{"id":33653,"date":"2026-01-16T09:37:58","date_gmt":"2026-01-16T14:37:58","guid":{"rendered":"https:\/\/turo.com\/blog\/canada\/?p=33653"},"modified":"2026-01-20T09:38:44","modified_gmt":"2026-01-20T14:38:44","slug":"turo-guide-winnipeg-to-chicago-drive","status":"publish","type":"post","link":"https:\/\/turo.com\/blog\/canada\/wayfaring\/turo-guide-winnipeg-to-chicago-drive\/","title":{"rendered":"Winnipeg to Chicago drive: The ultimate road trip guide"},"content":{"rendered":"\n<p class=\"wp-block-paragraph\">Swap wide open prairie skies for river cities, sandstone cliffs, and the shoreline of Lake Michigan on the Winnipeg to Chicago drive. This road trip guide gives you tips to make the trip smooth and must-see stops along the way so you can enjoy the drive itself instead of rushing to the finish line.<\/p>\n\n\n\n<p class=\"has-text-align-center has-medium-font-size wp-block-paragraph\"><strong>In this guide, we&#8217;ll be covering:<\/strong><\/p>\n\n\n\n<ul style=\"background-color:#f2e9ff\" class=\"wp-block-list has-background\">\n<li><a href=\"#tips-for-driving\">Tips for driving from Winnipeg to Chicago<\/a><\/li>\n\n\n\n<li><a href=\"#road-conditions\">How are the road conditions between Winnipeg and Chicago?<\/a><\/li>\n\n\n\n<li><a href=\"#best-time-of-year\">What is the best time of year to drive from Winnipeg to Chicago, IL?<\/a><\/li>\n\n\n\n<li><a href=\"#ev-chargers\">Are there EV chargers along the way between Winnipeg and Chicago?<\/a><\/li>\n\n\n\n<li><a href=\"#where-to-stop\">Where to stop while driving from Winnipeg to Chicago, Illinois<\/a><\/li>\n\n\n\n<li><a href=\"#faqs\">Frequently asked questions about the Winnipeg to Chicago road trip<\/a><\/li>\n\n\n\n<li><a href=\"#book-your-rental\">Book your rental car in Winnipeg with Turo<\/a><\/li>\n<\/ul>\n\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n\n\n\n<figure class=\"wp-block-image size-large\"><img loading=\"lazy\" decoding=\"async\" width=\"1024\" height=\"576\" src=\"https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/the-best-rental-cars-in-winnipeg-for-a-road-trip-to-chicago-1024x576.png\" alt=\"The best rental cars in Winnipeg for a road trip to Chicago.\" class=\"wp-image-33659\" srcset=\"https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/the-best-rental-cars-in-winnipeg-for-a-road-trip-to-chicago-1024x576.png 1024w, https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/the-best-rental-cars-in-winnipeg-for-a-road-trip-to-chicago-300x169.png 300w, https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/the-best-rental-cars-in-winnipeg-for-a-road-trip-to-chicago-768x432.png 768w, https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/the-best-rental-cars-in-winnipeg-for-a-road-trip-to-chicago.png 1366w\" sizes=\"auto, (max-width: 1024px) 100vw, 1024px\" \/><\/figure>\n\n\n\n<h2 class=\"wp-block-heading\" id=\"tips-for-driving\"><strong>Tips for driving from Winnipeg to Chicago<\/strong><\/h2>\n\n\n\n<p class=\"wp-block-paragraph\">The drive from Winnipeg to Chicago covers roughly 1,300 kilometres and takes about 13 to 14 hours behind the wheel. Most drivers split it over at least two days to keep things manageable. Crossing into the U.S. happens early, so keep your passports accessible and plan buffer time around the Pembina\u2013Emerson border.<\/p>\n\n\n\n<h2 class=\"wp-block-heading\" id=\"road-conditions\"><strong>How are the road conditions between Winnipeg and Chicago?<\/strong><\/h2>\n\n\n\n<p class=\"wp-block-paragraph\">The route follows major highways like I-29 and I-94, which are paved and well-maintained. North Dakota and Minnesota stretches are long and straight, and traffic builds closer to Minneapolis\u2013Saint Paul and again approaching Chicago.<\/p>\n\n\n\n<h2 class=\"wp-block-heading\" id=\"best-time-of-year\"><strong>What is the best time of year to drive from Winnipeg to Chicago, IL?<\/strong><\/h2>\n\n\n\n<p class=\"wp-block-paragraph\">Late spring through early fall offers the smoothest experience. Summer brings long daylight hours and dry roads, though cities can feel busier. Fall adds cooler temperatures and changing <a href=\"https:\/\/turo.com\/blog\/canada\/wayfaring\/best-canadian-scenic-drives-for-fall-colours\/\" target=\"_blank\" rel=\"noopener\" title=\"\">fall colours<\/a> across Minnesota and Wisconsin. Winter driving is possible, but storms and blowing snow can slow progress and make things challenging.<\/p>\n\n\n\n<figure class=\"wp-block-image size-large\"><img loading=\"lazy\" decoding=\"async\" width=\"1024\" height=\"576\" src=\"https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/browse-turo-for-the-best-car-rentals-for-the-winnipeg-to-chicago-drive-1024x576.png\" alt=\"Browse Turo for the best car rentals for the Winnipeg to Chicago drive.\" class=\"wp-image-33655\" srcset=\"https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/browse-turo-for-the-best-car-rentals-for-the-winnipeg-to-chicago-drive-1024x576.png 1024w, https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/browse-turo-for-the-best-car-rentals-for-the-winnipeg-to-chicago-drive-300x169.png 300w, https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/browse-turo-for-the-best-car-rentals-for-the-winnipeg-to-chicago-drive-768x432.png 768w, https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/browse-turo-for-the-best-car-rentals-for-the-winnipeg-to-chicago-drive.png 1366w\" sizes=\"auto, (max-width: 1024px) 100vw, 1024px\" \/><\/figure>\n\n\n\n<h2 class=\"wp-block-heading\" id=\"ev-chargers\"><strong>Are there EV chargers along the way between Winnipeg and Chicago?<\/strong><\/h2>\n\n\n\n<p class=\"wp-block-paragraph\">You can find fast chargers in towns that line the route and at rest stops along I-94. Charging stations cluster near downtown areas, shopping centres, and highway exits.<\/p>\n\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n\n\n\n<h2 class=\"wp-block-heading\" id=\"where-to-stop\"><strong>Where to stop while driving from Winnipeg to Chicago, Illinois<\/strong><\/h2>\n\n\n\n<p class=\"wp-block-paragraph\">Driving from Winnipeg to Chicago takes you through a stretch of the Midwest that&#8217;s well worth slowing down for. These stops break up the distance and give the drive a clear rhythm instead of feeling like one long push south.<\/p>\n\n\n\n<h3 class=\"wp-block-heading\" id=\"pembina-gorge\"><strong>Pembina Gorge State Recreation Area, North Dakota<\/strong><\/h3>\n\n\n\n<figure class=\"wp-block-image size-large\"><img loading=\"lazy\" decoding=\"async\" width=\"1024\" height=\"576\" src=\"https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/winnipeg-to-chicago-drive-pembina-gorge-state-recreation-area-north-dakota-1024x576.png\" alt=\"Winnipeg to Chicago drive: The ultimate road trip guide: Pembina Gorge State Recreation Area, North Dakota\" class=\"wp-image-33663\" srcset=\"https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/winnipeg-to-chicago-drive-pembina-gorge-state-recreation-area-north-dakota-1024x576.png 1024w, https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/winnipeg-to-chicago-drive-pembina-gorge-state-recreation-area-north-dakota-300x169.png 300w, https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/winnipeg-to-chicago-drive-pembina-gorge-state-recreation-area-north-dakota-768x432.png 768w, https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/winnipeg-to-chicago-drive-pembina-gorge-state-recreation-area-north-dakota.png 1366w\" sizes=\"auto, (max-width: 1024px) 100vw, 1024px\" \/><\/figure>\n\n\n\n<p class=\"wp-block-paragraph\">Pembina Gorge cuts sharply into North Dakota&#8217;s prairie, revealing a steep river valley filled with hardwood forest, winding trails, and lookout points above the Pembina River. It&#8217;s unique from anywhere else in the prairies, and a great stop after crossing the border.<\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li><strong>Distance from Winnipeg:<\/strong> ~130 km (~1.5 hours)<\/li>\n\n\n\n<li><strong>Distance to Chicago:<\/strong> ~1,170 km (~12 hours)<\/li>\n<\/ul>\n\n\n\n<h4 class=\"wp-block-heading has-text-align-center has-white-color has-black-background-color has-text-color has-background has-link-color wp-elements-1\"><strong>Why it&#8217;s great<\/strong><\/h4>\n\n\n\n<p class=\"wp-block-paragraph\">You can see a lot without going too far from the car. Short hikes lead to views of the valley, wooded slopes, and quiet river bends.<\/p>\n\n\n\n<h4 class=\"wp-block-heading has-text-align-center has-white-color has-black-background-color has-text-color has-background has-link-color wp-elements-2\"><strong>Practical tips<\/strong><\/h4>\n\n\n\n<p class=\"wp-block-paragraph\">Trail access roads can be uneven, and services are limited nearby. Bring water, snacks, and offline maps before leaving the highway.<\/p>\n\n\n\n<h4 class=\"wp-block-heading has-text-align-center has-white-color has-black-background-color has-text-color has-background has-link-color wp-elements-3\"><strong>How to get there<\/strong><\/h4>\n\n\n\n<p class=\"wp-block-paragraph\">Start with a <a href=\"https:\/\/turo.com\/ca\/en\/car-rental\/canada\/ywg\" target=\"_blank\" rel=\"noopener\" title=\"\">Winnipeg airport car rental<\/a> from Turo, with delivery available right to arrivals. From there, drive south on Highway 75 and cross into the U.S. at Emerson\u2013Pembina, then continue on I-29. Some access points are gravel with uneven shoulders. An <a href=\"https:\/\/turo.com\/ca\/en\/suv-rental\/canada\" target=\"_blank\" rel=\"noopener\" title=\"\">SUV<\/a> or <a href=\"https:\/\/turo.com\/ca\/en\/search?badges=ALL_WHEEL_DRIVE\" target=\"_blank\" rel=\"noopener\" title=\"\">all-wheel drive vehicle<\/a> from brands like <a href=\"https:\/\/turo.com\/ca\/en\/car-rental\/canada\/jeep\" target=\"_blank\" rel=\"noopener\" title=\"\">Jeep<\/a> or <a href=\"https:\/\/turo.com\/ca\/en\/car-rental\/canada\/subaru\" target=\"_blank\" rel=\"noopener\" title=\"\">Subaru<\/a> gives you extra clearance and space for gear.<\/p>\n\n\n\n<iframe src=\"https:\/\/www.google.com\/maps\/embed?pb=!1m18!1m12!1m3!1d2620.5457795290663!2d-98.06269652324013!3d48.94309269474158!2m3!1f0!2f0!3f0!3m2!1i1024!2i768!4f13.1!3m3!1m2!1s0x52c3af15baaaaaab%3A0x7cf9bf4e17c22a33!2sPembina%20Gorge%20State%20Recreation%20Area!5e0!3m2!1sen!2sca!4v1766173482321!5m2!1sen!2sca\" width=\"600\" height=\"450\" style=\"border:0;\" allowfullscreen=\"\" loading=\"lazy\" referrerpolicy=\"no-referrer-when-downgrade\"><\/iframe>\n\n\n\n<div style=\"height:35px\" aria-hidden=\"true\" class=\"wp-block-spacer\"><\/div>\n\n\n\n<div class=\"wp-block-buttons is-content-justification-center is-layout-flex wp-container-core-buttons-is-layout-fe48e5de wp-block-buttons-is-layout-flex\">\n<div class=\"wp-block-button has-custom-width wp-block-button__width-50\"><a class=\"wp-block-button__link has-black-background-color has-background has-text-align-center wp-element-button\" href=\"https:\/\/turo.com\/ca\/en\/search\" style=\"border-radius:9px\" target=\"_blank\" rel=\"noreferrer noopener\">Browse cars on Turo<\/a><\/div>\n<\/div>\n\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n\n\n\n<h3 class=\"wp-block-heading\" id=\"minneapolis-saint-paul\"><strong>Minneapolis\u2013Saint Paul, Minnesota<\/strong><\/h3>\n\n\n\n<figure class=\"wp-block-image size-large\"><img loading=\"lazy\" decoding=\"async\" width=\"1024\" height=\"576\" src=\"https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/winnipeg-to-chicago-drive-minneapolis-saint-paul-minnesota-1024x576.png\" alt=\"Winnipeg to Chicago drive: The ultimate road trip guide\" class=\"wp-image-33662\" srcset=\"https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/winnipeg-to-chicago-drive-minneapolis-saint-paul-minnesota-1024x576.png 1024w, https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/winnipeg-to-chicago-drive-minneapolis-saint-paul-minnesota-300x169.png 300w, https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/winnipeg-to-chicago-drive-minneapolis-saint-paul-minnesota-768x432.png 768w, https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/winnipeg-to-chicago-drive-minneapolis-saint-paul-minnesota.png 1366w\" sizes=\"auto, (max-width: 1024px) 100vw, 1024px\" \/><\/figure>\n\n\n\n<p class=\"wp-block-paragraph\">On the east and west banks of the Mississippi River, <a href=\"https:\/\/www.minneapolis.org\/\" target=\"_blank\" rel=\"noopener\" title=\"\">Minneapolis\u2013Saint Paul<\/a>&#8216;s waterfalls, riverfront paths, and historic bridges are woven right into the city grid. Minnehaha Falls and the Stone Arch Bridge are both minutes from downtown and easy to pair in a single stop.<\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li><strong>Distance from Winnipeg:<\/strong> ~720 km (~7.5 hours)<\/li>\n\n\n\n<li><strong>Distance to Chicago:<\/strong> ~580 km (~6 hours)<\/li>\n<\/ul>\n\n\n\n<h4 class=\"wp-block-heading has-text-align-center has-white-color has-black-background-color has-text-color has-background has-link-color wp-elements-4\"><strong>Why it&#8217;s great<\/strong><\/h4>\n\n\n\n<p class=\"wp-block-paragraph\">You can visit a 16-metre waterfall and walk across the Mississippi on a former rail bridge in the morning and dine in a world-class restaurant in the evening without leaving the city&#8217;s core.<\/p>\n\n\n\n<h4 class=\"wp-block-heading has-text-align-center has-white-color has-black-background-color has-text-color has-background has-link-color wp-elements-5\"><strong>Practical tips<\/strong><\/h4>\n\n\n\n<p class=\"wp-block-paragraph\">Parking around Minnehaha Falls and the riverfront fills quickly, especially on weekends. Metered zones and ramps dominate downtown, and event traffic can change access routes fast.<\/p>\n\n\n\n<h4 class=\"wp-block-heading has-text-align-center has-white-color has-black-background-color has-text-color has-background has-link-color wp-elements-6\"><strong>How to get there<\/strong><\/h4>\n\n\n\n<p class=\"wp-block-paragraph\">Follow I-29 south, then merge onto I-94 east into the Twin Cities. Expect tighter streets and structured parking near major sights. A compact <a href=\"https:\/\/turo.com\/ca\/en\/car-rental\/canada\" target=\"_blank\" rel=\"noopener\" title=\"\">car rental<\/a> with a smaller footprint keeps city driving simple, and sporty models from <a href=\"https:\/\/turo.com\/ca\/en\/car-rental\/canada\/bmw\" target=\"_blank\" rel=\"noopener\" title=\"\">BMW<\/a>, <a href=\"https:\/\/turo.com\/ca\/en\/car-rental\/canada\/mercedes-benz\" target=\"_blank\" rel=\"noopener\" title=\"\">Mercedes-Benz<\/a>, or <a href=\"https:\/\/turo.com\/ca\/en\/car-rental\/canada\/nissan\" target=\"_blank\" rel=\"noopener\" title=\"\">Nissan<\/a> are easy to maneuver without sacrificing comfort on the highway.<\/p>\n\n\n\n<iframe src=\"https:\/\/www.google.com\/maps\/embed?pb=!1m18!1m12!1m3!1d152017.71157089417!2d-93.34787779160284!3d44.92951727955196!2m3!1f0!2f0!3f0!3m2!1i1024!2i768!4f13.1!3m3!1m2!1s0x87f629fd5bb7538f%3A0xd070c186a8aea420!2sTwin%20Cities%2C%20MN%2C%20USA!5e0!3m2!1sen!2sca!4v1766174074284!5m2!1sen!2sca\" width=\"600\" height=\"450\" style=\"border:0;\" allowfullscreen=\"\" loading=\"lazy\" referrerpolicy=\"no-referrer-when-downgrade\"><\/iframe>\n\n\n\n<div style=\"height:35px\" aria-hidden=\"true\" class=\"wp-block-spacer\"><\/div>\n\n\n\n<div class=\"wp-block-buttons is-content-justification-center is-layout-flex wp-container-core-buttons-is-layout-fe48e5de wp-block-buttons-is-layout-flex\">\n<div class=\"wp-block-button has-custom-width wp-block-button__width-50\"><a class=\"wp-block-button__link has-black-background-color has-background has-text-align-center wp-element-button\" href=\"https:\/\/turo.com\/ca\/en\/search\" style=\"border-radius:9px\" target=\"_blank\" rel=\"noreferrer noopener\">Browse cars on Turo<\/a><\/div>\n<\/div>\n\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n\n\n\n<h3 class=\"wp-block-heading\" id=\"wisconsin-dells\"><strong>Wisconsin Dells, Wisconsin<\/strong><\/h3>\n\n\n\n<figure class=\"wp-block-image size-large\"><img loading=\"lazy\" decoding=\"async\" width=\"1024\" height=\"576\" src=\"https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/winnipeg-to-chicago-drive-wisconsin-dells-wisconsin-1024x576.png\" alt=\"Winnipeg to Chicago drive: The ultimate road trip guide: Wisconsin Dells, Wisconsin.\" class=\"wp-image-33665\" srcset=\"https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/winnipeg-to-chicago-drive-wisconsin-dells-wisconsin-1024x576.png 1024w, https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/winnipeg-to-chicago-drive-wisconsin-dells-wisconsin-300x169.png 300w, https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/winnipeg-to-chicago-drive-wisconsin-dells-wisconsin-768x432.png 768w, https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/winnipeg-to-chicago-drive-wisconsin-dells-wisconsin.png 1366w\" sizes=\"auto, (max-width: 1024px) 100vw, 1024px\" \/><\/figure>\n\n\n\n<p class=\"wp-block-paragraph\">Wisconsin Dells follows the Wisconsin River through narrow sandstone formations, with riverwalks, boat routes, and exposed rock walls running right through the area. It&#8217;s also known for its theme parks and large waterparks, many of which are minutes apart and easy to reach from the highway.<\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li><strong>Distance from Winnipeg:<\/strong> ~930 km (~9.5 hours)<\/li>\n\n\n\n<li><strong>Distance to Chicago:<\/strong> ~370 km (~4 hours)<\/li>\n<\/ul>\n\n\n\n<h4 class=\"wp-block-heading has-text-align-center has-white-color has-black-background-color has-text-color has-background has-link-color wp-elements-7\"><strong>Why it&#8217;s great<\/strong><\/h4>\n\n\n\n<p class=\"wp-block-paragraph\">The short distances between attractions make it easy to plan a full day of fun without long drives.<\/p>\n\n\n\n<h4 class=\"wp-block-heading has-text-align-center has-white-color has-black-background-color has-text-color has-background has-link-color wp-elements-8\"><strong>Practical tips<\/strong><\/h4>\n\n\n\n<p class=\"wp-block-paragraph\">Many attractions allow strollers, but stairs, splash zones, and narrow walkways are common. Plan to take out only what you need and store a stroller in the vehicle between stops.<\/p>\n\n\n\n<h4 class=\"wp-block-heading has-text-align-center has-white-color has-black-background-color has-text-color has-background has-link-color wp-elements-9\"><strong>How to get there<\/strong><\/h4>\n\n\n\n<p class=\"wp-block-paragraph\">Drive southeast on I-94 and follow the signs into Wisconsin Dells. Attractions are spread across the area, so if you&#8217;re planning a <a href=\"https:\/\/turo.com\/blog\/canada\/wayfaring\/family-size-adventure-planning-a-road-trip-with-kids\/\" target=\"_blank\" rel=\"noopener\" title=\"\">road trip with kids<\/a>, expect lots of short drives. Making your <a href=\"https:\/\/turo.com\/ca\/en\/car-rental\/canada\/winnipeg-mb\" target=\"_blank\" rel=\"noopener\" title=\"\">Winnipeg rental car<\/a> a <a href=\"https:\/\/turo.com\/ca\/en\/minivan-rental\/canada\" target=\"_blank\" rel=\"noopener\" title=\"\">minivan<\/a> or <a href=\"https:\/\/turo.com\/ca\/en\/van-rental\/canada\" target=\"_blank\" rel=\"noopener\" title=\"\">van<\/a> from <a href=\"https:\/\/turo.com\/ca\/en\/car-rental\/canada\/chrysler\" target=\"_blank\" rel=\"noopener\" title=\"\">Chrysler<\/a> or <a href=\"https:\/\/turo.com\/ca\/en\/car-rental\/canada\/ford\" target=\"_blank\" rel=\"noopener\" title=\"\">Ford<\/a> makes it easy to load and unload a stroller and bags between stops and keep everyone comfortable.<\/p>\n\n\n\n<iframe src=\"https:\/\/www.google.com\/maps\/embed?pb=!1m18!1m12!1m3!1d46200.21902485685!2d-89.81967699987021!3d43.63747977061765!2m3!1f0!2f0!3f0!3m2!1i1024!2i768!4f13.1!3m3!1m2!1s0x8807493e07cb769d%3A0x4acd26cd280b3378!2sWisconsin%20Dells%2C%20WI%2C%20USA!5e0!3m2!1sen!2sca!4v1766174730959!5m2!1sen!2sca\" width=\"600\" height=\"450\" style=\"border:0;\" allowfullscreen=\"\" loading=\"lazy\" referrerpolicy=\"no-referrer-when-downgrade\"><\/iframe>\n\n\n\n<div style=\"height:35px\" aria-hidden=\"true\" class=\"wp-block-spacer\"><\/div>\n\n\n\n<div class=\"wp-block-buttons is-content-justification-center is-layout-flex wp-container-core-buttons-is-layout-fe48e5de wp-block-buttons-is-layout-flex\">\n<div class=\"wp-block-button has-custom-width wp-block-button__width-50\"><a class=\"wp-block-button__link has-black-background-color has-background has-text-align-center wp-element-button\" href=\"https:\/\/turo.com\/ca\/en\/search\" style=\"border-radius:9px\" target=\"_blank\" rel=\"noreferrer noopener\">Browse cars on Turo<\/a><\/div>\n<\/div>\n\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n\n\n\n<h3 class=\"wp-block-heading\" id=\"milwaukee\"><strong>Milwaukee, Wisconsin<\/strong><\/h3>\n\n\n\n<figure class=\"wp-block-image size-large\"><img loading=\"lazy\" decoding=\"async\" width=\"1024\" height=\"576\" src=\"https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/winnipeg-to-chicago-drive-milwaukee-wisconsin-1024x576.png\" alt=\"Winnipeg to Chicago drive: The ultimate road trip guide: Milwaukee, Wisconsin.\" class=\"wp-image-33661\" srcset=\"https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/winnipeg-to-chicago-drive-milwaukee-wisconsin-1024x576.png 1024w, https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/winnipeg-to-chicago-drive-milwaukee-wisconsin-300x169.png 300w, https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/winnipeg-to-chicago-drive-milwaukee-wisconsin-768x432.png 768w, https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/winnipeg-to-chicago-drive-milwaukee-wisconsin.png 1366w\" sizes=\"auto, (max-width: 1024px) 100vw, 1024px\" \/><\/figure>\n\n\n\n<p class=\"wp-block-paragraph\"><a href=\"https:\/\/www.visitmilwaukee.org\/\" target=\"_blank\" rel=\"noopener\" title=\"\">Milwaukee<\/a> sits on Lake Michigan and carries a strong industrial and brewing history that still shapes the city today. Historic breweries, working riverfronts, and the <a href=\"https:\/\/mam.org\/\" target=\"_blank\" rel=\"noopener\" title=\"\">Milwaukee Art Museum<\/a>&#8216;s winged Quadracci Pavilion all sit within a tight downtown grid near the water.<\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li><strong>Distance from Winnipeg:<\/strong> ~1,020 km (~10.5 hours)<\/li>\n\n\n\n<li><strong>Distance to Chicago:<\/strong> ~150 km (~1.5 hours)<\/li>\n<\/ul>\n\n\n\n<h4 class=\"wp-block-heading has-text-align-center has-white-color has-black-background-color has-text-color has-background has-link-color wp-elements-10\"><strong>Why it&#8217;s great<\/strong><\/h4>\n\n\n\n<p class=\"wp-block-paragraph\">Culture and history come together on the shore of beautiful Lake Michigan, and you can see a lot in a single afternoon.<\/p>\n\n\n\n<h4 class=\"wp-block-heading has-text-align-center has-white-color has-black-background-color has-text-color has-background has-link-color wp-elements-11\"><strong>Practical tips<\/strong><\/h4>\n\n\n\n<p class=\"wp-block-paragraph\">Many brewery tours and museums run on set entry times, especially on weekends. Booking ahead helps you avoid waiting.<\/p>\n\n\n\n<h4 class=\"wp-block-heading has-text-align-center has-white-color has-black-background-color has-text-color has-background has-link-color wp-elements-12\"><strong>How to get there<\/strong><\/h4>\n\n\n\n<p class=\"wp-block-paragraph\">Follow I-94 southeast directly into Milwaukee. It&#8217;s easy to get around the downtown core, and charging stations are common near garages, museums, and shopping areas. An <a href=\"https:\/\/turo.com\/ca\/en\/electric-vehicle-rental\/canada\" target=\"_blank\" rel=\"noopener\" title=\"\">electric vehicle<\/a> is great here, and charging up <a href=\"https:\/\/turo.com\/ca\/en\/car-rental\/canada\/chevrolet\" target=\"_blank\" rel=\"noopener\" title=\"\">Chevrolet<\/a>, <a href=\"https:\/\/turo.com\/ca\/en\/car-rental\/canada\/toyota\" target=\"_blank\" rel=\"noopener\" title=\"\">Toyota<\/a>, or <a href=\"https:\/\/turo.com\/ca\/en\/car-rental\/canada\/tesla\" target=\"_blank\" rel=\"noopener\" title=\"\">Tesla<\/a> models between stops is easy.<\/p>\n\n\n\n<iframe src=\"https:\/\/www.google.com\/maps\/embed?pb=!1m18!1m12!1m3!1d1972132.9689767305!2d-88.82960636794219!3d43.67715814682874!2m3!1f0!2f0!3f0!3m2!1i1024!2i768!4f13.1!3m3!1m2!1s0x880502d7578b47e7%3A0x445f1922b5417b84!2sMilwaukee%2C%20WI%2C%20USA!5e0!3m2!1sen!2sca!4v1766176011225!5m2!1sen!2sca\" width=\"600\" height=\"450\" style=\"border:0;\" allowfullscreen=\"\" loading=\"lazy\" referrerpolicy=\"no-referrer-when-downgrade\"><\/iframe>\n\n\n\n<div style=\"height:35px\" aria-hidden=\"true\" class=\"wp-block-spacer\"><\/div>\n\n\n\n<div class=\"wp-block-buttons is-content-justification-center is-layout-flex wp-container-core-buttons-is-layout-fe48e5de wp-block-buttons-is-layout-flex\">\n<div class=\"wp-block-button has-custom-width wp-block-button__width-50\"><a class=\"wp-block-button__link has-black-background-color has-background has-text-align-center wp-element-button\" href=\"https:\/\/turo.com\/ca\/en\/search\" style=\"border-radius:9px\" target=\"_blank\" rel=\"noreferrer noopener\">Browse cars on Turo<\/a><\/div>\n<\/div>\n\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n\n\n\n<h3 class=\"wp-block-heading\" id=\"millennium-park\"><strong>Millennium Park, Chicago<\/strong><\/h3>\n\n\n\n<figure class=\"wp-block-image size-large\"><img loading=\"lazy\" decoding=\"async\" width=\"1024\" height=\"576\" src=\"https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/winnipeg-to-chicago-drive-millennium-park-chicago-1024x576.png\" alt=\"Winnipeg to Chicago drive: The ultimate road trip guide: Millennium Park, Chicago.\" class=\"wp-image-33660\" srcset=\"https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/winnipeg-to-chicago-drive-millennium-park-chicago-1024x576.png 1024w, https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/winnipeg-to-chicago-drive-millennium-park-chicago-300x169.png 300w, https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/winnipeg-to-chicago-drive-millennium-park-chicago-768x432.png 768w, https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/winnipeg-to-chicago-drive-millennium-park-chicago.png 1366w\" sizes=\"auto, (max-width: 1024px) 100vw, 1024px\" \/><\/figure>\n\n\n\n<p class=\"wp-block-paragraph\">Millennium Park is right at the centre of downtown <a href=\"https:\/\/www.chicago.gov\/city\/en\/depts\/dca\/supp_info\/millennium_park.html\" target=\"_blank\" rel=\"noopener\" title=\"\">Chicago<\/a>, framed by skyscrapers and the edge of Lake Michigan. It&#8217;s home to Cloud Gate, better known as &#8220;the Bean,&#8221; along with public art, open plazas, and direct access to the lakefront path.<\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li><strong>Distance from Winnipeg:<\/strong> ~1,300 km (~13.5 hours)<\/li>\n\n\n\n<li><strong>Distance to Chicago:<\/strong> 0 km (arrival point)<\/li>\n<\/ul>\n\n\n\n<h4 class=\"wp-block-heading has-text-align-center has-white-color has-black-background-color has-text-color has-background has-link-color wp-elements-13\"><strong>Why it&#8217;s great<\/strong><\/h4>\n\n\n\n<p class=\"wp-block-paragraph\">You can see Chicago&#8217;s skyline reflected in the Bean, walk through Crown Fountain, and step straight onto the Lakefront Trail. It&#8217;s a great place to get a feel for the city.<\/p>\n\n\n\n<h4 class=\"wp-block-heading has-text-align-center has-white-color has-black-background-color has-text-color has-background has-link-color wp-elements-14\"><strong>Practical tips<\/strong><\/h4>\n\n\n\n<p class=\"wp-block-paragraph\">The park is busiest late morning through early evening, especially on weekends. Early mornings offer more space around Cloud Gate and on nearby streets with metered parking.<\/p>\n\n\n\n<h4 class=\"wp-block-heading has-text-align-center has-white-color has-black-background-color has-text-color has-background has-link-color wp-elements-15\"><strong>How to get there<\/strong><\/h4>\n\n\n\n<p class=\"wp-block-paragraph\">Take I-94 into downtown Chicago and follow Lake Shore Drive along the edge of the park. The route runs beside Lake Michigan and gives you a clear view of the skyline as you approach. A <a href=\"https:\/\/turo.com\/ca\/en\/exotic-luxury-rental\/canada\" target=\"_blank\" rel=\"noopener\" title=\"\">luxury car<\/a>, <a href=\"https:\/\/turo.com\/ca\/en\/classic-rental\/canada\" target=\"_blank\" rel=\"noopener\" title=\"\">classic car<\/a> or <a href=\"https:\/\/turo.com\/ca\/en\/sports-rental\/canada\" target=\"_blank\" rel=\"noopener\" title=\"\">sports car<\/a>, like a model from <a href=\"https:\/\/turo.com\/ca\/en\/car-rental\/canada\/mercedes-benz\" target=\"_blank\" rel=\"noopener\" title=\"\">Mercedes-Benz<\/a> or <a href=\"https:\/\/turo.com\/ca\/en\/car-rental\/canada\/porsche\" target=\"_blank\" rel=\"noopener\" title=\"\">Porsche<\/a>, feels great to drive in the city, especially along the lakefront.<\/p>\n\n\n\n<iframe src=\"https:\/\/www.google.com\/maps\/embed?pb=!1m18!1m12!1m3!1d2970.474414060653!2d-87.6219796735407!3d41.882653265128404!2m3!1f0!2f0!3f0!3m2!1i1024!2i768!4f13.1!3m3!1m2!1s0x880e2ca70b00f081%3A0xcbf62372ee30a12b!2sMillennium%20Park%2C%20Chicago%2C%20IL%2C%20USA!5e0!3m2!1sen!2sca!4v1766176881578!5m2!1sen!2sca\" width=\"600\" height=\"450\" style=\"border:0;\" allowfullscreen=\"\" loading=\"lazy\" referrerpolicy=\"no-referrer-when-downgrade\"><\/iframe>\n\n\n\n<div style=\"height:35px\" aria-hidden=\"true\" class=\"wp-block-spacer\"><\/div>\n\n\n\n<div class=\"wp-block-buttons is-content-justification-center is-layout-flex wp-container-core-buttons-is-layout-fe48e5de wp-block-buttons-is-layout-flex\">\n<div class=\"wp-block-button has-custom-width wp-block-button__width-50\"><a class=\"wp-block-button__link has-black-background-color has-background has-text-align-center wp-element-button\" href=\"https:\/\/turo.com\/ca\/en\/search\" style=\"border-radius:9px\" target=\"_blank\" rel=\"noreferrer noopener\">Browse cars on Turo<\/a><\/div>\n<\/div>\n\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n\n\n\n<h2 class=\"wp-block-heading\" id=\"faqs\"><strong>Frequently asked questions about the Winnipeg to Chicago road trip<\/strong><\/h2>\n\n\n\n<h3 class=\"wp-block-heading\"><strong>Where is Chicago?<\/strong><\/h3>\n\n\n\n<p class=\"wp-block-paragraph\">Chicago is on the southwestern edge of Lake Michigan in northeastern Illinois. It&#8217;s close to the borders of Indiana and Wisconsin and acts as a major transportation hub for the Midwest. By road, it&#8217;s roughly 1,300 kilometres south of Winnipeg.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">Most visitors arrive through O&#8217;Hare International Airport or Chicago Midway International Airport, both outside the downtown core with direct highway access. Book your Winnipeg or <a href=\"https:\/\/turo.com\/us\/en\/car-rental\/united-states\/ord\" target=\"_blank\" rel=\"noopener\" title=\"\">Chicago airport car rental<\/a> with Turo and get out and explore as soon as you land!<\/p>\n\n\n\n<iframe src=\"https:\/\/www.google.com\/maps\/embed?pb=!1m18!1m12!1m3!1d190255.5023211657!2d-87.89668567937782!3d41.83384858171965!2m3!1f0!2f0!3f0!3m2!1i1024!2i768!4f13.1!3m3!1m2!1s0x880e2c3cd0f4cbed%3A0xafe0a6ad09c0c000!2sChicago%2C%20IL%2C%20USA!5e0!3m2!1sen!2sca!4v1766177317000!5m2!1sen!2sca\" width=\"600\" height=\"450\" style=\"border:0;\" allowfullscreen=\"\" loading=\"lazy\" referrerpolicy=\"no-referrer-when-downgrade\"><\/iframe>\n\n\n\n<h3 class=\"wp-block-heading\"><strong>How long does it take to drive from Winnipeg to Chicago?<\/strong><\/h3>\n\n\n\n<p class=\"wp-block-paragraph\">Driving straight through takes about 13 to 14 hours, depending on border wait times, traffic near Minneapolis\u2013Saint Paul, and congestion approaching Chicago. Many travellers split the drive over two days to stay rested.<\/p>\n\n\n\n<h3 class=\"wp-block-heading\"><strong>Do you need a passport to drive from Winnipeg to Chicago?<\/strong><\/h3>\n\n\n\n<p class=\"wp-block-paragraph\">You do. You&#8217;ll cross the Canada\u2013U.S. border early in the drive, so a valid passport is required. Keep all of your documents close at hand as you&#8217;re approaching the crossing to keep things efficient.<\/p>\n\n\n\n<figure class=\"wp-block-image size-large\"><img loading=\"lazy\" decoding=\"async\" width=\"1024\" height=\"576\" src=\"https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/exploring-chicago-in-the-perfect-rental-car-from-winnipeg-richardson-international-airport-1024x576.png\" alt=\"Exploring Chicago in the perfect rental car from Winnipeg Richardson International Airport.\" class=\"wp-image-33656\" srcset=\"https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/exploring-chicago-in-the-perfect-rental-car-from-winnipeg-richardson-international-airport-1024x576.png 1024w, https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/exploring-chicago-in-the-perfect-rental-car-from-winnipeg-richardson-international-airport-300x169.png 300w, https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/exploring-chicago-in-the-perfect-rental-car-from-winnipeg-richardson-international-airport-768x432.png 768w, https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/exploring-chicago-in-the-perfect-rental-car-from-winnipeg-richardson-international-airport.png 1366w\" sizes=\"auto, (max-width: 1024px) 100vw, 1024px\" \/><\/figure>\n\n\n\n<h3 class=\"wp-block-heading\"><strong>How much gas from Winnipeg to Chicago?<\/strong><\/h3>\n\n\n\n<p class=\"wp-block-paragraph\">Fuel costs depend on your vehicle and fuel prices at the time of travel. Most drivers can expect to use roughly 100 to 120 litres of gas for the full drive. Filling up before long rural stretches helps avoid price jumps near major cities.<\/p>\n\n\n\n<h3 class=\"wp-block-heading\"><strong>Is it easy to drive in Chicago?<\/strong><\/h3>\n\n\n\n<p class=\"wp-block-paragraph\">Chicago is straightforward once you&#8217;re familiar with the grid layout. Major roads are well-marked, but traffic builds during rush hour. Downtown driving feels busiest near the Loop and lakefront, but neighbourhood routes are calmer and easier to navigate.<\/p>\n\n\n\n<figure class=\"wp-block-image size-large\"><img loading=\"lazy\" decoding=\"async\" width=\"1024\" height=\"576\" src=\"https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/the-best-rental-cars-for-cant-miss-activities-in-chicago-1024x576.png\" alt=\"The best rental cars for can\u2019t-miss activities in Chicago.\" class=\"wp-image-33658\" srcset=\"https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/the-best-rental-cars-for-cant-miss-activities-in-chicago-1024x576.png 1024w, https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/the-best-rental-cars-for-cant-miss-activities-in-chicago-300x169.png 300w, https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/the-best-rental-cars-for-cant-miss-activities-in-chicago-768x432.png 768w, https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/the-best-rental-cars-for-cant-miss-activities-in-chicago.png 1366w\" sizes=\"auto, (max-width: 1024px) 100vw, 1024px\" \/><\/figure>\n\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n\n\n\n<h2 class=\"wp-block-heading\" id=\"book-your-rental\"><strong>Book your rental car in Winnipeg with Turo<\/strong><\/h2>\n\n\n\n<figure class=\"wp-block-image size-large\"><img loading=\"lazy\" decoding=\"async\" width=\"1024\" height=\"576\" src=\"https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/get-ready-for-the-ultimate-road-trip-to-chicago-illinois-1024x576.png\" alt=\"Get ready for the ultimate road trip to Chicago, Illinois.\" class=\"wp-image-33657\" srcset=\"https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/get-ready-for-the-ultimate-road-trip-to-chicago-illinois-1024x576.png 1024w, https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/get-ready-for-the-ultimate-road-trip-to-chicago-illinois-300x169.png 300w, https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/get-ready-for-the-ultimate-road-trip-to-chicago-illinois-768x432.png 768w, https:\/\/turo.com\/blog\/canada\/wp-content\/uploads\/sites\/3\/2026\/01\/get-ready-for-the-ultimate-road-trip-to-chicago-illinois.png 1366w\" sizes=\"auto, (max-width: 1024px) 100vw, 1024px\" \/><\/figure>\n\n\n\n<p class=\"wp-block-paragraph\">A long drive works best when the car fits the plan, not the other way around. With Turo, you choose the exact vehicle you want to drive and skip the long lines at rental counters altogether. Pickup and delivery options in Winnipeg let you get behind the wheel where and when it makes sense for you. So, what are you waiting for? Pack your bags and hit the road!<\/p>\n\n\n\n<p class=\"has-text-align-center is-style-lead has-white-color has-black-background-color has-text-color has-background has-link-color wp-elements-16 wp-block-paragraph\" style=\"font-size:18px\">Feeling inspired? <strong>Pitch a Trip<\/strong> and let Turo sponsor your vehicle rental to turn this adventure into a reality! Whether you&#8217;re a storyteller, photographer, or just love to travel, this could be your chance to share your experience with the world.<\/p>\n\n\n\n<div class=\"wp-block-buttons is-content-justification-center is-layout-flex wp-container-core-buttons-is-layout-fe48e5de wp-block-buttons-is-layout-flex\">\n<div class=\"wp-block-button has-custom-width wp-block-button__width-50\"><a class=\"wp-block-button__link has-background has-text-align-center wp-element-button\" href=\"https:\/\/turo.com\/ca\/en\/car-rental\/canada\/pitch-a-trip\" style=\"border-radius:9px;background-color:#593cfb\"><strong>Pitch a Trip<\/strong><\/a><\/div>\n<\/div>\n\n\n\n<div style=\"height:40px\" aria-hidden=\"true\" class=\"wp-block-spacer\"><\/div>\n","protected":false},"excerpt":{"rendered":"<p>Swap wide open prairie skies for river cities, sandstone cliffs, and the shoreline of Lake Michigan on the Winnipeg to Chicago drive. This road trip guide gives you tips to&#8230;<\/p>\n","protected":false},"author":2,"featured_media":33664,"comment_status":"closed","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[13],"tags":[19,389,330,334],"language":[2],"class_list":["post-33653","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-wayfaring","tag-canada","tag-local-recommendations","tag-road-trip-itinerary","tag-turo-travel-content"],"acf":[],"aioseo_notices":[],"aioseo_head":"\n\t\t<!-- All in One SEO 5.0.2.1 - aioseo.com -->\n\t<meta name=\"description\" content=\"The Winnipeg to Chicago drive isn\u2019t just about the destination. This road trip guide invites you to explore the cities, parks, and sights that make the trip special.\" \/>\n\t<meta name=\"robots\" content=\"max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n\t<meta name=\"author\" content=\"Turo\"\/>\n\t<meta name=\"keywords\" content=\"canada,local recommendations,road trip itineraries,turo travel content\" \/>\n\t<link rel=\"canonical\" href=\"https:\/\/turo.com\/blog\/canada\/wayfaring\/turo-guide-winnipeg-to-chicago-drive\/\" \/>\n\t<meta name=\"generator\" content=\"All in One SEO (AIOSEO) 5.0.2.1\" \/>\n\t\t<meta property=\"og:locale\" content=\"en_US\" \/>\n\t\t<meta property=\"og:site_name\" content=\"Field Notes: The Turo Blog Canada - Notes from the road and beyond\" \/>\n\t\t<meta property=\"og:type\" content=\"article\" \/>\n\t\t<meta property=\"og:title\" content=\"Winnipeg to Chicago drive: The ultimate road trip guide | Turo\" \/>\n\t\t<meta property=\"og:description\" content=\"The Winnipeg to Chicago drive isn\u2019t just about the destination. 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