Chicago to Sioux Falls Road Trip: A Complete Guide

This 580-mile route follows I-90 west across Illinois, Wisconsin, Minnesota, and into South Dakota. A little-known fact: the exit for Albert Lea, Minnesota, at mile marker 11 on I-90, marks the point where the route crosses the historic Jefferson Highway, an early transcontinental auto trail.

The drive typically takes 8–9 hours without stops. However, the journey is worth taking slowly, as the landscape shifts from the flat prairies of Illinois to the rolling hills of the Driftless Area, then to the vast plains of South Dakota. The question is it worth driving Chicago, IL to Sioux Falls, SD? For those who appreciate diverse scenery, charming small towns, and unique roadside attractions, the answer is a resounding yes.

Many travelers wonder how long to drive Chicago, IL to Sioux Falls, SD, but the real adventure lies in the things to do between Chicago, IL and Sioux Falls, SD. From the historic river town of Galena to the world-famous Spam Museum in Austin, the route is packed with memorable stops. Use our guide to how to find the best stops and hidden gems between cities to customize your trip.

I-90 is the backbone of this journey, a well-maintained interstate with ample services. The route is flat and straight through Illinois, becoming more scenic in Wisconsin. Gas stations are plentiful, but you'll want to plan stops as you move west.

Fuel prices vary: expect higher costs near Chicago and lower once you cross into South Dakota. To save money, fill up in the Rockford, IL area or just before the Minnesota border.

• Best gas stations: Kwik Trip (Wisconsin/Minnesota) for clean restrooms and coffee.
• Rest areas: Every 30–40 miles, often with picnic tables and vending machines.
• Toll roads: The Jane Addams Memorial Tollway (I-90) near Chicago requires an I-PASS or cash payment. Pay online within 14 days to avoid fines.
• Road quality: Excellent, with occasional construction in summer. Check 511 for up-to-date road conditions.

This route is also alternative-friendly: consider US-20 through northern Illinois and Iowa for a slower, more scenic drive if you have extra time.

I-90 is generally safe, but watch for deer, especially at dawn and dusk. In winter, ice and snow are common from November to March. Always carry an emergency kit and blankets.

For families, the best stops between Chicago, IL and Sioux Falls, SD include the Madison Children's Museum, the Minnesota Children's Museum in Rochester, and the Butterfly House & Aquarium in Sioux Falls. Pets are welcome at most rest areas and state parks, but keep them leashed.

• Fatigue management: Stop every 2 hours or 150 miles. Good rest zones include the Belvidere Oasis (IL) and the Blue Earth Rest Area (MN).
• Child-friendly: Use audio books or road trip bingo to keep kids engaged.
• Pet-friendly: Many hotels along I-90 accept pets; check policies in advance.

Hidden off-route spots: Just south of I-90 in Wisconsin, the town of Mineral Point is a hidden gem with Cornish heritage and artist studios. In Minnesota, the town of New Ulm offers German architecture and the Hermann Monument – a 102-foot statue honoring a Germanic leader.

The first major change in scenery occurs near Madison, where the landscape becomes hilly and dotted with glacial lakes. The Driftless Region in southwest Wisconsin remains unglaciated, offering rugged bluffs and deep valleys. As you cross the Mississippi River at La Crosse, the river’s broad floodplain creates a dramatic vista.

Minnesota’s plains are more subtle, with endless fields of corn and soybeans. Approaching Sioux Falls, you'll notice the land flattening into the Great Plains. The Big Sioux River cuts through the city, forming the namesake waterfall in Falls Park.

• Natural attractions: Devil's Lake State Park (WI), Blue Mounds State Park (MN), Falls Park (SD).
• Local commerce: Shop for Wisconsin cheese at the Mars Cheese Castle (Kenosha), or visit the Spam Museum (Austin, MN) for a quirky cultural experience.
• Farmers markets: Saturdays in La Crosse and Sioux Falls offer fresh produce and artisan goods.

UNESCO World Heritage Sites: While none exist directly on the route, the nearby Frank Lloyd Wright-designed buildings in Oak Park (Chicago) and the Taliesin estate in Spring Green, WI, are on the tentative list. The Effigy Mounds National Monument in Iowa is also a strong candidate for its prehistoric Native American mounds.