Chicago is one of the best launch pads for a road trip in the Midwest. Within a few hours you can reach sand dunes, sandstone canyons, a historic river town, the Wisconsin lakeshore and the very first mile of Route 66. These road trip ideas from Chicago are sorted by distance, so you can pick one that fits a day, a weekend or a full week.
All distances are approximate road miles from downtown Chicago. Add time for traffic on the expressways, which can be heavy at rush hour and on summer Friday afternoons.
Road trip ideas from Chicago at a glance
| Destination | Distance from Chicago | Best as |
|---|---|---|
| Indiana Dunes National Park | About 50 miles | Day trip |
| Milwaukee | About 90 miles | Day trip or weekend |
| Starved Rock State Park | About 95 miles | Day trip or weekend |
| Galena | About 165 miles | Weekend |
| Wisconsin Dells | About 200 miles | Weekend |
| Door County | About 250 miles (4 to 4.5 hours) | Long weekend |
| Sleeping Bear Dunes | About 335 miles | Long weekend or week |
| Route 66 to St. Louis | About 300 miles | Two to three days |
Day trips: dunes and canyons
Indiana Dunes National Park
About 50 miles from the Loop, Indiana Dunes is the closest national park to the city. It mixes Lake Michigan beaches, tall dunes and trails through woods and wetlands. Go early on summer weekends, when beach parking fills up.
Starved Rock State Park
Roughly 95 miles southwest, near Utica on the Illinois River, Starved Rock has 18 canyons carved into sandstone bluffs. French, LaSalle, Ottawa and St. Louis canyons have the most reliable waterfalls, which flow best in spring or after heavy rain.
Weekend road trips: Illinois and Wisconsin
Galena
Galena, in the far northwest corner of Illinois about 165 miles from Chicago, is a well-preserved 19th-century river town with a historic main street and rolling hills around it. The drive west gets prettier as you approach the Mississippi.
Milwaukee and Wisconsin Dells
Milwaukee is only about 90 miles north and makes an easy first stop. Continue to Wisconsin Dells, about 200 miles from Chicago, known for its sandstone river gorges and water parks. It is a strong pick for families.
Door County
Door County, the peninsula between Green Bay and Lake Michigan, is about 250 miles from Chicago, a drive of roughly four to four and a half hours on I-94, I-43 and WI-57. Plan at least three days to explore its small harbor towns, state parks and orchards. Fall color makes it especially popular in October.
Longer trips: around Lake Michigan
The Lake Michigan Circle Tour follows state highways all the way around the lake, through Illinois, Indiana, Michigan and Wisconsin. You do not need to drive the whole loop. A popular section heads up the Michigan side to Sleeping Bear Dunes National Lakeshore, about 335 miles from Chicago, then on to Mackinaw City, about 410 miles away. From there, ferries run to Mackinac Island, where cars are not allowed. Allow five to seven days for this northern swing.
The start of Route 66
Route 66 begins in downtown Chicago, on East Adams Street near Michigan Avenue, across from the Art Institute, where a “Begin” sign marks the spot. From there, the old road heads southwest across Illinois:
- Pontiac, about 100 miles out, is home to the Illinois Route 66 Hall of Fame and Museum.
- Springfield, the state capital, is about 200 miles from Chicago.
- St. Louis, about 300 miles away, is a natural end point for a short Route 66 sampler.
Two or three days is enough for the Illinois section. Parts of the historic alignment run next to I-55, so follow the brown Historic Route 66 signs to stay on the old road.
Sample weekend loop from Chicago
For a first trip, try this two-day loop. On day one, drive to Starved Rock State Park and hike the canyon trails in the morning, then continue west to Galena for the night. On day two, explore Galena’s main street, then head back to Chicago. The loop combines nature and history with no single leg much longer than the drive from Starved Rock to Galena.
How to pick your Chicago road trip
Start with how much time you have. A single day suits Indiana Dunes or Starved Rock. A weekend opens up Galena, Wisconsin Dells or Route 66 to Springfield. Door County and the Michigan shore need at least three days. For routes farther afield, our collection of trip ideas sorted by region and season covers the rest of the country, and the classic scenic drives of the United States shows how Route 66 compares with the other famous routes.
Timing also matters. Summer is peak season for the lake towns. Spring is best for waterfalls at Starved Rock. Fall brings color to Door County and Galena. Winter is quiet, and lake-effect snow can make driving in Michigan and Indiana difficult.
Chicago road trip FAQ
What is the best day trip from Chicago by car?
Indiana Dunes National Park, about 50 miles away, or Starved Rock State Park, about 95 miles away. Both offer hiking and scenery without an overnight stay.
How long is the drive from Chicago to Door County?
About 250 miles, roughly four to four and a half hours without long stops.
Where does Route 66 start in Chicago?
On East Adams Street near Michigan Avenue, across from the Art Institute of Chicago, where a “Begin” sign marks the start.
What is a good weekend road trip from Chicago?
Galena, Wisconsin Dells or the first section of Route 66 to Springfield all fit comfortably into two days.
