Regional Connected Routes
Best road trips passing through Chicago
We found 5 curated itineraries that include a stop in Chicago. Whether you want a weekend escape or a cross-country odyssey, these routes are fully enriched with stops, eats, and attractions.
5 Results
IL, MO, KS, OK, TX, NM, AZ, CA
Chicago, IL
Santa Monica, CA
$$ Tier
Route 66
2,448 miles
14-21 days
USA
Chicago, IL
Mackinac Island, MI
Family Gold$$$ Tier
The Great Lake Michigan Loop
450-500 miles
5-7 days
USA
Chicago, IL, USA
Door County, WI, USA
Family Gold$$ Tier
The Great Lakes Cherry Orchard Peninsula Run
250-300 miles
3-5 days
USA
Chicago, IL
Toronto, Canada
Family Gold$$$ Tier
The Great Lakes Cross-Border Corridor
500-550 miles
3-5 days
USA
Chicago, IL
Minneapolis, MN
Family Gold$$ Tier
The Upper Mississippi & Driftless Area
450-500 miles
3-5 days