31 days in Chicago and Beyond Itinerary

31 days in Chicago and Beyond Itinerary

Created using Inspirock Chicago and Beyond itinerary maker

Make it your trip
Fly to Chicago O'Hare International Airport, Drive to Rockford
1
Rockford
— 6 nights
Drive
2
Kankakee
— 3 nights
Drive
3
Chicago
— 17 nights
Drive
4
Waukegan
— 4 nights
Drive to Chicago O'Hare International Airport, Fly to Linton

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Rockford

— 6 nights
Rockford is the third largest city in the U.S. state of Illinois, the 171st most populous city in the United States, the largest city in Illinois outside of the Chicago metropolitan area, and the city of the 148th most populous metropolitan area in the United States. Explore Rockford's surroundings by going to Whiskey Acres Distilling Co. (in DeKalb), Freeport (Krape Park & Famous Fossil Winery) and Starved Rock State Park (in Utica). Next up on the itinerary: see the interesting displays at Historical Auto Attractions, make a trip to Dixon's Railroad Street Arches, admire the natural beauty at Anderson Japanese Gardens, and tour the pleasant surroundings at Stone Bridge Trail.

To see traveler tips, reviews, more things to do, and more tourist information, read our Rockford road trip site.

Linton, UK to Rockford is an approximately 15.5-hour combination of flight and car. You can also do a combination of car and flight. Traveling from Linton to Rockford, you'll gain 6 hours due to the time zone difference. When traveling from Linton in September, plan for a bit warmer days in Rockford, with highs around 30°C, while nights are about the same with lows around 15°C. Finish your sightseeing early on the 22nd (Wed) to allow enough time to travel to Kankakee.

Things to do in Rockford

Parks · Trails · Outdoors · Historic Sites

Side Trips

Kankakee

— 3 nights
Kankakee is a city in and the county seat of Kankakee County, Illinois, United States. Change things up with these side-trips from Kankakee: Gemini Giant (in Wilmington) and Weber House and Garden (in Streator). There's still lots to do: take a tour by water with Big River Fly Fishing, get outside with Haigh Quarry, and admire the striking features of B. Harley Bradley House.

To find more things to do, other places to visit, photos, and more tourist information, read our Kankakee trip itinerary builder website.

You can drive from Rockford to Kankakee in 2.5 hours. In September, plan for daily highs up to 30°C, and evening lows to 15°C. Finish up your sightseeing early on the 25th (Sat) so you can go by car to Chicago.

Things to do in Kankakee

Outdoors · Wildlife · Tours · Historic Sites

Side Trips

Chicago

— 17 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Explore Chicago's surroundings by going to Wheaton (First Division Museum at Cantigny & Cantigny Park). There's much more to do: explore the world behind art at The Art Institute of Chicago, enjoy breathtaking views from Skydeck Chicago - Willis Tower, take in the waterfront at Navy Pier, and take a stroll through The Magnificent Mile.

To see more things to do, traveler tips, and more tourist information, read Chicago sightseeing planner.

You can drive from Kankakee to Chicago in 1.5 hours. Traveling from Kankakee in September, Chicago is a bit warmer at night with lows of 19°C. Finish up your sightseeing early on the 12th (Tue) so you can go by car to Waukegan.

Things to do in Chicago

Parks · Museums · Historic Sites · Childrens Museums

Side Trips

Waukegan

— 4 nights
Waukegan is a city and the county seat of Lake County, Illinois, United States. Take a break from Waukegan with a short trip to Chicago Botanic Garden in Glencoe, about 32 minutes away. There's much more to do: relax in the rural setting at Elawa Farm, stroll through Prairie Wolf Slough, take a peaceful walk through Fort Sheridan Forest Preserve, and head outdoors with WindyCitySalmon.

To see traveler tips, ratings, maps, and other tourist information, you can read our Waukegan sightseeing planner.

Traveling by car from Chicago to Waukegan takes 1.5 hours. Traveling from Chicago in October, plan for slightly colder nights in Waukegan, with lows around 7°C. Wrap up your sightseeing on the 16th (Sat) early enough to travel back home.

Things to do in Waukegan

Parks · Wildlife · Nature · Museums

Side Trips