22 days in Chicago and Beyond Itinerary

Created using Inspirock Chicago and Beyond planner
Make it your trip
Fly to Chicago O'Hare International Airport, Drive to Waukegan
1
Waukegan
— 3 nights
Drive
2
Rockford
— 5 nights
Drive
3
Kankakee
— 2 nights
Drive
4
Chicago
— 11 nights
Fly to London Heathrow, Train to Cardiff

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Waukegan — 3 nights

Waukegan is a city and the county seat of Lake County, Illinois, United States. Explore Waukegan's surroundings by going to Chicago Botanic Garden (in Glencoe), Volo Museum (in Volo) and Baha'i House of Worship (in Wilmette). There's lots more to do: experience rural life at Elawa Farm, sample the tasty concoctions at ZumBier, walk around Independence Grove Dog Park, and immerse yourself in nature at Moraine Hills State Park.

Plan a Waukegan trip in moments using our itinerary builder.

Cardiff, UK to Waukegan is an approximately 16.5-hour combination of flight and car. Due to the time zone difference, you'll gain 6 hours traveling from Cardiff to Waukegan. While traveling from Cardiff, expect somewhat warmer days and about the same nights in Waukegan, ranging from highs of 27°C to lows of 15°C. Finish your sightseeing early on the 28th (Thu) so you can drive to Rockford.
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Parks · Wildlife · Outdoors · Nature
Side Trips

Rockford — 5 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. Venture out of the city with trips to Freeport (Jane Addams Recreation Trail, Krape Park, &more), Edwards Apple Orchard (in Poplar Grove) and Whiskey Acres Distilling Co. (in DeKalb). There's lots more to do: brush up on your military savvy at Historic Auto Attractions, contemplate the long history of Midway Village & Museum Center, get a taste of the local shopping with Rockford City Market, and admire the natural beauty at Anderson Japanese Gardens.

To find where to stay, reviews, other places to visit, and tourist information, read our Rockford attractions planner.

Getting from Waukegan to Rockford by car takes about 2 hours. Expect a daytime high around 30°C in September, and nighttime lows around 15°C. Cap off your sightseeing on the 3rd (Tue) early enough to go by car to Kankakee.
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Parks · Trails · Outdoors · Historic Sites
Side Trips

Kankakee — 2 nights

Kankakee is a city in and the county seat of Kankakee County, Illinois, United States. Start off your visit on the 4th (Wed): make a trip to Gemini Giant and then get a new perspective on things with Big River Fly Fishing. Here are some ideas for day two: admire the landmark architecture of B. Harley Bradley House, see the interesting displays at Kankakee County Museum, then examine the collection at Exploration Station...a children's museum, and finally look and learn at Strickler Planetarium.

To see traveler tips, maps, other places to visit, and more tourist information, go to the Kankakee online tour planner.

Traveling by car from Rockford to Kankakee takes 2.5 hours. In October, plan for daily highs up to 21°C, and evening lows to 8°C. Finish up your sightseeing early on the 5th (Thu) so you can go by car to Chicago.
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Museums · Outdoors · Wildlife · Tours
Side Trips

Chicago — 11 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for sightseeing, museums, and nightlife. Your trip includes some of its best attractions: admire the masterpieces at The Art Institute of Chicago, stop by The Magnificent Mile, engage your brain at Museum of Science and Industry, and get a new perspective on nature at Field Museum.

To see other places to visit, reviews, where to stay, and more tourist information, read Chicago attractions planner.

Traveling by car from Kankakee to Chicago takes 1.5 hours. In October, plan for daily highs up to 21°C, and evening lows to 11°C. Finish your sightseeing early on the 16th (Mon) to allow enough time to travel back home.
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Parks · Museums · Historic Sites · Childrens Museums
Side Trips