8 days in Chicago and Beyond Itinerary

8 days in Chicago and Beyond Itinerary

Created using Inspirock Chicago and Beyond trip planner

Make it your trip
Fly
1
Chicago
— 4 nights
Drive
2
Rockford
— 3 nights
Fly

S M T W T F S
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Chicago

— 4 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for museums, nightlife, and parks. Your trip includes some of its best attractions: admire the masterpieces at The Art Institute of Chicago, enjoy breathtaking views from Skydeck Chicago - Willis Tower, engage your brain at Museum of Science and Industry, and walk around Millennium Park.

For where to stay, photos, maps, and other tourist information, refer to the Chicago day trip app.

Philadelphia to Chicago is an approximately 3.5-hour flight. You can also drive; or take a bus. Due to the time zone difference, you'll gain 1 hour traveling from Philadelphia to Chicago. In June, daily temperatures in Chicago can reach 81°F, while at night they dip to 63°F. Finish up your sightseeing early on the 16th (Thu) so you can go by car to Rockford.

Things to do in Chicago

Museums · Parks · Childrens Museums · Zoos & Aquariums

Rockford

— 3 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 the numerous day-trip ideas around Rockford: Whiskey Acres Distilling Co. (in DeKalb) and Jane Addams Recreation Trail (in Freeport). There's lots more to do: take in nature's colorful creations at Anderson Japanese Gardens, hike along Stone Bridge Trail, and see the interesting displays at Historical Auto Attractions.

To find ratings, other places to visit, more things to do, and tourist information, refer to the Rockford trip itinerary app.

You can drive from Chicago to Rockford in 1.5 hours. Other options are to take a bus; or do a combination of subway and bus. In June, daily temperatures in Rockford can reach 81°F, while at night they dip to 60°F. Wrap up your sightseeing on the 19th (Sun) to allow time to fly back home.

Things to do in Rockford

Parks · Outdoors · Trails · Museums

Side Trips