39 days in Chicago Itinerary

39 days in Chicago Itinerary

Created using Inspirock Chicago tour itinerary planner

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Route & dates

39 days in Chicago Itinerary

Start: Los Angeles
Fly:  7​h
1
Chicago
— 38 nights
End: Chicago

38
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Millennium Park and Abraham Lincoln National Cemetery will appeal to history buffs. Explore hidden gems such as Starved Rock State Park and John Deere Historic Site. You'll find plenty of places to visit near Chicago: St. Joseph Catholic Church (in Joliet), Pontiac (Museum of the Gilding Arts, Pontiac-Oakland Automobile Museum, & more) and Washington Square (in Ottawa). There's lots more to do: explore the world behind art at The Art Institute of Chicago, tour the pleasant surroundings at Geneva Lake Shore Path, pause for some serene contemplation at Basilica of the Sacred Heart, and see what you can catch with a fishing tour.

For maps, photos, other places to visit, and other tourist information, use the Chicago itinerary planner .

Los Angeles to Chicago is an approximately 7-hour flight. You can also do a combination of bus and flight; or drive. You'll lose 2 hours traveling from Los Angeles to Chicago due to the time zone difference. Traveling from Los Angeles in May, expect a bit cooler with lows of 13°C in Chicago. Wrap up your sightseeing on the 28th (Fri) early enough to travel back home.

Things to do in Chicago

Parks Historic Sites Outdoors

Side Trips

Pontiac, Saint Joseph, Utica, South Bend, Rockford
Highlights from your plan
Starved Rock State Park ©
Starved Rock State Park
Millennium Park ©
Millennium Park
The Art Institute of Chicago ©
The Art Institute of Chicago

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