4 days in Chicago Itinerary

4 days in Chicago Itinerary

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Route & dates

4 days in Chicago Itinerary

Start: Cleveland
Fly:  3​h 15​min
1
Chicago
— 3 nights
Fly:  3​h 30​min
End: Cleveland

3
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Your day-by-day itinerary now includes Lake Michigan. Step off the beaten path and head to Basilica of the Sacred Heart and Notre Dame Stadium. Change things up with these side-trips from Chicago: Chicago Botanic Garden (in Glencoe) and Grotto of Our Lady Lourdes (in South Bend). And it doesn't end there: get to know the fascinating history of Chicago Riverwalk, trek along Lakefront Trail, appreciate the history behind Lincoln Square, and contemplate the waterfront views at Chicago River.

For photos, more things to do, other places to visit, and tourist information, you can read our Chicago travel route planner .

Cleveland to Chicago is an approximately 3.5-hour flight. You can also do a combination of flight, bus, and subway; or drive. Due to the time zone difference, you'll gain 1 hour traveling from Cleveland to Chicago. In October, daytime highs in Chicago are 65°F, while nighttime lows are 49°F. Finish your sightseeing early on the 7th (Mon) so you can travel back home.

Things to do in Chicago

Parks Historic Sites Nature

Side Trips

South Bend, Chicago Botanic Garden, Lake Michigan
Highlights from your plan
Lakefront Trail ©
Lakefront Trail
Grotto of Our Lady Lourdes ©
Grotto of Our Lady Lourdes
Basilica of the Sacred Heart ©
Basilica of the Sacred Heart

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