8 days in Chicago & Plymouth Itinerary

8 days in Chicago & Plymouth Itinerary

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Route & dates

8 days in Chicago & Plymouth Itinerary

Start: Chicago
1
Chicago
— 4 nights
Drive:  2​h 30​min
2
Plymouth
— 2 nights
Drive:  2​h
3
Chicago
— 1 night
End: Chicago

4
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
You've added 360 Chicago Observation Deck, The Magnificent Mile, Skydeck Chicago - Willis Tower, and other attractions to your itinerary. You'll explore the less-touristy side of things at Lakefront Trail and Richard H. Driehaus Museum. Millennium Park and The Art Institute of Chicago are good opportunities to explore the local culture. There's still lots to do: take in the spiritual surroundings of Holy Name Cathedral, get in on the family fun at Navy Pier, get a taste of the local shopping with Chicago Cultural Center, and examine the collection at The Field Museum.

To see maps, where to stay, reviews, and tourist information, go to the Chicago holiday planner.

If you are flying in from Mexico, the closest major airports are Chicago Midway International Airport, Chicago O'Hare International Airport and South Bend Regional Airport. July in Chicago sees daily highs of 33°C and lows of 22°C at night. Wrap up your sightseeing on the 31st (Wed) to allow time to travel to Plymouth.

Things to do in Chicago

Museums Shopping Parks
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Lakefront Trail ©
Lakefront Trail
Richard H. Driehaus Museum ©
Richard H. Driehaus Museum

2
nights
Plymouth

Plymouth ©
Plymouth is a city in Marshall County, Indiana, United States. To see other places to visit, where to stay, more things to do, and more tourist information, read our Plymouth day trip site .

Drive from Chicago to Plymouth in 2 hours. Plan for a bit cooler nights when traveling from Chicago in July since evenings lows in Plymouth dip to 17°C. On the 2nd (Fri), wrap the sightseeing up by early afternoon so you can travel to Chicago.

Things to do in Plymouth

Shopping Museums

Side Trip

The Village at Winona
Highlights from your plan
The Village at Winona ©
The Village at Winona

1
night
Chicago

Chicago ©
Your day-by-day itinerary now includes 360 Chicago Observation Deck, Chicago River Boat Architecture Tours and Skydeck Chicago - Willis Tower. Kick off your visit on the 2nd (Fri): admire the local landmark of Buckingham Fountain and then enjoy breathtaking views from Skydeck Chicago - Willis Tower.

To find ratings, where to stay, other places to visit, and tourist information, use the Chicago online day trip planner .

Drive from Plymouth to Chicago in 2 hours. Traveling from Plymouth in August, Chicago is somewhat warmer at night with lows of 22°C. Finish your sightseeing early on the 3rd (Sat) to allow enough time to travel back home.

Things to do in Chicago

Outdoors Tours
Highlights from your plan
Skydeck Chicago - Willis Tower ©
Skydeck Chicago - Willis Tower
Buckingham Fountain ©
Buckingham Fountain

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