9 days in Illinois, Wisconsin & Michigan Itinerary

9 days in Illinois, Wisconsin & Michigan Itinerary

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Route & dates

9 days in Illinois, Wisconsin & Michigan Itinerary

Start: Toronto
Ferry + Fly:  4​h 45​min
1
Chicago
— 2 nights
2
Chicago
— Few hours
Drive:  3​h 30​min
3
Springfield
— 1 night
Drive:  3​h
4
Madison
— 1 night
Drive:  2​h
5
Milwaukee
— 2 nights
Fly:  4​h
6
Ann Arbor
— Few hours
Train:  1​h
7
Detroit
— 1 night
Drive:  4​h 30​min
End: Toronto

2
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Your list of things to see and do now includes Frank Lloyd Wright Home and Studio, Emil Bach House by Frank Lloyd Wright, Charnley-Persky House, and other attractions. Kick off your visit on the 4th (Sun): admire the landmark architecture of The Rookery Building and then admire the striking features of Frank Lloyd Wright Home and Studio. On the 5th (Mon), you'll have a packed day of sightseeing: admire the landmark architecture of Charnley-Persky House and then don't miss a visit to Emil Bach House by Frank Lloyd Wright.

For maps, reviews, other places to visit, and more tourist information, go to the Chicago trip maker tool .

Traveling by flight from Ann Arbor to Chicago takes 4 hours. Alternatively, you can drive; or take a train. Due to the time zone difference, you'll gain 1 hour traveling from Ann Arbor to Chicago. Traveling from Ann Arbor in August, expect a bit warmer with lows of 22°C in Chicago. Wrap up your sightseeing on the 6th (Tue) early enough to drive to Springfield.

Things to do in Chicago

Historic Sites Museums

Side Trip

Frank Lloyd Wright Home and Studio
Highlights from your plan
Frank Lloyd Wright Home and Studio ©
Charnley-Persky House ©
Charnley-Persky House
The Rookery Building ©
The Rookery Building

few
hours
Chicago

Chicago
Frank Lloyd Wright's Robie House has been added to your itinerary.

To see traveler tips, more things to do, photos, and tourist information, you can read our Chicago trip planner .

Take a train from Milwaukee to Chicago in 1.5 hours. Alternatively, you can drive; or take a bus. You'll have a few hours on the 10th (Sat) to wrap things up before traveling to Detroit.

Things to do in Chicago

Nightlife Parks Fun & Games

1
night
Springfield

Springfield ©
Springfield is the capital of Illinois, but its real significance is as the hometown of Abraham Lincoln.
Start off your visit on the 6th (Tue): contemplate the long history of Dana-Thomas House, get advice or help at Abraham Lincoln Presidential Library and Museum, and then don't miss a visit to Lincoln Tomb & War Memorials.

To see more things to do, where to stay, traveler tips, and more tourist information, read Springfield online trip itinerary planner .

You can drive from Chicago to Springfield in 3.5 hours. Other options are to fly; or do a combination of flight and bus. In August, daily temperatures in Springfield can reach 34°C, while at night they dip to 20°C. Wrap up your sightseeing on the 7th (Wed) early enough to drive to Madison.

Things to do in Springfield

Historic Sites Museums
Highlights from your plan
Dana-Thomas House ©
Dana-Thomas House

1
night
Madison

Madison ©
Madison might be the capital of Wisconsin, but students rather than politicians give the city its identity.
Your day-by-day itinerary now includes Frank Lloyd Wright's Laurent House, Capitol Square and Monona Terrace Community and Convention Center. Start off your visit on the 7th (Wed): examine the collection at Frank Lloyd Wright's Laurent House, then admire the landmark architecture of Monona Terrace Community and Convention Center, and then don't miss a visit to Capitol Square.

For traveler tips and more tourist information, read Madison attractions planning app .

Traveling by car from Springfield to Madison takes 4.5 hours. Alternatively, you can do a combination of flight and bus; or do a combination of bus and flight. In August, plan for daily highs up to 31°C, and evening lows to 18°C. Wrap up your sightseeing by early afternoon on the 8th (Thu) to allow enough time to drive to Milwaukee.

Things to do in Madison

Museums

Side Trip

Frank Lloyd Wright's Laurent House
Highlights from your plan
Frank Lloyd Wright's Laurent House ©

2
nights
Milwaukee

Milwaukee ©
Milwaukee boasts well-preserved historical districts with a rich European past and a strong beer-brewing tradition.
Your day-by-day itinerary now includes Annunciation Greek Orthodox Church as well as SC Johnson Headquarters.

Use Inspirock's suggestions to plan your Milwaukee trip and find the best activities and attractions for your vacation.

You can drive from Madison to Milwaukee in 1.5 hours. Alternatively, you can take a bus. In August, daytime highs in Milwaukee are 30°C, while nighttime lows are 20°C. Wrap up your sightseeing by early afternoon on the 9th (Fri) to allow enough time to take a train to Chicago.

Things to do in Milwaukee

Historic Sites

Side Trip

SC Johnson Headquarters
Highlights from your plan
Annunciation Greek Orthodox Church ©
SC Johnson Headquarters ©
SC Johnson Headquarters

few
hours
Ann Arbor

Ann Arbor ©
Ann Arbor is a city in the U.S. Your day-by-day itinerary now includes Crazy Wisdom Bookstore & Tearoom, Nickels Arcade and Law Quadrangle. Start off your visit on the 3rd (Sat): don't miss a visit to Nickels Arcade, then explore and take pictures at Law Quadrangle, then make a trip to University of Michigan, and finally look for gifts at Crazy Wisdom Bookstore & Tearoom.

To see reviews, other places to visit, traveler tips, and other tourist information, go to the Ann Arbor road trip tool .

Toronto, Canada to Ann Arbor is an approximately 5-hour flight. You can also drive; or do a combination of train and car. Traveling from Toronto in August, Ann Arbor is little chillier at night with lows of 16°C. Finish up your sightseeing early on the 4th (Sun) so you can travel to Chicago.

Things to do in Ann Arbor

Historic Sites Shopping
Highlights from your plan
Crazy Wisdom Bookstore & Tearoom ©
Crazy Wisdom Bookstore & Tearoom
Law Quadrangle ©
Law Quadrangle
University of Michigan ©
University of Michigan

1
night
Detroit

Detroit ©
Founded in 1701 by a French explorer and adventurer, Detroit exerted a profound impact on the world for most of the 20th century.
You've now added Detroit Institute of Arts to your itinerary.

To find reviews, where to stay, maps, and more tourist information, go to the Detroit holiday planning website .

You can fly from Chicago to Detroit in 4 hours. Alternatively, you can do a combination of flight and bus; or drive. The time zone difference when traveling from Chicago to Detroit is 1 hour. Expect a daytime high around 32°C in August, and nighttime lows around 20°C. Wrap up your sightseeing by early afternoon on the 11th (Sun) to allow enough time to travel back home.

Things to do in Detroit

Museums
Highlights from your plan
Detroit Institute of Arts ©
Detroit Institute of Arts

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