9 days in Milwaukee, Chicago & Detroit Itinerary

9 days in Milwaukee, Chicago & Detroit Itinerary

Created using Inspirock United States trip builder

Make it your trip
Drive
1
Milwaukee
— 2 nights
Drive
2
Chicago
— 3 nights
Fly
3
Detroit
— 3 nights
Fly to Washington Dulles International Airport, Drive to Ashburn

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1

Milwaukee

— 2 nights

Brew City

Milwaukee boasts well-preserved historical districts with a rich European past and a strong beer-brewing tradition.
Your day by day itinerary now includes Harley-Davidson Museum as well as American Family Field.

To see reviews, ratings, other places to visit, and other tourist information, you can read our Milwaukee tour planning site.

Ashburn to Milwaukee is an approximately 9.5-hour combination of car and flight. You can also drive. Traveling from Ashburn to Milwaukee, you'll gain 1 hour due to the time zone difference. Expect slightly colder temperatures when traveling from Ashburn in July; daily highs in Milwaukee reach 80°F and lows reach 63°F. You will leave for Chicago on the 20th (Mon).

Things to do in Milwaukee

Museums

Chicago

— 3 nights

Windy City

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 Cloud Gate, 360 Chicago Observation Deck, Chicago Crime Tours and Experiences, and other attractions. There's much more to do: engage your brain at Museum of Science and Industry, meet the residents at Shedd Aquarium, learn more about the world around you at Field Museum, and take in panoramic vistas at Skydeck Chicago - Willis Tower.

To see ratings, traveler tips, where to stay, and tourist information, refer to the Chicago online itinerary planner.

You can drive from Milwaukee to Chicago in 1.5 hours. Alternatively, you can take a train; or take a bus. In July in Chicago, expect temperatures between 83°F during the day and 67°F at night. You'll have a few hours on the 23rd (Thu) to wrap things up before traveling to Detroit.

Things to do in Chicago

Childrens Museums · Museums · Parks · Zoos & Aquariums

Detroit

— 3 nights

The Motor City

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 added Motown Museum, Antique Touring Company, Ford Drive In, and other attractions to your itinerary. On the 23rd (Thu), gain interesting insight with Antique Touring Company and then take a leisurely stroll along Detroit RiverFront. Here are some ideas for day two: see the interesting displays at Motown Museum, then contemplate the long history of The Ford Piquette Avenue Plant, then see where the action happens at Comerica Park, and finally catch a movie at Ford Drive In.

To plan Detroit vacation without wasting time, ask Inspirock to design an itinerary.

You can fly from Chicago to Detroit in 4.5 hours. Other options are to drive; or take a train. Traveling from Chicago to Detroit, you'll lose 1 hour due to the time zone difference. In July, daily temperatures in Detroit can reach 82°F, while at night they dip to 65°F. Cap off your sightseeing on the 26th (Sun) early enough to travel back home.

Things to do in Detroit

Museums · Nightlife · Fun & Games · Tours

Side Trips