8 days in Detroit, Chicago & Milwaukee Itinerary

8 days in Detroit, Chicago & Milwaukee Itinerary

Created using Inspirock United States trip itinerary maker

Make it your trip
Drive
1
Detroit
— 2 nights
Drive
2
Chicago
— 4 nights
Drive
3
Milwaukee
— 1 night
Drive

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Detroit

— 2 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.
Your list of things to see and do now includes Motown Museum, Detroit RiverFront, Antique Touring Company, and other attractions. Start off your visit on the 18th (Sat): squeeze the most out of the city with Antique Touring Company and then take a leisurely stroll along Detroit RiverFront. Here are some ideas for day two: steep yourself in history at The Ford Piquette Avenue Plant, then see where the action happens at Comerica Park, and then steep yourself in history at Motown Museum.

For reviews, other places to visit, ratings, and more tourist information, go to the Detroit trip itinerary planner.

Ashburn to Detroit is an approximately 4.5-hour combination of car and flight. You can also drive. Expect little chillier weather when traveling from Ashburn in July: highs in Detroit hover around 82°F, while lows dip to 65°F. Finish up your sightseeing early on the 20th (Mon) so you can travel to Chicago.

Things to do in Detroit

Museums · Tours · Historic Sites

Side Trips

Chicago

— 4 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
You've added 360 Chicago Observation Deck, Wrigley Field, Chicago Crime Tours and Experiences, and other attractions to your itinerary. Next up on the itinerary: get curious at Museum of Science and Industry, get a new perspective on nature at Field Museum, take in panoramic vistas at Skydeck Chicago - Willis Tower, and meet the residents at Shedd Aquarium.

For traveler tips, where to stay, other places to visit, and tourist information, read Chicago online travel route planner.

You can drive from Detroit to Chicago in 5 hours. Alternatively, you can fly; or drive; or take a train. Due to the time zone difference, you'll gain 1 hour traveling from Detroit to Chicago. In July, plan for daily highs up to 83°F, and evening lows to 67°F. Wrap up your sightseeing on the 24th (Fri) to allow time to drive to Milwaukee.

Things to do in Chicago

Museums · Childrens Museums · Zoos & Aquariums · Parks

Milwaukee

— 1 night

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 Lakefront Brewery, Harley-Davidson Museum and American Family Field. On the 24th (Fri), sample the tasty concoctions at Lakefront Brewery, examine the collection at Harley-Davidson Museum, and then see where the action happens at American Family Field.

For maps, traveler tips, more things to do, and tourist information, use the Milwaukee itinerary maker.

Traveling by car from Chicago to Milwaukee takes 2 hours. Alternatively, you can drive; or take a train; or take a bus. July in Milwaukee sees daily highs of 80°F and lows of 63°F at night. You will leave for home on the 25th (Sat).

Things to do in Milwaukee

Museums · Breweries & Distilleries