9 days in Detroit, Milwaukee & Chicago Itinerary

9 days in Detroit, Milwaukee & Chicago Itinerary

Created using Inspirock United States planner
Make it your trip
Drive
1
Detroit
— 2 nights
Drive
2
Milwaukee
— 2 nights
Drive
3
Chicago
— 4 nights
Drive

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Detroit — 2 nights

Founded in 1701 by a French explorer and adventurer, Detroit exerted a profound impact on the world for most of the 20th century.
Your day by day itinerary now includes GM World, MGM Grand Detroit Casino, Motown Museum, and other attractions you added. Kick off your visit on the 22nd (Fri): steep yourself in history at The Ford Piquette Avenue Plant, see the interesting displays at GM World, and then try your luck at MGM Grand Detroit Casino. On the next day, shop like a local with Eastern Market, see the interesting displays at The Henry Ford, then examine the collection at Greenfield Village, and finally catch a live event at Comerica Park.

For where to stay, photos, ratings, and more tourist information, use the Detroit trip planner.

Ashburn to Detroit is an approximately 4.5-hour combination of car and flight. You can also drive. Expect slightly colder weather when traveling from Ashburn in July: highs in Detroit hover around 82°F, while lows dip to 65°F. You'll have a few hours on the 24th (Sun) to wrap things up before traveling to Milwaukee.
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Museums · Casinos · Fun & Games · Shopping
Side Trip

Milwaukee — 2 nights

Milwaukee boasts well-preserved historical districts with a rich European past and a strong beer-brewing tradition.
Your list of things to see and do now includes Harley-Davidson Museum, Best Place at the Historic Pabst Brewery, The Original Cheesehead Factory, and other attractions.

To see photos, maps, where to stay, and more tourist information, use the Milwaukee trip planner.

You can fly from Detroit to Milwaukee in 3 hours. Other options are to drive; or take a train. The time zone difference moving from Eastern Standard Time to Central Standard Time is minus 1 hour. In July, plan for daily highs up to 80°F, and evening lows to 63°F. You'll have a few hours on the 26th (Tue) to wrap things up before traveling to Chicago.
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Shopping · Historic Sites · Tours · Museums

Chicago — 4 nights

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Your day by day itinerary now includes Cloud Gate, Underground Donut Tour, Navy Pier, and other attractions you added. There's much more to do: enjoy breathtaking views from Skydeck Chicago - Willis Tower, admire nature's wide array of creatures at Shedd Aquarium, and engage your brain at Field Museum.

For ratings, maps, where to stay, and more tourist information, you can read our Chicago online driving holiday planner.

Traveling by car from Milwaukee to Chicago takes 1.5 hours. Alternatively, you can take a train; or take a bus. Expect a daytime high around 83°F in July, and nighttime lows around 67°F. You will have some time to spend on the 30th (Sat) before leaving for home.
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Childrens Museums · Museums · Tours · Theme Parks