8 days in Milwaukee, Chicago & Detroit Itinerary

8 days in Milwaukee, Chicago & Detroit Itinerary

Created using Inspirock United States journey planner

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

S M T W T F S
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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 American Family Field, Lakefront Brewery, The Original Cheesehead Factory, and other attractions you added. Kick off your visit on the 28th (Sun): examine the collection at Harley-Davidson Museum and then catch a live event at American Family Field. On your second day here, get behind the scenes at The Original Cheesehead Factory, indulge your thirst for a good beer at Miller Brewery Tour, and then indulge your thirst for a good beer at Lakefront Brewery.

To see traveler tips, photos, more things to do, and tourist information, use the Milwaukee trip itinerary tool.

Ashburn to Milwaukee is an approximately 9.5-hour combination of car and flight. You can also drive. The time zone changes from Eastern Standard Time (EST) to Central Standard Time (CST), which is usually a -1 hour difference. Plan for little chillier temperatures traveling from Ashburn in June, with highs in Milwaukee at 76°F and lows at 58°F. Finish your sightseeing early on the 29th (Mon) to allow enough time to drive to Chicago.

Things to do in Milwaukee

Breweries & Distilleries · Museums · Tours

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 Museum of Science and Industry, Wrigley Field, Shedd Aquarium, and other attractions. On the 30th (Tue), meet the residents at Shedd Aquarium, get curious at Museum of Science and Industry, and then see where the action happens at Wrigley Field. On your second day here, see the sky in a new way at Adler Planetarium.

Plan my Chicago trip by asking Inspirock to come up with tips and suggestions.

Traveling by train from Milwaukee to Chicago takes 1.5 hours. Alternatively, you can drive; or take a train; or take a bus. In June, daily temperatures in Chicago can reach 81°F, while at night they dip to 63°F. Finish up your sightseeing early on the 2nd (Thu) so you can travel to Detroit.

Things to do in Chicago

Museums · Childrens Museums · Parks · Zoos & Aquariums

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 day by day itinerary now includes The Ford Piquette Avenue Plant, Motown Museum, Detroit RiverFront, and other attractions you added. Kick off your visit on the 2nd (Thu): steep yourself in history at The Ford Piquette Avenue Plant, then explore the galleries of Motown Museum, and then take in the waterfront at Detroit RiverFront. On your second day here, get a taste of the local shopping with Eastern Market, then see the interesting displays at The Henry Ford, then get engrossed in the history at Holocaust Memorial Center, and finally catch a live event at Comerica Park.

For maps, other places to visit, and other tourist information, use the Detroit vacation planner.

Traveling by car from Chicago to Detroit takes 5 hours. Alternatively, you can fly; or drive; or take a train. The time zone difference moving from Central Standard Time (CST) to Eastern Standard Time (EST) is 1 hour. In July, plan for daily highs up to 82°F, and evening lows to 65°F. Cap off your sightseeing on the 4th (Sat) early enough to travel back home.

Things to do in Detroit

Museums · Historic Sites · Shopping

Side Trips