7 days in Chicago & Milwaukee Itinerary

7 days in Chicago & Milwaukee Itinerary

Created using Inspirock United States planner

Make it your trip
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Chicago
— 1 day
Drive
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Milwaukee
— 6 nights
Drive
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Chicago
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Chicago

— 1 day

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago’s First Lady Cruises has been added to your itinerary. Kick off your visit on the 12th (Sat): enjoy breathtaking views from Skydeck Chicago - Willis Tower, don't miss a visit to Cloud Gate, then get a new perspective on things with Chicago’s First Lady Cruises, and finally admire the landmark architecture of 360 Chicago Observation Deck.

For more things to do, maps, photos, and other tourist information, go to the Chicago trip planner.

Tampa to Chicago is an approximately 4-hour flight. You can also drive; or do a combination of bus and subway. The time zone difference moving from Eastern Standard Time to Central Standard Time is minus 1 hour. Prepare for slightly colder weather when traveling from Tampa in June: high temperatures in Chicago hover around 81°F and lows are around 63°F. Finish your sightseeing early on the 12th (Sat) to allow enough time to drive to Milwaukee.

Things to do in Chicago

Tours · Outdoors

Milwaukee

— 6 nights

Brew City

Milwaukee boasts well-preserved historical districts with a rich European past and a strong beer-brewing tradition.
You've added Miller Brewery Tour, Pabst Mansion, Milwaukee Boat Line, and other attractions to your itinerary. There's more to do: see the interesting displays at Harley-Davidson Museum.

To see traveler tips, maps, more things to do, and other tourist information, refer to the Milwaukee trip itinerary maker app.

Traveling by car from Chicago to Milwaukee takes 1.5 hours. Alternatively, you can take a train; or take a bus. Plan for a bit cooler temperatures traveling from Chicago in June, with highs in Milwaukee at 76°F and lows at 58°F. You will have some time to spend on the 18th (Fri) before leaving for Chicago.

Things to do in Milwaukee

Museums · Parks · Outdoors · Historic Sites

Side Trips

Chicago

Windy City

Shedd Aquarium has been added to your itinerary. Kick off your visit on the 18th (Fri): admire nature's wide array of creatures at Shedd Aquarium.

For more things to do, maps, traveler tips, and other tourist information, you can read our Chicago travel website.

You can drive from Milwaukee to Chicago in 1.5 hours. Alternatively, you can take a train; or take a bus. Wrap up your sightseeing by early afternoon on the 18th (Fri) to allow time for the flight back home.

Things to do in Chicago

Zoos & Aquariums · Parks
Highlights from your trip