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): appreciate the history behind Cloud Gate, get outside with Chicago’s First Lady Cruises, and then enjoy breathtaking views from 360 Chicago Observation Deck.

To find more things to do, traveler tips, ratings, and more tourist information, refer to the Chicago journey planning app.

Tampa to Chicago is an approximately 4-hour flight. You can also drive; or do a combination of bus and subway. The time zone changes from Eastern Standard Time to Central Standard Time, which is usually a -1 hour difference. Traveling from Tampa in June, things will get slightly colder in Chicago: highs are around 81°F and lows about 63°F. Wrap up your sightseeing on the 12th (Sat) to allow time to drive to Milwaukee.

Things to do in Chicago

Find places to stay Jun 12 — 13:

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 Bay Beach Amusement Park, Lambeau Field, Skydeck Chicago - Willis Tower, and other attractions to your itinerary. When in Milwaukee, make a side trip to see Shedd Aquarium in Chicago, approximately Chicago away. 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

Side Trips

Find places to stay Jun 12 — 18:

Chicago

Windy City

To see where to stay, reviews, maps, and more tourist information, you can read our Chicago travel planner.

You can drive from Milwaukee to Chicago in 1.5 hours. Other options are to take a train; or take a bus. You will leave for home on the 18th (Fri).

Things to do in Chicago

Nightlife · Parks · Fun & Games · Museums
Find places to stay Jun 18 — 19: