7 days in Chicago & Milwaukee Itinerary

7 days in Chicago & Milwaukee Itinerary

Created using Inspirock United States itinerary builder

Make it your trip
Fly
1
Chicago
— 1 day
Drive
2
Milwaukee
— 6 nights
Drive
3
Chicago
Fly

S M T W T F S
11
12
13
14
15
16
17
18
19
20
21
22
23
24

Chicago

— 1 day

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
On the 17th (Sat), pause for some photo ops at Cloud Gate, then take a tour by water with Chicago’s First Lady Cruises, and then enjoy breathtaking views from 360 Chicago Observation Deck.

For photos, ratings, other places to visit, and other tourist information, go to the Chicago holiday 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 changes from Eastern Standard Time to Central Standard Time, which is usually a -1 hour difference. In July, Chicago is a bit cooler than Tampa - with highs of 83°F and lows of 67°F. Finish your sightseeing early on the 17th (Sat) so you can drive to Milwaukee.

Things to do in Chicago

Outdoors · Tours

Milwaukee

— 6 nights

Brew City

Milwaukee boasts well-preserved historical districts with a rich European past and a strong beer-brewing tradition.
Your inner history buff will appreciate Pabst Mansion and North Point Lighthouse. Eschew the tourist crowds and head to Bay Beach Amusement Park and Sprecher Brewing Co.. Explore Milwaukee's surroundings by going to Green Bay (National Railroad Museum, The Automobile Gallery, &more), Kenosha (Southport Light Station Museum, Kenosha History Center, &more) and Chicago (Shedd Aquarium & Skydeck Chicago - Willis Tower). There's still lots to do: join in the after-dark buzz at Best Place at the Historic Pabst Brewery and examine the collection at Harley-Davidson Museum.

To find more things to do, photos, ratings, and tourist information, you can read our Milwaukee trip planner.

You can drive from Chicago to Milwaukee in 1.5 hours. Alternatively, you can take a train; or take a bus. In July in Milwaukee, expect temperatures between 80°F during the day and 63°F at night. On the 23rd (Fri), you'll have the morning to explore before heading off to Chicago.

Things to do in Milwaukee

Museums · Historic Sites · Parks · Breweries & Distilleries

Side Trips

Chicago

Windy City

For maps, more things to do, other places to visit, and other tourist information, use the Chicago trip tool.

Drive from Milwaukee to Chicago in 1.5 hours. Alternatively, you can take a train; or take a bus. You will leave for home on the 23rd (Fri).

Things to do in Chicago

Nightlife · Parks · Fun & Games · Museums