8 days in Chicago & Wisconsin Itinerary

8 days in Chicago & Wisconsin Itinerary

Created using Inspirock United States vacation planner

Make it your trip
Fly
1
Chicago
Fly
2
Madison
— 1 night
Drive
3
Stevens Point
— 3 nights
Drive
4
Chicago
— 3 nights
Fly

S M T W T F S
22
23
24
25
26
27
28
29
30
1
2
3
4
5

Chicago

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Kick off your visit on the 25th (Wed): ponder the design of Buckingham Fountain.

For more things to do, ratings, other places to visit, and more tourist information, read our Chicago trip planner.

Seattle to Chicago is an approximately 6-hour flight. You can also drive; or take a train. You'll lose 2 hours traveling from Seattle to Chicago due to the time zone difference. When traveling from Seattle in September, plan for a bit warmer days and about the same nights in Chicago: temperatures range from 78°F by day to 61°F at night. Wrap up your sightseeing by early afternoon on the 25th (Wed) to allow time for the flight to Madison.
Highlights from your trip

Madison

— 1 night

The City of Four Lakes

Madison might be the capital of Wisconsin, but students rather than politicians give the city its identity.
Chazen Museum of Art has been added to your itinerary. Start off your visit on the 25th (Wed): take in nature's colorful creations at Olbrich Botanical Gardens and then take a stroll through State Street & Downtown Madison.

To see ratings, reviews, traveler tips, and tourist information, use the Madison trip maker app.

Fly from Chicago to Madison in 2.5 hours. Alternatively, you can drive; or take a bus. Plan for a bit cooler nights when traveling from Chicago in September since evenings lows in Madison dip to 53°F. On the 26th (Thu), wrap the sightseeing up by early afternoon so you can travel to Stevens Point.

Things to do in Madison

Parks · Museums · Neighborhoods · Shopping

Stevens Point

— 3 nights
Stevens Point is the county seat of Portage County, Wisconsin, United States. Here are some ideas for day two: look for gifts at Mullins Cheese.

To find other places to visit, more things to do, traveler tips, and tourist information, read our Stevens Point visit planner.

Drive from Madison to Stevens Point in 2 hours. Traveling from Madison in September, Stevens Point is a bit cooler at night with lows of 48°F. Finish your sightseeing early on the 29th (Sun) so you can travel to Chicago.

Things to do in Stevens Point

Museums · Breweries & Distilleries · Shopping

Side Trips

Chicago

— 3 nights

Windy City

Your list of things to see and do now includes Chicago River Boat Architecture Tours, Wndr Museum, Laugh Factory, and other attractions. Satisfy your inner culture vulture at The Art Institute of Chicago and Field Museum. Museum of Science and Industry and Chicago Cultural Center will appeal to museum buffs. Enjoy Chicago some more: don't miss a visit to The Magnificent Mile, appreciate the history behind Cloud Gate, take in the spiritual surroundings of Fourth Presbyterian Church, and enjoy breathtaking views from Skydeck Chicago - Willis Tower.

To see other places to visit, reviews, and other tourist information, go to the Chicago day trip planning site.

Drive from Stevens Point to Chicago in 4 hours. Alternatively, you can do a combination of car and flight. Traveling from Stevens Point in September, expect Chicago to be a bit warmer, temps between 78°F and 61°F. Finish your sightseeing early on the 2nd (Wed) to allow enough time to fly back home.

Things to do in Chicago

Museums · Childrens Museums · Shopping · Neighborhoods

Wisconsin travel guide

4.2
Specialty Museums · Water Parks · Zoos
The Badger State
Wisconsin is known as "America's Dairyland" because of its status as the nation's most famous producer of milk and cheese. A growing favorite with foreign tourists, the state is a perfect holiday destination for nature lovers, offering year-round outdoor activities like fishing, boating, kayaking, and hiking. Dotted with thousands of inland lakes and waterways alongside apple and cherry orchards, Wisconsin also offers numerous urban tourist attractions, its cities hosting renowned beer and art festivals each year.