17 days in Chicago & Wisconsin Itinerary

17 days in Chicago & Wisconsin Itinerary

Created using Inspirock United States itinerary builder

This plan was created by another user. Make it your plan

Route & dates

17 days in Chicago & Wisconsin Itinerary

Start: Milwaukee
Train:  2​h 30​min
1
Chicago
— 3 nights
Drive:  1​h 30​min
2
Lake Geneva
— 3 nights
Drive:  1​h 30​min
3
Madison
— 3 nights
Drive:  1​h 15​min
4
Wisconsin Dells
— 2 nights
Drive:  30​min
5
Baraboo
— 3 nights
Train:  1​h 45​min
6
La Crosse
— 2 nights
Train:  3​h 30​min
End: Milwaukee

3
nights
Chicago

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
You've now added Kayaking & Canoeing to your itinerary. Kick off your visit on the 23rd (Fri): add some adventure to your tour with a kayaking and canoeing tour.

Discover how to plan a Chicago trip in just a few steps with Inspirock's itinerary builder.

Milwaukee to Chicago is an approximately 1.5-hour train ride. You can also drive; or take a bus. In August in Chicago, expect temperatures between 83°F during the day and 67°F at night. On the 25th (Sun), you'll travel to Lake Geneva.

Things to do in Chicago

Outdoors Adventure Tours
Highlights from your plan
Kayaking & Canoeing

3
nights
Lake Geneva

Lake Geneva ©
Lake Geneva is a city in Walworth County, Wisconsin, USA. You've now added Lake Geneva Canopy Tours to your itinerary. Take a break from the city and head to Big Foot Beach State Park and Williams Bay Beach. Discover out-of-the-way places like Southport Light Station Museum and Paradise Miniature Golf. When in Lake Geneva, make a side trip to see Hawthorn Hollow - Nature Sanctuary and Arboretum in Kenosha, approximately 46 minutes away. There's more to do: stroll through White River State Trail and get your game on at CMP Tactical Lazer Tag Lake Geneva.

To find more things to do, ratings, reviews, and more tourist information, use the Lake Geneva road trip app .

You can drive from Chicago to Lake Geneva in 1.5 hours. Alternatively, you can do a combination of train and taxi; or take a train. Traveling from Chicago in August, expect a bit cooler with lows of 55°F in Lake Geneva. Finish your sightseeing early on the 28th (Wed) to allow enough time to drive to Madison.

Things to do in Lake Geneva

Outdoors Parks Beaches

Side Trips

Kenosha, Williams Bay Beach, White River State Trail
Highlights from your plan
Lake Geneva Canopy Tours ©
Lake Geneva Canopy Tours
Big Foot Beach State Park ©
Big Foot Beach State Park
Southport Light Station Museum ©
Southport Light Station Museum

3
nights
Madison

Madison
Madison might be the capital of Wisconsin, but students rather than politicians give the city its identity.
Do some cultural sightseeing at Chazen Museum of Art and Wisconsin Historical Museum. You'll explore and learn at Wisconsin Veterans Museum and Livsreise. Take a break from Madison with a short trip to American Players Theatre in Spring Green, about 50 minutes away. And it doesn't end there: admire the striking features of Overture Center for the Arts, savor the flavors at Food & Drink, engage your brain at University of Wisconsin Geology Museum, and take in the spiritual surroundings of First Unitarian Meeting House of Madison.

For traveler tips, maps, ratings, and more tourist information, refer to the Madison online tour itinerary planner .

Drive from Lake Geneva to Madison in 1.5 hours. Alternatively, you can do a combination of taxi and bus. August in Madison sees daily highs of 80°F and lows of 60°F at night. Finish your sightseeing early on the 31st (Sat) to allow enough time to drive to Wisconsin Dells.

Things to do in Madison

Museums Nightlife Tours

Side Trips

American Players Theatre, Livsreise
Highlights from your plan
Wisconsin Veterans Museum
Wisconsin Veterans Museum
Chazen Museum of Art ©
Chazen Museum of Art
Overture Center for the Arts ©
Overture Center for the Arts

2
nights
Wisconsin Dells

Wisconsin Dells ©
Named after a nearby scenic gorge famous for its steep sandstone formations, Wisconsin Dells features more than 20 water parks, making it one of the most popular vacation areas in this region.
Discover out-of-the-way places like Wollersheim Winery & Distillery and Witches Gulch. Mr Marvel's Wondertorium and Portage WWII History Museum will appeal to museum buffs. Go for a jaunt from Wisconsin Dells to Montello to see John Muir Memorial County Park about 36 minutes away. Next up on the itinerary: steep yourself in history at H.H. Bennett Studio, indulge your thirst for a good beer at Port Huron Brewing Company, have some family-friendly fun at Laser Warfare, and look for gifts at Goody Goody Gum Drop.

For where to stay, reviews, traveler tips, and more tourist information, use the Wisconsin Dells itinerary website .

Traveling by car from Madison to Wisconsin Dells takes 1.5 hours. Alternatively, you can do a combination of bus and train. Expect a daytime high around 79°F in August, and nighttime lows around 59°F. Finish your sightseeing early on the 2nd (Mon) to allow enough time to drive to Baraboo.

Things to do in Wisconsin Dells

Parks Museums Wildlife

Side Trips

International Crane Foundation, Wollersheim Winery & Distillery, Portage WWII History Museum, John Muir Memorial County Park
Highlights from your plan
Wollersheim Winery & Distillery ©
Wollersheim Winery & Distillery
International Crane Foundation ©
International Crane Foundation
Witches Gulch ©
Witches Gulch

3
nights
Baraboo

Baraboo ©
Baraboo is a city in and the county seat of Sauk County, Wisconsin, United States. You've now added Parfrey's Glen State Natural Area to your itinerary. Start off your visit on the 3rd (Tue): experience rural life at Ski Hi Fruit Farm, learn about winemaking at Von Klaus Winery, then contemplate the long history of Aldo Leopold Foundation, and finally explore the stunning scenery at Parfrey's Glen State Natural Area. On the 4th (Wed), you'll have a packed day of sightseeing: see the interesting displays at Mr. Marvel's Wondertorium, browse the different shops at Wisconsin Dells Craft Mall, then stop by Baraboo Candy Company, and finally hike along Baraboo Riverwalk.

To find other places to visit, traveler tips, reviews, and more tourist information, you can read our Baraboo journey planner .

Baraboo is very close to Wisconsin Dells. In September in Baraboo, expect temperatures between 74°F during the day and 53°F at night. Finish your sightseeing early on the 5th (Thu) to allow enough time to travel to La Crosse.

Things to do in Baraboo

Parks Outdoors Nature
Highlights from your plan
Parfrey's Glen State Natural Area ©
Baraboo Riverwalk ©
Baraboo Riverwalk
Von Klaus Winery ©
Von Klaus Winery

2
nights
La Crosse

La Crosse ©
La Crosse is a city in the U.S. Start off your visit on the 5th (Thu): take an in-depth tour of Riverside Museum, examine the collection at Dahl Auto Museum, take in the spiritual surroundings of Franciscan Sisters of Perpetual Adoration Motherhouse, take in the architecture and atmosphere at Mary of the Angels Chapel, then look for gifts at The Wine Guyz, and finally make a trip to Pump House Regional Arts Center. On the 6th (Fri), you'll have a packed day of sightseeing: get engrossed in the history at Winona County Historical Society, then examine the collection at Watkins Museum and Store, then examine the collection at Polish Museum, and finally indulge your thirst for a good beer at Turtle Stack Brewery.

To find where to stay, ratings, photos, and tourist information, go to the La Crosse road trip planning app .

Traveling by train from Baraboo to La Crosse takes 2 hours. Alternatively, you can drive; or take a bus. Expect a daytime high around 78°F in September, and nighttime lows around 57°F. You'll have a few hours on the 7th (Sat) to wrap things up before traveling home.

Things to do in La Crosse

Museums Historic Sites Breweries & Distilleries

Side Trip

Winona
Highlights from your plan
Winona County Historical Society ©
Winona County Historical Society
Dahl Auto Museum ©
Dahl Auto Museum
Polish Museum ©
Polish Museum

Similar Plans

19 days in Michigan & Wisconsin BY A USER FROM UNITED STATES August, outdoors, relaxing, beaches, historic sites, wildlife, popular & hidden gems PREFERENCES: August, outdoors, relaxing, beaches, historic sites, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 18 days in Michigan & Wisconsin BY A USER FROM UNITED STATES August, outdoors, relaxing, beaches, historic sites, popular sights PREFERENCES: August, outdoors, relaxing, beaches, historic sites ATTRACTION STYLE: Popular sights PACE: Medium 15 days in Wisconsin BY A USER FROM UNITED STATES June, teens, kids, popular sights PREFERENCES: June, teens, kids ATTRACTION STYLE: Popular sights PACE: Medium 36 days in United States BY A USER FROM UNITED STATES July, teens, kids, popular & hidden gems PREFERENCES: July, teens, kids ATTRACTION STYLE: Popular & hidden gems PACE: Medium 34 days in United States BY A USER FROM UNITED STATES July, teens, kids, popular sights PREFERENCES: July, teens, kids ATTRACTION STYLE: Popular sights PACE: Medium 7 days in Wisconsin BY A USER FROM UNITED STATES September, relaxing, romantic, beaches, historic sites, popular sights PREFERENCES: September, relaxing, romantic, beaches, historic sites ATTRACTION STYLE: Popular sights PACE: Medium 3 days in Wisconsin BY A USER FROM UNITED STATES July, teens, outdoors, beaches, shopping, popular & hidden gems PREFERENCES: July, teens, outdoors, beaches, shopping ATTRACTION STYLE: Popular & hidden gems PACE: Medium 15 days in Michigan, Iowa & Wisconsin BY A USER FROM BRAZIL October, popular sights PREFERENCES: October ATTRACTION STYLE: Popular sights PACE: Medium 16 days in Summerfield, Wisconsin & Oklahoma City BY A USER FROM UNITED STATES July, slow & easy, hidden gems PREFERENCES: July ATTRACTION STYLE: Hidden gems PACE: Slow & easy 8 days in Wisconsin BY A USER FROM UNITED STATES June, shopping, popular sights PREFERENCES: June, shopping ATTRACTION STYLE: Popular sights PACE: Medium 6 days in Wisconsin BY A USER FROM UNITED STATES June, teens, outdoors, relaxing, beaches, historic sites, popular sights PREFERENCES: June, teens, outdoors, relaxing, beaches, historic sites ATTRACTION STYLE: Popular sights PACE: Medium 1 day in Wisconsin BY A USER FROM UNITED STATES June, shopping, popular sights PREFERENCES: June, shopping ATTRACTION STYLE: Popular sights PACE: Medium
View more plans