5 days in Wisconsin Itinerary

5 days in Wisconsin Itinerary

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Route & dates

5 days in Wisconsin Itinerary

Start: Chicago
train:  1​h 30​min
1
Milwaukee
— 1 day
train:  2​h
2
Wisconsin Dells
— 3 nights
Drive:  1​h 15​min
3
Madison
— 1 night
Drive:  2​h 45​min
End: Chicago

1
day
Milwaukee

Milwaukee ©
Milwaukee boasts well-preserved historical districts with a rich European past and a strong beer-brewing tradition.
On the 22nd (Sun), indulge your thirst for a good beer at Lakefront Brewery, explore the world behind art at Milwaukee Art Museum, and then examine the collection at Harley-Davidson Museum.

To find where to stay, traveler tips, and other tourist information, read our Milwaukee trip itinerary maker .

Chicago to Milwaukee is an approximately 1.5-hour train ride. You can also drive; or take a bus. In December, daily temperatures in Milwaukee can reach 35°F, while at night they dip to 23°F. Cap off your sightseeing on the 22nd (Sun) early enough to catch the train to Wisconsin Dells.

Things to do in Milwaukee

Museums Breweries & Distilleries
Highlights from your plan
Harley-Davidson Museum ©
Harley-Davidson Museum
Milwaukee Art Museum ©
Milwaukee Art Museum
Lakefront Brewery ©
Lakefront Brewery

3
nights
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.
You'll visit kid-friendly attractions like Mt. Olympus Resort and Zipline. Visiting Snowflake Ski Club and Devil's Lake State Park will get you outdoors. Change things up with a short trip to Taliesin Preservation: Frank Lloyd Wright Visitor Center in Spring Green (about 56 minutes away). It doesn't end there: cool off at Noah's Ark Water Park and see the interesting displays at Mr Marvel's Wondertorium.

To find reviews, traveler tips, maps, and tourist information, you can read our Wisconsin Dells online driving holiday planner .

Traveling by train from Milwaukee to Wisconsin Dells takes 2 hours. Alternatively, you can drive; or take a bus. Prepare for slightly colder weather when traveling from Milwaukee in December: high temperatures in Wisconsin Dells hover around 30°F and lows are around 18°F. Cap off your sightseeing on the 25th (Wed) early enough to go by car to Madison.

Things to do in Wisconsin Dells

Parks Outdoors Theme Parks

Side Trips

Taliesin Preservation: Frank Lloyd Wright Visitor Center , Devil's Lake State Park, Snowflake Ski Club
Highlights from your plan
Zipline
Noah's Ark Water Park ©
Noah's Ark Water Park
Mt. Olympus Water & Theme Park ©
Mt. Olympus Water & Theme Park

1
night
Madison

Madison ©
Madison might be the capital of Wisconsin, but students rather than politicians give the city its identity.
Start off your visit on the 26th (Thu): admire the natural beauty at Olbrich Botanical Gardens, ponder the world of politics at Wisconsin State Capitol, and then learn about wildlife with up-close encounters at Henry Vilas Zoo.

To find where to stay, more things to do, other places to visit, and tourist information, read our Madison travel itinerary planner .

Traveling by car from Wisconsin Dells to Madison takes 1.5 hours. Alternatively, you can do a combination of train and bus. Expect a daytime high around 32°F in December, and nighttime lows around 19°F. Wrap up your sightseeing on the 26th (Thu) to allow time to drive back home.

Things to do in Madison

Parks Zoos & Aquariums
Highlights from your plan
Henry Vilas Zoo ©
Henry Vilas Zoo
Wisconsin State Capitol ©
Wisconsin State Capitol
Olbrich Botanical Gardens ©
Olbrich Botanical Gardens

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