29 days in Chicago & Wisconsin Itinerary

29 days in Chicago & Wisconsin Itinerary

Created using Inspirock United States trip planner
Make it your trip
Fly
1
Chicago
— 5 nights
Drive
2
Milwaukee
— 4 nights
Drive
3
Sheboygan
— 3 nights
Drive
4
Green Bay
— 3 nights
Drive
5
Fish Creek
— 3 nights
Drive
6
Wausau
— 3 nights
Drive
7
Chippewa Falls
— 3 nights
Drive
8
Madison
— 4 nights
Fly

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Chicago — 5 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for sightseeing, museums, and nightlife. Your trip includes some of its best attractions: explore the world behind art at The Art Institute of Chicago, engage your brain at Field Museum, get a new perspective on things with Boat Tours & Water Sports, and observe the fascinating underwater world at Shedd Aquarium.

For where to stay, reviews, ratings, and more tourist information, you can read our Chicago journey planner.

San Francisco to Chicago is an approximately 6-hour flight. You can also drive; or do a combination of subway and train. The time zone difference when traveling from San Francisco to Chicago is 2 hours. In October, Chicago is a bit cooler than San Francisco - with highs of 65°F and lows of 49°F. Finish your sightseeing early on the 7th (Fri) so you can drive to Milwaukee.
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Museums · Parks · Childrens Museums · Zoos & Aquariums
Side Trips
Find places to stay Oct 2 — 7:

Milwaukee — 4 nights

Brew City

Milwaukee boasts well-preserved historical districts with a rich European past and a strong beer-brewing tradition.
Change things up with these side-trips from Milwaukee: Hawthorn Hollow - Nature Sanctuary and Arboretum (in Kenosha), Holy Hill (in Hubertus) and SC Johnson Headquarters (in Racine). Next up on the itinerary: contemplate in the serene atmosphere at Basilica of St. Josaphat, identify plant and animal life at Lion's Den Gorge Nature Preserve, stroll through Geneva Lake Shore Path, and test your team's savvy at popular escape rooms.

To find where to stay, photos, traveler tips, and tourist information, refer to the Milwaukee vacation planner.

Traveling by car from Chicago to Milwaukee takes 1.5 hours. Alternatively, you can take a train; or take a bus. In October, plan for daily highs up to 62°F, and evening lows to 46°F. Finish your sightseeing early on the 11th (Tue) to allow enough time to drive to Sheboygan.
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Side Trips
Find places to stay Oct 7 — 11:

Sheboygan — 3 nights

Sheboygan is a city in and the county seat of Sheboygan County, Wisconsin, United States. Explore the numerous day-trip ideas around Sheboygan: Cedar Valley Cheese (in Belgium), Horicon Marsh (in Mayville) and Wisconsin Maritime Museum (in Manitowoc). The adventure continues: admire the natural beauty at Bookworm Gardens, appreciate the history behind Acuity Flagpole, steep yourself in history at Wade House, and play a few rounds at Whistling Straits Golf Course - Straits and Irish.

For traveler tips, where to stay, reviews, and other tourist information, use the Sheboygan trip itinerary app.

Traveling by car from Milwaukee to Sheboygan takes an hour. In October in Sheboygan, expect temperatures between 60°F during the day and 42°F at night. Cap off your sightseeing on the 14th (Fri) early enough to go by car to Green Bay.
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Parks · Nature · Wildlife · Museums
Side Trips
Find places to stay Oct 11 — 14:

Green Bay — 3 nights

Home of the Packers

Home of the Green Bay Packers, the city of Green Bay centers around sports and is home to hundreds of notable football icons, including Brett Favre and Curly Lambeau.
You've now added Lambeau Field to your itinerary. Change things up with these side-trips from Green Bay: Sturgeon Bay (The Farm, Cave Point County Park, &more). There's much more to do: examine the collection at Green Bay Packer Hall of Fame, stroll around Titletown, take in nature's colorful creations at Rose-Hill Gardens, and pause for some photo ops at Shrine of Our Lady of Good Help.

To see where to stay, other places to visit, ratings, and tourist information, go to the Green Bay online trip itinerary maker.

You can drive from Sheboygan to Green Bay in 1.5 hours. In October in Green Bay, expect temperatures between 60°F during the day and 42°F at night. Finish up your sightseeing early on the 17th (Mon) so you can go by car to Fish Creek.
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Parks · Wildlife · Museums · Nature
Side Trips
Find places to stay Oct 14 — 17:

Fish Creek — 3 nights

Fish Creek is an unincorporated community located in Door County, Wisconsin, United States, within the town of Gibraltar and is located on Highway 42 along Green Bay.HistoryThe first settler of Fish Creek was Increase Claflin and his family circa 1844, but the village founder is considered to be entrepreneur Asa Thorp. Change things up with a short trip to Newport State Park in Ellison Bay (about 34 minutes away). There's still lots to do: get a taste of the local shopping with Edgewood Orchard Galleries, make a trip to Holy Transfiguration Chapel and Woods, stroll around Sunset Beach Park, and get interesting insight from Tours.

For reviews, more things to do, maps, and more tourist information, you can read our Fish Creek vacation app.

Getting from Green Bay to Fish Creek by car takes about 1.5 hours. In October, daily temperatures in Fish Creek can reach 57°F, while at night they dip to 42°F. Finish your sightseeing early on the 20th (Thu) so you can drive to Wausau.
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Parks · Nature · Shopping · Museums
Side Trips
Find places to stay Oct 17 — 20:

Wausau — 3 nights

Wausau is a city in and the county seat of Marathon County, Wisconsin, United States. Get out of town with these interesting Wausau side-trips: George W. Mead Wildlife Area (in Milladore), Sandhill Wildlife Refuge (in Babcock) and Stevens Point (Green Circle Trail & Schmeeckle Reserve). And it doesn't end there: explore the world behind art at Leigh Yawkey Woodson Art Museum, take a peaceful walk through Nine Mile Forest, admire the majestic nature at Rib Mountain State Park, and do a tasting at Lil' Ole Winemaker Shoppe.

To see more things to do, maps, and tourist information, refer to the Wausau online trip itinerary maker.

You can drive from Fish Creek to Wausau in 3 hours. October in Wausau sees daily highs of 58°F and lows of 40°F at night. Wrap up your sightseeing on the 23rd (Sun) early enough to drive to Chippewa Falls.
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Parks · Wildlife · Outdoors · Trails
Side Trips
Find places to stay Oct 20 — 23:

Chippewa Falls — 3 nights

Chippewa Falls is a city located on the Chippewa River in Chippewa County in the U.S. state of Wisconsin. Venture out of the city with trips to Alma (Wings Over Alma Nature & Art Center & Buena Vista Park), Cain's Orchard (in Hixton) and Red Cedar State Trail (in Menomonie). There's lots more to do: indulge your thirst for a good beer at Leinie Lodge, immerse yourself in nature at Tower Ridge Recreational Area, and admire the verdant scenery at Chippewa Valley.

Quickly create a custom-made itinerary for Chippewa Falls using our trip planner.

Getting from Wausau to Chippewa Falls by car takes about 1.5 hours. In October, plan for daily highs up to 59°F, and evening lows to 39°F. Finish your sightseeing early on the 26th (Wed) to allow enough time to drive to Madison.
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Parks · Nature · Breweries & Distilleries · Shopping
Side Trips
Find places to stay Oct 23 — 26:

Madison — 4 nights

The City of Four Lakes

Madison might be the capital of Wisconsin, but students rather than politicians give the city its identity.
Get out of town with these interesting Madison side-trips: Taliesin Preservation: Frank Lloyd Wright Visitor Center (in Spring Green), Brewery Pottery (in Mineral Point) and Anderson Japanese Gardens (in Rockford). Next up on the itinerary: brush up on your military savvy at Historic Auto Attractions, get a sense of history and politics at Wisconsin State Capitol, don't miss a visit to Memorial Union Terrace, and relax in the rural setting at The Apple Hut.

Quickly create a custom-made itinerary for Madison using our trip planner.

You can drive from Chippewa Falls to Madison in 3 hours. In October in Madison, expect temperatures between 62°F during the day and 43°F at night. Finish up your sightseeing early on the 30th (Sun) so you can catch the flight back home.
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Parks · Museums · Tours · Outdoors
Side Trips
Find places to stay Oct 26 — 30:

Wisconsin travel guide

4.3
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.
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