60 days in Indiana, Illinois & Wisconsin Itinerary

Created using Inspirock United States itinerary maker
Make it your trip
Fly
1
Evansville
— 5 nights
Fly
2
Chicago
— 8 nights
Drive
3
South Bend
— 6 nights
Train to Chicago Union Station, Fly to Bayfield
4
Bayfield
— 3 nights
Drive
5
Minocqua
— 6 nights
Drive
6
Madison
— 6 nights
Drive
7
Galena
— 6 nights
Fly
8
Milwaukee
— 6 nights
Fly
9
Springfield
— 6 nights
Drive
10
Indianapolis
— 7 nights
Fly

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Evansville — 5 nights

Venture out of the city with trips to Azalea Path Arboretum and Botanical Gardens (in Hazleton), Sultan's Run Golf Club (in Jasper) and The Graceful Lady Boutique (in Fort Branch). Spend the 24th (Fri) exploring nature at Hemlock Cliffs in Hoosier National Forest.

For more things to do, photos, other places to visit, and tourist information, you can read our Evansville online trip maker.

Atlanta to Evansville is an approximately 3-hour flight. You can also drive; or take a bus. Traveling from Atlanta to Evansville, you'll gain 1 hour due to the time zone difference. Traveling from Atlanta in January, things will get little chillier in Evansville: highs are around 42°F and lows about 24°F. Cap off your sightseeing on the 25th (Sat) early enough to catch the flight to Chicago.
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Parks · Nature · Outdoors · Museums
Side Trips

Chicago — 8 nights

Windy City

Chicago is known for sightseeing, museums, and nightlife. Your trip includes some of its best attractions: admire the masterpieces at The Art Institute of Chicago, engage your brain at Museum of Science and Industry, observe the fascinating underwater world at Shedd Aquarium, and get to know the resident critters at Lincoln Park Zoo.

To see traveler tips, photos, where to stay, and tourist information, go to the Chicago online trip builder.

Traveling by flight from Evansville to Chicago takes 3 hours. Alternatively, you can drive; or take a bus. Prepare for little chillier weather when traveling from Evansville in January: high temperatures in Chicago hover around 32°F and lows are around 18°F. Finish your sightseeing early on the 2nd (Sun) to allow enough time to drive to South Bend.
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Museums · Childrens Museums · Parks · Historic Sites
Side Trips

South Bend — 6 nights

Get out of town with these interesting South Bend side-trips: Krider Nurseries World's Fair Gardens (in Middlebury), Angola (Pokagon State Park & Glendarin Hills Golf Club) and Elkhart (Quilt Gardens & Linton's Enchanted Gardens).

To find reviews and more tourist information, you can read our South Bend travel planning tool.

Traveling by car from Chicago to South Bend takes 2 hours. Alternatively, you can drive; or take a train; or take a bus. Due to the time zone difference, you'll lose 1 hour traveling from Chicago to South Bend. In February, daily temperatures in South Bend can reach 34°F, while at night they dip to 17°F. Wrap up your sightseeing on the 8th (Sat) early enough to travel to Bayfield.
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Parks · Museums · Historic Sites · Outdoors
Side Trips

Bayfield — 3 nights

Venture out of the city with trips to Copper Falls State Park (in Mellen) and ABC Raceway (in Ashland).

To find photos, other places to visit, and tourist information, you can read our Bayfield trip site.

Getting from South Bend to Bayfield by combination of train and flight takes about 6 hours. Other options: fly; or drive. Traveling from South Bend to Bayfield, you'll gain 1 hour due to the time zone difference. Traveling from South Bend in February, things will get a bit cooler in Bayfield: highs are around 23°F and lows about 6°F. Finish your sightseeing early on the 11th (Tue) so you can drive to Minocqua.
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Nature · Parks · Winter Sports · Wineries
Side Trips

Minocqua — 6 nights

Venture out of the city with trips to Cable Natural History Museum (in Cable), WinMan Trails (in Winchester) and Wausau (The Center for the Visual Arts, Leigh Yawkey Woodson Art Museum, &more).

To see reviews, where to stay, traveler tips, and tourist information, you can read our Minocqua trip planner.

Drive from Bayfield to Minocqua in 2.5 hours. In February, daily temperatures in Minocqua can reach 24°F, while at night they dip to 6°F. Wrap up your sightseeing on the 17th (Mon) early enough to drive to Madison.
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Museums · Parks · Winter Sports · Outdoors
Side Trips

Madison — 6 nights

The City of Four Lakes

Explore Madison's surroundings by going to Snowflake Ski Club (in Westby), Bailey's Run Vineyard & Winery (in New Glarus) and Portage (Portage WWII History Museum & Cascade Mountain). The adventure continues: test your problem-solving skills at popular escape rooms, have fun and explore at Discovery Center Museum, tour or see a show at Monona Terrace Community and Convention Center, and make a trip to Memorial Union Terrace.

For maps, traveler tips, where to stay, and tourist information, read our Madison road trip app.

Drive from Minocqua to Madison in 3.5 hours. Traveling from Minocqua in February, expect Madison to be a bit warmer, temps between 30°F and 12°F. Finish up your sightseeing early on the 23rd (Sun) so you can go by car to Galena.
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Outdoors · Parks · Winter Sports · Museums
Side Trips

Galena — 6 nights

Explore Galena's surroundings by going to Rock Island (Jumer's Casino Rock Island & Atomic Cannon), Brewery Pottery (in Mineral Point) and Lock & Dam 13 Recreation Area (in Fulton).

To find where to stay, other places to visit, reviews, and other tourist information, go to the Galena day trip planning app.

Traveling by car from Madison to Galena takes 2 hours. Alternatively, you can do a combination of bus and taxi. Expect a daytime high around 30°F in February, and nighttime lows around 12°F. Finish your sightseeing early on the 1st (Sat) to allow enough time to fly to Milwaukee.
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Museums · Shopping · Golf · Outdoors
Side Trips

Milwaukee — 6 nights

Brew City

Venture out of the city with trips to Lapham Peak (in Delafield), SC Johnson Headquarters (in Racine) and Highway 42 (in Sheboygan). The adventure continues: learn more about the world around you at Milwaukee Public Museum, get engrossed in the history at Mitchell Gallery of Flight, sample the tasty concoctions at Silver Creek Brewing, and brush up on your military savvy at Civil War Museum.

For photos, where to stay, reviews, and tourist information, read Milwaukee journey maker tool.

You can fly from Galena to Milwaukee in 3 hours. Other options are to drive; or take a bus. Expect a daytime high around 41°F in March, and nighttime lows around 27°F. Finish your sightseeing early on the 7th (Fri) to allow enough time to fly to Springfield.
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Museums · Breweries & Distilleries · Parks · Fun & Games
Side Trips

Springfield — 6 nights

Flower City

Get out of town with these interesting Springfield side-trips: Children's Discovery Museum (in Normal), McLean County Museum of History (in Bloomington) and Great Rivers Scenic Route (in Alton). There's much more to do: take an in-depth tour of Abraham Lincoln Presidential Library and Museum, get a taste of the local shopping with The Vault Art Gallery, steep yourself in history at Dana-Thomas House, and see the interesting displays at Memories: Route 66 Museum.

For maps, where to stay, photos, and other tourist information, read Springfield day trip planning app.

You can fly from Milwaukee to Springfield in 2.5 hours. Other options are to drive; or take a train. Expect a bit warmer weather when traveling from Milwaukee in March: highs in Springfield hover around 51°F, while lows dip to 31°F. Finish your sightseeing early on the 13th (Thu) to allow enough time to drive to Indianapolis.
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Museums · Outdoors · Historic Sites · Shopping
Side Trips

Indianapolis — 7 nights

Circle City

Explore Indianapolis' surroundings by going to Perfect North Slopes (in Lawrenceburg), Clifty Falls State Park (in Madison) and Westfield (Urban Vines Winery & Brewery Co. & Collective Beauty Salon & Spa). There's much more to do: test your problem-solving skills at popular escape rooms, look for all kinds of wild species at Exotic Feline Rescue Center, deepen your understanding at Indiana University, and make a trip to Central Canal.

For more things to do, maps, traveler tips, and tourist information, you can read our Indianapolis trip planner.

You can drive from Springfield to Indianapolis in 3.5 hours. Other options are to drive; or fly; or do a combination of train and bus. You'll lose 1 hour traveling from Springfield to Indianapolis due to the time zone difference. In March in Indianapolis, expect temperatures between 49°F during the day and 31°F at night. Finish up your sightseeing early on the 20th (Thu) so you can catch the flight back home.
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Parks · Wineries · Museums · Breweries & Distilleries
Side Trips

Indiana travel guide

4.1
Casinos · Room Escape Games · Specialty Museums
The Hoosier State
With an extensive history of motorsports, Indiana's main claim to fame is the popular automobile race held each year in its capital city. A mostly rural state, Indiana is a land of till plains and lakes, its appearance a result of traces left behind by receding glaciers. The central section of the state, mostly flat with some rolling hills, contains some of the country's most fertile farmland. The state also contains almost 39,000 km (24,000 mi) of waterways, including the Wabash River, the longest free-flowing river east of the Mississippi. For a genuine "Hoosier" experience, tour the state's slow-paced small towns, noted for their hospitality and outstanding local cuisine. You'll remember the warmth and charm long after your vacation is over.
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Illinois travel guide

4.3
Observation Decks · Parks · Art Museums
The Prairie State
The most populous state in the country's Midwest region, Illinois features a diverse landscape that includes both the enormous urban sprawl of Chicago and flat central plains, devoted almost entirely to farmland. With a great selection of things to do, Chicago is the state's centerpiece, featuring world-famous architecture and renowned museums. Farther away from this giant urban center, you can explore historical landmarks dedicated to local heroes Abraham Lincoln and Ernest Hemingway. The state also includes a prehistoric Native American site, one of only 20 World Heritage Sites in the United States, a unique feature well-worth adding to your itinerary.
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Wisconsin travel guide

4.3
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.
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