8 days in Chicago, Madison & Two Harbors Itinerary
Created using Inspirock United States sightseeing planner
Start: Chicago
1
Chicago
— 2 nights
Fly
2
Madison
— 1 night
Fly
3
Two Harbors
— 4 nights
Drive
End: Chicago
Mon, Apr 17 - Mon, Apr 24
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Chicago — 2 nights

Windy City
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.On the 18th (Tue), stroll around Millennium Park, then enjoy breathtaking views from Skydeck Chicago - Willis Tower, then engage your brain at Museum of Science and Industry, and finally take in panoramic vistas at 360 Chicago Observation Deck.
Ask Inspirock to suggest an itinerary and make planning a trip to Chicago fast, fun, and easy.
If you are flying in from Ireland, the closest major aiports are Chicago Midway International Airport, Chicago O'Hare International Airport and Gary Chicago International Airport. In April in Chicago, expect temperatures between 17°C during the day and 5°C at night. Wrap up your sightseeing on the 19th (Wed) to allow time to fly 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.Start off your visit on the 19th (Wed): make a trip to Memorial Union Terrace and then learn about wildlife with up-close encounters at Henry Vilas Zoo.
For ratings, maps, photos, and tourist information, refer to the Madison day trip website.
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 April since evenings lows in Madison dip to 1°C. On the 20th (Thu), you're off to Two Harbors.
Highlights from your trip
Two Harbors — 4 nights

Two Harbors is a city in and the county seat of Lake County, Minnesota, United States, along the shore of Lake Superior. Venture out of the city with trips to Onyx Beach (in Silver Bay), Ely (North American Bear Center & International Wolf Center) and Father Baraga's Cross (in Schroeder). Next up on the itinerary: explore the landscape on two wheels at Gooseberry Falls State Park, contemplate the waterfront views at Caribou River, tour the pleasant surroundings at Tettegouche Trail, and stop by Great Lakes Candy Kitchen.
For maps, traveler tips, and tourist information, go to the Two Harbors online route planner.
Fly from Madison to Two Harbors in 5.5 hours. Alternatively, you can drive; or do a combination of bus and taxi. Prepare for a bit cooler weather when traveling from Madison in April: high temperatures in Two Harbors hover around 9°C and lows are around -2°C. Wrap up your sightseeing on the 24th (Mon) to allow time to fly back home.
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For maps, traveler tips, and tourist information, go to the Two Harbors online route planner.
Fly from Madison to Two Harbors in 5.5 hours. Alternatively, you can drive; or do a combination of bus and taxi. Prepare for a bit cooler weather when traveling from Madison in April: high temperatures in Two Harbors hover around 9°C and lows are around -2°C. Wrap up your sightseeing on the 24th (Mon) to allow time to fly back home.
Side Trips
Highlights from your trip
Wisconsin travel guide
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.