10 days in Midwest Itinerary

10 days in Midwest Itinerary

Created using Inspirock Midwest vacation builder

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Route & dates

10 days in Midwest Itinerary

Start: Cleveland
Fly:  3​h 15​min
1
Chicago
— 1 night
Fly + Drive:  6​h 30​min
2
Mackinaw City
— 1 night
ferry:  30​min
3
Mackinac Island
— Few hours
+2
ferry + bus + Drive:  9​h 45​min
4
Egg Harbor
— 2 nights
Drive:  3​h 15​min
5
Milwaukee
— 2 nights
Fly:  3​h 30​min
End: Cleveland

1
night
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
On the 11th (Wed), admire the masterpieces at The Art Institute of Chicago, get to know the fascinating history of Chicago Riverwalk, and then sample some tasty brews at a beer tour and tasting. On your second day here, take in the pleasant sights at Chicago Botanic Garden, then explore the landscape on two wheels at Lakefront Trail, then appreciate the extensive heritage of Millennium Park, and finally pause for some photo ops at Cloud Gate.

For other places to visit, maps, traveler tips, and other tourist information, refer to the Chicago online tour planner .

Cleveland to Chicago is an approximately 3.5-hour flight. You can also do a combination of flight and bus; or drive. Traveling from Cleveland to Chicago, you'll gain 1 hour due to the time zone difference. In September, daytime highs in Chicago are 78°F, while nighttime lows are 61°F. Cap off your sightseeing on the 12th (Thu) early enough to travel to Mackinaw City.

Things to do in Chicago

Parks Tours Outdoors

Side Trip

Chicago Botanic Garden
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Beer Tastings & Tours
Chicago Riverwalk ©
Chicago Riverwalk

1
night
Mackinaw City

Mackinaw City ©
Mackinaw City is a village in Emmet and Cheboygan counties in the U.S. On the 13th (Fri), visit a coastal fixture at Old Mackinac Point Lighthouse, tour the pleasant surroundings at Colonial Michilimackinac, then take in the views from Mackinac Bridge, and finally visit a coastal fixture at McGulpin Point Lighthouse & Historic Site.

To see other places to visit, where to stay, ratings, and tourist information, use the Mackinaw City trip itinerary maker site .

Traveling by combination of flight and car from Chicago to Mackinaw City takes 6.5 hours. Alternatively, you can do a combination of flight and bus; or drive. Due to the time zone difference, you'll lose 1 hour traveling from Chicago to Mackinaw City. Prepare for little chillier weather when traveling from Chicago in September: high temperatures in Mackinaw City hover around 67°F and lows are around 54°F. Finish up your sightseeing early on the 14th (Sat) so you can catch the ferry to Mackinac Island.

Things to do in Mackinaw City

Historic Sites Parks Museums

Side Trip

Mackinac Bridge
Highlights from your plan
Mackinac Bridge ©
Mackinac Bridge
Colonial Michilimackinac ©
Colonial Michilimackinac

few
hours
Mackinac Island

Mackinac Island ©
Mackinac Island is a city in Mackinac County in the U.S. On the 14th (Sat), contemplate the long history of Biddle House, then pause for some serene contemplation at Trinity Church, then immerse yourself in nature at Mackinac Island State Park, and finally take in the architecture and atmosphere at St Anne's Catholic Church.

For traveler tips, photos, reviews, and tourist information, you can read our Mackinac Island online driving holiday planner .

Mackinac Island is just a stone's throw from Mackinaw City. In September, plan for daily highs up to 67°F, and evening lows to 54°F. Finish your sightseeing early on the 14th (Sat) so you can travel to Egg Harbor.

Things to do in Mackinac Island

Parks Nature Historic Sites
Highlights from your plan
Mackinac Island State Park ©
Mackinac Island State Park
St Anne's Catholic Church ©
St Anne's Catholic Church
Trinity Church ©
Trinity Church

2
nights
Egg Harbor

Egg Harbor ©
Egg Harbor is a village in Door County, Wisconsin, United States. Start off your visit on the 15th (Sun): enjoy the sea views from Eagle Bluff Lighthouse, then immerse yourself in nature at Peninsula State Park, then take in the exciting artwork at Francis Hardy Gallery, and finally visit a coastal fixture at Cana Island Lighthouse. Here are some ideas for day two: learn about winemaking at Harbor Ridge Winery, hunt for treasures at Schartner's Farm Market, learn about winemaking at Lautenbach's Orchard Country, then tour the pleasant surroundings at Sunset Beach Park, and finally look for gifts at Wood Orchard.

To find ratings, reviews, more things to do, and other tourist information, read our Egg Harbor day trip planner.

Explore your travel options from Mackinac Island to Egg Harbor with the Route module. You'll gain 1 hour traveling from Mackinac Island to Egg Harbor due to the time zone difference. In September in Egg Harbor, expect temperatures between 70°F during the day and 55°F at night. Finish up your sightseeing early on the 17th (Tue) so you can go by car to Milwaukee.

Things to do in Egg Harbor

Shopping Wineries Parks

Side Trips

Fish Creek, Francis Hardy Gallery, Cana Island Lighthouse
Highlights from your plan
Schartner's Farm Market ©
Schartner's Farm Market
Peninsula State Park ©
Peninsula State Park
Cana Island Lighthouse ©
Cana Island Lighthouse

2
nights
Milwaukee

Milwaukee ©
Milwaukee boasts well-preserved historical districts with a rich European past and a strong beer-brewing tradition.
On the 17th (Tue), explore and take pictures at Miller Park, then examine the collection at Harley-Davidson Museum, and then indulge your taste buds at Food & Drink. Get ready for a full day of sightseeing on the next day: admire the striking features of SC Johnson Headquarters, take an in-depth tour of Mitchell Gallery of Flight, then admire the masterpieces at Milwaukee Art Museum, and finally take in the spiritual surroundings of Holy Hill.

To see ratings, photos, and more tourist information, read our Milwaukee online route builder .

Traveling by car from Egg Harbor to Milwaukee takes 3.5 hours. Alternatively, you can do a combination of car and bus; or do a combination of car, bus, and flight. Expect a daytime high around 74°F in September, and nighttime lows around 58°F. On the 19th (Thu), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Milwaukee

Museums Tours Parks

Side Trips

Holy Hill, SC Johnson Headquarters
Highlights from your plan
Harley-Davidson Museum ©
Harley-Davidson Museum
Milwaukee Art Museum ©
Milwaukee Art Museum
SC Johnson Headquarters ©
SC Johnson Headquarters

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