45 days in Minnesota & Chicago Itinerary

45 days in Minnesota & Chicago Itinerary

Created using Inspirock United States trip maker

Make it your trip
Fly
1
Minneapolis
— 5 nights
Drive
2
Lake Itasca
— 3 nights
Drive
3
Orr
— 3 nights
Drive
4
Ely
— 5 nights
Drive
5
Silver Bay
— 3 nights
Drive
6
Grand Marais
— 5 nights
Drive
7
Duluth
— 5 nights
Drive
8
Winona
— 3 nights
Drive
9
Chicago
— 11 nights
Fly

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Minneapolis

— 5 nights

The City of Lakes

Located on both banks of the Mississippi River, Minneapolis salutes the state's love of the outdoors with numerous lakes, wetlands, creeks, and waterfalls--many connected to one another by a national scenic byway great for sightseeing.
Attractions like Minnehaha Park and Chain of Lakes make great kid-friendly stops. Explore the numerous day-trip ideas around Minneapolis: Carpenter St. Croix Valley Nature Center (in Hastings), Mini Met (in Jordan) and Baker Park Reserve (in Maple Plain). There's lots more to do: explore the world behind art at Minneapolis Institute of Art, tee off at Rush Creek, stroll through The Belwin Conservancy, and learn about wildlife with up-close encounters at Como Park Zoo & Conservatory.

To find where to stay, more things to do, reviews, and tourist information, you can read our Minneapolis holiday builder app.

Bangkok, Thailand to Minneapolis is an approximately 23-hour flight. You'll gain 13 hours traveling from Bangkok to Minneapolis due to the time zone difference. When traveling from Bangkok in September, plan for slightly colder days in Minneapolis, with highs around 28°C, while nights are colder with lows around 16°C. Cap off your sightseeing on the 19th (Sun) early enough to go by car to Lake Itasca.

Things to do in Minneapolis

Parks · Outdoors · Nature · Wildlife

Side Trips

Lake Itasca

— 3 nights
Step out of Lake Itasca with an excursion to Rabideau CCC camp in Blackduck--about 54 minutes away.

For maps, more things to do, other places to visit, and tourist information, go to the Lake Itasca online trip maker.

Traveling by car from Minneapolis to Lake Itasca takes 4 hours. Traveling from Minneapolis in September, Lake Itasca is slightly colder at night with lows of 11°C. Finish your sightseeing early on the 22nd (Wed) to allow enough time to travel to Orr.

Things to do in Lake Itasca

Parks · Nature · Outdoors · Historic Sites

Side Trip

Orr

— 3 nights
Orr is a city in Saint Louis County, Minnesota, United States. Explore the numerous day-trip ideas around Orr: Scenic State Park (in Bigfork), Voyageurs National Park (in Ray) and Lake Kabetogama (in Kabetogama). There's still lots to do: take in the dramatic scenery at Vermilion Falls and contemplate the waterfront views at Crane Lake.

To find other places to visit, ratings, more things to do, and other tourist information, refer to the Orr online tour itinerary planner.

Getting from Lake Itasca to Orr by car takes about 3 hours. In September, daily temperatures in Orr can reach 23°C, while at night they dip to 9°C. Wrap up your sightseeing on the 25th (Sat) early enough to drive to Ely.

Things to do in Orr

Nature · Parks

Side Trips

Ely

— 5 nights
Ely is a city in Saint Louis County, Minnesota, United States. Bring the kids along to North American Bear Center and Kawishiwi Falls Trail. Take a break from Ely with a short trip to Flathorn - Gegoka Cross Country Ski Trails in Isabella, about 40 minutes away. There's still lots to do: admire the majestic nature at Soudan Underground Mine, explore the activities along Birch Lake, make a trip to Listening Point, and look for gifts at Piragis Northwoods Company.

To find photos, reviews, and more tourist information, use the Ely trip planner.

Traveling by car from Orr to Ely takes 1.5 hours. In September in Ely, expect temperatures between 22°C during the day and 9°C at night. Finish your sightseeing early on the 30th (Thu) to allow enough time to drive to Silver Bay.

Things to do in Ely

Parks · Outdoors · Nature · Trails

Side Trips

Silver Bay

— 3 nights
Silver Bay is a city in Lake County, Minnesota, United States. Bring the kids along to Gooseberry Falls State Park and Shovel Point. Next up on the itinerary: admire the majestic nature at Tettegouche State Park, tour the pleasant surroundings at Superior Hiking Trail, and contemplate the waterfront views at Baptism River.

For other places to visit, where to stay, photos, and other tourist information, use the Silver Bay road trip planning app.

You can drive from Ely to Silver Bay in 1.5 hours. In September in Silver Bay, expect temperatures between 22°C during the day and 9°C at night. Wrap up your sightseeing on the 3rd (Sun) to allow time to drive to Grand Marais.

Things to do in Silver Bay

Parks · Nature · Trails · Outdoors

Side Trips

Grand Marais

— 5 nights
Grand Marais is a city in Cook County, Minnesota, United States. Kids will appreciate attractions like Cascade River State Park and Grand Portage State Forest. Change things up with these side-trips from Grand Marais: Grand Portage (Grand Portage National Monument, High Falls, &more), Temperance River State Park (in Schroeder) and Points Unknown (in Hovland). And it doesn't end there: ski along the peaceful trails at Pincushion Mountain Trail System, get outside with Joe's Inland Fishing, and immerse yourself in nature at Judge C.R. Magney State Park.

For where to stay, traveler tips, maps, and more tourist information, read our Grand Marais travel route tool.

Getting from Silver Bay to Grand Marais by car takes about 1.5 hours. Expect a daytime high around 13°C in October, and nighttime lows around 5°C. Wrap up your sightseeing on the 8th (Fri) to allow time to travel to Duluth.

Things to do in Grand Marais

Parks · Nature · Outdoors · Tours

Side Trips

Duluth

— 5 nights

Zenith City of the Unsalted Seas

Situated on the westernmost point of the Lake Superior, Duluth represents a booming port city.
Family-friendly places like Oberg Mountain Loop and Self Discovery Adventures will thrill your kids. Fill the 13th (Wed) with the natural beauty at Jay Cooke State Park. There's much more to do: admire all the interesting features of Minnesota's North Shore Scenic Drive, take a tour by water with Boat Tours & Water Sports, stroll around Canal Park, and get engrossed in the history at Glensheen, The Historic Congdon Estate.

For reviews, where to stay, ratings, and tourist information, use the Duluth attractions planner.

Traveling by car from Grand Marais to Duluth takes 2.5 hours. Expect a daytime high around 15°C in October, and nighttime lows around 6°C. Wrap up your sightseeing on the 13th (Wed) early enough to travel to Winona.

Things to do in Duluth

Parks · Nature · Outdoors · Museums

Side Trip

Winona

— 3 nights
Winona is a city in and the county seat of Winona County, in the state of Minnesota. Explore Winona's surroundings by going to National Eagle Center (in Wabasha), Houston (Harmony-Preston Valley Trail & Root River State Trail) and Whitewater State Park (in Altura). There's more to do: admire the masterpieces at Minnesota Marine Art Museum and cruise along Garvin Heights City Park.

To see where to stay, more things to do, traveler tips, and tourist information, use the Winona trip planner.

Getting from Duluth to Winona by car takes about 4 hours. Other options: do a combination of flight and car. In October in Winona, expect temperatures between 18°C during the day and 6°C at night. Finish up your sightseeing early on the 16th (Sat) so you can travel to Chicago.

Things to do in Winona

Parks · Outdoors · Trails · Wildlife

Side Trips

Chicago

— 11 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Kids will enjoy The Art Institute of Chicago and Skydeck Chicago - Willis Tower. And it doesn't end there: stroll around Millennium Park, take in the waterfront at Navy Pier, wander the streets of The Magnificent Mile, and take in panoramic vistas at 360 Chicago Observation Deck.

Plan my trip to Chicago with suggested itineraries provided by Inspirock.

Drive from Winona to Chicago in 5 hours. Alternatively, you can do a combination of car and flight. Traveling from Winona in October, you can expect nighttime temperatures to be a bit warmer in Chicago, with lows of 11°C. Wrap up your sightseeing by early afternoon on the 27th (Wed) to allow time for the flight back home.

Things to do in Chicago

Parks · Museums · Childrens Museums · Tours

Side Trips

Minnesota travel guide

4.4
Room Escape Games · History Museums · Shopping Malls
The Land of 10,000 Lakes
Deriving its name from the Dakota word for "land of sky-tinted water," Minnesota is a land of pristine lakes, pockets of dense green forests, and sprawling prairieland. Spend your vacation exploring the state's diverse landscape for endless outdoor activity and a chance to see some of the area's national monuments, or take a trip to the bustling St. Paul-Minneapolis area, a network of commerce and cultural attractions, including the famous Mall of America.