28 days in Chicago & Minnesota Itinerary

28 days in Chicago & Minnesota Itinerary

Created using Inspirock United States journey planner

Make it your trip
Fly
1
Chicago
— 10 nights
Drive
2
Winona
— 2 nights
Drive
3
Duluth
— 4 nights
Drive
4
Grand Marais
— 3 nights
Drive
5
Ely
— 3 nights
Fly
6
Minneapolis
— 4 nights
Fly

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Chicago

— 10 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Take a break from Chicago with a short trip to Illinois Holocaust Museum & Education Center in Skokie, about 30 minutes away. There's still lots to do: admire the masterpieces at The Art Institute of Chicago, meet the residents at Shedd Aquarium, get to know the resident critters at Lincoln Park Zoo, and find something for the whole family at Fox in a Box Chicago.

For where to stay, traveler tips, reviews, and other tourist information, refer to the Chicago trip planner.

Jeddah, Saudi Arabia to Chicago is an approximately 19-hour flight. The time zone difference when traveling from Jeddah to Chicago is minus 9 hours. Plan for much colder temperatures traveling from Jeddah in February, with highs in Chicago at 2°C and lows at -7°C. Cap off your sightseeing on the 11th (Fri) early enough to travel to Winona.

Things to do in Chicago

Museums · Parks · Shopping · Childrens Museums

Side Trips

Winona

— 2 nights
Winona is a city in and the county seat of Winona County, in the state of Minnesota. Start off your visit on the 12th (Sat): cruise along Garvin Heights City Park and then explore the world behind art at Minnesota Marine Art Museum. On your second day here, make a trip to The Fremont Store and then cruise along Old Hwy 61.

To see ratings, other places to visit, and tourist information, refer to the Winona vacation maker.

Traveling by car from Chicago to Winona takes 5 hours. Alternatively, you can do a combination of flight and car. Plan for slightly colder temperatures traveling from Chicago in February, with highs in Winona at -1°C and lows at -13°C. Wrap up your sightseeing on the 13th (Sun) to allow time to travel to Duluth.

Things to do in Winona

Outdoors · Scenic Drive · Museums

Side Trip

Highlights from your trip

Duluth

— 4 nights

Zenith City of the Unsalted Seas

Situated on the westernmost point of the Lake Superior, Duluth represents a booming port city.
Explore Duluth's surroundings by going to Tettegouche Trail (in Silver Bay) and Gooseberry Falls State Park (in Two Harbors). And it doesn't end there: get to know the fascinating history of Lakewalk, explore and take pictures at Minnesota's North Shore Scenic Drive, stroll around Leif Erikson Park, and don't miss a visit to Canal Park.

To see where to stay, more things to do, ratings, and tourist information, you can read our Duluth road trip app.

You can drive from Winona to Duluth in 4 hours. Alternatively, you can do a combination of car and flight. When traveling from Winona in February, plan for little chillier days in Duluth, with highs around -5°C, while nights are about the same with lows around -15°C. Finish your sightseeing early on the 17th (Thu) so you can travel to Grand Marais.

Things to do in Duluth

Parks · Outdoors · Trails · Wildlife

Side Trips

Grand Marais

— 3 nights
Grand Marais is a city in Cook County, Minnesota, United States. Go for a jaunt from Grand Marais to Grand Portage to see Grand Portage State Park about 54 minutes away. Next up on the itinerary: get a new perspective on things with Joe's Inland Fishing, ski along the peaceful trails at Pincushion Mountain Trail System, tour the pleasant surroundings at Honeymoon Bluff, and take a peaceful walk through Grand Portage State Forest.

To find traveler tips, maps, where to stay, and more tourist information, go to the Grand Marais trip itinerary planner.

Traveling by car from Duluth to Grand Marais takes 2.5 hours. In February in Grand Marais, expect temperatures between -6°C during the day and -16°C at night. Finish your sightseeing early on the 20th (Sun) to allow enough time to drive to Ely.

Things to do in Grand Marais

Parks · Outdoors · Nature · Wildlife

Side Trip

Ely

— 3 nights
Ely is a city in Saint Louis County, Minnesota, United States. Take a break from Ely with a short trip to Flathorn - Gegoka Cross Country Ski Trails in Isabella, about 40 minutes away. Next up on the itinerary: surround yourself with nature on White Wilderness Sled Dog Adventures, tour the pleasant surroundings at Chilly Dogs Sled Dog Trips, relax and rejuvenate at The Pebble Spa Co., and immerse yourself in nature at Soudan Underground Mine.

To find reviews, where to stay, ratings, and more tourist information, you can read our Ely visit planner.

You can drive from Grand Marais to Ely in 3 hours. Traveling from Grand Marais in February, you can expect nighttime temperatures to be a bit cooler in Ely, with lows of -23°C. Finish your sightseeing early on the 23rd (Wed) to allow enough time to fly to Minneapolis.

Things to do in Ely

Outdoors · Parks · Wildlife · Tours

Side Trips

Minneapolis

— 4 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.
Step out of Minneapolis to go to Stillwater and see Washington County Historic Courthouse, which is approximately 36 minutes away. And it doesn't end there: explore the world behind art at Minneapolis Institute of Art, walk around Central Park Ice Skating Trail, buy something for everyone on your list at Mall of America, and don't miss a visit to Rice Park.

To find ratings, reviews, where to stay, and other tourist information, go to the Minneapolis route builder.

Traveling by flight from Ely to Minneapolis takes 2.5 hours. Alternatively, you can drive; or do a combination of taxi and bus. Plan for a bit warmer temperatures traveling from Ely in February, with highs in Minneapolis at -3°C and lows at -14°C. Wrap up your sightseeing on the 27th (Sun) early enough to fly back home.

Things to do in Minneapolis

Parks · Museums · Outdoors · Breweries & Distilleries

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.