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  • Posing for a photo in front of The Bean in Millennium Park in Chicago, Illinois
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    Day 1: The Best of City Life in Chicago, Illinois

  • Aerial view of the Mississippi River and the Minneapolis, Minnesota, skyline
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    Day 2: The Skyways and Airwaves of Minneapolis

  • Family posing for a photo outside Mall of America in Bloomington, Minnesota
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    Day 3: The Iconic Mall of America in Bloomington

  • Spoonbridge and Cherry sculpture by Claes Oldenburg and Coosje van Bruggen in the Minneapolis Sculpture Garden in Minnesota
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    Day 4: More Fun in Minneapolis and St. Paul

  • Photographing Minnehaha Falls and Minnehaha Regional Park in Minneapolis, Minnesota
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    Day 5: Exploring Local Favorites in Minneapolis and St. Paul

Appreciating views of the Mississippi River from the Guthrie Theater in Minneapolis, Minnesota
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Ryan Taylor

Art, Food and Fun: Chicago, Illinois, to Minnesota’s Twin Cities

By Kristin Trummer

  • Route distance:
    670 km
  • Suggested Time:
    5 days

Discover the eclectic music scenes, green spaces and creative hubs of Chicago, Minneapolis and St. Paul with plenty of foodie jaunts in between.

Charting a course from Chicago across Minnesota, this midwestern USA road trip features eye-catching art, epic shopping, major attractions and exciting sports. Catch a flight into Chicago O’Hare International Airport in Illinois and check in to the W Chicago - Lakeshore to kick off your vacation.

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Posing for a photo in front of The Bean in Millennium Park in Chicago, Illinois
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Illinois Office of Tourism

Day 1: The Best of City Life in Chicago, Illinois

There’s no better place to begin your exploration of this vibrant cultural metropolis than Millennium Park downtown. Arrive in the morning to beat the crowds and snap a pic of the impressive and reflective Cloud Gate Sculpture, known as “The Bean.” This colossal work created by British artist Anish Kapoor is one of the largest of its kind in the world. Lurie Garden is an award-winning oasis amid skyscrapers and the perfect place to meander; take a free guided tour or be a kid again with the free family-friendly scavenger hunt. Pop into nearby Cindy’s Rooftop restaurant, where you can dine while taking in sweeping views of Millennium Park, Lake Michigan and The Art Institute of Chicago. If it’s brunch you’re craving, Wildberry Pancakes and Cafe’s mouthwatering menu has stacked pancakes, omelets, savory skillets, crepes and more. After lunch, head back toward Millennium Park to get lost in The Art Institute of Chicago’s sprawling collection from around the world and across centuries. Founded in 1879, it’s one of the oldest and largest art museums in the world and hosts 1.5 million awe-inspired visitors annually. For the quintessential Chicago dinner, indulge in a stuffed deep-dish pizza from Giordano’s, which has topped “Best Pizza” lists over the past 40 years. End your day with possibly the best sunset of your life from the third tallest building in the Western Hemisphere at Skydeck Chicago in the Willis Tower. Feel suspended in air as you step out on The Ledge, an all-glass viewing platform on the 103rd floor – incredible!

658 km
6.5 hours by car
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Aerial view of the Mississippi River and the Minneapolis, Minnesota, skyline
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Day 2: The Skyways and Airwaves of Minneapolis

Wake up the next morning and drive 6.5 hours through Wisconsin to Minneapolis, Minnesota. Ideal stops along the way include charming capital city and college town Madison, the water parks of the Wisconsin Dells, or quaint and scenic Eau Claire. If you’d prefer to fly, catch a quick flight from O’Hare to Minneapolis-St. Paul International Airport. Check in at The Marquette Hotel downtown and start exploring the bustling, creative energy of this major city. Endless entertainment awaits right outside your door as this Curio Collection hotel by Hilton is linked to the IDS Center skyscraper’s shopping, restaurants and award-winning Crystal Court urban park. Strolling along the Nicollet Mall, Minneapolis’ pedestrian-friendly strip for shopping and entertainment, you’ll notice beautiful greenery and more than 12 kilometers of overhead skyways connecting 80 city blocks. When you’re ready to eat, Barrio’s bold Latin cuisine and creative tequila bar make it an excellent spot to unwind and people watch. Or check out the News Room’s varied American fare, whether on its large outdoor patio or in the clever newspaper-themed interior. End your first night in Minnesota getting to know the city’s eclectic music scene. See music seven nights a week at the Dakota Jazz Club, or check the calendar at First Avenue. You may just catch your favorite band (or discover a new one) at one of the longest-running independently owned venues in the USA.

38 km
1 hour by car
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Family posing for a photo outside Mall of America in Bloomington, Minnesota
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Day 3: The Iconic Mall of America in Bloomington

Get ready to shop until you drop because day 3 is all about the famed Mall of America in Bloomington. Known the world over as the largest shopping center in the USA, it’s just a 30-minute drive from Minneapolis. It’s not only shopping, though – the Mall of America has exciting on-site attractions like the SEA LIFE Aquarium, the immersive FlyOver America flight simulation ride and frequent events such as concerts and fashion shows. After a morning filled with finding deals and the latest fashion, grab a quick lunch in the mall – for example, crispy Korean chicken at Bonchon or a juicy hamburger with a milkshake at the Shake Shack. Then gear up for an afternoon at Nickelodeon Universe, the sprawling indoor theme park filled with rides and attractions for all ages featuring Nickelodeon cartoon favorites. By evening, you’ll no doubt be ready for a slower, sit-down meal, and Cedar + Stone’s thoughtful farm-to-table menu provides the perfect spot to linger. For lighter fare, Masu Sushi & Robata’s sustainable menu has super-fresh sushi and ramen. For a local touch, Twin City Grill’s home cooking elevates beloved Midwestern classics like meatloaf, fish-n-chips and steaks. After a day at Mall of America, head back to Minneapolis to catch live music at Varsity Theater. With eclectic headliners most nights of the week, the art deco venue has gained international acclaim as a premier music venue.

26 km
0.75 hours by car
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Spoonbridge and Cherry sculpture by Claes Oldenburg and Coosje van Bruggen in the Minneapolis Sculpture Garden in Minnesota
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Meet Minneapolis

Day 4: More Fun in Minneapolis and St. Paul

Start the fourth morning of your trip with a meander through The Minneapolis Sculpture Garden in the heart of downtown, where you’ll discover larger-than-life sculptures in an urban garden setting. From a gigantic cherry perched on a spoon to a towering cobalt blue rooster and 43 other whimsical installations, it’s sure to bring a smile to your face. At the adjacent Walker Art Center, you’ll find contemporary visual arts and design exhibitions and a rotating curation of dance, theater, music performances and film screenings. For lunch, The Market at Malcolm Yards’ artfully repurposed Harris Machinery Building is a mixed-use space that houses nine different culinary concepts from local chefs. One favorite feature is the ingenious self-pour tap wall, where you can sample a range of beer, wine and cider. Walk off that hearty meal along the Mississippi riverfront with green spaces showcasing the best of Minneapolis’ skyline and architecture, old and new. From roughly February through October, catch a Minnesota United Major League Soccer (MLS) game at Allianz Field, just a 15-minute drive away in neighboring St. Paul. Inspired by the lakes of Minnesota, this modern soccer stadium was built with forward-thinking design and mindful sustainability. Win or lose, grab a team jersey afterward at the Black & Blue team store as a memento of your trip.

77 km
1.5 hours by car
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Photographing Minnehaha Falls and Minnehaha Regional Park in Minneapolis, Minnesota
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Day 5: Exploring Local Favorites in Minneapolis and St. Paul

It’s the last day of your trip and time to escape the city for the morning at Minnehaha Regional Park. The city’s oldest and most popular park features a 16-meter waterfall, layered limestone bluffs and scenic river overlooks. Rent bikes or hike to explore the park’s abundant trail system that connects with Fort Snelling State Park. For lunch, head into St. Paul to the Keg & Case Market food hall. Enjoy a casual lunch on the green from one of the many tasty food vendors housed within. Clutch Brewing Company’s retro Airstream trailer serves up cold craft beers right on the lawn to pair with whatever you choose. Load up on American football trivia and history at the Vikings Museum, about 20 minutes away in Eagan. Experience the comprehensive history of the Minnesota Vikings National Football League (NFL) team firsthand with interactive exhibits, artifacts and a 360-degree video theater. After a jam-packed day, the evening calls for a more leisurely pace. You’ll find just that at Aster Cafe, beneath the shade trees on one of the prettiest streets in Minneapolis. With its candlelit bar, string-lit patio and backdrop of the Mississippi River and city skyline, Aster Cafe serves up romantic ambiance and inviting small plates — making it the perfect spot for your final evening on the town. After one more restful night at The Marquette Hotel, begin your return trip home from Minneapolis-St. Paul International Airport or drive back to Chicago to fly out of O’Hare International Airport.

Golden Gate Bridge, San Francisco, California
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