The northern states of Mississippi River Country have a bounty of uniquely American attractions to offer, from Route 66 (which starts in downtown Chicago) to the Harley-Davidson Museum in Milwaukee to the Mall of America in Minnesota to charming towns on the Great River Road.
Follow this nine-day itinerary—the perfect route for fall colors in the Midwest—and see the sights in Illinois, Wisconsin, and Minnesota.
Day 1
Afternoon/Evening
- Fly into Chicago O’Hare International Airport in Chicago, Illinois
- Check into your hotel
Chicago has an impressive array of hotels, from boutique arts enclaves to historic renovated buildings; notable luxury accommodations in downtown Chicago include The Gray Hotel, The Langham, and Four Seasons Chicago
- Explore downtown Chicago and the Magnificent Mile
If you don’t need a night of rest after your travels, head over to the Magnificent Mile, a 13-block stretch of Michigan Avenue near Chicago’s lakefront that’s home to more than 450 stores and 275 restaurants
Day 2
Morning
- Explore more of Chicago
Take some time to enjoy the sights around downtown Chicago, including Millennium Park (which home to the iconic Cloud Gate sculpture, also known as “The Bean”) and world-famous attractions like the Art Institute of Chicago, the Field Museum, and the Shedd Aquarium
Afternoon
- Depart for Milwaukee, Wisconsin (1 hour, 30 minutes)
- Visit the Harley-Davidson Museum and other Milwaukee attractions
Harley-Davidson motorcycles were born in Wisconsin, and the Harley-Davidson Museum tells the story of this celebrated brand; other attractions to visit include the Instagram-worthy Milwaukee Art Museum and the Milwaukee Public Museum
Evening
- Check into your hotel
Milwaukee’s downtown lodging properties offer a wide array of experiences, from the trendy boutique vibe at Saint Kate – The Arts Hotel to the historical elegance of The Pfister Hotel
- Take in a show at one of Milwaukee’s historic theaters
Milwaukee is home to several historic theaters that welcome national and international touring acts throughout the year—see who’s playing at the Riverside Theater, the Pabst Theater, or Turner Hall Ballroom
Day 3
Morning
- Depart for Madison, Wisconsin (1 hour, 15 minutes)
- Explore Downtown Madison and State Street
Madison is the state capital of Wisconsin and is home to the state’s flagship university and the campus and the Capitol building are connected via State Street, a seven-block pedestrian-only zone that’s filled with shops and restaurants; grab lunch here after taking in the sights
Afternoon
- Depart for Minneapolis-Saint Paul, Minnesota (4 hours)
Evening
- Check into your hotel in Minneapolis-Saint Paul
Minneapolis and Saint Paul are known as the Twin Cities offer a wide range of hotels and accommodations, from the high-end Hotel Ivy in downtown Minneapolis to the Chambers Hotel in the city’s theater district to the Radisson Blu at the Mall of America in Bloomington
Day 4
Morning
- Explore the Mall of America
The Mall of America, located in the Twin Cities suburb of Bloomington, is the largest shopping center in the United States (take note: there is no sales tax on clothing or shoes in Minnesota), boasting more than 500 stores and 60 restaurants, as well as an indoor amusement park and an aquarium; spend a few hours shopping and grab lunch here
Afternoon
- Take a Twin Cities attractions tour
There is a lot to see and do across the Twin Cities region, from professional sports to outdoor recreation, but a quick attractions tour could include sites like Minnehaha Falls, the Walker Art Center & Minnesota Sculpture Garden, or Paisley Park (Prince’s home and studio)
Evening
- Explore Minneapolis-Saint Paul nightlife
If you don’t want to turn in for the night after you check into your hotel, you can find great nightlife in the Twin Cities, including live music at First Avenue or the Dakota Jazz Club
Day 5
Morning
- Depart Minneapolis-Saint Paul for Red Wing, Minnesota (1 hour, 15 minutes on the Minnesota Great River Road)
- Explore downtown Red Wing
Red Wing is a charming city nestled along the Mississippi River southeast of Minneapolis-Saint Paul; explore the charming downtown to find local favorites like the Red Wing Shoe Store & Museum (home to the world’s largest boot), Hanisch Bakery and Coffee Shop, and the Uffda Shop
Afternoon
- Depart Red Wing for Galena, Illinois (4 hours, 15 minutes)
Continue to enjoy the views along the Great River Road in Minnesota (or Wisconsin, if you decide to cross the Mississippi River) as you travel south toward Galena; the northern Great River Road is an excellent place to see fall colors in the United States
Evening
- Check into your hotel in Galena
Galena, located in northwestern Illinois, is often called one of the most charming small towns in America, and its lodging options reflect that: The Jail Hill Inn has been rated as the #1 B&B in the country and #2 worldwide, and Goldmoor Inn & Resort sits on a bluff overlooking the Mississippi River
- Find a bite to eat in downtown Galena
Historic Main Street in downtown Galena boasts more than 100 independently owned shops and restaurants, all tucked into 1800s-era buildings; popular dining spots include Vinny Vanucchi’s and Log Cabin Steakhouse
Day 6
Morning
- Explore more of Galena’s shops and restaurants
Galena’s Main Street is home to everything from spas to bookshops to candy stores, so there are plenty of retailers to explore
- Depart for Moline, Illinois (1 hour, 45 minutes on the Illinois Great River Road)
Afternoon
- Explore Moline
Moline is one of the Quad Cities, a region that spans both sides of the Mississippi River in Illinois to the east and Iowa to the west; some of Moline’s top attractions include the John Deere Pavilion (Moline is the home of the famous agricultural company) and the Celebration Belle paddlewheeler, which offers cruises on the Mississippi River
- Depart for Alton, Illinois (4 hours)
Evening
- Check into your hotel in Alton
Alton, located along the Mississippi River in southwestern Illinois, is where Route 66 meets the Great River Road, so it’s the perfect region to explore during the height of fall color season; unique lodging properties include the Cracker Factory, which has apartments and suites in the upstairs of a historic downtown building, and the Beall Mansion bed & breakfast
- Explore spooky sights
Alton is known as “one of the most haunted small towns in America,” and there are lots of ways to explore these eerie attractions, including tour groups, self-guided tours, and special events
Day 7
Morning
- Explore Alton’s scenery and Route 66 attractions
There are lots of unique Route 66 attractions in and around Alton, including the Chain of Rocks Bridge, the Pink Elephant Antique Mall, the world’s largest ketchup bottle (Collinsville); don’t’ miss scenic stops like Pere Marquette State Park and Cahokia Mounds State Historic Site, a UNESCO Word Heritage Site
- Depart for Springfield, Illinois (1 hour, 30 minutes)
Afternoon
- Explore Route 66 attractions in Springfield
First, stop for lunch at the Cozy Dog Drive In, a historic diner that’s been serving customers for more than 85 years; other Route 66 attractions in Springfield include Route 66 Motorheads Bar, Grill & Museum, the historic Route 66 brick road outside town, and the Ace Sign Museum
- Depart for Pontiac, Illinois (1 hour, 45 minutes)
- Explore downtown Pontiac
Pontiac is another charming city with a small-town feel on Route 66 in Illinois; don’t miss engaging attractions like the Route 66 Hall of Fame & Museum, the Pontiac-Oakland Auto Museum, and downtown’s historic murals
Evening
- Depart for Chicago, Illinois (1 hour, 45 minutes)
- Check into hotel and grab dinner
End your day with a relaxing stay in your hotel (grab a room at a famous spot like The Drake or Nobu) or get out and explore Chicago’s amazing dining scene—it’s home to 21 Michelin Star restaurants, including Indienne and Alinea
Day 8
Morning/Afternoon
- Explore more of Chicago
If you didn’t hit up Chicago’s Museum Campus (which includes the Field Museum and Adler Planetarium) last time, be sure to check out those intriguing stops; you can also stroll along the Lake Michigan lakeshore or visit engaging attractions like Navy Pier, 360 Chicago, or the Skydeck at the Willis Tower
Evening
- Get out on the water on a river or lake cruise
Take in the stunning sights of Chicago’s skyline at night on a cruise along the Chicago River or the Lake Michigan lakefront—you can find architecture cruises, dinner cruises and more with companies like Wendella Boats, Shoreline Sightseeing, City Experiences, and First Lady
Day 9
Morning
- Depart from Chicago-O’Hare International Airport
