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Midwestern Mileposts
Discover the heart of the Midwest on a road trip where iconic sports, regional flavors, and cultural landmarks define each spot.
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Louisville, KY
While not “technically” in the Midwest, Louisville is just two hours south of Indianapolis, and a great way to expand your Midwest road trip options. If you are a fan of baseball, check out the Louisville Slugger Museum and Factory where you can hold bats used by Mickey Mantle, Cal Ripken Jr. and Derek Jeter. Bourbon is the drink of choice in Kentucky, and Louisville offers visitors a chance to explore different distilleries through the Urban Bourbon Trail, a collection of bars and restaurants in the city offering a wide variety of bourbons to casual fans and aficionados. Check off one of the greatest bucket list sporting events in America and visit the famous Kentucky Derby. Even if you are not into horse racing, the people watching will keep you entertained.
Start
Where to Stay: Omni Louisville Hotel
What to see: Louisville Slugger Museum and Factory, Kentucky Derby Museum
Where to Eat: Jack Fry’s
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Pit Stop
+A food stop worth pulling over for is Schrimpff’s Confectionary for nostalgic sweet treats.
Location: Schimpff's Confectionery, 347 Spring St, Jeffersonville, IN 47130
Distance: 4 Miles
Pit Stop
+If you want some year-round holiday cheer, make a detour to visit Santa Claus, Indiana.
Location: 452 E Christmas Blvd, Santa Claus, IN 47579
Distance: 76 Miles
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Indianapolis, IN
Indianapolis is primarily a sports town, and a first class one at that. And no event is more synonymous with the city than the Indianapolis 500, the largest single-day sporting event in the world. But don’t worry if you can’t make it for the Indy 500, The Indianapolis Motor Speedway Museum has an incredible collection of race memorabilia and offers visitors a chance to take a lap around the track. If you have kids, The Children’s Museum of Indianapolis is a must. Indianapolis has top rated restaurants like Milktooth and Bluebeard, but if you're looking for their most famous dish head to Jonesy’s Junction to have a giant tenderloin sandwich.
Distance: 112 Miles with detour 147 Miles
Where to Stay: Omni Severin Hotel
What to see: Indianapolis Motor Speedway Museum
Where to Eat: Jonesy’s Junction
Pit Stop
+Optional detour to leave your legacy and add a layer to World’s Largest Ball of Paint
Location: 10696 N 200 W, Alexandria, IN 46001
Distance: 54 Miles
Pit Stop
+Nothing beats a Midwest diner and Triple XXX Family Restaurant is the place to go (especially if you like root beer floats).
Location: Triple XXX Family Restaurant, 2 N Salisbury St, West Lafayette, IN 47906
Distance: 72 Miles
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Chicago, Il
Chicago is known for many things — deep-dish pizza, brutally cold winters, Michael Jordan — but once you see the Chicago skyline on your Midwest road trip, you’ll be reminded it's also home to some of America’s most iconic architecture. While there, go on a walking tour or guided boat ride to really soak up the beauty of the city. If you want to get a bird’s-eye view, check out the 360 Chicago Observation Deck at the John Hancock Center. You could spend a month in Chicago and not scratch the surface on all the great cuisine. We recommend hitting Gino’s East for deep dish, Lou Mitchell’s for a diner, and the Navy Pier for a Chicago style hot dog.
Distance: 123 Miles
Where to Stay: Omni Chicago Hotel
What to see: Millenium Park to see “The Bean” Cloud Gate
Where to Eat: Gino’s East
Pit Stop
+Stop by the iconic pit stop that’s been around since 1947 to load up on cheese and tasty snacks.
Location: Mars Cheese Castle, 2800 W Frontage Rd, Kenosha, WI 53144
Distance: 61 Miles
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Minneapolis, MN
Minneapolis is a city filled with vibrant art, great food and stunning waterfalls. If you are someone who likes to shop, Minneapolis is the city for you. Home to the largest mall in the United States, the Mall of America has endless stores and attractions, including the Nickelodeon Universe Theme Park and an aquarium, making it a fun place for everyone. Nothing is more comforting than Minneapolis’s food scene. Make sure to get the city's famous Juicy Lucy, a burger filled with cheese inside the patty. If you’re in the mood for something other than burgers, Minneapolis has great Scandinavian food culture in large part due to its Nordic heritage.
Distance: 365 Miles
Where to Stay: Omni Viking Lakes
What to see: Minneapolis Sculpture Garden
Where to Eat: Matt’s Bar and Grill, FIKA café
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More Adventures to Enjoy
From sea to shining sea, America’s Hotel Company plays host to coastal escapes, desert drives, city breaks, and more. Hop in and hit the road.
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Route 66 Centennial Cruise
There is no better year than 2026 to go on the classic American road trip celebrating the 100th anniversary of Route 66.
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Blue Ridge Rhythm Route
Experience the best of the Southeast on a road trip from Nashville to Asheville, and Charlotte, where music, mountain scenery and Southern culture come together.
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