People who've never really considered a visit to “Flyover Country” usually find themselves pleasantly surprised – and sometimes even downright shocked – just by just how much there is to see, do and experience in the truly amazing American Midwest, often for free.
Defined by wide-open swathes of farmland, friendly small towns and attractive urban cities (as well as the bonus of great importance and lower prices for gas and lodging than you'd count on paying on the coasts), this down-to-earth territory holds all of the makings of the memorable road trip.
Editor's note: Book the latest travel restrictions before planning any trip and try to follow government advice.
St. Louis – Missouri
With affordable attractions, tasty food and river city culture, St. Louis constitutes a great starting place to kick off a Midwestern road trip. At 630ft, the iconic Gateway Arch is required viewing, and America's tallest man-made monument. The CityArchRiver project recently revamped the land that surrounds the landmark, updating facilities and adding green space and bike trails.
Take the tram ride to the top for the best bird's eye view around, or catch a ride to cruise the mighty Mississippi on a paddlewheel-powered riverboat (snagging an America the Beautiful Pass could save you a few bucks on ticket prices). During baseball season, Busch Stadium and Ballpark Village come to life with avid Cardinals fans rooting for that home team. If you are not attending the game, the sports energy in town is contagious.
Site of the 1904 World's Fair, 1300-acre Forest Park is really a one-stop cultural cache that includes museums, a zoo, a science center, a greenhouse, lakes and pedestrian paths – all free to access. There is no charge to tour the historic Anheuser-Busch Brewery grounds and admire the Budweiser Clydesdales either. After exploring, sample some classic fried ravioli at any of the old-school Italian restaurants around the Hill and order up some ice cream or frozen custard at Ted Drewe's.
Route 66 Heritage Project – Illinois
Get your kicks! Gearing up to celebrate its centennial in 2026, America's Mother Road accounts for 300 miles of scenic byway on its Central Illinois leg between St. Louis and Chicago, (running 2,400 all told out to California). Encounter Route 66 by crossing the Mississippi River at the Chain of Rocks Bridge and make a day of it heading northeast to take in the scenery through Litchfield, Springfield, Bloomington/Normal and Pontiac.
Commemorate the journey by snapping selfies against Americana-rich backdrops like the 30ft Gemini Giant at Wilmington's Launching Pad drive-in (temporarily closed), Paul Bunyon holding a warm dog in Atlanta and also the Joliet Correctional Center where Jake and Elwood served amount of time in the Blues Brothers. Hole up in a mom-and-pop motel if you need a break from the long day's driving, and keep your personal motor running having a pit pause and refuel at Dell Rhea's Chicken Basket in Willowbrook.
Chicago – Illinois
Route 66 ultimately deposits travelers in Chicago at the end of the street. A two-time World's Fair host, the Windy City delivers a winning combination of history, sports, food and culture, inviting visitors to hang in there and look for as long as they like.
Take your pick of Museum Campus attractions such as the Shedd Aquarium, the Adler Planetarium (temporairly closed to public) and the Field Museum, then venture north up Michigan Avenue towards the renowned Art Institute of Chicago. Hot tip: a CityPASS packages these and a couple other top attractions to save visitors 50% on premium admission prices overall.
After strolling through Millennium Park and taking a few photos in the Bean, have a spin on the Ferris wheel at Navy Pier and window-shop your way the Magnificent Mile. Chicago boasts a strong theater community with performing arts showcases, concerts and events happening every evening of the week, often with last-minute or day-of ticket discounts available.
You definitely won't lack for excellent eats, whether you opt to enjoy affordable local favorites like deep-dish pizza, Chicago-style hot dogs and global cuisine galore, or splurge on the high-end meal at among the city's finest dining establishments.
Milwaukee – Wisconsin
From Chicago, it's just a fast 90-minute journey north up I-94/I-41 to Milwaukee, an urban area that manages to stay humble while still impressing visitors using its style and substance. The Harley-Davidson Museum is a pilgrimage destination for legions of brand-loyal customers.
After a visit, learn by pointing out city's beer heritage with a tour of Miller Brewery or Sprecher Brewery. You will need something to eat, and wholesome dairy is what's on the menu (this is Wisconsin, after all), namely by means of cheese curds, butter burgers and frozen custard. Milwaukee's Public Market in the Third Ward offers a one-stop chance to sample everything under one roof.
When the weather's nice, the river and lakefront encourage locals and people to get outside and revel in water recreation. Meanwhile, the Milwaukee Art Museum (the Santiago Calatrava-designed “wings” that fan open and shut twice daily are a free show in as well as themselves), an established repertory theater and a rocking roster of summer festivals keep Milwaukee solidly rooted within the arts. At the end of the day, the historic (and haunted?) Pfister Hotel proposes stylish confines in which to rest your weary head.
Green Bay – Wisconsin
Keep on trucking up I-43 for around two hours and join “the Pack” in Green Bay, Wisconsin's oldest settled community where pro football reigns supreme. Don some green and yellow and visit Lambeau Field; saving money Bay Packers Hall of Fame, tours of the stadium and the Titletown entertainment district next door are available throughout the year.
Sports aren't the only attraction here, though – breathtaking hiking territory abounds with landscapes that show off dolomite cliffs, waterfalls and beachfronts. Made from hearty stock, Green Bay residents don't be put off by the long cold winters, opting instead to make the most of the season with roller skating, tubing, snowshoeing and cross-country skiing.
You can always thaw out in front associated with a from the local restaurants, cafes and brewpubs that feature cozy fireplaces. Or, belly up to and including local bar for a traditional traditional Friday-night Wisconsin fish fry.
Duluth – Minnesota
It's a five-hour jaunt across S.R. 29 to Chippewa Falls and then up US 53 over the Minnesota state line into Duluth. Across the idyllic banks of Lake Superior, the truly amazing outdoors are alive and well here, especially throughout the fall when the Northwoods foliage bursts into spectacular shades of burnished orange, red and gold. Settled through the Sioux and Chippewa tribes, the town now can serve as entrance towards the Northern coast Scenic Drive that runs 154 miles up to Grand Portage, just shy of the Canadian border.
The Aerial Lift Bridge is Duluth's crown-jewel landmark, raising and lowering nearly two dozen times every day to support the passage of ships and boats traveling into and from the harbor. The Canal Park district attracts visitors with charming local restaurants to frequent and also the Lakewalk to wander.
Gooseberry Falls State Park – Minnesota
From Duluth, follow the Northern coast Scenic Byway 40 miles northeast past glimpses from the lake, forests and rock formations to chill the journey at Gooseberry Falls, one of Minnesota's most stunning state parks.
Stretch your legs with a walk around the Falls View Loop to drink in the namesake Upper, Middle minimizing cascades. A slice of cherry crunch or French Silk at Betty's Pies in nearby Two Harbors makes the perfect sweet finale.
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