People who’ve never really considered a visit to “Flyover Country” usually find themselves pleasantly surprised — and sometimes even downright shocked — by just how much there is to see, do and experience in the great American Midwest, often for free.
Defined by wide-open swathes of farmland, friendly small towns and attractive urban cities (not to mention the bonus of much lower prices for gas and lodging than you’d expect to pay on the coasts), this down-to-earth territory holds all the makings of a memorable road trip.
St. Louis, Missouri
With affordable attractions, tasty food and river city culture, St. Louis makes a great starting point 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 in town, or catch a ride to cruise the mighty Mississippi on a paddlewheel-powered riverboat (snagging an America the Beautiful Pass will save you a few bucks on ticket prices). During baseball season, Busch Stadium and Ballpark Village come alive with avid Cardinals fans rooting for the home team. Even if you’re not attending the game, the sports energy in town is contagious.
Site of the 1904 World’s Fair, 1300-acre Forest Park is a one-stop cultural cache that includes museums, a zoo, a science center, a greenhouse, lakes and pedestrian paths — all free to access. There’s 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 on 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). Meet up with 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, Paul Bunyon holding a hot dog in Atlanta and the Joliet Correctional Center where Jake and Elwood served time in the Blues Brothers. Hole up in a mom-and-pop motel if you need a break from the long day of driving, and keep your own motor running with a pit stop to refuel at Dell Rhea’s Chicken Basket in Willowbrook.
Chicago, IL
Route 66 ultimately deposits travelers in Chicago at the end of the road. A two-time World’s Fair host, the Windy City delivers a winning combination of history, sports, food and culture, inviting visitors to stick around and explore for as long as they like. Take your pick of Museum Campus attractions like the Shedd Aquarium, Adler Planetarium and the Field Museum, then venture north up Michigan Avenue to the renowned Art Institute of Chicago.
After strolling through Millennium Park and taking a few photos at the Bean, take a spin on the Ferris wheel at Navy Pier and window-shop your way up the Magnificent Mile. Chicago boasts a strong theater community with performing arts showcases, concerts and events happening every night of the week, often with last-minute or day-of ticket discounts available. You definitely won’t lack for great eats, whether you opt to indulge in affordable local favorites like deep-dish pizza, Chicago-style hot dogs and global cuisine galore, or splurge on a high-end meal at one of the city’s finest dining establishments.
F-Local 