The best Amtrak train trips from Chicago

Illinois Service Line 
Train time from Chicago: 4 hours and 45 minutes

The Gateway City is best known for the 630-foot arch towering over downtown (it’s worth visiting the historic landmark for a great aerial view of the city), but venture to neighborhoods like Central West End, Lafayette Square and Maplewood for art, Victorian architecture and locally-owned shops and restaurants.

Say cheers to St. Louis’s brewing past with a tour of the Anheuser-Busch flagship brewery, an ornate 1850s-era facility housing over 30 of the company’s brands. Afterwards, head to one of the nearly 65 crafts breweries St. Louis boasts—start with Earthbound, Schlafly and 4 Hands Brewing Co. Before hopping back on the train, fill up at nearby Levels, a Nigerian-inspired restaurant aiming to bring the spirit—and delicious food—of Lagos to the Midwest.

Cardinal Line 
Train time from Chicago: 10 hours and 49 minutes 

A two-state riverfront, historic German pork and beer manufacturing neighborhood and—if you time it right—a kitschy pig-themed road race are only an Amtrak away in Ohio’s third largest city. Head to the aptly named Over-the-Rhine district, where a world of 19th century European architecture, the Cincinnati Symphony Orchestra, meat and cheese markets, breweries, and Cincy’s favorite scoops, Graeter’s, await. Finish off the historic charm admiring the over 80,000 volumes at downtown’s Mercantile Library, an impressive, brightly-lit space with a good sense of humor—especially when it comes to the terms of its 10,000-year lease.

Cardinal Line 
Train time from Chicago: 4 hours and 54 minutes 

With the perks of a big city and the friendly and affordable atmosphere of a small town, it’s easy to feel at home in Indiana’s capital. Olympic-sized swimming pools were recently constructed inside Lucas Oil Stadium to house competitors just weeks before the Paris Olympics—a first for an NFL stadium and an expected record for the largest swim meet ever. Whether you visit to cheer on the swimmers or the Colts, savor brunch carbonara and a croissant at Gallery Bistro & Bar under a wall-sized Anthony Bourdain painting (the late chef visited Indy in 2010) and head across the street to snap your photo with a one of the many NDY sculptures.

Southwest Chief Line 
Train time from Chicago: 12 hours and 30 minutes 

Though forming distinct identities throughout its history, both sides of this city—often differentiated as either KCK or KCMO—captivate visitors with delightful recreation, thrilling sports and unexpected arts and culture, like boasting the most public fountains of any city in the world. After your train ride, stretch your legs on a walking tour with Urban Hikes KC (you’re bound to run into a fountain or two), offered in English or Spanish. Keep moving—and fill up—on the Missouri side at Chicken N Pickle, an indoor/outdoor recreation complex and restaurant with pickleball courts. Don’t miss the chance to catch a Kansas City Current game at the 11,500-seat CPKC Stadium, the first ever to be purpose-built for a professional women’s sports team.

Illinois Service Line 
Train time from Chicago: 5 hours and 30 minutes

What could be more perfect for a city esacpe than wine and the outdoors? Just outside the home of Southern Illinois University, you’ll find over 40 miles of vineyards and some of the best hiking in Illinois. Between the eleven wineries comprising the Shawnee Hills Wine Trail (tasting ranges from $1-$12 depending on the pour) and the endless private and public camping, trailer and RV sites in and around Shawnee National Forest, the Carbondale region provides a welcome escape from the city bustle. There are plenty of shuttle services between wineries, including affordable commutes in five Southern Illinois counties through Shawnee MTD Public Transportation.

Capitol Limited Line
Train time from Chicago: 7 hours and 8 minutes 

Along the shores of Lake Erie, Cleveland—”The Land” as it's known—is bursting with charm, proving it’s far from its ill-fitting reputation as another piece of the rundown Rust Belt. The city of neighborhoods has farm-to-table restaurants, cafes, bookstores and a diverse population ready to set the record straight. In Ohio City, stroll the cocktail bar-lined streets and take home a souvenir, and maybe even the scent of the city with a candle making class at Cleveland Candle Co. Explore the other areas of the city as you learn about Black history in Cleveland on a self-guided mural tour and even book an overnight stay at the house where A Christmas Story was filmed—holiday season or not.

Hiawatha Line
Train time from Chicago: 1 hour and 29 minutes

Chicago’s northern neighbor is an easily accesible getaway no matter the season, but head to the Cream City in the summer for an unbelievable array of water recreation and relaxation, international festivals and live music every night as the sun goes down. Delight in the painstakingly friendly atmopshere, whether you kayak between some of the city’s best breweries, jam out at weekly Chill on the Hill concerts or celebrate Black culture and heritage on Juneteenth.

Borealis Line 
Train time from Chicago: 7 hours and 24 minutes 

Set your sights on urban nature and Native American heritage when your train crosses the Mississippi into the Twin Cities. In fact, with 180 parks in Minneapolis, six blocks is the furthest you’ll have to walk to find one. Take in the flowing waters of the 53-foot waterfall at Minnehaha Regional Park or wind a kayak through the 22 miles of Minnehaha Creek, between the park and Lake Minnetonka. Before heading back to Chicago, graze on crickets with popcorn and elk tacos at James Beard Award winner Owamni, a one-of-a-kind indigenous restaurant using decolonized ingredients.