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The 6 Best Train Trips To Take From Chicago

By Staff in Arts & Entertainment on Oct 9, 2015 4:00PM

The Midwest loves its trains, and as the autumn leaves change colors, this might be the most beautiful time of year to take a weekend getaway by train. Take in the countryside views of Illinois, Michigan, Wisconsin and beyond from a cushioned seat aboard one of these trains bound for some of our favorite cities outside of Chicago. Here are our favorite train trips to take from Chicago—and if your favorite getaway isn't here, let us know in the comments.

Milwaukee: In under two hours on the Amtrak, Chicagoans will find themselves at the train station in the heart of downtown Milwaukee to begin either an eclectic day trip or a weekend getaway to check out the many gems the city has to offer. From bars and great food, to art, bookstores and the river walk, visitors from the Second City will experience a getaway with an cosmopolitan feel while enjoying the city's quintessential Midwestern personality.

Highlights include the Milwaukee Art Museum and the Betty Brinn Children's Museum for excellent exhibits, Woodland Pattern Book Center for readings and a decidedly unique book shop, especially for poetry lovers. For food and drink, the classic German tavern, Von Trier's and the cozy bar with a hipster edge, Hotel Foster will satisfy if you find yourself on the East Side.

While downtown, must-do highlights include the Newsroom bar for great cocktails and beer in a classic, noir pub with a journalism theme. As a bonus, it is located next to Safe-House, just another extension of this best-kept secret gem.

Grab some well above average pub food at Swinging Door Saloon, a place that also has an engaging and casual "locals" energy to it with a friendly staff within a classic space. With every part of the city offering a diverse array of places to see and things to do, it is ideal for a weekend trip so many of its nooks can be fully explored.
—Carrie McGath

Kalamazoo: Just over two hours away from Chicago on the Amtrak, writers and artists as well as beer lovers and foodies will be equally content in this charming and bohemian Southwest Michigan city. Do your own brewery hop or schedule one with West Michigan Beer Tours since Kalamazoo is home to over a dozen microbreweries both downtown and in the surrounding area.

For fine art, be sure to go to the Kalamazoo Institute of Arts to see a solid and significant permanent collection as well as compelling exhibitions. Also a literary hub that only continues to grow, see all manner of events from readings, to poetry slams and other spoken word performances. The presence of Kazoo Books and the Michigan News Agency just adds to the writer-friendly oasis Kalamazoo is at its core.

For foodies, Food Dance and Rustica are absolute musts. Off the beaten path is Rupert's Brew House a laid-back brewery with free shows, great beer (and housemaid rum!) and a pub dog, Captain Stooby, the brewery's 200 lb. Great Dane. O'Duffy's in the Vine Neighborhood is an authentic, friendly and cozy Irish pub with excellent pub fare and great rotating taps. For the "local watering hole," The Green Top Tavern is not to be missed as the bar with a mixture of beer tourists, hipsters and all other manner of longtime natives of the city.
—Carrie McGath

If you've only got a little bit of travel time, hope the Metra and get off at the Libertyville stop one weekend. It's a little over an hour of train time, and the train station is a short walk from fantastic places to eat, drink and shop. For finer dining, head to Tavern, or the newest sushi place in the area gaining great accolades, Shakou. If bar food is more your speed, check out Mickey Finn's, a newly relocated brew-pub that's long been a Libertyville favorite, both for its craft beers and its food.

Shopping includes everything from boutique home design stores to specialty shoe shops and Savory Spice shop, a gourmet spice purveyor on par with Evanston's Spice House. You can even catch a movie on the cheap at the old school Liberty Theatre.

Finally, if you could only spend time or money in one place, we recommend that it be Firkin. With amazing, creative entrees, a full bar of fantastic beers and wines, and an incredibly knowledgeable and friendly waitstaff, this tiny treasure will not disappoint.
—Marielle Shaw

New Buffalo: Easily accessible via the Amtrak or the South Shore, this quaint resort town is especially a must-visit in the summer months, but is equally beautiful in the fall. Boasting a captivating lakeshore and pleasant beaches, it is a wonderful place to decompress and refuel from life in the big city. Also home to Oink's, once visited by Vice President, Joe Biden, is a wacky and wondrous spot to indulge in the joy of ice cream with huge selection of flavors.

For dining overlooking Lake Michigan, right near the beach, enjoy The Stray Dog pub and restaurant and Jimmy's bar for that local bar feel and an excellent New American menu and a rooftop patio. And of course, you can always try your luck at Four Winds Casino and free shuttles are available to get you there and back.
—Carrie McGath

If there’s a place to slowdown and not be bothered by human drama, it’s on wheels of steel headed toward Memphis, Tennessee. On this ten-and-a-half hour train ride, let the city fade away and immerse yourself in a book, music or the scenery out your window as you slice through the cornfields of southern Illinois and ultimately the countryside of the upper south. Remember to pack some Soul with you too—you’re riding into Memphis, the home of Stax Records! For those who don’t know the label, they introduced the world to Soul greats such as Otis Redding and Isaac Hayes.
—Ben Kramer

via Meijer Gardens

Grand Rapids, Michigan
Here is a city that has culture, great food and lively nightlife. From the Urban Institute for Contemporary Arts with cutting-edge exhibitions and film viewings, to Meijer Gardens for public artworks among a beautiful and sprawling park, the opportunity for fine art culture is diverse and appealing.

Stella's burger and whiskey bar has what GQ called the best burger in America in 2012 with the added asset of arcade games, pinball and a great bar in a fun atmosphere. Across the street, continue your pinball game at Pyramid Scheme and stay later for a show, with events almost nightly in a hipster-punk atmosphere. Vault of Midnight is a must-do for comic book lovers, and it is worth crossing the street for a superbly crafted coffee at Madcap.
—Carrie McGath