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The 6 Best Weekend Getaways From Chicago

By Staff in Arts & Entertainment on Jun 19, 2013 7:20PM

Summer in Chicago can be such a magical, yet fleeting, experience people don't want to leave town for fear of missing something. But there are nearby destinations reachable by plane, car, train and even light rail that are worth a visit and make perfect weekend getaways.

Here are our picks for the six best weekend getaways from Chicago. Break out the GPS and start booking rooms on AirBNB now.

The next time you're in Milwaukee, schedule a trip to the city's public market. (Photo via Milwaukee Public Market Facebook page.)

Jump on the Amtrak at Union Station and in one hour and twenty-nine minutes you'll find yourself in a sleepy, cheaper version of Chicago that's also cool in its right: Milwaukee. Lurk on Hotwire or and you can easily find a cheap hotel; I once got a room at the Hilton City Center for $51 a night, though I preferred the vintage charm of Hotel Metro (which has some nice package deals). What's there to do in Milwaukee? Among other things they have a slam bang art museum that makes for a perfect half-day excursion, a really solid used bookstore (Downtown Books), and a splendid riverwalk that has a lot more charm than Chicago's. It's an extremely walkable city. Foodwise, there's so much tasty grub around that you won't know what to do with yourself. The Milwaukee Public Market, Smyth at the Iron Horse Hotel, and (of course) the Wisconsin Cheese Mart are all great. But the real reason I love Milwaukee? They have two tiki bars (Foundation and Lucky Joe's Tiki Room) and they're both awesome. —Rob Christopher

Ann Arbor
Ann Arbor, home to the University of Michigan, Zingerman’s Deli, and a whole lot of beer, is about a four-hour drive from Chicago. Or, hop a quick flight to Detroit then rent a car and drive about 40 minutes. The city is ideal to tackle in a weekend—just make sure you’re wearing your drinking pants. Beer lovers can drink sours at Jolly Pumpkin CafĂ© and Brewery, try one of the many beers on draft at Arbor Brewing Company, or sip the seasonal beer at Grizzly Peak Brewing Company. Wine drinkers should head to Vinology, where glasses are half off Monday-Friday from 11 a.m. until 6 p.m. And spirit drinkers need to beeline for The Raven’s Club, which is turning out really excellent cocktails and snacks like deviled eggs, chicken liver butter with shallot marmalade, and a sandwich with medjool date jam, smoky peanut butter, and morbier cheese. The sandwich may sound familiar to fans of the CB&J—chef Frank Fejeran had a stint at the Hopleaf. Order anything with the spicy housemade ginger beer (like a Fernet shot with a ginger beer chaser) and thank me later. When you’re not drinking, you need to eat, so make a pilgrimage to Zingerman’s Deli for sandwiches, ice cream, and treats to bring back to Chicago; everyone swears the bread freezes really well. Another spot to eat is Frita Batidos, a bright, airy restaurant that sells Cuban street food like chorizo burgers and coconut milkshakes along with sangria and mojitos. And when you’re not eating or drinking, visit the University Art Museum, pick up a summer read at Literati, a brand new bookstore, or gallery hop downtown. —Amy Cavanaugh

No visit to New Glarus is complete without loading up the trunk of your car with beer from New Glarus Brewing. (Chuck Sudo/Chicagoist)

New Glarus, Wisconsin
There's nothing neutral about "America's Little Switzerland." It's only a two-hour drive from Chicago and teeming with antique stores, cheese and meat shops, wood-paneled taverns and—oh, yeah—a brewery very popular with beer geeks. But there's more to New Glarus than meat, cheese and beer. New Glarus Woods State Park offers 435 acres of the most scenic and beautiful wildlife in Wisconsin and is popular with campers. If you don't want to rough it, rent a room at any number of local bed and breakfasts. The New Glarus Chamber of Commerce has a list of festivals throughout the year like the upcoming Heidi Festival/Taste of New Glarus June 28-30. —Chuck Sudo

The Garage is Louisville's answer to Big Star. (Chuck Sudo/Chicagoist)

Whether you choose to drive five hours or fly one, there are many reasons to make a weekend trip to what news stations in Louisville call "Kentuckiana." The food and drink scene here is growing and more diverse than we anticipated, with popular restaurants like Harvest, Milkwood, Hillbilly Tea, The Blind Pig, Doc Crow's and Proof on Main all worth visiting. If Big Star had a killer charcuterie menu and focused on wood-fired pizzas, it would be The Garage. Bourbon still rules here, but a visit to Against the Grain Brewery and Restaurant should be on your agenda, as well as a trip over the Ohio River to New Albanian Brewing Company in New Albany, Indiana. Head to the Muhammad Ali Center for an in-depth, interactive look at the life and career of The Greatest of All Time. The 21c Museum Hotel is a combination contemporary art museum and boutique hotel. The museum displays some very provocative art exhibits. —Chuck Sudo

New Buffalo/Three Oaks, Michigan
The New Buffalo/Three Oaks area is becoming the place to go for any Chicagoan, especially those who love to eat. It's just a two-hour drive from Chicago and, once you arrive, there is enough good food to keep you occupied for at least a long weekend. Start in New Buffalo, where the bacon jam and local meats at P&G Mullins Local have gained a cult following. Stop at the local grocery store, which has a better beer selection than most specialty stores in Chicago, before heading off to Journeyman Distillery in Three Oaks for some whiskey and a great menu filled with bar snacks. Take a road trip to Greenbush Brewing, New Holland Brewery or Bell's Brewing, all within a short distance. It's such a popular destination that when Chicago's own Pleasant House Bakery opened their second location, they didn't pick a North Side neighborhood—they picked Three Oaks. —Anthony Todd

Pierogi Fest isn't the main reason to explore Northwest Indiana, but it's a good one. (Chuck Sudo/Chicagoist)

Northwest Indiana
For a great weekend getaway from Chicago, you don't even really need to get in a car. A CTA ride to the Millennium Park South Shore station is your gateway to fun weekend destinations right in Northwest Indiana.

You think I'm joking? Was Nelson Algren joking when he moved Simone de Beauvoir to his beach cottage in Gary, Indiana? Northwest Indiana has everything you need for a fun escape from Chicago, at half the price and none of the hassle of a road trip, whether it's walking the main drag in Miller Beach, hiking the Indiana Dunes, exploring the ruins of Gary, or having a drink at the Shoreline brewery in Michigan City (after a day at the outlet mall). All of these destinations are easily accessible with a South Shore ticket and two feet.

Feeling ambitious? Hop in a car for a ride down Kennedy Avenue in Hammond (take the North exit off of I-80/94) for a run of real dive bars, including the bar that was founded by Jean Shepherd's friend Flick (who would kick people out when they asked why he stuck his tongue on that flagpole in the first place). Have lunch at Schoop's, Zel's, Aurelio's or Freddie's Steak House for a taste of local cuisine and true NWI atmosphere. And if you can time your visit right, you can even gorge yourself at Pierogi Fest in Whiting (which has much more to offer year-round besides a classic Midwestern ethnic street fest). —Kevin Robinson