How to Spend a Weekend in Chicago

Hit the ground running and take in everything the Windy City has to offer.
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Sports, pizza, hot dogs and stunning architecture are just a few of the things that make up the great city of Chicago. 237 square miles and 77 neighborhoods leaves for a lot of ground to cover in just 48 hours—but we’re up to the task. So hop on the El train from the airport—it’s the easiest way to get into the city center, after all—and take the Windy City by storm.

Kick the weekend off with happy hour—Chicago is filled with good dives. “Rossi’s Bar and Liquors is one of Chicago’s true dive bars, and a great escape from the heart of River North,” says Kevin Beary, beverage director of the much-revered Three Dots and a Dash tiki bar on N. Clark Street. With it’s dim lighting, an electronic dart board and jukebox, Rossi’s has brought pure joy to dive bar-loving Chicagoans for over 50 years. “I’ll always head there after work to unwind and relax.”

Photo courtesy of John W. Iwanski/Flickr.
Photo courtesy of John W. Iwanski/Flickr.

For more upscale cocktailing, check out Grant Achatz’s Aviary for whimsical concoctions served in portholes, or Jim Meehan’s new Prairie School, recently opened on North Morgan Street. At Prairie School, Meehan shows inspiration from his days at PDT (Please Don’t Tell) in New York City on his cocktail list, as well as the organic architectural style from Frank Lloyd Wright; the Falling Water is made with coffee, plum brandy and cardoon-infused Amaro.

On Saturday, do as the locals do: grab a coffee and head to the farmer’s market. “I live very close to the Green City Market in Lincoln Park, so I like to go to check out the new produce and say hello to my many farmer friends who vend there,” says Lee Wolen, chef/partner of BOKA and recently-opened Somerset restaurants. Other Green City Markets can be found in the West Loop and the Park at Wrigley and are open seasonally from May through October. The indoor market at the Peggy Notebaert Nature Museum is open year-round.

No trip to Chicagoland is complete without a trip to historic Wrigley Field, home to the Chicago Cubs for over 100 years. (There may be no happier baseball fans than Cubs fans, regardless of whether or not the Cubs didn’t get a redeeming chance at the World Series title this year.) “My husband and I are huge Cubs fans,” says Stephanie Izard, chef/owner of Girl & The Goat, Little Goat, and Duck Duck Goat. “Our son, Ernie, is named after the late great Ernie Banks, and we jump at any chance to go to a game.”

Photo courtesy of Deirdre Hayes/Flickr.
Photo courtesy of Deirdre Hayes/Flickr.

When baseball isn’t in season, hit the indoors—there’s a reason approximately 2,000,000 people visit the impressive Shedd Aquarium. Situated on Chicago’s lakefront, Shedd is one of the largest aquariums in the world, and home to 32,000 animals with more than 1,500 species of fish, reptiles, amphibians, birds and mammals found in waters around the world.

With some 7,300 restaurants in Chicago, dinner spots are hard to pare down. Those looking for a slice should head to Piece Brewery & Pizzeria in Wicker Park. “It’s my favorite spot for pizza and beers in Chicago,” says Izard. “I always get their veggie pizza, but love when they have guest chef pies as well.” Izard herself has been a guest chef; her little goat pizza with goat chili, pickled peppers, cheddar, “goat spice” and sour cream was featured earlier this year.

Beary also likes to keep it casual: “Calumet Fisheries serves some of Chicago’s best seafood hands down,” he says. The South Chicago fish shack is known for smoking fish on-site. “Can’t miss items are the smoked salmon, smoked shrimp and fried scallops.”

The Windy City also has it’s fair share of high-end tasting menus. Curtis Duffy offers two seasonally-changing menus at his three-starred Grace, the vegetarian “Flora” and the omnivore “Fauna.” At Alinea, which has received three Michelin stars since the Chicago guide launched in 2011, Grant Achatz offers three tasting menus in The Salon, Gallery and Kitchen Table. Highlights are “sometimes experimental, and may include scented vapors, smoke and balloons,” state Michelin inspectors.

And no weekend getaway is complete without brunch. “My wife, son and I love going out for Sunday brunch and Lula Cafe has one of the best brunches in Chicago,” adds Wolen of the North Kedzie Blvd. eatery. Lula Cafe touts itself as a “boheme bistro of the unclassifiable kind,” serving sophisticated dishes like sweet corn and grits with cherry tomatoes, tropea onions, smoked pasilla oil, Parmesan and a slow-cooked egg, and “The Royale” shrimp po’boy with green tomato chow-chow, cabbage and fried shallots.

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