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Stay at the Old Chicago Inn Bed and Breakfast, which includes a room decked out in all-Cubs décor. oldchicagoinn.com
Snooze old-school at the Flemish House of Chicago Bed and Breakfast, built in a converted 1892 row house. innchicago.com
Sleep in after a late night at the Hotel Sax, next to the House of Blues and near a hip bowling alley and bar with the apt name of 10pin. hotelsaxchicago.com
Wake up at the Sutton Place Hotel, right across the street from Chicago’s best apple pancake at the Original Pancake House. chicago.suttonplace.com
Watch a baseball game with a Cubby Blue Bomb in hand at the Cubby Bear, directly across from Wrigley Field. cubbybear.com
Fill up on mussels at the Gage. thegagechicago.com
Sip a gourmet cocktail—try the gin-fueled Juliet and Romeo—at the Violet Hour. theviolethour.com
Chomp down on a genuine Chicago dog at Hot Doug’s. Or browse the menu for other items served on a bun, like bratwurst, Thuringer, andouille, Polish, and Italian sausages. The restaurant’s specials can include such gems as the foie gras dog. hotdougs.com
Indulge in the multilayered sea of cheese and sauce that makes up the gut-busting Chicago-style pizza at Giordano’s. giordanos.com
Sample the homemade hot fudge sundae served in all its old-fashioned, cherry-on-top glory at the kitschy Margie’s Candies. margiescandies.nv.switchboard.com
Cultural Attractions: Chicago
Chicago’s architectural treasures include office towers by Daniel Burnham and Prairie School houses by Frank Lloyd Wright. But the city’s real diamond is the home of its beloved Cubs, Wrigley Field. cubs.mlb.com
When train car magnate George Pullman dreamed up what is now called the Pullman Historic District in the late 1800s, he set out to create an ultra-modern factory town south of Chicago. He succeeded, and the Prague International Hygienic and Pharmaceutical Exposition of 1896 named the district the world’s most perfect town. Remnants of this historic marvel still exist today. Stroll past the redbrick houses of Arcade Row, where employees rented homes from the company. Some of the forward-thinking amenities here included gaslights, indoor plumbing, and daily trash pickup. Across Arcade Park lies the Hotel Florence—you might recognize its Victorian facade from the movie Road to Perdition—once the location of the only bar in town. pullmanil.org
Pay your respects to notables like Marshall Field and architect Mies van der Rohe at the Graceland Cemetery. gracelandcemetery.org
The Green Mill looks like the jazz club that time forgot. Against one wall, an old jukebox spins warped records, and the well-worn cash registers—the newer one hails from the ’40s—add to the aged ambiance. Al Capone once favored a central booth, the better to see the front and the back of the club. A trapdoor behind the bar leads to tunnels below the building, handy for a quick exit. Today, owner Dave Jemilo keeps the cover price between $6 and $12, ensuring a diverse crowd that ranges from long-time locals to Hollywood A-listers like Johnny Depp and Marion Cotillard. greenmilljazz.com
Fun Stuff: Chicago
Catch improv comedy shows at iO, just a few doors down from Wrigley. chicago.ioimprov.com
Imagine the city is your oyster at the John Hancock Observatory, where the 94th-story Skywalk viewing deck stays open until 11 p.m. hancock-observatory.com
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