Top 10 Things to Do in Chicago: Hot Dogs, Tiki Bars, Tours & More

If you’re visiting Chicago

…and looking for the best of the best in food and fun, you’re in the right place. We make it our business to identify the most interesting and exciting nooks and crannies of cities while putting together our challenging and original scavenger hunts. And we love to share them!

Read on for 10 of the best things to do in Chicago, from historic sites to epic bites.

1. Grant Park: Far more than just the home of Millennium Park and its world-famous Bean, Chicago’s answer to Central Park is 319 acres of nature, culture, and adventure. Take a stroll, check out the skating ribbon, or scale the 19,000-square-foot rock wall. Admire yourself in the Cloud Gate sculpture (above), aka “The Bean.” Or catch a show at Pritzker Pavilion. Or stop into the Art Institute and goggle at the impressive new contemporary art galleries. Or visit the beautiful Buckingham Fountain. Or…well, you get the idea.

2. Museum Campus: You’ll find an awful lot of culture next door to Grant Park, too. Along the shores of Lake Michigan lie the Field Museum, most famous for Sue, the largest and most complete T-rex on earth; the Shedd Aquarium, whose relatively new Polar Play Zone lets kids touch starfish and visit a miniature submarine; and the Adler Planetarium, part space museum, part modern planetarium—one of the oldest in the world.

3. Architectural Tour: Arguably the best way to view—and appreciate—the Chicago skyline is via boat. Specifically, on a river cruise with Chicago’s First Lady. Plenty of companies here offer boat tours, but First Lady is the only one featuring tours lead by the Chicago Architecture Foundation. Or, if 90 minutes on a boat isn’t adventurous enough for you, consider an architectural tour…by kayak!

4. Old Town: As one of the few Chicago neighborhoods to survive the 1871 fire, this Victorian neighborhood keeps history alive—with an assist from its neighbor, Goose Island. See the gorgeous St. Michael’s Church and the architectural masterpiece that is the Chanley-Persky House Museum; catch a play at A Red Orchid or a movie at the ArcLight; or munch on some rich chocolatey goodness at the Fudge Pot.

5. The Second City: Speaking of Old Town, you can hardly swing a smartphone without hitting a Yelp review for one of the area’s various improv comedy theaters—but nothing beats the legendary Second City. It’s the place that brought us the likes of Stephen Colbert, Tina Fey, Amy Poehler, Bill Murray, and Dan Aykroyd, so you could be seeing the next comedy kingpin.

6. Wrigleyville: Even before the breaking of the century-long curse, Wrigley Field and the surrounding neighborhood was a must-visit for baseball fans. Catch a game and take in the mystique of a baseball stadium right in the middle of a neighborhood. And whether you’re a connoisseur of suds or not, give Old Style beer a try.

7. Murphy’s Bleachers: While it used to be a simple hot dog joint 80 years ago, Murphy’s Bleachers is now widely regarded as the best sports bar in the nation. This rags-to-riches dive bar has TVs everywhere and serves as the alternative to catching a game at Wrigley. Come hungry, because that lean half-pound burger isn’t going to eat itself.

8. Chicago-Style Hot Dogs: Now, if you’re in the mood for a classic Chicago hot dog or Italian beef, you get yourself to Portillo’s Hot Dogs, on Ontario a couple blocks west of Michigan Ave. This retro chain serves up the street food you crave, and the chocolate cake shake is famous in its own right. Or if you’re still over at Grant Park, grab a char dog to go at Gold Coast Dog.

9. Rick Bayless Restaurants: The celebrity chef’s empire of Mexican cuisine is a Chicago mainstay. His original restaurant, Frontera Grill, draws diners from around the world (and offers only limited reservations, fyi). And Topolobampo next door serves unforgettable Michelin-starred tasting menus. For a quicker, more affordable taste of the Bayless brand, his counter-service Xoco sits on the same block and doles out Mexican street food and tap beers.

10. Tiki Bars: Every town worth its salt rim has a bar scene, but for something a little different, Chicago’s tiki-bar scene is crushing it. Three Dots and a Dash stocks more than 200 rums and a bunch of flaming cocktails right around the corner from Frontera Grill, and Lost Lake in Logan Square wins points for its tiki-hut environs. New spots pop up regularly, including relative newcomer Flamingo Rum Club, with its Cuban vibe and immense rum selection.

Watson Adventure Scavenger HuntBonus Pick! Watson Adventures Scavenger Hunts: Solve a murder mystery, immerse yourself in the Wizarding world, or snack your way through Lincoln Park on one of the many Chicago team building scavenger hunts offered by Watson Adventures. On each hunt, teams search for answers to tricky, humorous questions while exploring a great location, from tours in museums—such as the Art Institute and the Field Museum—to hunts around town.

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