8 Quintessential Chicago Experiences for Every First-Time Visitor

05 June 2016

Chicago offers the kind of attractions you would expect in a big city: historic architecture and museums, ample shopping neighborhoods, a busy nightlife scene, brilliant green spaces and a breathtaking water front. If you're visiting the Windy City for the first time, follow this list to take part in the most quintessential experiences my home base has to offer.

8 Quintessential Chicago Experiences for Every First-Time Visitor | Brave Little Cheesehead

1 | Wander through Millennium Park
Millennium Park stretches nearly 25 miles within the Loop along Lake Michigan. Here you'll find The Cloud Gate, the city's iconic giant, silver bean-shaped sculpture offering pristine reflections of the city's skyscrapers. It's the perfect opportunity for an obligatory bean selfie. In the summer months, you might even catch a free open-air concert or movie showing at the Jay Pritzker Pavillion. Take a cue from the locals and spread out on the lawn over blankets, sharing bottles of wine and all sorts of munchies.

8 Quintessential Chicago Experiences for Every First-Time Visitor | Brave Little Cheesehead

2 | Shop the Magnificent Mile
Stretching from the Chicago River to Oak Street, Chicago's Michigan Avenue offers approximately 12 blocks of some of the world's most well-known department stores like Neiman Marcus, Saks Fifth Avenue and Bloomingdale's. And when you're ready to rest your tootsies, head to the John Hancock building and take the elevator up to the top floor where you'll find The Signature Room, a restaurant and lounge with an observation deck. It's great place to grab a cocktail (ranging from about $12-$20) and admire some of the best views of the city skyline, and surprisingly enough, the ladies bathroom boasts a stellar view, too. If shopping is your thing, be sure to make time for a jaunt to some of Chicago's other best spots.

8 Quintessential Chicago Experiences for Every First-Time Visitor | Brave Little Cheesehead

3 | Pick Your Preference at Museum Campus
Located in the South Loop area, Chicago's best museums, including the Field Museum, the Adler Planetarium and the Shedd Aquarium are all nestle together just beside Soldier Field, home of the Chicago Bears. Any of these are a good choice for families, but my personal preference is the Adler Planetarium because of the Grainger Sky Theater, an orb-shaped room with celestial objects like stars and planets projected across the curved walls and ceilings. If you have a longer stay planned, you can get admission to all museums with a Chicago City Pass.  

4 | Take a History Lesson Along the Chicago River
Even as a local, the Chicago Architectural Boat Tour is a highlight. Chicago is legendary for its architecture, and what better way to experience it than on a relaxing cruise down the river. Tickets are a bit steep at $44 for a 90-minute ride, but it's well worth it.

5 | Stand Above the Skyline at the Willis Tower
Though localsmyself includedwill still refer to this famous building as the Sears Tower, it remains one of the city's top attractions. The observation deck on the 103rd floor is called the Skydeck, featuring ceiling to floor windows and one of the city's newest attractions, The Ledgeglass boxes that extend out from the building, offering some of the most remarkable views of the city.

8 Quintessential Chicago Experiences for Every First-Time Visitor | Brave Little Cheesehead

6 | Stroll along Lakefront Path
Along Lake Michigan, you'll find the Lakefront Path, a lovely biking, jogging, rollerblading or walking path that stretches from the downtown area all the way to the northern suburbs. Rent a bike from a self-serve kiosk or just walk along the paved path past plenty of parks and your fill of beaches. And don't forget to stop and look back over your shoulder every once and a while for stunning lakefront views of the city.

8 Quintessential Chicago Experiences for Every First-Time Visitor | Brave Little Cheesehead

7 | Catch a Game at Wrigley Field
About a 25-minute ride north on the elevated "el" train and just off the Addison Red Line stop, you'll find Wrigleyville, a neighborhood named for the baseball park that resides at its center. This area of the city looks like it eats, sleeps and breathes baseball, full of pizza joints, burger spots and bars called Sluggers and Murphey's Bleachers. During baseball season, the streets will be blocked off and full of Cubs fans, heading to catch the day's game. Grab a baseball cap and scalp some tickets in the neighborhood to enjoy one of the most charmingly nostalgic ballparks in the nation. And what a perfect time to try a Chicago-style hot dog! Just don't put ketchup on it. If Wrigley is high on your list, make sure you visit soon, as the park is currently under renovation, and its eclectic vibe may start to fade.

8 Quintessential Chicago Experiences for Every First-Time Visitor | Brave Little Cheesehead

8 | Have a Laugh at Second City
The city has a vast comedy culture, and Chicago's The Second City is the most famous comedy theaters by far, with famous alumni like John Belushi, Steve Carrell, Stephen Colbert, Chris Farley and Tina Fey, to name a few. Still a favorite among locals, check the calendar to see what's playing and reserve tickets in advance so you don't miss out! 

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