The Guide To Your First Trip to Chicago, IL

If you’re visiting Chicago for the first time, you’re in for a treat. With so many amazing sites to see, restaurants to eat at, and attractions to check out, you’ll have a blast exploring the city. Read on to discover six popular things to do during your first-time visit to Chicago so you can make the most of your trip.

Walk Around Navy Pier

first trip to chicago il
Photo by rigel on Unsplash

With so much to see and do, you could spend an entire day at Navy Pier. This family-friendly destination has everything from scenic boat rides and outdoor music to carnival rides and indoor gardens. Of course, you’ll instantly recognize the Centennial Wheel. The inspiration for the Centennial Wheel comes from the very first Ferris wheel, which made its big debut at Chicago’s World Fair. Step into one of the ride’s climate-controlled gondolas to soar nearly 200 feet in the air.

If you’re planning to spend a few days in Chicago this summer, we suggest checking out Navy Pier on a Wednesday or Saturday to enjoy one of the incredible, free firework displays. You can even get tickets for one of the cruise boats to watch the fireworks from the water for a truly magical experience.

Explore Millennium Park

From unique art and live music to amazing restaurants and outdoor festivals, Millennium Park has something to offer everyone. In the summer, you can splash around Crown Fountain, wander through Lurie Garden, grab lunch at Park Grill in the McCormick Tribune Plaza, and watch a movie under the stars in the Jay Pritzker Pavilion. If you have children, take them to Maggie Daley Park to frolic around the playground, enjoy a round of mini-golf, or attempt the lakefront climbing wall.

During the winter, enjoy ice skating around the plaza, warm up with a tour of the Chicago Cultural Center, and then peruse the Art Institute of Chicago. There’s plenty to do at Millennium Park any time of the year. Just make sure you take a photo with Chicago’s famous art installation, Cloud Gate, before you leave. Also known as The Bean, this reflective sculpture is a must-see for anyone visiting the windy city for the first time.

Get a 360-degree View of the City

Experience Chicago in a whole new way by taking in a 360° view of this gorgeous city from one of two observation decks in the area. Formerly known as Sears Tower, the Skydeck at Willis Tower allows visitors to see the city from 1,353 feet in the air. Step into a glass box, known as The Ledge, that hangs more than four feet off the side of the Skydeck to really get your adrenaline pumping.

For an alternate view, head over to Michigan Avenue and make your way up TILT at the 360 CHICAGO Observation Deck. This unique ride tips you over The Magnificent Mile from 1,030 feet in the air so you can get a thrilling, downward-facing view of the city and Lake Michigan.

Relax Along the Chicago Riverwalk

If you’d rather relax during your first visit to the windy city, head over to the Chicago Riverwalk to sip a glass of wine on the patio or go for a cruise with your friends on a tiki party boat. Cast a line in the water to fish along the pier or spend some time on the water laying through the Riverwalk’s skyscraper canyon.

If you enjoy art, take a stroll down the Chicago Riverwalk to view all of the sculptures, murals, and banners on public display. Stick around in the evening to check out the world’s biggest video-projected artwork. Presented in partnership with the Shedd Aquarium, Art on theMART features nightly shows from 8:30 p.m. to 9 p.m. every evening.

Enjoy a Broadway Show in Chicago

For something fun to do indoors, get tickets for an amazing theater performance from Broadway In Chicago. Choose a show at one of five historic venues in the downtown theater district, including the Cadillac Palace Theatre, the James M. Nederlander Theatre, the CIBC Theatre, the Auditorium Theatre, and the Broadway Playhouse at Water Tower Place. You’ll find amazing prices on productions that come directly from Broadway and see world premieres of productions that are sure to be big Broadway hits soon.

For a truly luxurious night out, treat yourself to suite service when you buy your tickets online. With room for up to 50 guests, suite service gets you a full private bar, light snacks, private restroom facilities, and upgraded menu options. You’ll even get access to the suite 45 minutes before the show starts so you can settle in and get comfortable.

Grab a Bite To Eat in the West Loop

To see a different side of the city, check out the hip and industrial West Loop neighborhood. Known for its popular nightlife attractions and exquisite dining options, you’ll find a ton of unique things to do in this area. If you need a little pick-me-up, we suggest stopping by Sawada Coffee for handcrafted cortado and one of the famous Doughnut Vault donuts. Explore the West Loop’s rich history and diverse cultural traditions by taking a walk around the neighborhood.

Then, pop into the restaurant Cira to order a few small plates featuring fresh, coastal ingredients for lunch. We love the culatello toast, which comes topped with red wine fig preserves, lemon mascarpone, and basil. For dinner, visit the Girl and The Goat on restaurant row to indulge in dishes that feature global flavors and local ingredients. You’ll find many unique items on the menu, like goat empanadas with smoked blueberries, pippara, and idiazabal cheese. Make sure you try the crunchy nutty toasty choco mousse, which features hazelnut praline, toasted meringue, balsamic ganache, and a chocolate crumble.

Our team at Gurnee Podiatry & Sports Medicine Associates hopes you enjoyed our list of six popular things to do during your first-time visit to Chicago. We’d love to hear which restaurants, sites, and attractions were your favorite after your trip. Drop us a line to tell us all about your experience and let us know if there are any additional things we should add to our list so our readers can explore everything Chicago has to offer.