Tips To Eat, Drink, & Experience Chicago Like a Local

From stunning architecture to drool-inducing famous Chicago foods, this city should be on everyone’s list of places to visit in the United States.

There are plenty of touristy things to do in Chicago, but many of us like to forgo the touristy spots and experience cities like a local. I've asked travel blogger Valentina to share her insider tips about how to experience Chicago the way the locals do! Whether you’ve visited Chicago a thousand times or are visiting for the first time, you'll find some truly helpful, genuinely local tips here.

Over to you, Valentina!

Navy Pier

Most know of Navy Pier as one of the most popular of all Chicago attractions. Navy Pier is home to Chicago’s famous Centennial Ferris Wheel, the Chicago Children’s Museum, the Shakespeare Theater, and the impressive Crystal Gardens. While this sounds like a lot of family-friendly fun, Navy Pier has so much more to offer!

Among these attractions, however, the most popular tourist activity at Navy Pier is riding the Centennial Wheel. One reason is that from the top of the Centennial Wheel, you’ll get beautiful views of Chicago’s skyline.

Local’s Secrets for Navy Pier

But what if you don’t want to pay the big bucks to ride around in a few slow circles? I have the perfect alternative for you: Make your way to the top floor of Navy Pier’s parking garage for equally impressive—yet completely free—views!

The parking garage can be accessed from inside Navy Pier. It’s at the furthest east end of the structure, and you’ll know you’re on the right floor when you exit the elevators and find yourself outside.

In addition to providing a top-notch Instagram-worthy experience, Navy Pier is one of Chicago’s great cultural hubs. Year round, you’ll find free or paid events, activities, and expos. This is how locals experience Navy Pier!

Every year, Navy Pier hosts EXPO Chicago, a massive international contemporary art exhibition. Navy Pier is also home to Chicago’s branch of the Great American Lobster Fest.

In the fall, you can see movies from the International Film Festival at Navy Pier’s movie theatre. Every weekend during the warmer months there’s a host of different free concerts, dance performances, and other events at Chicago’s Navy Pier.

During summer, the pier has firework shows every Wednesday and Saturday, and the Navy Pier Beer Garden is a great place to catch the show.

So, check the events calendar and experience Chicago’s Navy Pier like a local!

The Lakefront

Chicago’s lakefront is a favorite meeting place of locals. Chicagoans flock to the lakefront to bask in the sun, exercise, and even party!

North Avenue Beach is where you’ll find high energy, dance music, and a younger crowd. It’s illegal to bring alcoholic beverages to Chicago beaches, but you’ll find all the drinks you need at North Avenue Beach’s Castaways Bar.

In addition, there’s a new and exciting pop-up bar on North Avenue Beach: Shore Club. Shore Club is a cute, coastal lounge on the beach between North Avenue and Fullerton Avenue.

In Chicago’s ritzy Gold Coast neighborhood, you’ll find Oak Street Beach. It offers a more mature, relaxed vibe than the norm at North Avenue Beach.

Experience Chicago’s Lakefront Like a Local

The best way to experience the Chicago lakefront like a local is to join in the action. Weather permitting, the lakefront trail is busy and just the right amount of overwhelming and fun!

You can run, walk, rollerblade, bike, or whatever else it is that you do. The action is especially intense between Oak Street and North Avenue Beach. This is also the best area to catch cool views of Chicago’s skyline.

For tourists, I recommend renting Divvy Bikes, and casually riding the lakefront trail. If you’re athletically inclined and looking for a challenge, you can ride all the way south to Chicago’s Museum Campus.

In exchange for burning those additional calories, you’ll gain access to the Field Museum of Natural History, the Adler Planetarium, and the Shedd Aquarium. You’ll even get more great skyline views!

Festivals and street markets

Chicago has unique festivals and street markets throughout the year, but particularly during the summer. The most famous festivals in Chicago are Taste of Chicago and Lollapalooza.

Taste of Chicago brings together the best flavors and dishes from local restaurants. Lollapalooza is Chicago’s famous music festival that never fails to deliver an impressive lineup.

Local Festivals and Markets

Aside from these big events, Chicagoans also love other local festivals and markets. Favorites include the yearly Lincoln Park Wine festival, the Old Town Art Fair, and West Fest (in the West Loop). While you may not be able to sync up your visit to Chicago with a specific festival, you should at least check out which festivals and events are going on during the time of your visit. You’ll certainly find something worth exploring!

One final note about a recurring Chicago street market: The Maxwell Street Market is held every Sunday year-round. While the market is primarily a flea market, it’s also the best place to find authentic and delicious homemade Mexican food in Chicago.

Millennium Park

The most touristy Millennium Park attractions are the Bean and Crown Fountain. The Bean is the unofficial name for Cloud Gate, the enormous bean-shaped outdoor sculpture. Crown Fountain is a set of two 50-foot LED towers joined by a reflecting pool.

While these attractions are certainly worth a visit, locals know that there’s so much more to Millennium Park.

Local Tips for Millennium Park

In the winter months, Millennium Park is a scenic place to ice skate. In the summer, the city organizes many free events. For instance, you can take workout classes, watch movies, and listen to free concerts in Millennium Park. So, be sure to check out what events are going on during your visit.

Photo tip: Make your way to the BP Pedestrian Bridge (the bridge that links Millennium Park to Maggie Daley Park). Towards the east end of this bridge, the city opens up, and you’ll have fantastic photo opportunities!

The Magnificent Mile and Chicago Riverwalk

The south section of the DuSable Bridge is a great place to access the Chicago Riverwalk. You should start your walk near the 900 N Michigan Avenue shops. Enjoy the famous Magnificent Mile of North Michigan Avenue as you walk south towards the DuSable Bridge.

This is where Chicagoans shop! All the best stores are on Michigan Avenue. From favorites like TopShop to high-end jewelers like Tiffany & Co, it’s all on Michigan Avenue.

Local Experiences on Magnificent Mile & Chicago Riverwalk

When you reach the DuSable Bridge, make sure to snap a few pics of the view. You’ll see fantastic vistas of the skyscrapers that frame the Chicago River. At the southern end of the bridge, take the stairs down to the Riverwalk.

If you choose to continue your journey west, you’ll hit the always-busy City Winery. This is a great place to experience Chicago and relax outside with friends while enjoying a fancy drink or two.

If you head east from the bridge, you’ll happen upon the Island Party Hut. The Island Party Hut is a more relaxed place to grab beers, play cornhole, or rent a pontoon boat.

If you continue east, past Island Party Hut, you’ll hit the lakefront just south of Navy Pier.

Hottest restaurants in Chicago

Yes, Chicagoans love their deep dish pizza, but I promise you there are even cooler places to dine than Giordano’s and plenty of great restaurants that are perfect for a romantic Chicago date.

Of course, if you don’t mind being a little touristy, Chicago food tours are a great way to learn all about the local eats.

Local Restaurants in Chicago

Chicagoans have been obsessed with a few particular restaurants for a long time now. Among these is Girl & the Goat in Fulton Market. Since opening in 2010, this hot spot has been packing them in! You’ll need to book a table here weeks to months in advance of your visit.

Girl & the Goat offers a family style menu of global influence. It's operated by the extremely influential Boka restaurant group, which also brought us Duck Duck Goat and Little Goat. Duck Duck Goat focuses on Chinese cuisine, while Little Goat is more casual.

Another Chicago restaurant that everyone is obsessed with is Aba. A trendy Mediterranean spot with a stunning outdoor garden terrace, Aba is owned by the Lettuce Entertain You group, a big restaurant conglomerate in Chicago. They’re also famous for bringing us RPM Steak and RPM Italian (two more upscale dining favorites). Make your reservations far in advance for any of these eateries.

One final favorite that I'll mention is Gilt Bar. Gilt Bar serves decadent American favorites in a romantic yet non-fussy setting. You must try their orecchiette dish.

On the weekends, ask to be seated in the Library. Downstairs at Gilt Bar, you’ll find a photo booth. Take advantage of it! You’ll look back on those photos and fondly remember your dining experience in Chicago.

Chicago rooftop bar scene

With such a stunning skyline, you can’t blame Chicagoans for loving their rooftop bars. The rooftop scene is as hot as the summers! Skip the crowds and long lines at the Signature Room, and instead go where the locals go.

Hidden Gem Rooftop Bars

The most low-key rooftop bars include NoMI Garden and the J Parker. The best rooftops for partying include London House, ROOF on theWit and IO Godfrey at the Godfrey Hotel.

Be prepared to tip the bouncer at London House if you’re not willing to wait in line. London House has certainly been the hottest rooftop bar since it opened a few years ago. All of these places have indoor seating and outdoor patios with fantastic views.

Find a way to fit in a few of these must-dos on your visit to Chicago, and you’ll be sure to experience Chicago like a local!

Where to stay in Chicago

There are a ton of places to stay in Chicago, with hotels to suit every budget.

Luxury

A new-ish hotel in Chicago, the five-star Langham Hotel has stunning decor and the classy service that you’d expect of the Langham brand (330 N Wabash Ave). Check availability and pricing online: Langham Hotel | Read guest reviews

Moderate

theWit is a stylish hotel close to both Millenium Park and the river (201 N State St). Check availability and pricing online: theWit | Read guest reviews

Budget

Hotel Felix has been recognized for its eco-friendly activities. It even has a spa on site—unusual for a hotel at this price point (111 W Huron St). Check availability and pricing online: Hotel Felix | Read guest reviews
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About the Author

Valentina is the blogger behind Valentina’s Destinations. The site was born from her obsession with meticulously researching, organizing, and planning travel itineraries. Valentina is originally from Nis, Serbia. Her passion is traveling the world. When she's not traveling, she works as a physician’s assistant in the psychiatry field. She finds the mental health field to be as rewarding as traveling can be.