Deep Dish Pizza

Giordano’s, Lou Malnati’s, and Gino’s East are the most famous of the Chicago deep dish pizza places – and they each have very loyal followings. They’re known for their buttery crusts, chunky tomato sauces, and gooey layers of cheese. Typically the toppings, like meats or veggies, are stuffed inside of the pizza, and the sauce sits on top. It’s significantly heavier than a New York style slice. It can take 30 – 45 minutes to cook a deep dish pizza, so go a little before you’re hungry so you’re not starving while you wait.

Pequod’s
This spot offers a unique twist on deep dish pizza. Rather than a buttery crust, Pequod’s pizza has a flaky, caramelized crust that sets it apart from the classic Chicago style.

Cheap Eats

Chiya Chai
This trendy waterfront stall offers delicious Indian street food, but the best part is their chai. Grab a hot tea to take with you on a lakefront walk.

Big Star Tacos
Big Star Tacos has great food and an even better environment. You can sit inside or outside and enjoy your tacos. Make sure to get a Frito Pie if they have it as a special item. It’s basically nachos, but instead of tortilla chips, they use Fritos. 

Garrett Popcorn Shops
A Chicago staple, Garrett Popcorn offers unique and addictive popcorn flavors, both sweet and savory. It’s a perfect souvenir or afternoon snack. I personally love the cheddar flavor.

High-End Options

Girl and the Goat
This Michelin-starred restaurant has some of the best food in Chicago (and a sister restaurant in LA). Try the chickpea fritters, goat empanadas, and the short rib.

Duck Duck Goat
This restaurant is by the same people behind Girl and the Goat, but it is very different in both food and vibe. Duck Duck Goat is a bit more casual and focuses on delicious Chinese fare with a twist. All of the dishes are great, but the duck fried rice was our table’s unanimous favorite.

Au Cheval
Au Cheval has the best burgers in Chicago. Get the burger – optional to add on a piece of thick-cut bacon and an egg. You won’t be disappointed. For drinks, the Paper Plane and Bee’s Knees were both excellent.

The Perch
The Perch is a great brunch spot on the fringe of the Wicker Park neighborhood. Their cinnamon rolls are so gooey and come in a cast iron skillet – don’t miss out on them!

Cafe Robey
Cafe Robey is another solid Wicker Park brunch spot.

SEE CHICAGO LANDMARKS

Millennium Park
Millennium Park is a sprawling green space in downtown Chicago. Take a walk and see these highlights:

The Bean
Officially called Cloud Gate, this iconic sculpture in Millennium Park is a giant, reflective bean-shaped structure made of polished stainless steel.

Crown Fountain
Right outside of the Art Institute you’ll see an interactive fountain featuring videos of faces that “spit” water.

Buckingham Fountain
Buckingham Fountain is a beautiful large fountain near the waterfront in Grant Park.

Marina City Complex Towers
If you’ve seen the Wilco album cover Yankee Hotel Foxtrot, then you’ll recognize these towers. They kind of look like a beehive or corn on the cob – they’re actually a mix of residential and commercial spaces. You can find the towers along the Chicago River near State Street.

what to DO in chicago

Willis Tower (formerly Sears Tower)
This iconic skyscraper offers breathtaking 360-degree views of the city from the Skydeck (called The Ledge), a glass balcony extending out 103 stories above the ground.

Boat Cruise
Explore Chicago’s scenic waterfront and architecture from the water on a relaxing boat tour along the Chicago River. There are a bunch of different excursions available ranging from historical to architecture-focused. We did the tour around sunset and thought it was cool to see the skyline from the water during the day, and at night with the skyline all lit up.

Art Institute of Chicago and Outdoor Garden
Chicago’s Art Institute houses an impressive collection of Impressionist and Post-Impressionist paintings by artists like Monet, Van Gogh, and Picasso. Make sure to see: A Sunday on La Grande Jatte by Georges Seurat, The Bedroom by Van Gogh, Nighthawks by Edward Hopper, and American Gothic by Grant Wood. Don’t miss the outdoor portion with some sculptures and lots of shade!

Shop on the Magnificent Mile
Go shopping on Michigan Avenue, a stretch lined with high-end designer stores and popular department stores.

See a Comedy Show at Second City Comedy Club
Catch an improv comedy show at the world-famous Second City, known for launching the careers of comedy giants like Tina Fey, Amy Poehler, and Bill Murray.

Baseball or Hockey Game
Depending on the season, catch a baseball, hockey, or football game.

Go For a Walk

Explore the Navy Pier and go on the Ferris Wheel (Centennial Wheel)
This lively entertainment complex on Lake Michigan features shops, restaurants, amusement rides, and iconic landmarks like the Centennial Wheel, a giant Ferris wheel offering stunning views.

Walk or Bike the Lakefront Trail
Enjoy a scenic ride or stroll along the paved Lakefront Trail, offering beautiful views of Lake Michigan and the Chicago skyline.

Walk Around River North
Explore this trendy neighborhood known for its art galleries, upscale boutiques, bars, and nightlife.

Walk Around Wicker Park
Wicker Park is another trendy neighborhood known for its vintage shops, boutiques, art galleries, bars, and restaurants. It’s worth spending some time strolling the streets here.