Things To Do

FOOD & DRINK

Lou Malnati's Pizzeria

Neighborhood: River North Our number pick for a the deep dish experience. Just be prepared to wait 45 minutes for the the pizza to come out, using a knife and fork to eat a slice, and a two hour post meal food coma.

Portillo's & Barnelli's Chicago

You haven't truly lived until you've indulged in a Chicago-style hot dog with cheese fries, a classic Italian beef sandwich, or creamy penne alla vodka from Portillo's. For the ultimate experience, try all three—and earn extra credit if you take on the legendary Chocolate Cake Shake challenge!

Au Cheval

Neighborhood: West Loop Nothing beats a slab of thick cut bacon and egg on a perfectly cooked burger patty.

Wildberry Pancakes & Cafe

Neighborhood: Loop Great spot for brunch. Get in line early to nab a table.

Ann Sather Restaurant

Neighborhood: Lakeview Excellent place for breakfast. You cannot leave here without trying the cinnamon rolls.

The Green Mill

Neighborhood: Uptown A historic jazz club with a cozy, vintage vibe, known for live music, classic cocktails, and a connection to Chicago’s Prohibition-era past.

Gilt Bar

Neighborhood: River North Great place for bite or drinks. Ask about a seat at The Library, the hidden speakeasy downstairs.

Cindy's Rooftop

Neighborhood: Loop Excellent place for brunch and drinks with a stunning view of Millennium Park and the Chicago skyline in a bright, open space.

ACTIVITIES

Chicago River Boat Architecture Tours

Best way to take in Chicago’s skyline and architecture from the water.

Chicago Riverwalk

Lakefront Trail

Great trail for biking, running, or walking along the lakefront. Best way to get amazing views of Chicago's skyline.

The Art Institute of Chicago

Historic and famed art museum. Do not miss if you are an art lover.

Field Museum

Come see Sue the T. rex.

Millennium Park

The Bean. Maggie Daley Park. Crown Fountain. Definitely worth the stroll for what has become an iconic part of Chicago

Wrigley Field

Historic stadium and home to the Chicago Cubs. If we are lucky enough, you might be able to catch a game and see the Cubs play some October baseball.

Second City

See an improv comedy show at the legendary theater where many comedy greats got their start.

The iO Theater

Another historic improv theater and training center. Many SNL alums performed here prior to their fame.