Things To Do
Architecture River Tour
Everyone's favorite Chicago activity! Head to the river along Michigan Avenue and get on one of the many Architectural Boat Tours. They're funny, educational, and a unique way to take in the city's beauty.
Skydeck Chicago
Located in the Sears Tower (or Willis Tower if you want to be incorrect), the Sky Deck is a lookout at the top of what was once the tallest skyscraper in the world. Step into the glass box if you're not afraid of heights!
Cindy's Rooftop
One of the *other* best views in Chicago. Order a cocktail at the bar and go to the terrace to gaze over Millennium Park and Lake Michigan. (Cindy's is also located across from the famous Bean if you want to check off two things at once.)
Pequod's Pizza
What is Chicago's best deep dish pizza? You have stumbled onto a very controversial topic. For Candice and Alvaro, that is Pequod's Pizza in Lincoln Park. If you want try deep dish but don't want to travel as far, Lou Malnati’s is another acceptable option with several downtown locations.
Luke's Italian Beef
In the holy trinity of Chicago foods—Deep Dish, Chicago Hot Dog, and Italian Beef—Italian Beef is our favorite. We recommend getting it dry with a side of gravy, but the classic way is to get it "baptized" by having it completely submerged in the sauce. Don't forget to add hot peppers! Luke's Italian Beef also serves Chicago Dogs and we won't side-eye you if you get both.
City Winery at the Riverwalk
This is a classic spot to take in Chicago without being super touristy. Grab a drink and settle in for some top-tier people watching. Enjoy the architecture, watch finance bros try to dock their boats, and play 1-2-3 He's Yours (Gilmore Girls fans will know).
Lakefront Trail
While it will probably be too cold to have a true beach day, you can still experience Chicago beaches by walking along the Lakefront Trail. Start at Oak Street Beach and head north on the concrete slab. Question if you're looking at Lake Michigan or some random ocean that somehow ended up in the Midwest.
Three Dots and a Dash
This is a fun, underground tiki bar that fully commits to the theme. Watch out for the skull-and-crossbones icons next to each drink—three means you’ll want to pace yourself. The entrance is hidden, but don't panic! Head to Firecakes Donuts on Hubbard Street, turn into the alley, and look for the thatched roofs and bouncer outside.
The Art Institute of Chicago
Did you know Chicago is home to the second-largest art museum in the United States? You do now! Marvel at iconic paintings such as A Sunday on La Grande Jatte, Nighthawks, American Gothic, The Old Guitarist, Monet's Water Lilies, Van Gogh's Self-Portrait, and The Great Wave.
The International McDonald's
Because McDonald's is headquartered in Chicago, we get a special restaurant: The International McDonald's. Here you can try a rotating menu of global items like the Teriyaki Chicken Filet-O from Japan or the Big Spicy Paneer Wrap from India. Who says the Midwest doesn't have culture?