Things To Do
Riverfront Plaza
Chicago invested heavily to create a riverwalk reaching from downtown all the way to Lake Michigan. Daniella and Kevin run this trail throughout the year and it is a beautiful place to take in the sights.
Millennium Park
Millennium Park is located in the heart of downtown Chicago and is an award-winning center for art, music, architecture and landscape design. It is where iconic Chicago moments are hosted every year: Chicago Marathon, Lollapalooza, and more. It includes Chicago's infamous "Bean" and Buckingham Fountain nearby.
Hancock Tower 360 Deck
Soak in an arial view of the entire city from the top of the Hancock Tower. There is a 360 Observation deck at the top with tickets purchased.
The Art Institute of Chicago
The Art Institute of Chicago, founded in 1879, is one of the oldest and largest art museums in the United States. The museum is based in the Art Institute of Chicago Building in Chicago's Grant Park.
Field Museum
The Field Museum, is a natural history museum in Chicago, Illinois, and is one of the largest such museums in the world.
The Second City
The world's premier comedy club, comedy theater, and school of improvisation. Live shows every night in Chicago and a great option while in town.
The Aviary
If you're into cocktails, this place is worth getting a tasting reservation!
Lazy Bird
Another great cocktail option with live music on select nights. No reservations available, so recommend getting there closer to opening time or be open to standing at the bar!
Cindy's Rooftop
Hip, stylish rooftop bar/eatery at the Chicago Athletic Association Hotel with beautiful views of Millenium Park
Au Cheval
This is our go-to burger spot and dubbed one of the best burgers in the city! No reservations possible, so either get their early or put in your name and grab a beverage nearby. The wait is usually not as long as they say. Also - try the fried chicken wings too!
Pequod's Pizza
Another Chicago staple is the deep dish pizza. Pequod's is a great environment and pizza!
Alla Vita
One of our favorite Italian spots in the city. Great pasta, pizza, and wine!
Maple & Ash
An incredible steakhouse with a cool vibe, delicious cocktails, and incredible seafood too! In the heart of the Gold Coast neighborhood, there is plenty to walk around and see nearby.
Great Central Brewing Company
This is one of our favorite breweries in the city. It has a great selection of drinks made in house and other Chicago local drinks. It is a big open space with boardgames and 3-4 other breweries are within walking distance.