Things To Do & Places To Eat!
Cloud Gate aka “The Bean”
It’s not a trip to Chicago without a Bean pic. Super touristy, but super fun!
Architecture Boat Tour
Hop on a boat, cruise along the Chicago River, and learn all about the city’s beautiful skyline and architectural history.
Willis Tower (formerly known as “The Sears Tower”)
Don’t let the locals hear you call it Willis Tower — it’s still the Sears Tower to us! This is the tallest skyscraper in Chicago and has the famous Skydeck with glass boxes that extend out over the city. You can step out onto the ledge - scary, but a cool photo!
Magnificent Mile
A go-to shopping street with everything from luxury stores to fun boutiques.
Navy Pier
A pier on Lake Michigan with shops, restaurants, rides, and beautiful lake and skyline views. Firework shows every Wednesday and Saturday night in the summer!
Wrigley Field
Catch a game where we got engaged at the famous Wrigley Field — the second-oldest Major League Baseball stadium and the oldest in the National League.
The Art Institute of Chicago
Chicago’s world-class art museum with iconic lions out front.
National Museum of Puerto Rican Arts & Culture
The only Puerto Rican museum in the U.S. outside of the island itself, celebrating PR heritage through art, history, and community. Admission is free!
Portillo's Chicago – Canal and Taylor
For great burgers or the ultimate Chicago-style hot dog (don’t ask for ketchup!). Tania learned the hard way.
Giordano's
Iconic deep dish pizza. If you’ve never had it, now’s your chance! Multiple locations throughout the city.
Mr. Beef
Visit the famous beef sandwich shop featured in The Bear!
Harold's Chicken Shack
Fried chicken, and a Chicago staple. There are multiple locations throughout the city, or you can just Uber Eats it straight to your hotel. Don’t skip the mild sauce — trust us!