Things To Do
Chicago Architecture River Cruise
A must-do, even for locals. This boat tour cruises down the Chicago River and shows off the city’s iconic skyline while sharing the stories behind the buildings. It’s relaxing, informative, and gives you the best views of the city, especially on a sunny summer day.
Millennium Park & "The Bean"
Home to the famous Cloud Gate sculpture (aka The Bean), Millennium Park is perfect for a stroll, photos, and people-watching. It’s centrally located and right near the Art Institute and the lake.
Navy Pier
A lively spot with lake views, restaurants, bars, boat rides, and even a Ferris wheel. It’s touristy in the best way and great if you’re looking for something easy and walkable.
Wrigleyville
Even when the Cubs are out of town, Wrigleyville is a lively neighborhood full of classic Chicago bars, restaurants, and energy. Grab a drink at iconic spots like The Cubby Bear, Sluggers (yes, the one with batting cages upstairs), Murphy’s Bleachers, or Draft Kings, or wander Clark Street and pop into whatever looks fun. It’s a great area for casual bar hopping and getting a feel for Chicago’s sports-bar culture.
Neighborhood Exploring
Chicago is a city of neighborhoods, each with its own personality: -River North: packed with cocktail bars, rooftop lounges, and some of the city’s best dining -Lincoln Park: tree-lined streets, the zoo, and lake access -West Loop: trendy restaurants and great bars
The Couple's Favorite Restaurants & Bars
Upscale Restaurants: -Shaw's Crab House (River North) -Girl & the Goat (West Loop) -Il Porcellino (River North) -Topo Gigio (Old Town) -Aba (West Loop) -Zarella (River North) Casual Restaurants: -Ranalli's (West Loop or Lincoln Park) -Al's Beef (River North or Lakeview) -Gilt Bar (River North) -Stans Donut (Gold Coast or Lakeview) -Pequod's Pizza (Lincoln Park) Bars: -Parlay (River North) -Flight Club (Loop) -Butch McGuire's (Gold Coast) -Electric Shuffle (River North) -Gus' Sip & Dip (River North) -Texan Taco Bar (West Loop) Rooftop Bars: -London House (Loop) -Cindy's Rooftop (Loop) -ROOF at the Wit (Loop)