Travel the Chicago River in style with a bartender, an entertaining tour guide and killer views as you explore the city's architecture on all three main branches of the Chicago river
Enjoy a Cubs home game at historical Wrigley Field or just head over to Wrigleyville to experience the game day energy at one of the many bars and restaurants!
Located on the south bank of the Chicago River, the award-winning, pedestrian-friendly Chicago Riverwalk stretches 1.25 miles from Lake Michigan to Lake Street. Along the way you’ll discover intimate coves, breezy cafes, wineries and bars, public art, monuments, museums, and a boatload of excursions on the water.
Chicago’s 26 miles of scenic lakefront includes numerous public parks and free beaches. We recommend Oak Street Beach or North Ave Beach. Rent paddle boards, kayaks, or jet skis for water activities. Rent bikes and cruise down the Lakefront Trail, take a beachfront yoga class, play beach volleyball, or just kick back in the sand and soak in the sun and skyline views.
Millennium Park is a can’t-miss attraction for any Chicago visit. The lakefront campus, located in the heart of downtown, is home to the iconic Cloud Gate statue (aka “The Bean”), interactive fountains, tranquil gardens, free events, public art, skating rinks, rock climbing, and plenty of green space.
The Magnificent Mile is one of the most famous shopping areas in the world — home to a dizzying array of popular stores, restaurants, attractions, and architecture all on one iconic street.
Check out some of the couples favorite spots:
Dinner
- Gibson's Italia
- Pizzeria Portofino
- Trivoli Tavern
- Gibson's Bar & Steakhouse
- Robert's Pizza and Dough
- Sushi Dokku
Drinks
- Green Door Tavern (John and Chelsea's first date)
- Clark Street Ale House (The couple's neighborhood pub)
- Texan Taco Bar
- Ranalli's (also has great pizza)
- LondonHouse Chicago (great views!)
- Bub City (live music wed-sat nights!)
There's no shortage of restaurants, bars, or things to do across Chicago's many neighborhoods!