Exciting 3-Day Bachelorette Party Itinerary in Chicago with Top Tourist Attractions

Day 1: Arrival and Lakefront Fun

Chicago, Illinois on September 26, 2025

9:00am

Breakfast at Wildberry Pancakes and Cafe

Start your day with hearty breakfasts featuring American classics and incredible pancakes near Millennium Park, a favorite spot for locals and tourists alike.
USD15, 1h

10:30am

Millennium Park Tour

Explore this iconic park featuring Cloud Gate (The Bean), Crown Fountain, and Lurie Garden for stunning photo opportunities and a vibrant atmosphere.
Free, 1h30m

12:00pm

Lunch at The Gage

Enjoy upscale gastropub fare with a lively ambiance right across Millennium Park, perfect for a bachelorette group.
USD25, 1h

1:30pm

Architectural Boat Tour

Take a 90-minute Chicago River architectural tour to learn about the city's stunning skyline and rich history from the river's perspective.
USD50, 1h30m

3:30pm

Walk Along Chicago Lakefront Trail

Leisurely stroll along Lake Michigan’s shoreline with beautiful views, public art, and gardens.
Free, 1h

6:30pm

Dinner at Lou Malnati’s Pizzeria

Taste Chicago’s famous deep-dish pizza at Lou Malnati’s, a classic and must-try dining experience.
USD30, 1h30m

8:30pm

Night Out in River North

Enjoy cocktails and vibrant nightlife in River North, a lively area with numerous bars and lounges perfect for a bachelorette party.
Varies, Until late
View Hotel Availability

Day 2: Culture and Entertainment

Chicago, Illinois on September 27, 2025

8:30am

Breakfast at Yolk - South Loop

Savor hearty and creative breakfast options in a casual setting, setting you up for an active day.
USD20, 1h

10:00am

Shedd Aquarium

Explore one of the world’s largest indoor aquariums featuring thousands of aquatic animals and engaging exhibits open from 9am to 6pm.
USD40, 2h

12:30pm

Lunch at Café Brauer

Dine in this historic lakeside café in Lincoln Park, offering American cuisine with beautiful views and outdoor seating.
USD30, 1h

2:00pm

Field Museum of Natural History

Discover fascinating exhibits including dinosaur skeletons and ancient artifacts in this iconic museum open from 9am to 5pm.
USD40, 2h

4:30pm

Walk through Grant Park

Relax and explore Chicago’s premier park featuring gardens, fountains, and sculptures near the museum campus.
Free, 1h

6:30pm

Dinner at Cindy's Rooftop

Enjoy delicious New American cuisine with a spectacular view of Millennium Park and the city skyline.
USD35, 1h30m

8:30pm

Comedy Show at Second City

Laugh the night away at this famous comedy club where many legendary comedians got their start; shows start at 8:30pm.
USD35, 2h
View Hotel Availability

Day 3: Views and Farewell

Chicago, Illinois on September 28, 2025

8:30am

Breakfast at Goddess and the Baker

Enjoy fresh pastries, coffee, and hearty breakfast dishes in a bright and charming café with multiple Chicago locations.
USD20, 1h

10:00am

360 Chicago Observation Deck at John Hancock Center

Take in sweeping panoramic views from the 94th floor plus experience TILT, an engaging tilting glass lookout; open from 10am.
USD35, 1h

11:30am

Visit Navy Pier

Explore this iconic lakeside entertainment destination featuring rides, gardens, and food vendors; enjoy lakeside views and activities.
Free entry, attractions vary, 1h30m

1:00pm

Lunch at Big Bowl

Stop for fresh Asian-inspired cuisine in a lively setting at Navy Pier offering great group dining options.
USD25, 1h

2:30pm

Chicago Riverwalk Stroll

Enjoy a leisurely walk along the scenic Riverwalk featuring public art, cafes, and beautiful river views.
Free, 1h

4:00pm

Departure or Relaxing Drinks

Wrap up your trip with drinks at a nearby rooftop bar like Cindy's or a cozy lounge to toast the bachelorette party.
Varies, Varies
View Hotel Availability