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Chic Chicago Bachelorette Party Itinerary: September 26-28, 2025

Viewed by 214 travelers

Day 1: City highlights

Chicago, Illinois on September 26, 2025

9:00am

Breakfast at Wildberry Pancakes and Cafe

Start your day with delicious pancakes and breakfast favorites near Millennium Park, known for fresh ingredients and excellent coffee. A perfect way to fuel up for the day.
USD20, 1h

10:30am

Millennium Park & The Bean

Explore the iconic Cloud Gate sculpture (
Free, 1h

12:00pm

Lunch at The Purple Pig

Dine on Mediterranean small plates and charcuterie in a lively atmosphere on Michigan Avenue, perfect for sharing with your party.
USD35, 1h30m

2:00pm

Architectural River Cruise

Experience the famous Chicago River architecture cruise (usually 1.5 hours) to see and learn about the stunning skyline and history of the city.
USD50, 1h30m

4:00pm

Relax at the hotel or explore River North shops

Rest or stroll through River North's vibrant boutiques and art galleries.
Free, 1h

7:00pm

Dinner at Girl & The Goat

Enjoy award-winning plates by Chef Stephanie Izard in a trendy, energetic setting, perfect for a celebratory dinner.
USD60, 2h

9:30pm

Night out in River North

Hit the lively bars and lounges like Three Dots and a Dash or Celeste for cocktails and dancing.
Variable, Until late
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Day 2: Shopping & Relaxation

Chicago, Illinois on September 27, 2025

9:30am

Breakfast at Lou Mitchell's

Enjoy a classic Chicago breakfast at this famous and historic spot known for warm service and hearty dishes.
USD20, 1h

11:00am

Shopping on the Magnificent Mile

Explore high-end shops and boutiques along Michigan Avenue, ideal for bachelorette party gift shopping and fashion finds.
Variable, 2h

1:30pm

Lunch at Eataly Chicago

Relish authentic Italian food and vibrant marketplace atmosphere, offering a great variety of fresh options for all tastes.
USD30, 1h

3:00pm

Spa Time at AIRE Ancient Baths Chicago

Indulge in rejuvenating baths and massages at this serene spa, perfect for relaxation mid-trip but requires prior booking.
USD150, 2h

6:00pm

Dinner at RPM Steak

Experience upscale steakhouse dining with a modern vibe, ideal for a glamorous bachelorette dinner.
USD70, 2h

8:30pm

Comedy Show at The Second City

Enjoy an evening of hilarious improv and sketch comedy at Chicago's legendary comedy theater. Shows typically start at 8:30pm.
USD40, 2h
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Day 3: Brunch & Departure

Chicago, Illinois on September 28, 2025

11:00am

Brunch at Beatrix in River North

Celebrate your last day with wholesome and creative brunch dishes in a casual, stylish atmosphere.
USD25, 1h30m

12:45pm

Walk along the Chicago Riverwalk

Take a scenic and relaxing stroll along the revitalized Chicago Riverwalk with views of the city and public art.
Free, 1h

2:00pm

Last minute shopping or coffee at Intelligentsia Coffee

Grab an artisanal coffee and enjoy boutique shopping nearby before heading out of town.
USD10, 1h
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