Ultimate Chicago Bachelorette Party Itinerary

Viewed by 423 travelers

Day 1: Arrival and Exploration

Chicago, USA

10:00AM

Check-In at Hotel

Upon arrival, check in at the luxurious Hotel Felix to drop off your bags and get settled into your stylish accommodations.
Hotel Felix, 111 W Huron St, Chicago, IL 60654
USD 250, 1 hour

11:30AM

Brunch at Beatrix

Indulge in a lovely brunch at Beatrix, where you can savor delicious breakfast bowls and their renowned caramel crunch cake.
Beatrix, 519 N Clark St, Chicago, IL 60654
USD 25, 1.5 hours

1:00PM

Millennium Park and Cloud Gate

Stroll through Millennium Park, snap stunning photos by the Cloud Gate sculpture, and enjoy the vibrant atmosphere.
Walk from Beatrix to Millennium Park, approximately 10 minutes
Free, 2 hours

3:00PM

Navy Pier

Explore Navy Pier, visit shops, and enjoy breathtaking views of Lake Michigan.
Take the #65 bus from Millennium Park to Navy Pier, about 15 minutes
Free, 3 hours

6:30PM

Dinner at RPM Italian

Savor a chic dinner at RPM Italian, featuring delectable handmade pasta and a trendy atmosphere perfect for a bachelorette party.
Take a rideshare from Navy Pier to RPM Italian, about 10 minutes
USD 70, 2 hours

9:00PM

Cocktails at Aviary

Finish off the night with creative cocktails at Aviary, a swanky bar known for its innovative drinks and stunning views.
Take a rideshare from RPM Italian to Aviary, about 5 minutes
USD 15, 2 hours
Find Hotels in Chicago

Day 2: Shopping and Spa Day

Chicago, USA

9:00AM

Breakfast at Wildberry Pancakes

Start the morning with breakfast at Wildberry Pancakes, famous for their amazing pancakes and berry parfaits.
Wildberry Pancakes, 130 E Randolph St, Chicago, IL 60601
USD 20, 1.5 hours

10:30AM

Shopping on Mag Mile

Shop till you drop on the Magnificent Mile, featuring a mix of luxury brands and unique boutiques.
Walk from Wildberry Pancakes to Magnificent Mile, approximately 5 minutes
Free to explore, 3 hours

1:30PM

Lunch at The Purple Pig

Enjoy lunch at The Purple Pig, where Mediterranean-inspired dishes and a rustic environment await you.
Walk back to The Purple Pig, 444 N Michigan Ave, Chicago, IL 60611, about 10 minutes
USD 30, 1.5 hours

3:00PM

Spa Treatments at The Peninsula Spa

Pamper yourselves with rejuvenating treatments at The Peninsula Spa, a luxurious relaxation experience that will leave you feeling blissful.
Take a rideshare to The Peninsula Spa, about 5 minutes
USD 150, 3 hours

7:00PM

Dinner at Girl & The Goat

Indulge in a lively dinner at Girl & The Goat, known for its inventive dishes and vibrant atmosphere.
Take a rideshare to Girl & The Goat, 809 W Randolph St, Chicago, IL 60607, about 10 minutes
USD 60, 2 hours

9:30PM

Bar Hopping in Wicker Park

Experience Chicago's nightlife by bar hopping in Wicker Park, filled with unique bars and hip hangouts.
Take a rideshare to Wicker Park, about 15 minutes
Free to explore, drinks extra, 3 hours
Find Hotels in Chicago

Day 3: Fun and Adventure

Chicago, USA

9:00AM

Breakfast at Toast

Fuel up for the day at Toast, known for its creative breakfast menu and cozy atmosphere.
Toast, 746 W Armitage Ave, Chicago, IL 60614
USD 20, 1.5 hours

10:30AM

Bike Ride Along Lakefront Trail

Rent bikes and enjoy a scenic ride along the Lakefront Trail, taking in stunning views of the skyline and the lake.
Rent bikes at Divvy Station near the restaurant, approx. 5 minutes
USD 15, 2 hours

1:00PM

Lunch at Lou Malnati's

Savor Chicago's iconic deep-dish pizza at Lou Malnati's, a must-have experience on your trip.
Return the bikes, then take a rideshare to Lou Malnati's, about 15 minutes
USD 30, 1.5 hours

2:30PM

Escape Room Adventure

Engage your minds with a thrilling escape room adventure at Escape Artistry, testing your team's problem-solving skills.
Take a rideshare to Escape Artistry, 3411 W Fullerton Ave, Chicago, IL 60647, about 20 minutes
USD 40, 1.5 hours

5:00PM

Dinner at The Capital Grille

Enjoy a sophisticated dinner at The Capital Grille with mouthwatering steaks and a fine wine list.
Take a rideshare to The Capital Grille, 633 N St Clair St, Chicago, IL 60611, about 10 minutes
USD 70, 2 hours

8:00PM

Comedy Show at The Second City

Wrap up the day with laughter by attending a comedy show at The Second City, a classic Chicago venue.
Take a rideshare to The Second City, 1616 N Wells St, Chicago, IL 60614, about 15 minutes
USD 25, 2 hours
Find Hotels in Chicago

Day 4: Relax and Celebrate

Chicago, USA

10:00AM

Brunch at The Bongo Room

Enjoy a laid-back brunch at The Bongo Room, with their delicious brunch fare and eclectic environment.
The Bongo Room, 1470 N Milwaukee Ave, Chicago, IL 60622
USD 25, 1.5 hours

11:30AM

Visit the Art Institute of Chicago

Immerse yourselves in art by visiting the Art Institute of Chicago, home to stunning collections and exhibitions.
Take a rideshare to the Art Institute, 111 S Michigan Ave, Chicago, IL 60603, about 10 minutes
USD 25, 2 hours

2:00PM

Lunch at Vienna Beef Hot Dogs

Experience a true Chicago staple by grabbing lunch at Vienna Beef Hot Dogs, indulging in classic Chicago-style hot dogs.
Walk to Vienna Beef at 739 N Western Ave, Chicago, IL 60612, about 25 minutes
USD 10, 1 hour

3:00PM

Shopping at Oak Street

Enjoy high-end shopping along Oak Street, perusing luxury boutiques and trendy shops as a final treat.
Take a rideshare to Oak Street, about 15 minutes
Free to explore, 2 hours

6:00PM

Farewell Dinner at The Signature Room

Celebrate the end of the bachelorette weekend with a memorable dinner at The Signature Room, enjoying breathtaking views from the 95th floor of the John Hancock Center.
Take a rideshare to The Signature Room, 875 N Michigan Ave, Chicago, IL 60611, about 15 minutes
USD 80, 2 hours

8:00PM

Nightcap at The Roof on theWit

End your Chicago bachelorette bash with a nightcap at The Roof, offering panoramic city views and a lively atmosphere.
Take a rideshare to The Roof on theWit, 201 N State St, Chicago, IL 60601, about 10 minutes
USD 20, 2 hours
Find Hotels in Chicago
0

More About Chicago

Trip Packing List: Chicago (Late February 2026)
Packing List
Trip Packing List: April 3–12 — DC, New Haven, Boston, Chicago, Denver, San Francisco
Packing List
Chicago Weather & Climate Guide: Seasons in the Windy City
Weather Guide
Full Guide to Michelin Star Cities: 2025 Updated List
Travel Expert
Global Michelin Cities & US Travel Tiers from New York
Travel Expert
Itinerary created by AI-assisted, human-reviewed