Make this trip your own
Create your own free, personalized itinerary in seconds — then sign up to save and edit it.
Create my version

Ultimate Bachelor Party Weekend in Chicago

Viewed by 170 travelers

Day 1: Party in River North

Chicago, USA

10:00AM

Brunch at Yolk

Start your day with a delicious brunch at Yolk in River North to fuel up for the exciting day ahead.
Yolk is a short walk from most hotels in River North.
$$, 1 hour

12:00PM

Architectural Boat Tour

Embark on an Architectural Boat Tour to admire the stunning skyline of Chicago while learning about its history and architecture.
Walk to the boat dock at Michigan Avenue. The tour lasts 1.5 hours.
$$$, 2 hours

3:00PM

Explore The Art Institute of Chicago

Immerse yourself in art and culture at The Art Institute of Chicago, home to an impressive collection of masterpieces.
Take a short walk from the boat tour dock to the museum.
$, 2 hours

6:00PM

Dinner at Girl & the Goat

Indulge in a fantastic dinner experience at the renowned Girl & the Goat in the West Loop, known for its inventive dishes.
Take a rideshare to the West Loop from the museum.
$$$, 2 hours

9:00PM

Bar Hopping in West Loop

Experience the vibrant nightlife of Chicago by hopping between the trendy bars in the West Loop neighborhood.
Explore the West Loop on foot to visit different bars.
$$, 3 hours
Find Hotels in Chicago

Day 2: Explore Hip Neighborhoods

Chicago, USA

10:00AM

Brunch at Big Star

Kick off your day with a delicious Mexican brunch at Big Star in Wicker Park.
Take a rideshare to Wicker Park from your accommodation.
$$, 1 hour

12:00PM

Street Art Tour in Logan Square

Join a guided street art tour in Logan Square to admire the vibrant murals and graffiti art in the neighborhood.
Travel by rideshare from Wicker Park to Logan Square.
$, 2 hours

3:00PM

Visit Lincoln Park Zoo

Spend the afternoon at Lincoln Park Zoo, a free and family-friendly attraction showcasing a variety of animals.
Take a short rideshare to Lincoln Park from Logan Square.
Free, 2 hours

6:00PM

Dinner at RPM Italian

Enjoy a sophisticated Italian dinner at RPM Italian in River North, known for its modern twist on classic dishes.
Travel back to River North by rideshare for dinner.
$$$, 2 hours

9:00PM

Night Out in Wicker Park

Experience the eclectic nightlife of Wicker Park by bar hopping and enjoying live music at local venues.
Explore Wicker Park on foot to discover the best bars and music spots.
$$, 3 hours
Find Hotels in Chicago

Day 3: Shop, Sail, and Celebrate

Chicago, USA

10:00AM

Shopping on The Magnificent Mile

Spend the morning shopping at the upscale boutiques and flagship stores along The Magnificent Mile.
Walk or take a short rideshare to The Magnificent Mile from your accommodation.
$$$, 2 hours

12:00PM

Navy Pier Adventure

Head to Navy Pier for a fun-filled afternoon of rides, attractions, and stunning views of Lake Michigan.
Take a leisurely walk or rideshare to Navy Pier from The Magnificent Mile.
$$, 3 hours

4:00PM

Sail on Lake Michigan

Embark on a private yacht cruise on Lake Michigan for a luxurious and unforgettable experience.
Meet at the designated pier for the yacht cruise.
$$$, 2 hours

7:00PM

Dinner at Gibsons Bar & Steakhouse

Indulge in a classic steakhouse dinner at Gibsons Bar & Steakhouse in the iconic Wrigleyville area.
Take a rideshare to Wrigleyville for dinner.
$$$, 2 hours

9:00PM

Celebrate at Wrigleyville Bars

Conclude the bachelor party with a night of celebration at the lively bars and pubs in Wrigleyville.
Hop between bars in Wrigleyville to experience the vibrant nightlife of the area.
$$, 3 hours
Find Hotels in Chicago
0
Like this trip? Make your own version.
A free, personalized itinerary in seconds — sign up to save and edit it.
Create my version

More About Chicago

Trip Packing List: Chicago (Late February 2026)
Packing List
Trip Packing List: Ahmedabad → Abu Dhabi → Chicago (4 Jun–11 Jul)
Packing List
Chicago Weather Guide: Mid-May Transitions & Lake Breezes
Weather Guide
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

Plan Your Chicago Trip

Cost Estimator
Estimate your trip budget
Packing List
Get a custom checklist
Weather Expert
Check weather & best time to go