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Ultimate Bachelor Party Weekend in Chicago

Day 1: Arrival and Nightlife

Chicago, USA

3:00PM

Check into Hotel

Upon arrival in Chicago, check into your hotel in the lively River North neighborhood, known for its trendy bars and restaurants.
Cost varies depending on hotel choice, 30 minutes

5:00PM

Happy Hour at Three Dots and a Dash

Kick off the bachelor party with tropical cocktails and tiki vibes at this renowned tiki bar. Enjoy discounted drinks during happy hour.
$10-$20 per person, 1-2 hours

8:00PM

Dinner at RPM Steak

Indulge in a high-end steakhouse experience at RPM Steak, known for its chic ambiance and delicious cuts of meat.
$50-$100 per person, 1.5-2 hours

10:00PM

Night Out in River North

Experience the vibrant nightlife of River North by hopping between popular bars and clubs like The Underground, Celeste, and Tao Chicago.
Cost varies depending on venues, 3-4 hours
Find Hotels in Chicago

Day 2: Exploring Downtown Chicago

Chicago, USA

10:00AM

Brunch at The Bongo Room

Start the day with a delicious brunch at The Bongo Room, known for its creative and indulgent breakfast dishes.
$20-$30 per person, 1-2 hours

12:00PM

Architectural Boat Tour

Embark on a scenic boat tour along the Chicago River to admire the city's iconic architecture and skyline.
$40-$50 per person, 1.5 hours

2:30PM

Visit Millennium Park

Take a leisurely stroll through Millennium Park to see the famous Cloud Gate sculpture, also known as 'The Bean', and enjoy the serene Lurie Garden.
Free, 1-2 hours

5:00PM

Craft Beer Tasting at Revolution Brewing

Head to Revolution Brewing for a tasting flight of locally brewed craft beers in a laid-back and hip setting.
$15-$25 per person, 1-2 hours

8:00PM

Dinner at Girl & the Goat

Savor inventive small plates and globally inspired cuisine at the acclaimed Girl & the Goat restaurant, known for its lively atmosphere.
$50-$75 per person, 2 hours

10:00PM

Bar Hopping in Wicker Park

Experience the eclectic nightlife of Wicker Park by bar hopping between unique venues like The Violet Hour, The Robey, and Emporium Arcade Bar.
Cost varies depending on venues, 3-4 hours
Find Hotels in Chicago

Day 3: Lakefront Activities and Nightlife

Chicago, USA

11:00AM

Brunch at The Hampton Social

Enjoy a leisurely brunch at The Hampton Social, known for its coastal-inspired vibes and Instagram-worthy decor.
$30-$40 per person, 1-2 hours

1:00PM

Rent Jet Skis at Montrose Beach

Get your adrenaline pumping by renting jet skis at Montrose Beach and enjoy exhilarating rides on Lake Michigan.
$100-$150 per jet ski, 1-2 hours

4:00PM

Beach Volleyball at North Avenue Beach

Unwind with some friendly beach volleyball games at North Avenue Beach, a popular spot for outdoor activities and people-watching.
Free, 1-2 hours

6:00PM

Dinner at Navy Pier

Head to Navy Pier and dine at one of the waterfront restaurants while enjoying panoramic views of Lake Michigan and the Chicago skyline.
$40-$60 per person, 1.5-2 hours

8:00PM

Pub Crawl in Riverwalk

Conclude the bachelor party with a lively pub crawl along the Chicago Riverwalk, stopping at waterfront bars like Island Party Hut and City Winery.
Cost varies depending on venues, 2-3 hours
Find Hotels in Chicago
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