The Last Hurrah: Planning the Ultimate Bachelor Party in Chicago

Are you interested in hosting your bachelor party in Chicago? In a city this large, it's the perfect destination for some wild nights out with your boys. Celebrate your impending nuptials by experiencing nightlife with a chauffeured charter bus rental in Chicago.

Book with us for an easy and stress-free experience on your next trip.

Your Chicago Bachelor Party

Are you planning a bachelor party in Chicago? In a metropolis as large as the Windy City, there’s no shortage of activities to enjoy, especially on the nightlife side. Celebrate in style with a group of any size, and take in everything the city has to offer.


Your Chicago Bachelor Party

So you’re ready to tie the knot, but you want to go all out one last time before the big day. Because of its large size and myriad of cultural experiences, Chicago is the perfect city to host your bachelor party in. Regardless of how large your bachelor party group may be, Total Charters can accommodate your transportation needs. We offer an array of charter bus and minibus rental options that drastically improve your traveling experience while in Chicago, all at competitive prices.

Never been to Chicago before? No worries-- we’ve compiled a list of the best restaurants, hotels, and night spots for you to visit, ensuring you have a the best bachelor party possible.

Wild Out in Wicker Park

One of Chicago’s most popular neighborhoods, Wicker Park is located on the Western side of the city. It’s a noted hipster hangout, placing an emphasis on the art community, dining, and nightlife.

A group of people dancing in a nightclub

Debonair Social Club

Address: 1575 N Milwaukee Ave, Chicago, IL 60622

Phone: (773) 227-7990

This is a late-night spot that features a variety of sounds and styles. Each floor in the space plays different music, catering to several crowds.


Address: 1469 N Milwaukee Ave, Chicago, IL 60622
Phone: (773) 384-1439
This bumping night spot features daily food and drink specials, but also showcases an array of DJs during weekends. Sports games are also frequently watched here, with games such as billiards available for guests.


Address: 2011 W North Ave, Chicago, IL 60647
Phone: (773) 278-6600

This large, two-floor space offers a variety of live entertainment options throughout the week, ranging from DJs and musicians to dancers and bands.

The Violet Hour

Address: 1520 N Damen Ave, Chicago, IL 60622
Phone: (773) 252-1500
One of the more upscale bars in the Wicker Park area, Violet Hour is a sophisticated space with high-key lighting, signature cocktails, and small tapas options.

The Flat Iron

Address: 1565 N Milwaukee Ave, Chicago, IL 60622
Phone: (773) 365-9000
One of Chicago’s most eclectic bars, Flat Iron has an unorthodox vibe, attracting a large portion of the art community. This space infuses affordable drinks, billiards games, and a jukebox full of classic records.

Party in Lincoln Park

Located on the North Side of Chicago, Lincoln Park is a community bordering the coastline of the city. Well known for its dining and music venues, the area is also home to a few highly sought-after night spots.

A group of men in a lounge having a conversation and drinking

The Apartment

Address: 2251 N Lincoln Ave, Chicago, IL 60614
Phone: (773) 348-5100
One of the larger nightlife venues in Lincoln Park, The Apartment is a dance club and lounge where DJs play records from a variety of genres, offering unique vibes for everyone in attendance.

The Drop Lounge

Address: 1909 N Lincoln Ave, Chicago, IL 60614
Phone: (312) 574-0898

A premier late-night spot designed like an underground, cave like venue, this shot and cocktail bar features some of the most requested DJs in the city.

The J. Parker

Address: 1816 N Clark St, Chicago, IL 60614
Phone: (312) 254-4747
Upscale and high class, The J. Parker is a rooftop bar and lounge located on top of Hotel Lincoln. J. Parker is known for its Latin cocktails and amazing views of the city.

Lincoln Avenue Social

Address: 2263 N Lincoln Ave, Chicago, IL 60614
Phone: (773) 348-7200
This late-night sports bar has a large selection of craft beers, handmade cocktails, and light eats for long nights of partying.

The Arrogant Frog Bar

Address: 1365 W Fullerton Ave, Chicago, IL 60614
Phone: (773) 248-9119
One of the more traditional-style bars in Chicago, the Arrogant Frog Bar is a tavern full of craft beers, sports television, and space for conversation.

Get Loose in the Loop

Centered in the heart of downtown Chicago, the Loop is one of the busiest, most vibrant areas in the city. Packed full of great restaurants, shops, parks, and entertainment spots, the Loop is home to a number of great bars and clubs.

A group of men toasting beers Brando’s Speakeasy

Address: 343 S Dearborn St, Chicago, IL 60604
Phone: (773) 216-3213
This lounge and club has an intimate vibe, offering drinks, karaoke, dancing, and an old school appearance to the Chicago scene.

2Twenty2 Tavern

Address: 2303, 222 S Wabash Ave, Chicago, IL 60604
Phone: (312) 878-9994
A late-night staple in Chicago, 2Twenty2 Tavern has an array of snacks and crafted cocktails to keep you satisfied.

Cerise Rooftop

Address: 203 N Wabash Ave 26th floor, Chicago, IL 60601
Phone: (312) 940-4774
Another popular rooftop hotel venue, Cerise Rooftop is a swanky, popular night spot that frequently features guests drinking and dancing alongside amazing city views.

Bar Allegro

Address: 171 W Randolph St #101, Chicago, IL 60601
Phone: (312) 696-2420
Highly sought-after rooftop hotel bar found at the Hotel Allegro. While small, this lounge has an amazing snack menu and a great selection of cocktails.

Howl at the Moon Chicago

Address: 26 W Hubbard St, Chicago, IL 60654
Phone: (312) 863-7427
One of the liveliest bars in Chicago, this hotspot is very popular for its intense party vibe, frequently featuring piano shows and bucket drinks.

Lounge in Logan Square

Logan Square is another large neighborhood found on the northwestern side of Chicago. Although Logan Square is primarily known for historical areas and large homes, it’s also popular for its diversity and rich cultural prominence.

A group of men toasting beers and one of them is taking a group selfie The Owl

Address: 2521 N Milwaukee Ave, Chicago, IL 60647
Phone: (773) 235-5300

One of the more eclectic bars in Logan Square, this late-night spot has a jukebox, indoor waterfall, and a ton of craft beers for every taste.

Slippery Slope

Address: 2357 N Milwaukee Ave, Chicago, IL 60647
Phone: (773) 799-8504
One of the most famous venues in Chicago, this bar is filled with red lights that illuminate an active dance floor and seating area. Games and original cocktails coincide with a revolving selection of local DJs.

East Room

Address: 2354 N Milwaukee Ave, Chicago, IL 60647
Phone: (773) 698-8774

One of the most iconic and well-known venues in Chicago, East Room draws crowds from every corner of the city. This indoor/outdoor establishment features games such as cornhole, a myriad of cocktails, and a low-lit atmosphere.

Emporium Logan Square

Address: 2363 N Milwaukee Ave, Chicago, IL 60647
Phone: (773) 360-8774
Emporium is an extremely eclectic bar hangout; set in an enormous loft full of video games, the space has over 60 different types of whiskeys.

Logan Bar

Address: 2230 N California Ave, Chicago, IL 60647
Phone: (773) 252-1110
Logan Bar is a neighborhood spot with traditional tavern fare, dozens of craft beers on tap, coupled with a vaulted ceiling and heated patio.

Get Situated

So, you know where you’re going to be enjoying your evenings in Chicago, but you’re not quite sure where you’re going to be resting your head and getting fueled up for your late-night shenanigans. Not to worry-- we’ve listed some of the best hotels to stay at, as well as the best restaurants in town to enjoy a great dinner.

A two-bed hotel room

Places to Stay

Kimpton Hotel Allegro

Address: 171 W Randolph St, Chicago, IL 60601
Phone: (312) 236-0123

Hyatt Centric Chicago Magnificent Mile

Address: 633 N St Clair St, Chicago, IL 60611
Phone: (312) 787-1234

Ambassador Chicago

Address: 1301 N State Pkwy, Chicago, IL 60610
Phone: (312) 787-3700

The Whitehall Hotel

Address: 105 E Delaware Pl, Chicago, IL 60611
Phone: (312) 944-6300

Hotel Felix

Address: 111 W Huron St, Chicago, IL 60654
Phone: (312) 447-3440

A resturant dining room with elegant seating

Places to Eat


Address: 1729 N Halsted St, Chicago, IL 60614
Phone: (312) 337-6070


Address: 1723 N Halsted St, Chicago, IL 60614
Phone: (312) 867-0110

Gibsons Bar & Steakhouse

Address: 1028 N Rush St, Chicago, IL 60611
Phone: (312) 266-8999

RPM Italian

Address: 52 W Illinois St, Chicago, IL 60654
Phone: (312) 222-1888


Address: 3500 N Elston Ave, Chicago, IL 60618
Phone: (773) 654-1460


Plan Your Bachelor Party, Today

Are you ready to start preparing for your bachelor party? Total Charters has handled hundreds of bachelor parties for parties of every size, so we know exactly what it takes to handle transportation for your group. Whether you need a shuttle from the suburbs, like a charter bus rental in Joliet, or you need a bus service to pick up you and your group from O'Hare International Airport, count on us to provide safe and reliable services for your Chicago bachelor party. To learn more about how we can assist you with your bachelor party or any other trip types, contact us today at 312-766-2242, and check out our beginner’s guide to Chicago!