Pool Halls in Chicago, IL

$11 for One Hour of Pool and $15 Toward Drinks and Snacks at Elite Cafe & Billiards ($25 Value)

Elite Cafe & Billiards

Melrose Park

Retro pool hall gives players plenty of space to maneuver around its 17 billiards tables

$25 $11

Maxwell and Mary J. Blige on December 14 at 7 p.m.

Maxwell and Mary J. Blige: King and Queen of Hearts Tour

United Center

The royalty of ’90s neo-soul join forces on a nationwide tour that simultaneously looks forward while hearkening back to a classic sound

$76.71 $35

25% Cash Back at Duffy's Tavern and Grille

Duffy's Tavern and Grille

North Side

Claim this deal and get 25% cash back rewards when you pay with your linked Visa card at Duffy’s Tavern and Grille

$0 $0

25% Cash Back at Weather Mark Tavern

Weather Mark Tavern


Get 25% cash back on your first purchase and 20% cash back on all additional purchases

$0 $0

20% Cash Back at Graffiti Chicago

Graffiti Chicago

Near North Side

Claim this deal and get 20% cash back rewards when you pay with your linked Visa card at Graffiti Chicago

$0 $0

Laugh Out Loud Chicago Improv-Comedy Show Through January 28

Laugh Out Loud Chicago

Laugh Out Loud

Improvisers perform both family-friendly and adults-only shows with spontaneous scenes, games, and songs

$20 $10

Toby Love and Judy Santos on October 27 at 8:30 p.m.

Toby Love

Rio Chicago

Bachata superstar Toby Love reconnects with his former Aventura collaborator Judy Santos, along local producer DJ Extreme, for Bachataween

$26.62 $19

Halloween Bar Crawl on October 28 or 29 or Trolley Bar Crawl: Crawl-o-ween on October 29, at 8 p.m.

Halloween Trolley Bar Crawl or Halloween Bar Crawl: Crawl-o-ween

Multiple Locations

Don creative Halloween costume, then walk or hop on a trolley to hit Chicago bars featuring drink specials, scavenger hunts, and prizes

$17.36 $8

"The Christmas Schooner"

Mercury Theater


$45 $24.25

The Second City Presents Urban Twist for Two (October 14–December 16)

Second City Diversity and Inclusion presents: "Urban Twist", a hip sketch comedy revue featuring Bob Curry Fellows

The Blackout Cabaret - 2nd Floor Pipers Alley

The famed Chicago institution presents a night of political satire and sketch comedy written and performed by a diverse cast

$32 $16


Under the Gun Theater

Under the Gun Theater

$12 $9

"Thrones! The Musical Parody": A Parody of "Game of Thrones" (October 12-October 30)

"Thrones! A Musical Parody"

Apollo Theater

This send up of the HBO phenomenon puts a humorous, musical spin on the world of Westeros, including spoilers all the way through Season 6

$59.75 $18

"Dating IRL" - Sunday October 23, 2016 / 7:30pm

Under the Gun Theater

Under the Gun Theater

$12 $9

"Are You Still Afraid of the Dark?"

Under the Gun Theater

Under the Gun Theater

$12 $9

LUSH: An Interactive Female Burlesque Show and Drinking Game (October 14, November 11, or December 9)

LUSH – An Interactive Female Burlesque Show & Drinking Game

Original Mothers

Part burlesque, part drinking game, these Friday-night shows feature talented performers and plenty of audience interaction

$30 $20

Sugar Brown Burlesque: The Diaries of a Submissive on October 29 or 30 at 8 p.m.

"Sugar Brown Burlesque: The Diaries of a Submissive"

Humility Gallery

Sugar Brown explores her newly submissive side through lusty yet elegant choreography and poetry

$43.19 $20

"Ghost Stories"

Under the Gun Theater

Under the Gun Theater

$12 $9

2nd Annual Haunted Halloween Ball - Saturday October 29, 2016 / 8:00pm

Navy Pier Grand Ballroom

Amazing Chicago's Funhouse Maze at Navy Pier

$20 $13.75

A Nightmare on Hubbard Street-The 5th Annual River North Halloween Costume Bar Crawl on Saturday, October 29, at 12 pm

A Nightmare on Hubbard Street – The 5th Annual River North Halloween Costume Bar Crawl

Bar Louie

Annual Halloween-themed bar crawl weaves through River North, with drink specials, live DJs, and a costume contest along the way

$27.95 $15

"Girl Found"

The Cornservatory

North Side

$20 $13.75

"How We Got On"

The Den Theatre - Janet Bookspan Theatre

Wicker Park

$32 $20.75

Haunted Hotel Bash at Hard Rock Hotel - Saturday October 29, 2016 / 10:00pm-3:00am (Plus Pre- and After-Parties)

Hard Rock Hotel

Chicago, IL

$50 $17.50

Saints & Sinners Halloween Party - Saturday October 29, 2016 / 9:00pm-2:00am

Lucky Strike


$15 $4.75

Craft-Beer Tasting for Two or Four at Beermiscuous (Up to 43% Off)


North Side

Each guest selects four draft craft beer samples from a wide variety of options at a unique beer café

$30 $18

Tangerine: A Two-Man Show

The Cornservatory

North Side

$10 $7.50

River North Whiskey Fest - Saturday November 12, 2016 / Noon - 4:00pm

Moe's Cantina and Old Crow Smokehouse River North

Near North Side

$50 $29.25

"RejecTED Talks"

Under the Gun Theater

Under the Gun Theater

$12 $9

Two Well Drinks and $10 in Tokens at Emporium Arcade Bar (Up to 60% Off). Two Options Available.

Emporium Arcade Bar

Multiple Locations

Visitors juggle drinks and joysticks at the arcade bar’s two locations, where vintage video games and pinball tables abound

$20 $8

"Skooby Don't"

Mary's Attic at Hamburger Mary's


$28 $18.25

General, VIP, or VIP Admission with a Drink to Laugh Factory Chicago Weekend or Tuesday-Night Comedy Shows

Laugh Factory

Laugh Factory

Legendary standup-comedy venue hosts some of the best local and touring comedians around during weekend and Tuesday night comedy shows

$10 $7

Select Local Merchants

  • Pressure Billiards and Cafe
    Though you wouldn’t expect to find professional pool tables in a café nor freshly crafted deli sandwiches in a pool hall, Pressure Billiards and Cafe has managed to seamlessly combine these elements into a single all-encompassing amusement space. On the billiards side of the facility, 13 9-foot Brunswick Metro tables bask in the glow of contemporary wall sconces and ample overhead light as players aim for pocket dominance like a keys-versus-wallet grudge match. A slate of eight LCD televisions displaying seasonal sports games, meanwhile, ensures that adrenaline levels never wane between turns. After billiards bouts conclude, guests can saunter over to the café side of the establishment to dine on classic pub dishes flanked by a range of mixed drinks and a dozen bottled beers. Once fully refueled, clients can wind down in the lounge or partake in one of the bar’s nightly activities, such as an open mic, trivia night, or comedy showcase. Explore Edgewater Groupon has partnered with the Edgewater Chamber of Commerce to offer this special collection from Edgewater merchants. The North Side neighborhood is home to one-of-a-kind shops such as Edgewater Workbench, where customers create custom gifts with 3D printing and laser cutting, and pioneering restaurants such as Uncommon Ground, home of the country’s first certified organic rooftop garden. Shop the full collection.
    Read More
    Chicago, IL US
  • City Pool Hall
    Rack 'em up! Pool hall City Pool Hall in Chicago is a great spot for an evening out. The drink list at this restaurant has everything you need to complete your meal (and your night out). City Pool Hall is the perfect spot to enjoy a great meal outside (weather permitting). If you're hitting City Pool Hall on a weeknight, it's best to make a reservation since the place can really fill up. Guests of City Pool Hall's W Hubbard St location can park their vehicles on the street. For those who wish to avoid traffic, City Pool Hall is also accessible via public transportation, with stops at Grand-blue (Blue Line) and Clinton-green (Green Line, Pink Line). Bicyclists will also find lots of space to safely lock up their bikes. Meals at City Pool Hall usually set you back about $30 per diner. Early risers and night owls alike can enjoy City Pool Hall since it offers breakfast, lunch, and dinner. So head on over to City Pool Hall and enjoy some great eats and a game of pool. So when you need to cure your hunger craving, visit City Pool Hall and treat yourself to a tasty American dish. When you're in need of a casual night out, head to City Pool Hall and enjoy some great American classics. You deserve an excellent meal, so head on over to City Pool Hall and enjoy some of the highly-rated American fare.
    Read More
    Chicago, IL US
  • Chicago Billiard Cafe
    Clacking pool balls echo across 16 9-foot tables at the Chicago Billiard Café, where rising and renowned cue masters can snack on items from a menu of tasty pub grub while admiring a century-old authentic snooker table. Donated by an altruistic band of Muppets, vivid red and green felt carry an enchanting aura and stretch across tables from Brunswick Gold Crown and Soren Sogard, which host 8- and 9-ball tournaments on Mondays and Thursdays, respectively. Frappuccinos and fizzy sodas fuel accurate strokes and gallant cue duels, and winners can rejoice with deep-fried Twinkies preluded by all-beef hot dogs and gooey pizzas from the café’s menu. Dulcet tunes unite with the even more mellifluous sound of patrons’ corner-pocket prophecies to underscore bouts that take place on a glittering pinball machine, which glimmers amid the softly lit interior ensconced by exposed brick.
    Read More
    Chicago, IL US
  • Waveland Bowl
    The pin pioneers at Waveland Bowl have provided Chicagoans with the latest in bowling amenities since its opening in 1959, when AMF's automatic pinsetters and Magic Triangle indicators superseded the rusted, tough-to-maintain human staff members behind every lane. Though the alley's original neon sign has since been replaced, the constant improvements have continued throughout the years, and the facility now boasts automatic bumpers on 40 Brunswick Armour Plate lanes and buys new pins every year. Throughout the week, the facility hosts open bowling and leagues for children and adults, and Thursday–Monday, cosmic bowling recreates the thrill of playing under the aurora borealis without the risk of polar bears ruining all the rental shoes.
    Read More
    Chicago, IL US
  • Chicago Billiards
    Chicago's Chicago Billiards features an impressive selection of adult beverages, so everyone in your group will find something they like to drink. Parking is plentiful, so visitors can feel free to bring their vehicles.
    Read More
    Chicago, IL US
  • Nick's Billiard Academy
    It's an absolutely satisfying experience to knock a ball into a pocket. Get your pool game on at Nick's Billiard Academy in Chicago. Parking is plentiful, so visitors can feel free to bring their vehicles.
    Read More
    Chicago, IL US