Nightlife in Crestwood

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

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

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

Movie with Popcorn and Drinks for One, Two, or Four at Village of Bensenville (Up to 57% Off)

Village of Bensenville


Guests grab buckets of popcorn and large sodas before heading into intimate twin theaters to view recent releases

$22 $11

$39 for Date Night with Two Movie Tickets and $100 eGift Card ($124 Value*)

Ultimate Date Night Package

Online Deal

Create your own ultimate date with movie tickets and a $100 eGift Card for dinner

$124 $39

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

"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

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

"Hip Hop Nutcracker" on Friday, December 9, at 7:30 p.m.

Hip Hop Nutcracker

Rosemont Theatre

A dozen dancers pair with a DJ and electric violinist to put an explosive hip-hop spin on this holiday classic

$42.55 $25

Murder-Mystery Dinner for One or Two at The Murder Mystery Co. (Up to 55% Off)

The Murder Mystery Co.


Interactive murder mystery dinner starring professional actors testing guests’ sleuthing skills throughout a three course meal

$60 $27

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

Beer Tastings, Flights, and Unfilled Growlers for Two or Four at Metal Monkey Brewing (Up to 33% Off)

Metal Monkey Brewing

Metal Monkey Brewing

Learn about beer and enjoy plenty of samples at the brewery, such as Goodall Day Blonde and Big Chimpin IPA

$21 $14

Improv-Comedy Show with Popcorn (Through January 28)

Laugh Out Loud Theater Schaumburg

Laugh Out Loud

Improvisers perform shows with spontaneous scenes, games, and songs

$22 $11

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

Movie Theater Ticket Subscription Plans from MoviePass (Up to 44% Off). Four Options Available.


Online Deal

Smartphone app lets users reserve movie theater tickets at major theaters nationwide, saving them time and money

$17.99 $12.99

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

"The Wild Side: A Bad Ass Pole Show" on October 7, November 4, or December 2

The Wild Side: A Bad Ass Pole Show

Original Mothers

Chicago’s sexiest pole dancers dazzle with high-fyling acrobatics and titillating dance moves

$30 $20

Standup or Improv Comedy Show at The Comedy Shrine Theater through January 28

The Comedy Shrine

The Comedy Shrine Theater

Comics and resident improvisers fill standup showcases and a flagship show of short-form improv a la Whose Line Is It Anyway?

$20 $10

"Naughty Little Cabaret" Burlesque, Fridays at 8 p.m. through October 28

Naughty Little Cabaret

Original Mothers

Male and female burlesque performers, including some from RuPaul’s Drag Race, dazzle with acrobatics, teasing, and titillating dance moves

$30 $20

The Dancing Horses from September 1 through October 30

The Dancing Horses

The Dancing Horses Theatre

Equestrians & various horse breeds do a Vegas-style performance, followed by an exotic bird show featuring Echo from America’s Got Talent

$37.50 $18

"Kiss Kiss Cabaret"

Uptown Underground


$27.50 $18

Tasting Experience for Two with Pint Glasses and "Crowlers" at Noon Whistle Brewing (Up to 50% Off)

Noon Whistle Brewing


Sip beers and take home 32-oz. canned crowlers at the brewery behind such beers as Cozmo, American Pale Ale and Bernie milk stout

$54 $27

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 Red Star Cocktail Lounge

Red Star Cocktail Lounge


Claim this deal and get 20% cash back rewards when you pay with your linked Visa card at Red Star Cocktail Lounge

$0 $0

"A Christmas Carol"

Metropolis Performing Arts Centre

Arlington Heights

$30 $19.75

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

Groupon Exclusive: Girls Night Out The Show with Meet and Greet on (November 15 or November 17)

Girls Night Out The Show

Multiple Locations

Muscle-bound hunks unleash ripped abs and sexy dance moves in a tantalizing evening of girls’ night out fun; meet and greet included

$45 $30

"The Christmas Schooner"

Mercury Theater


$45 $24.25

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

$17 for $30 Worth of Tropical Appetizers and Tiki-Bar Drinks at Hala Kahiki

Hala Kahiki

River Grove

Tropical cocktails named for Pelé and coral reefs poured in Polynesian-themed bar opened in 1963

$30 $17

Select Local Merchants

  • At The Office
    Catch the game and knock back a few beers with friends at At the Office. Great food plus TV equals the perfect fan meal. This restaurant is kid-friendly, so little ones are welcome to tag along. At the Office has a large dining room, making it easy to seat large parties. At the Office provides seasonal outdoor seating — be sure to grab a chair before it's too late. The restaurant can fill to capacity on the weekends, so don't forget to call ahead to reserve your table. Great food is best enjoyed comfortably, so At the Office encourages less-than-fancy attire. Or, take your food to go. A nearby parking lot is readily available for At the Office's diners. Prepare to spend about $30 per person when dining at At the Office. When you're looking for a fun place to watch the big game, At the Office is where you want to be. There's a classic American dish waiting to be made for you at At the Office. When you come to At the Office, you'll be beyond satisfied with a casual American meal.
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    Crestwood, IL US
  • Brazen Head
    Brazen Head serves American-style cuisine in the middle of Crestwood's Crestwood district. Being a fan is serious business; don't miss a minute of your team's game. Brazen Head offers patio seating in the warmer months. Patrons have the pleasure of listening to live music while they dine. A tad noisy, the restaurant is well-suited for those who don't mind a little extra hustle and bustle. Weekends are when crowds really head to Brazen Head, so plan accordingly. If you prefer to drive to the restaurant, go right ahead. Parking is abundant in the area. Hitting the mid-range mark, Brazen Head s prices are perfectly reasonable for food that goes above and beyond. The best American dishes are cooked up by the great crew at Brazen Head, and they're waiting to serve you! So what are you waiting for? Come see what the highly-rated American food at Brazen Head is all about. Come see why Brazen Head is one of the top British pubs in Crestwood.
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    Crestwood, IL US
  • Mitch's Pub and Eatery
    Order all of your favorite pub classics and munch away at Mitch's Pub and Eatery in Crestwood. Those in search of a stiff drink can also peruse the bar menu, where a range of beer, wine, and cocktails are available. Mitch's Pub and Eatery caters to all party sizes, both large and small. Be sure to make reservations so you can get seated right away. Put the suit away when heading to Mitch's Pub and Eatery — dress is casual, as are the vibes. You can also serve food from Mitch's Pub and Eatery at your next party — the bar offers catering. Mitch's Pub and Eatery is located in a prime area for those who wish to park in lots. When you need great food that is not going to cost an arm and a leg, stop by Mitch's Pub and Eatery. For simply amazing pub food, Mitch's Pub and Eatery has all of your favorites to continuously satisfy your hunger. Mitch's Pub and Eatery has everything you could want from a British pub in Crestwood.
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    Crestwood, IL US
  • AMC Loews Crestwood 18
    Sitting in a comfy seat watching an absolutely thrilling movie sounds like the perfect night. Visit AMC Loews Crestwood 18 in Crestwood for a great time with family and friends. Next time you're in the neighborhood, this theater should be at the top of your list with their amazing restaurant. Tots are more than welcome to hang with their parents at this theater. Parking is plentiful, so patrons can feel free to bring their vehicles.
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    Crestwood, IL US
  • Dillagafs Pub
    For bar nibbles and pub food par excellence, Dillagafs Pub is a top pick. You can also serve food from Dillagafs Pub at your next party — the restaurant offers catering. At Dillagafs Pub, service is a priority. That why we provide parking spaces on site. So when you want some amazing food to complement your drinks, Dillagafs Pub will be there for you.
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    Crestwood, IL US
  • Sony Crestwood Theatre
    Rainy day? Head on over to Sony Crestwood Theatre in Crestwood and check out that film you have been dying to see. Check out the restaurant at this theater for a delicious meal. A great date night can be spent at the drive-in theater. Parking is plentiful, so guests can feel free to bring their vehicles.
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    Crestwood, IL US