Win 2 hours of bowling for 8 people at Lucky Strike Chicago. Lucky Strike package includes free shoe rental & 2 appetizers for 8 people.

Enjoy a great brunch with this $40 gift card at Donovan's Pub and Restaurant, one of the oldest comfort food hot spots in Chicago, complete with a sidewalk café and giant beer garden, then laugh until you cry at a hilarious performance by the cast of The Second City. Certificate is good towards 2 tickets to a Second City performance.

Use your $50 gift card to eat dinner at one of the premier steak houses in Chicago then explore Chicago's notorious past on an Untouchable Tour of Prohibition-era mobster hangouts.

Use this package to sample the best that Chicago has to offer in vegetarian cuisine at the Chicago Diner before heading to The Annoyance Theatre, which has created some of Chicago's finest comedy. Package includes a $50 gift card to Chicago Diner and a vegetarian cookbook.

See the 2017 Tony Award-winning "Best Musical" that gives a contemporary look on life and the way we live it. Win two tickets for the February 12th opening night performance. Mid-Balcony seats, Row M, Seats 309 and 310.

See the 2017 Tony Award-winning "Best Musical" that gives a contemporary look on life and the way we live it. Win two tickets for the February 12th opening night performance. Orchestra seats.

Enjoy a night on the town by using your $100 gift card to get a nice dinner at DeClan's Irish Pub before using your voucher for 2 tickets to the Chicago Opera Theater.

Use your 2 $50 gift cards to eat at the Boundary Tavern & Grille before heading to the About Face Theatre, where you will use your voucher good for 2 tickets to the About Face Theater to see "This Bitter Earth." It'll be a night to remember.

A night of food and entertainment. First, use your $100 in gift cards to enjoy food in the festive atmosphere of Carnivale, a lively Latin-American eatery. Then watch the Tony Award winning musical Hello Dolly at the Oriental Theatre.

Get Wilde on the Northside of Chicago! Start by using your $70 in gift cards, to a great dinner at Wilde, a literary-themed upscale pub with an extensive beer list and good food. Follow this up with a performance at Timeline Theatre. You'll have a great time!

Let's go to the show! Win 4 VIP passes to any film at any Landmark Theatre. Passes are good until 12/31/19.

Love Shakespeare? This package includes tickets to a Chicago Shakespeare Theater production at Navy Pier, plus tickets to Babes with Blades Theatre Company's Othello, which features non-traditional actors taking on Shakespearean characters. If you're a fan of Shakespeare, this is the package for you!

Dance, Dance, Dance! Watch a great dance performance when you win this voucher for 2 VIP tickets to Giordano Dance Chicago's October 26 or 27, 2018 performances.

Enjoy dinner and music all on Michigan Avenue. First use your $100 gift card to dine at the Gage, an iconic restaurant across from the Millennium Park and the Art Institute. You can then walk just a short distance to the Chicago Symphony Orchestra on South Michigan Avenue, where you enjoy the best of the CSOcourtesy of Sue Yellen.

Win a gift certificate good towards 2 tickets to "A Gentleman's Guide to Love & Murder" at Porchlight, Chicago's leader in music theatre. Porchlight Music Theatre is known for its bold, edgy, and intimate music theater, offering audiences drama, song, and dance using Chicago and Broadway's brightest music theater talent.

Use your $50 gift card to Flemings Steakhouse to enjoy a great dinner before using your voucher good towards 2 tickets to the Joffrey Ballet's World Premiere of Anna Karenina, which runs from February 13-24, 2019.

Enjoy dinner at Optima/The Rabbit Hole, an upscale eatery in Old Town. Then head off for a laugh fest at Zanies Comedy Club. This package includes a $50 gift card to Optima/The Rabbit Hole and 6 tickets to Zanies Comedy Club.

Use your $100 gift card to enjoy dining in the Milk Room, Cherry Circle, or the Game and Drawing Room at the Chicago Athletic Club, then head over to the Chicago Sinfonietta, where you can use your gift certificate good for 2 A-level tickets to any Sinfonietta concert.

Enjoy a great Italian meal at Petterino's when you use your $75 gift card then watch Goodman Theatre's production of "How to Catch Creation."

Long recognized as one of the region's top classical groups, Music of the Baroque's professional chorus and orchestra is one of the leading ensembles in the country devoted to the performance of eighteenth-century works.

Party at Sidetrack! Win this gift certificate for bottle service for up to six people at this Boystown bar famous for its diverse crowd and exuberant showtunes.

Enjoy happy hour for 10 people, including draft beer and Tito's cocktails! Have fun on Clark just south of Foster in Andersonville.

Let Meeting House Tavern entertain you and your friends, when you win this certificate good towards a happy hour for 10 people, with draft beer and Tito's cocktails. This Andersonville hot spot offers various types of interactive and passive entertainment including theme nights, arcade games, as well as traditional pub and board games.

Two hours of private karaoke and $200 for food and drink! ! Sing for your supper when you win the gift certificate for this karaoke package at this stylish, Asian hot spot. Blind Dragon has 4 luxury "Sing Or Die" Karaoke Suites.

Ping-Pong parties, great food and drinks....give this place a SPiN, This package includes a private party for up to 25 in a VIP room with Ping Pong table and lounge seating.

See the Broadway favorite Hello Dolly before checking into the renovated LaQuinta Suite Chicago for a 2-Night Stay in a spacious guestroom suite, including breakfast.

On February 2, attend the largest LGBTQ soiree in the Midwest! The 2019 Equality Illinois Gala draws nearly 1,500 supporters of LGBTQ civil rights for an exciting night of food, fun and inspiration. Two tickets to the winner of this prize.

Enjoy the bright lights of the Las Vegas strip, when you win a 2 night stay for 2 at the MGM Resorts International Las Vegas. Visit Brad Garrett's Comedy Club, or the intimate Hollywood Theatre. Relax in style at the Grand Spa, 6-acre Pool Complex, and Wet Republic. Indulge in gourmet cuisine at a variety of award-winning restaurants including Craftsteak, FiAMMA, and the renowned Joël Robuchon. Grab a drink at one of the lounges, and revel in the beauty of the stunning new nightclub Hakkasan, all-star DJs Tiesto, Calvin Harris, and Steve Aoki. It's easy to see why MGM Grand is Las Vegas' Entertainment Authority. This Las Vegas package includes 2 tickets to the Grand Garden Arena, KÀ by Cirque du Soleil at the MGM Resort in Las Vegas.