If your birthday happens to be on February 29th, we owe you a Happy Birthday and an I’m sorry. You haven’t had that many opportunities to celebrate (how old are you turning? 8? or 16? the big 20?), these Chicago restaurants and bars want to make the most out of this Leap Year. From free food to 2.29-priced items, these spots go all out with Chicago Leap Day Deals.
1. Sip on the “Leap Year” Cocktail at Central Park Bar
Central Park Bar in Avondale will feature one of the best Chicago Leap Day deals with a special $10 “Leap Year” cocktail available only on Thursday, February 29. Named after the classic cocktail of the same name created by a bar in London in 1928, the drink features Beefeater London Dry Gin, Grand Marnier, Carpano Antica Sweet Vermouth, and lemon juice.
Address: 2924 N Central Park Ave, Chicago, IL 60618
2. Dance to Leap Day Live Music at aliveOne
AliveOne will feature FREE live music from the resident band Bonzo Squad, who will perform an “extra long” jam in honor of Leap Day on Thursday, February 29, at 9:30 p.m. If the live music isn’t your final draw, then the Half-price happy hour will. The Chicago Leap Day deals will be available from 5 p.m. to 7 p.m. along with all-night specials, including $3 Miller High Life and $8 Eve of Destruction cocktails.
Address: 2683 N Halsted St, Chicago, IL 60614
3. Grab Leap Year Cocktails at the I|O Godfrey Rooftop
Head to Chicago’s largest and only year-round rooftop lounge and savor the moment with their exclusive Leap Year cocktail, “Look Before You Leap.” This delightful concoction features Bombay Sapphire Gin, St. Germain Elderflower Liqueur, fresh grapefruit topped with Prosecco and garnished with a slice of dehydrated dragon fruit. While not one of the Chicago Leap Day deals, the cocktail is the perfect way to leap into a toast to the extra day.
Address: 127 W Huron St, Chicago, IL 60654
4. Celebrate a Chicago Leap Year Birthday at Old Town Pour House
Old Town Pour House, a vibrant bar and restaurant featuring 90 beers on tap and modern American food with chef-driven twists, extends a special invitation to all leaplings. One of the best Chicago Leap Day deals, anyone born on Feb. 29 can celebrate their unique birthday with a FREE entree of their choice.
Address: 1419 N Wells St, Chicago, IL 60610
5. Leap Day Brunch Delights: A 29-percent Discount at Wake’n Bacon
Chicagoans who visit Wake ‘n Bacon, the vibrant Insta-worthy brunch spot in East Lakeview, on Leap Day will enjoy a special 29-percent discount when they dine for brunch or lunch on Thursday, February 29. Anyone who dines on Leap Day will also be entered to win a free private party space at Wake ‘n Bacon for up to 50 guests, with the rental fee waived!
Address: 420 W Belmont Ave, Chicago, IL 60657
6. Munch on $2.29 Cookies and $29 Cakes at Sweet Mandy B’s
To celebrate the Leap Year, Sweet Mandy B’s in Lincoln Park and Streeterville will offer one of the Best Chicago Leap Day deals. All their regular cookies (not iced) are $2.29 each (normally $3.30), including their famous Chocolate Chip, Confetti, and Snickerdoodle cookies. Regular 6-inch three-layer house cakes will also be available for $29 (normally $34).
Address: 254 E Ontario St, Chicago, IL 60611
Address: 1208 W Webster Ave, Chicago, IL 60614