Best Chicago Spots for Third Wheel-ing a Date
via Ina Mae Tavern
While it may not officially be “cuffing season,” warm weather is upon us and if you’re in between summer flings, have a boo that lives out of town, or just don’t care to be tied down, you’re inevitably going to be caught as the third (or fifth) wheel in a group of couples. Summertime Chi is no doubt the best time to embrace being single, so follow along as we list our all time favorite spots to third wheel….
Ina Mae Tavern {1415 North Wood Street, Chicago; 773.360.8320}
When it comes to warm weather in Chicago, there’s nothing better than sipping on your favorite cocktails, biting into delicious food, and listening to live music. If your vibe skews towards southern food + funky vibes and good music, head over to Ina Mae Tavern in Wicker Park. Bring your coupled up besties and bite into menu items like Nola Hot Sausage Sliders and Hush Puppies.
via Cafe Ba-Ba-Reeba
Cafe Ba-Ba-Reeba! {2024 North Halsted Street, Chicago; 773.935.5000}
If you’re third wheeling with two of your besties that love to share, head to Cafe Ba-Ba-Reeba in Lincoln Park. Since 1985, this well-loved tapas bar has been serving up authentic Spanish cuisine. No matter if you want lighter bites like Garlic Potato Salad or House-Marinated Spanish Olives or you prefer something a little heartier like Grilled Beef Skewers, there’s something for everyone here.
Daisy's Po-Boy and Tavern {5215 South Harper Avenue, Chicago; 773.675.8767}
Looking for something different than the same old burger and fries? Try Hyde Park’s Daisy's Po-Boy and Tavern. If you’re looking for a fun way to spend your Saturday, sip on the Chatham Artillery Punch while you wait for your meal of Barbeque Gulf Shrimp Po’ boys or Fried Chicken + Biscuits. The casual environment is perfect for a group!
Clever Coyote at The Robey {2016 West North Avenue, Chicago; 872.315.3063}
Let’s be honest, nothing says “summer vacation” quite like a tiki bar. Clever Coyote is located on the second floor of The Robey Hotel and they’re pulling out all the stops for this classic rock meets 90s nostalgia. Enjoy drinks like the Black Hole Sun (mezcal, tequila, roasted grapefruit syrup, lime, and activated charcoal) or the Suckerpunch (a clarified gin milk punch with pineapple and lime topped with a lollipop).
via bar avec
bar avec {640 North La Salle Drive, 8th Floor, Chicago; 312.736.1740}
Pull out your favorite warm weather outfits, throw on your sunnies, and bring your favorite couples to enjoy an airy roof deck that defines summertime Chicago. bar avec has all things bright and seasonal when it comes to their Mediterranean bites and creative cocktails, but the views are where this spot really shines. Don’t miss out!
Big Star {Multiple Locations}
This one should be no surprise! A visit to Big Star is a fun (sometimes rowdy) way to spend a night with friends. The ever-popular honky-tonk-esque hangout serves up the perfect country combination of beer and bourbon alongside tacos and nachos. Do a group date, meet your significant other’s friends, or just hang with your bestie and your date.
Pompette {1960 North Damen Avenue, Chicago; 773.799.8072}
For a low-key kind of night, Pompette is the perfect choice. This neighborhood cafe and wine bar comes packed with small items like olives and cheeses to share tapas style and larger entrees like Grilled Texas Shrimp Risotto and CDK Ranch Hanger Steak. This is a great spot to meet the boyfriend or girlfriend for the first time - Grab a drink with them, then stay to debrief over dinner afterwards with your friend.
By Madison Freeman | Special Correspondent