5. Untitled Supper Club
8.4
111 W Kinzie St (btwn N LaSalle St & N Clark St), Chicago, IL
Restaurant · River North · 141 tips and reviews
Amy Graff: Small, unassuming storefront opens into a gorgeously sultry, sexy, dark, and romantic space with a whiskey library to rival the best of 'em. Killer tunes and small plates too.
Jen Marquez Ginn: Their schtick is to emulate a speakeasy, which they do pretty well via the atmosphere and drink selection. Drinks are pricey but worth it. Good spot for date night.
Chicity82: Whiskey me up! Very spacious, great for intimate concerts. Dance floor is fairly large and the DJs are ok
6. 3 Arts Club Cafe
9.1
1300 N Dearborn St (at W Goethe St), Chicago, IL
Café · Gold Coast · 83 tips and reviews
OkCupid Daters' Choice: 3 Arts Club Cafe was voted the Best Instagramable Date Spot by OkCupid users in the first-ever Daters' Choice Awards! Tap Read more for additional date spot categories in Chicago. #daterschoice Read more.
Bianca: A must see in the city. Get ready to wait 60 to 90 minutes during weekends. It’s a beautiful & romantic spot but the food is just ok, nothing special.
ISC Chicago: ROASTED HALF CHICKEN (Garlic Confit, Potato Purée, Natural Jus)
BuzzFeed: The ambiance feels like you've stepped back in time with dark mood lighting, jazz music, and an almost a mysterious yet romantic feel. Read more.
Sarah Eckstein: Best restaurant in all of Chicago. Dinner, drinks, service, all things exceed my expectations. What are you waiting for?
Crain's Chicago Business: The wine cellar is stocked with Old World vintages, while the signature cocktails start with powerful brown spirits. Read more.
9. Maple & Ash
8.8
8 W Maple St (at State St), Chicago, IL
Steakhouse · Near North Side · 60 tips and reviews
Eric C: Beautiful interior, romantic and hip decor. Food was very very good. If you're up for a splurge get the "I don't give a f..." Chef's 5 course meal.
Christine Gobran: This was delicious!! Caesar salad,bone in filet were amaaaaazing
Alex Flis: Filet mignon was to die for. Save room for dessert and get the sundae tower😍 literally the best
11. The Kitchen
8.8
316 N Clark St, Chicago, IL
American Restaurant · River North · 22 tips and reviews
Bianca: I loved their food, the meatballs are a must! Try a seat on the patio - is romantic! 😎
Myka England: The food is awesome, that goes without saying, Anything ‘slagel farms’ burger- tartare- steak is ... soooo good. As a T girl, everyone here is so supportive and sweet ;-)
Dan Stamer: Get the Sticky Toffee Pudding!
12. Travelle
8.5
330 N Wabash Ave, Chicago, IL
Lounge · Near North Side · 37 tips and reviews
Reserve: Travelle Kitchen + Bar is a sophisticated lounge and restaurant, offering stunning river views. Enjoy a romantic meal with their prix fixe menu on Saturday or Sunday for $185 per couple. Read more.
Terri P: Amazing food! Great place to try for restaurant week - lunch. I will go back
Brock Wanless: If having brunch, order the signature Travelle Benedict for a delicious combo of eggs Benedict, lobster, spinach, and potatoes!
13. Prosecco
8.5
710 N Wells St (at W Superior St), Chicago, IL
Italian Restaurant · River North · 30 tips and reviews
Edward Henry: Great for a date night
Mike: The food and service is perfect every time. Best Italian in River North.
Crain's Chicago Business: For a more substantial starter or light entree, pick from the carpacci menu of air-dried beef filet, beef tenderloin or duck, thinly sliced and garnished sparely. Read more.
14. The Comedy Bar
8.3
500 N La Salle Dr (btwn W Illinois St & W Grand Ave), Chicago, IL
Comedy Club · Streeterville · 16 tips and reviews
Mingle Around Matchmaker: Cheap but classy date spot. Xoxo
Tonya McSwain: Cool, intimate setting to hang out and have a laugh.
The Comedy Bar: Don't break the bank on your next date night! Treat your special someone to some great laughs, food, and drinks - at an affordable price!