1. The Florentine
7.9
151 W Adams St (at S LaSalle St), Chicago, IL
Italian Restaurant · 52 tips and reviews
Crain's Chicago Business: "She is My Cherry . . . Gimlet" mixes vodka, cherry purée and lime juice; "Siamese Dream" — now off the menu — matched dark rum with pumpkin purée, Grand Marnier and spiced syrup. Read more.
Chicago magazine: The masterpiece is a lamb shank with farro risotto, peperonata, and mint gremolata: dramatic, tender, and unforgettable.
Alicia Bryant: The flan dessert and coffee were excellent. Great atmosphere. Very warm and cozy.
Dan Pyatetsky: One of the most memorable pizzas I’ve had. Everything was surprisingly under-seasoned but it was still excellent. Walk in the Woods tasted great once we added salt, and Where’s Ruby was the favorite.
Christopher Floss: The best #pizza in #streeterville! Over twenty years in the making to perfect their crust. The meatballs are worth a try, too!!!
Magda Brej: We stumbled upon this place after the architecture tour, great thin crust pizza!
4. The Terrace at Trump
7.8
Trump International Hotel & Tower Chicago, Chicago, IL
Restaurant · Near North Side · 52 tips and reviews
hooeyspewer .: Try a Motu Ahe (Cruzan dark rum and mango, papaya, and guava juices) and if you *really* like it, you can order it by the punchbowl.
Christopher Floss: The best views of the #chicago river! Awesome and elegant #rooftop venue.
💋JinkyJane✈✈✈🇺🇸: Fireworks in the summertime on Wednesdays and Saturdays @ 10 pm...Very nice view esp. from The Trump Tower Terrace!
6. The Franklin Room
9.1
675 N Franklin St, Chicago, IL
American Restaurant · River North · 26 tips and reviews
Katie: My go-to spot for anyone - fantastic menu, always excellent service and the music is always on-point. Perfect for dates, family dinners, visitors, or just grabbing $1 Oysters at Happy Hour.
Eric Munn: The shrimp pot pie is outstanding. Great whiskey list as well.
Andy Swindler: $1 oysters from 5-6:30pm. Get some.
10. Mercadito
8.3
108 W Kinzie St (btwn Clark St & LaSalle Blvd), Chicago, IL
Mexican Restaurant · River North · 249 tips and reviews
@MisterHirsch: Must try cocktail ----> b.n.g.t.m. (Big nose goes to mexico) with Herradura Blanco & reposado, dark rum, guava, orgeat, and a touch of fire ... No really, FIRE. :)
Marco Morelli: torrejas de bolillo dessert (creme anglaise soaked mexican bread, vanilla ice cream, cajeta sauce - like french toast with ice cream on top!), Camaron Ceviche and the Toreado Guacamole are must gets.
Michael Caputo: Try the Camaron tacos. It's shrimp, roasted garlic, chipotle mayo, avocado and it's amazing! Read more.
11. Cité
8.2
505 N Lake Shore Dr (btwn Grand Ave & Illinois St), Chicago, IL
French Restaurant · Streeterville · 25 tips and reviews
InterContinental Chicago: Definitely the place to be at sunset. American/French cuisine and impeccable service, right on the lake. Has a small lounge area for those that want to sip a beverage while drinking in the view
Cite Elegant: Come on Wednesday or Saturday nights to watch the fireworks literally come at you from Navy Pier
Cite Elegant: Make reservations 5-6pm to witness the sunset and city alive during your dinner. The lights in the rest. are just dim enough to complement the city view.
Redeye Chicago: This Colombian steakhouse specializes in traditional dishes ranging from arepas (cornbread with cheese and chorizo) to the entrana, a skirt steak doctored up with a secret blend of spices. Read more.
Brian Wesselman: BYOB nights are now Mon to Thurs only. Sun used to be included but no longer.
Food Porn .it: You've got to try the Entraña! It's marinated skirt steak that will stand up to or beat any steak in Chicago. Can you afford to not trust a guy whose name is Food Porn? Entraña is #FoodPornCertified
14. Sixteen
7.1
401 N Wabash Ave (Floor 16), Chicago, IL
New American Restaurant · Near North Side · 62 tips and reviews
@MisterHirsch: Pretty much any cocktail goes great with the view here, but try The Lagoon (light & dark rum, blue curacao, grenadine, pineapple, orange, & lime juice.
Michelle B: Terrace is table service only, but well worth the wait. The hazelnut, chocolate nutella and caramel ice cream mini waffle cones are the perfect sweet treat - they come in a pair perfect for sharing.
TripExpert: This high-end spot still knows fun. "Can a four-star meal begin with fried smelts and end with a Butterfinger bar? My last dinner at Sixteen says yes." -Chicago Tribune on TripExpert Read more.