2. 3 Arts Club Cafe
9.1
1300 N Dearborn St (at W Goethe St), Chicago, IL
Café · Gold Coast · 83 tips and reviews
C Rey: Ah yes, the comfort of RH furniture, design, and ambiance in the confines of a swanky Streeterville building. The café menu is decent but let's be honest, you want to come for the experience.
daisy liu: Very fancy place. Healthy food. Good view.
Noha Qari: The ambience is beautiful and fancy
4. Maple & Ash
8.9
8 W Maple St (at State St), Chicago, IL
Steakhouse · Near North Side · 60 tips and reviews
Eater: This swanky New American Steakhouse offers an excellent selection of wines and cocktails. No matter what you order on the menu, we recommend trying a side of their spicy onion rings! Read more.
Eater: Maple & Ash is a seriously swanky spot in the Gold Coast with an all-star staff excellent people-watching, and standout wine and cocktails. Read more.
Cole Kennedy: A transcendent dinner experience. Sublime steaks, perfect sides (get Brussels sprouts), thoughtful wine program, and comforting desserts. Did I mention the swanky atmosphere and world-class service?
5. Alinea
9.1
1723 N Halsted St (btwn W North Ave & W Willow St), Chicago, IL
Molecular Gastronomy Restaurant · Lincoln Park · 142 tips and reviews
Michael Tran: Bloody fancy!
Tasting Table: For an incredible fine dining experience, reserve a table at Alinea and enjoy a unique interplay of tastes, aromas, textures and sights. Read more.
Nate Ellis: Very fancy but more about the experience around the food than the food itself.
Stefanie: Cool spot on Millennium Park. Several spots within for food/drinks. Skip the more formal Cherry Circle Room & head to Cindy's for great shared plates (meatballs!) and a stunning view.
R N: Great place to get formal or informal drinks...
Vivian Ramirez: Food or cocktails here pretty standard, nothing fancy or special. The winner here is the awesome space, friendly staff, and perfect location to regroup at some point over cocktails.
9. Chicago Q
8.7
1160 N Dearborn St (at W Division St.), Chicago, IL
BBQ Joint · Near North Side · 167 tips and reviews
Myra Rubin: BBQ happiness :-) Loved the Brûlée'd Mac&Cheese. Really beautiful restaurant, upscale yet comfortable.
Bullfrog & Baum: Pulled pork, mac n' cheese, and killer bloody mary's are go-to's at this upscale BBQ joint. Can't decide on your smoked meat? Go for the BBQ Flight.
Time Out Chicago: Upscale touches include Kobe brisket and “competition” ribs. Spare ribs (the standard, not the $10-more-expensive “competition” slab), proved tender, with a good dose of smoke and a slightly sweet rub Read more.
10. Steak 48
8.9
615 North Wabash Avenue (Wabash and Ontario), Chicago, IL
Steakhouse · Near North Side · 37 tips and reviews
Kevin M. McNally, CMP: There are many steak offerings here in Chicago. I love the upscale feel, service & the great menu offerings. Reservations a must. Staff is friendly and you won't go home hungry. Full. Very Full.
Irene Tjahjadi: Plain shirt only here or business formal attire
Stacey Etchison: Just WOW! Appetizers are OUT OF THIS WORLD. Fantastic fancy date night spot.
11. The Aviary
8.7
955 W Fulton Market (at Morgan St.), Chicago, IL
Cocktail Bar · Fulton Market · 174 tips and reviews
Spike: Expertly crafted cocktails and a quiet night out; go here for the upscale treatment.
Erik Rowley: Inventive drinks, seductive atmosphere. Perfect place for dates or group get togethers, don't recommend for single explorers. In the Rocks is a classy riot, use a sling shot to break the ice, bourbon.
Adrian Phillips: This is an experience. It’s like fine dining for cocktails. Each drink you order is unique. The old fashioned that comes in an ice cube, the oatmeal one that comes in an inflated plastic bag. Worth it
13. Gilt Bar
9.1
230 W Kinzie St (at N. Franklin St.), Chicago, IL
Lounge · River North · 186 tips and reviews
Stephen Spiewak: Cool ambiance. Upscale, but didn't feel too pretentious. Menu is very reasonable, and great for sharing. Definitely get the roasted garlic/olive oil appetizer.
Thrillist: GB’s got a 30-40 bottle global wine list, 12 beers on tap ranging from Maudite to $2 PBR in a frozen goblet. To be fancy, nab a sig cocktails made with local vodka Death's Door. Read more.
Erin Burke: Truffle Pasta was awesome. Very swanky atmosphere
14. Cherry Circle Room
8.9
12 S Michigan Ave (at E Madison St), Chicago, IL
American Restaurant · The Loop · 45 tips and reviews
Redeye Chicago: This elegant restaurant feels like straddling different points in history, without any windows, a curved wooden bar, and slick tufted booths. The menu boasts both craft cocktails and creative food. Read more.
Teddy: Classy joint. The room itself is gorgeous, the cocktails are delicious, and they have some badass matchbooks at the front.
Lucille Fisher: Very retro-as in Don Draper & his crew may come any moment. Beautifully restored, like the rest of the Chicago Athletic Association.Breakfast,lunch, dinner. Great for date nights. Eclectic menu.
Kelly Nash: Feels similar to a speakeasy. Great cocktails in a classy setting. Only one unisex bathroom though, which seems a little crazy.
Jen Kane: Yes it's pricey, but this is the kind of place you come to for a fancy drink not a $2 PBR. Great cool vibe,interesting cocktails(order the Weston), oh and don't forget the Cracker Jacks!
Kathryn Jill: Swanky atmosphere