The Violet Hour is one of The 15 Best Fancy Places in Chicago.

1. The Violet Hour

8.9
1520 N Damen Ave (at Pierce Ave), Chicago, IL
Speakeasy · Wicker Park · 255 tips and reviews

JessicaJessica: Very trendy drink spot. Upscale and classy!

Jon D.Jon Du Prey: Great drinks classy place

Caroline W.Caroline Wu: Had the Sunday Best. One of the best cocktails I've ever tasted - incredible. Ambience is dark and private but classy

3 Arts Club Cafe is one of The 15 Best Fancy Places in Chicago.

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 R.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 l.daisy liu: Very fancy place. Healthy food. Good view.

Noha Q.Noha Qari: The ambience is beautiful and fancy

Bavette's Bar and Boeuf is one of The 15 Best Fancy Places in Chicago.

3. Bavette's Bar and Boeuf

9.2
218 W Kinzie St (at N Wells St), Chicago, IL
Steakhouse · River North · 129 tips and reviews

Pauline K.Pauline K: Swanky place

Phillip W.Phillip Wharton: The meatloaf is delicious, the chocolate pie is exceptional, and the atmosphere is cool and classy.

Maryam M.Maryam Malik: #DateNight #SpecialOccasion #FineDining & really good value for the buck . Fancy Ambience & cultured place.

Maple & Ash is one of The 15 Best Fancy Places in Chicago.

4. Maple & Ash

8.9
8 W Maple St (at State St), Chicago, IL
Steakhouse · Near North Side · 60 tips and reviews

EaterEater: 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.

EaterEater: 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 K.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?

Alinea is one of The 15 Best Fancy Places in Chicago.

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 T.Michael Tran: Bloody fancy!

Tasting TableTasting 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 E.Nate Ellis: Very fancy but more about the experience around the food than the food itself.

Chicago Athletic Association is one of The 15 Best Fancy Places in Chicago.

6. Chicago Athletic Association

9.3
12 S Michigan Ave (at E Madison St), Chicago, IL
Hotel · The Loop · 58 tips and reviews

StefanieStefanie: 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.R N: Great place to get formal or informal drinks...

Vivian R.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.

Le Colonial is one of The 15 Best Fancy Places in Chicago.

7. Le Colonial

8.9
57 E Oak St, Chicago, IL
Vietnamese Restaurant · Streeterville · 86 tips and reviews

SuperbSuperb: Vietnamese fine dining? Awesome.We loved the Sup Do Bien and the shrimp-stuffed beignets!

feliciafelicia: pho broth was a little sweet for my taste, and they put all the fixin's in for you. small bowl, fancy place.

MJ C.MJ Cao: Fancy Vietnamese. Not as good as authentic Vietnamese.

RPM Italian is one of The 15 Best Fancy Places in Chicago.

8. RPM Italian

9.0
52 W Illinois St (at N Dearborn St), Chicago, IL
Italian Restaurant · Near North Side · 238 tips and reviews

JohnJohn: Swanky.... just there for drinks but service was excellent

Joseph B.Joseph B.: A fun, classy place to hang out if you can elbow your way to the bar.

AbdulAbdul: Nice classy atmosphere and nice Italian food selections. Bravo!

Chicago Q is one of The 15 Best Fancy Places in Chicago.

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 R.Myra Rubin: BBQ happiness :-) Loved the Brûlée'd Mac&Cheese. Really beautiful restaurant, upscale yet comfortable.

Bullfrog & BaumBullfrog & 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 ChicagoTime 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.

Steak 48 is one of The 15 Best Fancy Places in Chicago.

10. Steak 48

8.9
615 North Wabash Avenue (Wabash and Ontario), Chicago, IL
Steakhouse · Near North Side · 37 tips and reviews

Kevin M.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 T.Irene Tjahjadi: Plain shirt only here or business formal attire

Stacey E.Stacey Etchison: Just WOW! Appetizers are OUT OF THIS WORLD. Fantastic fancy date night spot.

The Aviary is one of The 15 Best Fancy Places in Chicago.

11. The Aviary

8.7
955 W Fulton Market (at Morgan St.), Chicago, IL
Cocktail Bar · Fulton Market · 174 tips and reviews

SpikeSpike: Expertly crafted cocktails and a quiet night out; go here for the upscale treatment.

Erik R.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 P.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

Tous Les Jours is one of The 15 Best Fancy Places in Chicago.

12. Tous Les Jours

8.7
2144 S Archer Ave, Chicago, IL
Bakery · Armour Square · 4 tips and reviews

Dan R.Dan Richardson: Good mix of fancy pastries, pretty cakes, macarons, bread. Tasty and affordable

AlisonAlison: Insanely fancy pastries and they are all so delicious!

ISC C.ISC Chicago: Modern bakery in Chinatown

Gilt Bar is one of The 15 Best Fancy Places in Chicago.

13. Gilt Bar

9.1
230 W Kinzie St (at N. Franklin St.), Chicago, IL
Lounge · River North · 186 tips and reviews

Stephen S.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.

ThrillistThrillist: 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 B.Erin Burke: Truffle Pasta was awesome. Very swanky atmosphere

Cherry Circle Room is one of The 15 Best Fancy Places in Chicago.

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 ChicagoRedeye 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.

TeddyTeddy: Classy joint. The room itself is gorgeous, the cocktails are delicious, and they have some badass matchbooks at the front.

Lucille F.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.

The Berkshire Room is one of The 15 Best Fancy Places in Chicago.

15. The Berkshire Room

8.5
15 E Ohio St, Chicago, IL
Bar · Near North Side · 71 tips and reviews

Kelly N.Kelly Nash: Feels similar to a speakeasy. Great cocktails in a classy setting. Only one unisex bathroom though, which seems a little crazy.

Jen K.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 J.Kathryn Jill: Swanky atmosphere