The Matchbox is one of The 15 Best Places for Fancy Cocktails in Chicago.

1. The Matchbox

8.6
770 N Milwaukee Ave, Chicago, IL
Bar · River West · 73 tips and reviews

Joanna E.Joanna Ericson: Vodka gimlets are the best in the city!!

Cris F.Cris Franco: Must haves: Margarita, Sidecar and Brandy Manhattan.

Adam S.Adam Seger: Localize your Manhattan (which they do amazingly here) with locally made hum in place of the sweet Vermouth

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

2. The Violet Hour

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

Nikol H.Nikol Hasler: Order a Julietta y Romeo- Wonderful gin fizz with champagne. If possible get a seat in the back. It is worth the wait.

Elyse H.Elyse Hudson: The Old Fashioned is to die for!

Rafique J.Rafique Jiwani: The old fashioned here is one of the best I've had but request it to be mixed with Wild Turkey rare breed bourbon for a more potent finish

The Doughnut Vault is one of The 15 Best Places for Fancy Cocktails in Chicago.

3. The Doughnut Vault

8.7
401 1/2 N Franklin St (at W Kinzie St), Chicago, IL
Donut Shop · River North · 144 tips and reviews

Gloria C.Gloria Chin: super popular in the morning & weekends!! go after 10 am for a shorter line. choose between the buttermilk old fashioned ($2.00) or the yeasty glazed ($3.00) doughnuts

Danielle N.Danielle Nash: Buttermilk old fashioned... Straight up out of this world amazing

Christopher F.Christopher Floss: Awesome old fashioned donuts!!! Get there early (especially on the weekend) otherwise they may run out!!! The buttermilk donut is THE BEST!!!!!!!

Firecakes Donuts is one of The 15 Best Places for Fancy Cocktails in Chicago.

4. Firecakes Donuts

9.2
68 W Hubbard St (at N Clark St), Chicago, IL
Donut Shop · Near North Side · 165 tips and reviews

Eric M.Eric Munn: Hands down the best buttermilk old fashioned donut I've ever had

hooeyspewer ..hooeyspewer .: Great doughnuts, but - Seriously excellent buttermilk old fashioned. Also try the doughnut ice cream sandwich. You won't be sorry :)

Erika D.Erika Davis: Ice cream sandwich is good, but I love their old fashion donuts. My favorite donuts place in Chicago so far.

The Whistler is one of The 15 Best Places for Fancy Cocktails in Chicago.

5. The Whistler

8.9
2421 N Milwaukee Ave (at W Fullerton Ave), Chicago, IL
Cocktail Bar · Logan Square · 110 tips and reviews

Brian M.Brian MacQueen: Get here early! That way you can find a spot to sit down and enjoy the seasonal craft cocktails.

Sheriff S.Sheriff Scabs: The best Old Fashioned I've ever had. A whiskey lover's dream come true.

Nick G.Nick G: The best old fashion in the city. The bearded mixologist is a god among men.

Stan's Donuts & Coffee is one of The 15 Best Places for Fancy Cocktails in Chicago.

6. Stan's Donuts & Coffee

8.5
1560 N Damen Ave (at N Milwaukee Ave), Chicago, IL
Donut Shop · Wicker Park · 131 tips and reviews

Laura C.Laura Caputo: Delicious! I had the old fashioned pistachio glazed donut and it was yummy.

Tim M.Tim M.: Chocolate old fashioned donut was amazing! Strawberry ice cream was rich, but tasty.

Jen M.Jen Marquez Ginn: Fantastic donuts. The Lemon Pistachio Old Fashioned and the Buttercream Bismark are my favorites. This place is the only one that rivals Doughtnut Vault for me. They also partner with Popular Pays.

Scofflaw is one of The 15 Best Places for Fancy Cocktails in Chicago.

7. Scofflaw

9.3
3201 W Armitage Ave (at Kedzie Ave), Chicago, IL
Cocktail Bar · Logan Square · 149 tips and reviews

Samantha K.Samantha Kuhn: Cute, vintage atmosphere with helpful and unpretentious servers, what more could you want at a Mixology bar? Enjoy a Diplomat's Daughter and get there at midnight for free chocolate chip cookies.

Kate F.Kate Fifield: KICK ASS BAR. Candlelight makes for a very sexy atmosphere. Excellent, elevated food to match craft cocktails makes for a killer combination.

Caitlin W.Caitlin White: One of the best bars I've been to. One side has a cozy living room feel where you can TALK to people. Great house made cocktails and my boyfriend like their old fashioned. Free cookies at 12!

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

8. The Aviary

8.8
955 W Fulton Market (at Morgan St.), Chicago, IL
Cocktail Bar · Fulton Market · 174 tips and reviews

Thompson HotelsThompson Hotels: Our concierge Samantha at The Sax Chicago says that she was stunned with the Old Fashioned in the Rocks. The presentation of the drink in an ice egg was amazing.

Euclid W.Euclid Walker: Go to the Office & for your second drink, try telling the bartender what you enjoy (e.g scotch with an exotic spicy twist) & let them make you a custom cocktail. Jason made us some amazing drinks!

Chris N.Chris Nickerson: Thos one of the only bars in the world I can get pappy 23 bourbon. If you have never had it or just like bourbon....this is THE bourbon. Also try the old fashion and the potato.. amazing

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

9. Gilt Bar

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

Kevin R.Kevin Ragland: Great meal. Best of my Chicago trip. Get the pot roast, pork belly or any of the homemade pastas and you'll be very happy you did. Also, great craft cocktails.

Dan C.Dan Carroll: Great sazeracs

Munjal M.Munjal Munshi: The Manhattans here are excellent!

Weegee's Lounge is one of The 15 Best Places for Fancy Cocktails in Chicago.

10. Weegee's Lounge

8.6
3659 W Armitage Ave (btwn N Monticello Ave & N Lawndale Ave), Chicago, IL
Cocktail Bar · Logan Square · 24 tips and reviews

Rachel C.Rachel C.: Sloe gin fizz delicious

Time Out ChicagoTime Out Chicago: Owner Alex Huebner says the flicker of a television would spoil the speakeasy vibe of his candlelit bar, where you can enjoy an expertly mixed Sazerac and classic jazz on the stereo. Read more.

Frank B.Frank B.: THE best Manhattan in Chicago. Awesome.

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

11. The Berkshire Room

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

Alex F.Alex Flis: Love how you pick the presentation, and flavors and the mixologists craft you a unique cocktail. Love the concept, I ordered the same options twice and got a different drink each time... So cool

AngelaAngela: Fantastic and eclectic place for a craft cocktail. Cozy with a warm and inviting staff.

Joonas M.Joonas M. 🚴💉: Great old fashioned!

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

12. Cherry Circle Room

8.8
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.

Rob H.Rob Hohmann: Best Manhattan in Chicago (ask for Buffalo Trace) if the burger is on the menu do not pass this up! Service is exemplary!

Andi P.Andi Pepin: Delicious craft cocktails, the duck hash was excellent. The service was great.

The Dawson is one of The 15 Best Places for Fancy Cocktails in Chicago.

13. The Dawson

8.6
732 W Grand Ave (at N Halsted St), Chicago, IL
New American Restaurant · Fulton River District · 96 tips and reviews

Nai W.Nai W: Nice. Great burger. Good pulled pork tacos. Best vodka gimlet in Chicago!

Loren M.Loren Morris: Great deviled eggs with white anchovies and deviled eggs. Great old school Manhattan

Redeye ChicagoRedeye Chicago: The BBQ Bloody offers plenty of kick, blending vodka, Dr. Pepper barbecue sauce, tomato, cheddar, jalapeno and onion. If whiskey's more your style, try the Brunch Manhattan. Read more.

Watershed is one of The 15 Best Places for Fancy Cocktails in Chicago.

14. Watershed

8.4
601 N State St (at E Ohio St), Chicago, IL
Cocktail Bar · Near North Side · 57 tips and reviews

bartend4funbartend4fun: Nice cozy craft cocktail atmosphere. Awesome Bartenders and staff

Abby M.Abby Meixner: My kind of bar, their mixologists take pride and i love everything about the decor and laid back attitude.

ArdvaarkArdvaark: The House Manhattans are absolutely first-rate.

Stan's Donuts & Coffee is one of The 15 Best Places for Fancy Cocktails in Chicago.

15. Stan's Donuts & Coffee

8.6
259 E Erie St Ste 1-100 (N Fairbanks Ct), Chicago, IL
Donut Shop · Streeterville · 46 tips and reviews

Zachary F.Zachary Fuentes: The Lemon Pistachio Old Fashioned and the Blueberry Fritter are my two absolute favorites.

Sarah R.Sarah Ross Matteson: Best donuts in Chicago! Get the Old Fashioned - you will not be disappointed.

Amy R.Amy Robertson: Old fashioned donuts are good but not out of this world