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Cheers to that! | Top 5 Bars in Chicago

When you think about drinking in Chicago, you're probably thinking sports bar. While there most certainly are plenty of great sports bars in Chicago, there are also a lot (and I mean a LOT) of really great cocktails bars, speakeasys, wine / champagne bars - you name it! When it's freezing cold 9 months out of the year... you might as well drink! So cheers to that!

Here is my (first of many) list of Top 5 Bars in Chicago!


In Scrolling Order:

  1. Longman and Eagle (credit: Chicago Tribune)

  2. The Violet Hour (credit: Architecture Digest)

  3. Three Dots and a Dash (credit: Three Dots and a Dash)

  4. The Aviary (credit: The Aviary)

  5. The Office (credit: Architecture Digest)


Longman and Eagle

I hated Bloody Marys. That is... until I got to Chicago. Chicago's Bloody Mary game is on a whole different level. The range of garnishes is endless - from oysters (The Savoy) to mini Chicago Dogs on top (Jimmy Green's) to everything else... literally there are at minimum 18 garnishes on the Bloody Mary at Rockit Bar. But if you want a really really good Bloody Mary that isn't a full-on meal - go to Longman & Eagle. You probably know about Longman & Eagle for its food, but it's the Bloody Mary that should earn itself a spot on your list. And if you want something really special - try ordering a Bloody Lawrence. Longman and Eagle is known for their whiskey selection - so might as well put it to good use in a Bloody Mary!!!

Velvet Hour

The Velvet Hour is one of my favorite speakeasys in the world. Chicago - the city notorious for Prohibition bootleggers in the 1920s - naturally has its own great speakeasy. The drinks are amazing, and the décor is good enough to be in Architecture Digest. To quote them: "The single lightbulb designating the entrance of the Violet Hour is a nod to the secrecy of the bygone era. Inside, patrons are treated to a marble bar that spans the length of the room, as well as crystal chandeliers and hardwood floors." Regardless if you're going for the architecture or the really really good, classic cocktails... just go!

Three Dots and a Dash

Where The Violet Hour is clean and crisp... Three Dots and a Dash is just pure fun. You never know when the bartender will light a drink on fire at the bar! Three Dots and a Dash is probably the most well-known tiki bar in Chicago. Hidden away in an alley, you're transported to a tropic island the moment you head downstairs. Anything and everything you have ever imagined about a tiki-bar - it has it! All the gimmicks, without giving up any quality on the drinks! If you happen to be in Chicago during the winter and can't afford to fly to Hawaii... try escaping for a little bit at Three Dots and a Dash.

The Aviary

The Aviary is the best known bar in Chicago - hands-down. It has won every single bar award under the sun - Top 50 Best Bars in the World, James Beard, Food & Wine... even Forbes. The Aviary is part of the Alinea Group - the brainchild of Grant Achatz and his team. It specializes in unique, modern cocktails that are really really good. On top of that... each cocktail is an unforgettable experience (I think about the old-fashioned like cocktail that came inside a frozen ice sphere, you then use a "slingshot" to break the sphere and let the cocktail and ice fall into the glass... what?!?!)!

The Library

You are pretty darn special if you can get a reservation at The Aviary. But if you get an invite down to The Office... that is something else. "An unmarked door at chef Grant Achatz's experimental cocktail bar the Aviary leads to the Office, a clubby—and very exclusive—speakeasy with 14 seats. The Office focuses on reinvented classics, rather than the Instagram-worthy creations upstairs. Admission is by invitation only, so be extra nice to your server at the Aviary." I had gone once - random weekday, first reservation. I had to text a random number I found online, and took their first (and only) available spot. It was incredible. We went downstairs and was given a book of poetry. There were five or six short poems.. and we were asked to pick the one that spoke to each of us the most. Then the server asked us for a base liquor of choice. We each picked something different, and LOVED it. There were five of us, and we each tried the others' drinks (obviously this was pre-COVID) and we STILL loved our own drink the most. I'm not sure what magic was in that book of poems... but it was definitely an experience to remember!



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