London and New York always seem to get all the noise when it comes to raving about cocktails. Lest you not forget, there is a city in the Midwest winning award after award and just might be the most exciting cocktail town in the world. The best bars in Chicago are getting on and doing their thing, without fussing about it.
If you are headed there, don’t miss a chance to try one or more of the Chicago bars on this list. It might be known for its cold and wind, but there’s something super hot about Chicago!
Chicago’s Best Bars
Aviary is not for faint-hearted – these are serious drinks made by serious artists at serious prices. Reservations are mandatory and prepayment is required, even for that reservation.
Aviary is the output of Chef Grant Achatz and his drinks guru, Micah Melton. You are at the Alinea of drinks. No Sex on the Beach or Fuzzy Navel here.
You will, however, find slingshots, smoke and several cocktails that change flavor as ice melts or ingredients macerate. The only flair you’ll find is happening behind the grate in the back where the staff is performing miracles.
It’s all very Emerald city and, of course, a whole lot of fun. It’s a pilgrimage for any cocktail enthusiast. Not surprisingly, Aviary has won the James Beard Award for Outstanding Bar Program.Outstanding Bar.
- The Aviary, 955 W Fulton Market, Chicago, IL 60607
The Violet Hour
Another James Beard Foundation Bar Program award winner, The Violet Hour is the granddaddy of Chicago’s great cocktail renaissance of the early 21st C.
Like Leonardo, Raphael and Michelangelo coming out of Florence, Toby Maloney, owner of The Violet Hour, was one of the lucky few to have worked in a little bar in New York called Milk & Honey. He left the banks of the Hudson to lay claim to Chi-town and that he did.
With its combination of fresh ingredients, friendly staff, and warm interior, it was destined to change the cocktail world in Chicago forever.
A few of the cocktails have become modern classics in their own right, like the The Art of Choke and the Juliet & Romeo – which have never been off their ever changing menu.
- The Violet Hour, 1520 N Damen Ave, Chicago, IL 60622
Owners Shelby Allison & Paul McGee took Chicago by storm when they left Vegas to make Chicago their home. Also on the James Beard Foundation Award playbook as finalist for Best Bar Program, they are the tiki bar that makes one of the coldest cities in the USA glow with warmth. Once the doors open at 5pm, you better claim your spot.
I don’t usually tell people what to drink, but you have to try the Bunny’s Banana Daiquiri. No one uses banana much in a cocktail and I love it. It is one of my favorite cocktails ever and I hear it calling me from London.
- Lost Lake, 3154 W Diversey Ave, Chicago, IL 60647 (Tragically Lost Lake has had to close due to Covid! I’ll let you know if I hear anything.)
The Z Bar at the Peninsula Chicago
The glamorous Peninsula Hotel is home to The Z Bar on the Magnificent Mile, running straight through the heart of Chicago and a magnet for those looking for the poshest spot in town.
The Z Bar answers to all that! Not only is the view spectacular, but the drinks are equal to the view. Many were inspired by the former travels of Vlad Novikov, the bar manager.
One sip of the Parali and you know he set his sights on Greece. It’s rare to find Mastiha, and even rarer to see Tsipouro, outside of Greece, let alone on the same menu.
- The Z Bar at the Peninsula, 108 E Superior St, Chicago, IL 60611
Her reputation preceded her. Juia Momose is one of the most talked about bar-owners in Chicago. I say bar-owner because, after years of bartending, she is the proud owner of Kumiko.
Upon entering, it’s not hard to guess that she was channeling her Japanese heritage when designing Kumiko, a slice of calm is a super frenetic city. Trained at the Aviary, as well as a few other Michelin Starred restaurants, Julie has created a temple to perfection and simplicity.
The cocktail menu reads like the The Tale of Genji with cocktails named Walk Softly and Sunshine Follows. Don’t be intimidated if you forgot to study Japanese poetry in college, there’s also her take on the Old-Fashioned and Manhattan, plus the most glamorous Gin & Tonics you’ve seen!
- Kumiko, 630 W Lake St, Chicago, IL 60661
The Milk Room
Bars talk about being “speakeasy’ style, but The Milk Room was an actual speakeasy. In the early 20th C, members of the very glam Chicago Athletic Association would scuffer behind a wall, where the Milk Room was waiting. With only eight seats, this mini-bar is as popular today as it was in the 1920’s.
You have to pre-book your two-hour experience, then you’ll have access to a menu filled with a selection of “spirit-heavy” cocktails, containing your brown liquids, such as whisky, bourbon and rye. It’s all curated by bartender- extraordinaire Paul McGee. After two hours are up, head to his other place, Lost Lake, for some Tiki fun!
- The Milk Room, 12 S Michigan Ave, Chicago, IL 60603
All the rest that I didn’t have time to do
When you only have three days in Chicago, there are only so many bars and restaurants you can visit and still drink responsibly. I missed out on so many, but that’s just an excuse to return.
Here are a few that are on my list for next time:
- Lone Wolf
- The Ladies Hour
- The Drifter
- Neon Wilderness
- Best Intentions
Where to eat when you’re drinking
You have to eat in Chicago. Some of the best restaurants in America, if not the world, are located here. A few have amazing bar menus and, we’ve made it easier for you to find a good meal to accompany your great cocktails. Just remember, Chicago sized portions are as big as their generosity!
When a bartender suggests you try a restaurant, you are assured that the cocktails won’t disappoint, but how about the food? Well, I am here to vouch for Bad Hunter. One bite into Bad Hunter’s Chicken-Fried Hen-of-the-Woods Sandwich and I was gob-smacked. For those who speak only American-English, it means that I think it is now one of my favorite sandwiches of all time.
This is technically a fried-mushroom sandwich slathered with American cheese, pickles and what they’ve called White BBQ Sauce. It was so tasty it almost made me forget the Red Spritz – a warm mix of cabernet, cinnamon, mace, and orange peel – next to me!
- Bad Hunter, 802 W Randolph St, Chicago, IL 60607
Gibsons Bar & Steakhouse
I want a bit of Gibsons in my life here in London. Although we have great steak houses here with fabulous bar programs, we just can’t transport the atmosphere of a great American legend like Gibsons over the pond. Filled to the brim with locals, the bar was about to explode if one more person entered its hallowed doors. Steak and martinis were what we came for, not to forget the Loaded Wedge on the side.
To be more precise, that would be a Bone-In Strip (24 oz) accompanied with a half a head of Iceberg lettuce smothered with Bacon, Tomato & Blue Cheese. The only drinks that could join in the dance was a Vodka Martini, Dirty with Olives stuffed with Blue Cheese. If you’re going to have it, here is the place!
- Gibsons Bar & Steakhouse, 1028 N Rush St, Chicago, IL 60611
Portillo’s Hot Dog
Portillo’s Hot Dogs are not the culinary wonder that you might be looking for, but it has got to be done! Opened in 1963 and, although they sell more food that just hot dogs now, Portillo’s Hot Dogs are known near and far.
The Jumbo Hot Dog may not be as big as expected, just a tad thicker than then normal one, but it was stuffed to the edges with mustard, relish, celery salt, freshly chopped onions, sliced red ripe tomatoes, kosher pickle and peppers.
We also couldn’t resist the Jumbo Chili Cheese Dog. All washed down with a Root Beer!
- Portillo’s, 100 W Ontario St, Chicago, IL 60654
Revival Food Hall
We got our dose of deep dish pizza at the Revival Food Hall. I love the food hall option these days. You can graze on one or more of each and every option that the food hall has to offer and then go back for more. We went for the pizza then followed it with the cocktail option, all without leaving the building.
On the ground floor of the National Bank of Chicago Building, designed by one of the most famous of Chicago’s turn of the century architects, Daniel Burnham. I feel slightly sorry for him that the food hall didn’t exist then, as the employees of the National Bank might have been able to nip down for a boilermaker before heading back to work.
- Revival Food Hall, 125 S Clark St, Chicago, IL 60603
That’s just four food choices for city bursting at the seams with great food. I highly recommend the 2Foodtrippers Guides to the Restaurants in Chicago for more recommendations.
What to do when you’re not drinking
If you love your modern architecture, then you will be ecstatic in Chicago. The Great Chicago Fire ravaged the city in 1871 destroying almost every building. The architects of the time, named you hear cited over and over again, such as Daniel Burnham, John Root, Dankmar Adler and Louis Henry Sullivan are known as the “fathers of modernism” and embraced the skyscraper whole heartedly.
Thus, Chicago became, and still is, a pilgrimage for architects and architecture-lovers worldwide. We can’t forget the most famous of all, the singular Frank Lloyd Wright whose influence is seen all over the world. He practiced in Chicago’s Oak Park and many of his buildings can be visited, or seen from outside.
- FLW Home and Studio, 951 Chicago Ave, Oak Park, IL 60302
- Unity Temple, 875 Lake St, Oak Park, IL 60301
- Robie House, 5757 S Woodlawn Ave, Chicago, IL 60637
Frank Lloyd Wright is an icon and, if you are in Chicago, the best way to get to know him is to start off by visiting his home and studio. In the heart of Oak Park, is his first studio where he lived from 1889 until 1909.
There, he designed his groundbreaking works, the Robie House and the Unity Temple, two other of the buildings that you shouldn’t miss if you are in Chicago.
The Unity Temple is unmissable really. Named a World Heritage Site and considered one of the most important buildings of the entire 20thC, the Unity Temple is considered to be the first modern building in the America.
One look at the square block of reinforced concrete, you realize it’s unlike any other church you’ve probably seen. Step inside and it’s a wonder of sequence of space that plays with your emotions without you even realizing it until it happens.
The Robie House is on the other side of town in Hyde Park, close to the University of Chicago and Former President Obama’s home. It is the first example of Wright’s Prairie Style of architecture, much copied the whole world round.
At each Frank Lloyd Wright museum, the tours are led by fantastic volunteers, who can tell you a whole lot more than I can about each building. Be sure to book a tour beforehand as they get filled up very fast and it’s the only way you can enter.
A shout out to Gene, our tour guide for the Unity Temple, who was divine. He had just come back after battling a stroke, and was thrilled to be with us. He complained that not enough millennials took the tours – so if you are a millennial – go book a tour!
The Chicago river winds it way smack down in the middle of downtown Chicago. By experiencing Chicago’s famed skyscrapers from the water, you get a completely different perspective on what the pioneers of modernist architecture were trying to achieve. Skyline’s tour guides are most impressive, considering that the tours go every hour, you would think they would be jaded. Ours was not only crazy for architecture, but a stand-up comedian. We were chuckling all the way from the Mies Van Der Rohe to the Jeanne Gang buindings!
Take an Architecture Tour on foot
One more option is to explore architecture in Chicago on foot. No one does this better than the Chicago Architectural Association. They have masses of different tours, from the Historic Treasure of Chicago’s Golden Age to a tour of the “L” Train. Something for everyone!
See Your Favorite Art
Anyone who’s seen Ferris Bueller’s Day Off will remember this scene! It’s a love letter to the Art Institute of Chicago, which is like a warehouse to the best artist that was ever creating from Seurat to Picasso to Chagall to Hopper to Van Gogh. It’s one of the great museums of the world.
Where to Stay When You are in Chicago
Like any great city of the world, there are as many of the best bars in Chicago as there are great to choose from. We stayed on the Magnificent Mile at The Gwen and we couldn’t have been happier.
Upon arrival, they greeted us with a welcome drink – a hot gin toddy which I wasn’t going to turn away. They upgraded us to a suite, which is also fabulous. It ticked all the boxes I demand from a Lush hotel – great service, great towels, great bed and a great bar!
- The Gwen, 521 North Rush Street, Chicago, IL 60611
If you are eager to hear a few stories from the bartenders who are making the drinks, listen to Shelby of Lost Lake, Vlad at The Z and Abe at The Violet Hour on Lush Life Podcast.