Rocco Smith
Chicago is the third-largest city in the United States, so you can bet there are some great bars to check out.
Whether it is the end of a long day of work or you want to relax after sightseeing, going to a Chicago bar brings a lot of culture and fun to your day.
This list contains bars from all over the city, so you will not have to travel far to get to one. Here are my picks for the best bars in Chicago.
The Green Mill
4802 N Broadway, Chicago, IL 60640
Phone: 773-878-5552
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The Green Mill does not double as a breakfast place. They have late hours in the afternoon and evening, with live music on some nights.
They have specific bands for specific nights. For example, they will feature bands that play dance music on Tuesdays and Thursdays, allowing you to get up and move for a bit.
Otherwise, live music plays from 8 p.m. to midnight. Keep in mind that the Green Mill does not serve food, and they do not take cash.
Hopleaf
5148 N Clark St, Chicago, IL 60640
Phone: 773-334-9851
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Hopleaf, located in Andersonville, looks like a regular bar, but the dining options have a distinct Belgian flavor.
You can try their famous mussels and frites alongside one of the 68 beers on top and in-bottle, though the menu does change every season.
You may even find some new house beers crafted at Illinois distilleries. Hopleaf also stays open every day, and they take reservations if you crave some Belgian atmosphere, which is open, friendly, and warm.
So while you eat and drink, you can enjoy the different Belgian signs and posters on the walls.
Scofflaw
3201 W Armitage Ave, Chicago, IL 60647
Phone: 773-252-9700
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In Chicago’s Logan Square neighborhood, Scofflaw is a great place to visit when late-night gin cravings hit.
It is a great mix of comfort and sophistication since the dining salon has a Victorian-era style, while the bar area lets you grab a beer or a shot. On the whole, I would describe it as “cozy vintage.”
Plus, if you stay until midnight, you might snag a few fresh-baked cookies, which is my favorite part. I enjoy sitting on the cocktail patio on a warm day, but coming here when it is a little later and the lights are low is quite relaxing.
Sportsman’s Club
948 N Western Ave, Chicago, IL 60622
Phone: 872-206-8054
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Sportsman’s Club mixes the sophisticated with the affordable, although the atmosphere is a touch more rustic.
Taxidermied animals are hanging on the wall, making it feel more like a hunter than a sportsman’s club, but that is just me.
There is an outdoor patio if you stop by while walking your dog. However, I like the inside better, since checkerboards are etched into each table.
Sometimes I like to bring my chess set and play with a friend while we enjoy a drink. Plus, the vintage wood tables and art deco lighting make you feel right at home.
The Hideout
1354 W Wabansia Ave, Chicago, IL 60642
Phone: 773-227-4433
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The Hideout goes as far back as 1934, where workers used to meet for beer and eggs and play games.
Before it became a legal restaurant and bar, it used to be a “hideout” for undocumented workers and people who wanted to drink in secret during Prohibition.
Nowadays, the Hideout involves many of the same activities: drinking, playing games, and enjoying music, and draws workers from all over the city.
Its industrial feel, and the factories surrounding it, give it an authentic city flavor. You can see which stand-up comedians and musicians are performing on their website above.
The Violet Hour
1520 N Damen Ave, Chicago, IL 60622
Phone: 773-252-1500
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Walking into the Violet Hour makes you feel like you are about to watch a 1920s murder mystery or scandal unfold.
Do not worry, this speakeasy-themed place is truly sophisticated, with a shaken and stirred cocktail menu with some adorable names, like Little Black Dress and Diamond Rose.
You can get reservations for the patio and indoor eating area, but the bar is first-come-first-serve.
It is more of a place to drink than eat but is great for a date night since the space and lighting are so intimate. The drinks are pretty strong, of course, so pace yourself.
Cove Lounge
1750 E 55th St, Chicago, IL 60615
Phone: 773-684-1013
The Cove Lounge is a great dive bar stop for your next visit to Hyde Park. They have plenty of games to play while you enjoy your drinks, like darts and bowling, plus a jukebox to play your favorite song.
I like to go there if I need a little personal time or am in the mood to bowl with a friend. Their tap selection is a little small, but they luckily have many bottled beers.
Although it markets itself as a cocktail lounge, it is more casual than that, especially since they only take cash. Fortunately, there is an ATM inside.
Delilah’s Chicago
2771 N Lincoln Ave, Chicago, IL 60614
Phone: 773-472-2771
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Delilah’s prides itself on its music scene, with a different kind of music playing most nights. Similarly, they have over a thousand beers and spirits to sample while sampling the music, especially oldies or punk.
You might even catch an art opening, a film screening, or other special events. The hanging sign for the bar is pretty striking since the cartoon looks just like the Evil Queen from Disney’s Snow White and the Seven Dwarfs.
You may especially like Delilah’s if you are a whiskey fan. They have a binder full of whiskey options, which may seem overwhelming, but it is truly a treasure trove.
Kumiko
630 W Lake St, Chicago, IL 60661
Phone: 312-285-2912
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We have our first Japanese-themed bar, where Japan’s tastes and spirits (pun intended) come in full swing.
The place is low-lit and intimate at nighttime, with a full bar and lots of sitting space for enjoying Japanese drinks and cuisine.
The component flights are great to try since Kumiko’s creator Julia Momosé put them all together, putting a different spin on traditional Japanese saké.
However, there are exciting drinks you may not expect here, like the New Wave cocktail, which has hints of curry.
If you like spicy drinks, it is surprisingly delicious. Kumiko is pretty popular, so make reservations.
Map Room
1949 N Hoyne Ave, Chicago, IL 60647
Phone: 773-252-9351
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The Map Room’s interior is pretty cool, with international flags hanging from the ceiling and cutouts of every country spread over the walls.
The beer selection also includes selections from over the world, catering to the traveler in all of us. Although the Map Room does not have its own kitchen, you are allowed to bring your food to enjoy with your drink.
They are also open every day except Thanksgiving and Christmas, so you can count on their friendly service whenever you need them.
You can sign up for their Beer School with Chicago brewer Greg Browne at $25 a ticket.
Maria’s Packaged Goods and Community Bar
960 W 31st St, Chicago, IL 60608
Phone: 773-890-0588
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If you need to pick up some small items before heading home, Maria’s has you covered. They serve pints of yummy beer and have packaged items for sale on the way out.
Plus, Maria herself greets you at the door. While they do not have a kitchen, they encourage customers to order food from other surrounding restaurants for delivery to Maria’s.
The beer selection includes a lot of Midwestern favorites for relatively cheap, too. The interior is not too much to write home about, but it is still cozy, and the staff is friendly every time I go there.
Matchbox Bar
770 N Milwaukee Ave, Chicago, IL 60642
Phone: 312-666-9292
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The Matchbox Bar is supposedly the smallest bar in Chicago, but it comes with no small amount of charm. The lighting is a soft, calming red, with plenty of beers on top behind the counter.
They have even expanded their seating outdoors. There is a cozy white porch with tables underneath the roof and plants and fairy lights hanging all over.
It is one of my favorite places to hang out on a warm night, especially when I am on a date. The Matchbox Bar is open until 2 am every day, except Monday when they close at 11 pm.
Osito’s Tap
2553 S Ridgeway Ave, Chicago, IL 60623
Phone: 773-277-8117
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Many people say you can get the best margarita in Chicago at Osito’s. They are not far from the truth since their margaritas are great.
Osito’s is an excellent place for a quick Mexican-themed brunch, although it is a bit pricier. The Sunshine Mimosa and the omelet are my favorites.
Like any bar worth its salt, they also have some creative cocktails and good craft beer options. There is almost nothing more relaxing than a Mexican cocktail and tapas, and Osito’s chill atmosphere helps create that effect.
Rainbo Club
1150 N Damen Ave, Chicago, IL 60622
Phone: 773-489-5999
Rainbo Club is not much to look at from the outside, but on the inside, it feels old-fashioned but cozy with the classic bar stools and checkered floor.
It used to be a cabaret building back in the day, which is fantastic to imagine. There is a photo booth in the corner if you want to have some fun with a camera.
Not to mention the few classic arcade games and pinball machines. There is not a lot of sitting room, so you may need to come closer to opening for a seat.
Once again, we have a cash-only venue, so come prepared.
Sidetrack
3349 N Halsted St, Chicago, IL 60657
Phone: 773-477-9189
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Sidetrack is an experience of a gay bar, with lots of lights and space to accommodate plenty of people.
It has been open since 1982 and has won tons of accolades, such as Most Popular Bar in Illinois and Most Visited Bar in Chicago.
The drink menu changes with the seasons, but they are always colorful and delicious. Luckily, the place is open 365 days a year, so you have plenty of chances to explore the vast space, which spans eight storefronts.
This is the one bar on this list with a legitimate dance floor.
Final Thoughts
While there is plenty to do in Chicago, it is always fun to go to a bar to enjoy a drink or grab a quick bite.
That makes it impossible to talk in one place about all the best bars in Chicago. I hope you go to Chicago and discover some other amazing bars for yourself.
If you really want to treat yourself, be sure to check out these incredible michelin star restaurants around the city as well!
So, did we leave a restaurant out of this list? Make sure you leave us a comment and we’ll check it out!
