Chicago is one of the most fun and lively cities in America (even in the wintertime), and with that comes no shortage of incredible bars and restaurants. I explored the ins and outs of Chicago for 10 months, and have come up with a list of the best bars in Chicago (I’m picky, so trust me – these are all excellent).
Below you’ll find 10+ of the best places to go in Chicago based on whether you’re looking for cocktails, a night out, or a wine bar.
If you want to check out the Chicago dining scene, don’t miss: The Best Restaurants in Chicago
The Very Best Bars in Chicago
If You’re Looking for Cocktails…
CABRA
Location: West Loop
Created by one of the top chefs in Chicago, Stephanie Izard, Cabra is the go-to place for drinks on the weekend. It’s the perfect choice if you’re looking for a lively atmosphere, fun appetizers, and beautiful city views. Located on the top of the Hoxton Hotel, Cabra is a Peruvian themed bar/restaurant, and a great place to day drink or sit at the bar for cocktails before heading to dinner.
LAZY BIRD
Location: West Loop
Also located in the Hoxton Hotel, Lazy Bird is the speakeasy in the bottom of the hotel. Because of its popularity, Lazy Bird can get crowded on the weekends with long wait times. I suggest arriving early or trying to sneak in during the week to see what the buzz is all about. Plus, there’s oftentimes live music so you can sip on cocktails while listening to breakout artists who come through town.
MAPLE & ASH
Location: Gold Coast
Maple & Ash is quite the scene and one of the hottest places in the Gold Coast. Its fancy decor, stylish bartenders, and great cocktail menu make it for an excellent place to sit at the bar, sip on cocktails, and people watch (I’ve seen a celebrity or two in there before). There are two bars in Maple & Ash (one when you walk in, and one upstairs), I suggest heading to the bar upstairs to get the full feel of the restaurant.
Pro tip: Maple & Ash serves $30 seafood towers and $10 martinis Monday-Friday from 5pm-6pm. If you want to snag a seat at this coveted time, make sure to show up right at 5pm when the restaurant opens. This only applies to bar seating.
SPARROW
Location: Gold Coast
Sparrow is one of my all time favorite cocktail bars in the city. Not only is it the perfect date spot, but it’s also the perfect spot to cozy up in when the weather gets cold and you need a warm escape. The building has been around since 1927 so it has an old, rustic, speakeasy like feel to it. Sparrow specializes in rum drinks and craft beers.
THREE DOTS AND A DASH
Location: River North
A fun and lively tiki bar, Three Dots and a Dash is a must see if you’re visiting Chicago. The tiki drinks are strong, the decor is on point, and the atmosphere is next level. There are over 200 different types of rum in this Polynesian-island type setting.
If You’re Looking for Late Night/Live Music…
BANDIT
Location: West Loop
Bandit is the place to go if you’re looking for a wild night out. The walls are adorned in all things 90s including old pictures of Britney Spears, Destiny’s Child, and more. At night they have a live DJ, someone playing live music, and table service. It’s high energy and a downright blast.
KINGSTON MINES
Location: Lincoln Park
Kingston Mines is a live blues bar located in Lincoln Park. You have to pay to get in, but I promise its worth it. Open until 4 am, expect a late night out of fun, dancing, and blues when you visit.
ZEBRA LOUNGE
Location: Gold Coast
A smaller, but equally as fun bar to visit is the Zebra Lounge. Zebra Lounge is a piano bar with live music each night; generally catering to a younger crowd. Because it’s small with limited seating, I suggest arriving early if you want to sit down and relax while listening to the live performer.
If You’re Looking for Wine…
ALL TOGETHER NOW
Location: Ukrainian Village
Of the three wine bars listed, All Together Now is by far my favorite wine bar in Chicago (and perhaps in the United States!). Located in Chicago’s Ukrainian Village, I suggest grabbing a bottle of wine and some bites to share with friends, and sit down and take your time. The decor is timeless and the vibe is impeccable. It’s the perfect place to go for day drinking or a bottle of wine before dinner.
CITY WINERY CHICAGO
Location: Chicago Riverwalk
City Winery Chicago on the riverwalk is strictly a summer wine bar. (There is another City Winery open year-round, but I don’t suggest it). Here you can purchase a bottle of wine and sit out on the river, or on the patio near the river. It’s the perfect place to watch the boats sail by.
POPS FOR CHAMPAGNE
Location: Gold Coast
Pops for Champagne has been around since 1982 and not only does it have an impressive champagne list, but also an impressive wine list. Plus there’s often live jazz on the weekends and small plates to munch on while you sip your champagne.
The bar scene in Chicago is ever-evolving. While these are my all time favorite spots, I can’t wait to go back and discover even more of what this incredible city has to offer. If I missed any “must-visit” bars, let me know in the comments below so I can add them to my Chicago bucket list!
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Kylee is a Neonatal Intensive Care (NICU) nurse passionate about making travel affordable and accessible to nurses. Inspiring nurses to travel both near and far, Kylee began Passports and Preemies in 2017 while volunteering in Skopje, North Macedonia as a way to reach nurses and advocate for the prevention of nurse burnout by traveling. Kylee is the original creator of the “8 Day Vacay” – a vacation geared towards nurses who aim to take advantage of the potentially 8 days off between work weeks with no need to use PTO.
