If you’re planning a big night out or just want to squeeze in one more stop for the evening after visiting 360 CHICAGO, keep reading. This is your local guide to the city’s most captivating bars. From hidden speakeasies and skyline rooftops to historic institutions and cocktail labs, we're sharing the ultimate lineup of Chicago's coolest spots. Every pick includes insider tips on when to go, what to expect, and more so you can spend less time scrolling and more time sipping.
No list of Chicago’s best bars is complete without CloudBar—Chicago’s highest bar—located 94 stories above the Magnificent Mile right here at 360 CHICAGO. Purchase a Sip & View ticket and get observation deck access with a signature cocktail and souvenir cup to take home. Keep reading to discover more of our favorite spots across the city!
We know what you're thinking—what makes a bar cool? For this guide, we're talking about places with a distinctive vibe, a killer story, and drinks so good you'll be raving about them all week. We’ve scattered them across a bunch of different neighborhoods, with a mix of prices so there's something for everyone.
A Quick Heads-Up: Just so you know, things can change. Rooftop hours, live music schedules, and even wait times can shift, so it’s always a good idea to double-check their websites or social media before you head out.
Getting There: Most of these spots are just a quick rideshare away from 360 CHICAGO and the Magnificent Mile. We've included some tips on reservations and when things get busy. Remember that street parking can be a real challenge on a Saturday night.
Ready for More? For more ways to fill your day, be sure to check out our Plan Your Visit page for hours, directions, and tips that pair perfectly with a night out on the town.
Hidden doors, hushed vibes, and seriously good drinks—these Chicago speakeasy spots bring all the old-school cool with a modern twist.
Why it's cool: Tucked away in a 100-year-old basement, this place keeps things fresh with a rotating cocktail menu printed on vintage tarot cards.
Heads up: It's a small space, so you might have to wait for a spot.
When to go: Hit it up on a weeknight for a laid-back vibe, or on a late weekend for pop-up performances.
Getting there: It's right in River North, so it's a super quick rideshare from 360 CHICAGO.
Price range: $$–$$$
Pro tip: Keep an eye out for nightly showtimes because seats fill up fast.
Why It's Cool: Hidden behind a "very cool wall" inside Pilsen Yards, this place feels like a true secret. With only 16 seats, it's a cozy and exclusive spot with plush velvet banquettes and a small, four-seat bar. They focus on seasonal and classic American cocktails, making it the perfect spot for a date night or a casual night out with a close friend.
Heads Up: With such a small space, you'll want to get there early to grab one of the few seats available.
When to Go: They are open Wednesday through Thursday from 4:30 p.m. to 10 p.m., Friday and Saturday from 4 p.m. to 11 p.m., and Sunday from 3 p.m. to 9 p.m.
Getting There: The bar is located in Pilsen, and because it's hidden, a rideshare is probably your best bet to get there smoothly.
Price Range: $$$ - $$$$$
Why it's cool: Think velvet booths and Moorish decor in a hidden upstairs spot. It feels both dramatic and intimate, with live jazz and burlesque shows to boot.
Heads up: Make a reservation, especially if you're going for a show.
When to go: Thursday through Saturday after 9 pm for the live acts, or earlier if you just want to grab a cocktail and chat.
Getting there: It's in Wicker Park, so a rideshare is your best bet on the weekend.
Price range: $$–$$$
Pro tip: Ask the bartender about their off-menu classic cocktails; you won't be disappointed!
Why it's cool: A neon-lit, Japanese-inspired basement bar hiding beneath Sushi Dokku. They specialize in Japanese whiskies and highballs, with a DJ setting the mood.
Heads up: The entrance can be a little tricky to find, so look for the signs from the host stand.
When to go: Go late on a weekend for a high-energy party or on a weeknight for more space.
Getting there: It’s in the West Loop/Fulton Market area, so a rideshare is definitely the easiest way to go.
Price range: $$
Pro tip: Grab a quick snack from upstairs before the dance floor revs up.
Nothing beats a Chicago rooftop on a perfect summer day or a crisp, clear winter night (hello, heat lamps!), so these downtown spots are always a good time. And if you're thirsty for more, we have a whole other guide to the best Rooftop Bars in Chicago.
Why it's cool: You get incredible, sweeping views of Lake Michigan and Millennium Park from the top of the Chicago Athletic Association. They're also famous for their seasonal punch bowls and chic, open-air terrace.
Heads up: Walk-ins are an option, but expect a line around sunset during the busy season.
When to go: Hit it up in the late afternoon for some awesome daylight views, or go after dinner to see the city lights sparkle.
Getting there: It's just a quick rideshare from 360 CHICAGO.
Price: $$–$$$
Why it's cool: This place is famous for its tiered terraces overlooking the Chicago River. It’s the perfect spot to snap that classic postcard shot of the Wrigley Building and the bridges.
Heads up: They have a host-managed line and a smart-casual dress code, so don’t forget your ID.
When to go: Try to go on a weekday during golden hour for the best light and fewer crowds.
Getting there: It’s a super easy walk from the Magnificent Mile or a short rideshare.
Price: $$–$$$
Why it's cool: Get ready for a seriously luxurious experience. This rooftop offers sophisticated cocktails and a cosmopolitan vibe right off Michigan Avenue.
Heads up: Make a reservation if you can. They have great inside seating, too, which is a perfect backup if the weather turns.
When to go: It’s a great spot for an early evening cocktail before dinner or a late-night drink after a show.
Getting there: Just a few minutes from 360 CHICAGO by rideshare, or a nice little walk if you're up for it.
Price: $$$
Pro tip: For the ultimate sky-high experience, start your evening at CloudBar at 360 CHICAGO. You can sip on local craft flavors while taking in panoramic views from 1,000 feet up before you head to your next stop.
Looking for bars with a story? These Chicago legends are like time machines, serving up a slice of history with your drink. Think wood-paneled walls, jazzy secrets, and century-old vibes.
Why it's cool: This place is a true Chicago classic. Step inside and you'll feel the Al Capone-era history, surrounded by glowing neon and live jazz almost every night.
Heads up: Bring some cash for the cover charge on certain nights, and remember that seating is first-come, first-served.
When to go: Late weekend sets are when the energy is at its peak, while weeknights are great for really soaking in the music.
Getting there: It’s in Uptown, so a rideshare or the "L" train is your best bet.
Price: $–$$
Pro tip: Grab a seat near the stage to get the full throwback experience.
Why it's cool: A Chicago institution since the 1800s! This spot is all about classic German food, house-brewed beers, and a historic stand-up bar.
Heads up: It's perfect for groups or an early evening get-together.
When to go: Try to go in the late afternoon to avoid the post-work crowd.
Getting there: It's right in the Loop with easy access to public transit.
Price: $–$$
Why it's cool: Dimly lit and delightfully old-school. With its colorful, quirky art and no-frills attitude, it's the perfect mix of a classic dive and a local icon.
Heads up: Service is straightforward, so cash is the fastest way to pay.
When to go: It's the quintessential late-night stop after dinner in the neighborhood.
Getting there: It's in Old Town, just a quick rideshare from 360 CHICAGO.
Price: $
Why it's cool: This bar has a kind of creaky, vintage charm that you just can't fake. Think old signs and a vibe that feels like it’s been there forever (because it has!).
Heads up: It can get pretty busy before and after dinner.
When to go: Go for a late lunch or an early evening drink to snag a spot at the bar.
Getting there: It’s centrally located in River North.
Price: $–$$
Chicago’s LGBTQ+ scene is famous for being super vibrant and welcoming, no matter where you go. These bars strike the perfect balance between great drinks, friendly service, and a party you won't want to leave.
Why it's cool: This huge, multi-room video bar is a Chicago legend, known for its themed nights, epic singalongs, and massive crowds ready to have a good time.
Heads up: Lines can get long on weekends, so have your ID ready.
When to go: Weeknights are perfect for a casual hang, while Sundays and event nights bring some major energy.
Getting there: It's in the heart of Northalsted, and you'll definitely want to plan on a rideshare for weekend trips.
Price: $–$$
Why it's cool: A true classic. This spot is always buzzing with a mix of locals and visitors, and you can count on a lively dance floor and incredible drag shows.
Heads up: The shows and events change nightly, so check their schedule before you head over.
When to go: After 10 pm on Thursday through Saturday is when the party really gets started.
Getting there: It's on the same block as Sidetrack, making it super easy to bar hop.
Price: $–$$
Why it's cool: This intimate, Black-owned cocktail bar is all about a warm, inclusive vibe and expertly crafted drinks. It's a true neighborhood gem.
Heads up: It's a smaller space, so you might have to wait for a spot.
When to go: Arrive early if you want to snag a seat, or head in later for a lively community feel.
Getting there: Located in Andersonville, a rideshare is your best bet.
Price: $$
Why it's cool: This spot has been a neighborhood staple forever. It’s got awesome art on the walls, a super friendly crowd, and DJs spinning on the weekends.
Heads up: There's an adjacent restaurant, so you can grab some food before you start your night.
When to go: Late on Friday and Saturday for the full party vibe, or on a weeknight if you're looking for a chill spot to chat.
Getting there: It's in Uptown, and you'll find it close to the lakefront.
Price: $–$$
Looking for a place where the music is as cool as the drinks? These Chicago bars are keeping the city's incredible blues tradition alive, one nightly set at a time.
Why it's cool: This legendary spot is a blues lover's dream. With two stages and a rotating lineup of bands, it's the perfect place to get a late-night blues education all under one roof.
Heads up: There's a cover charge, and it's 21+. But don't worry; the lines move fast.
When to go: Hit it up on the weekend for those late-night sets to get the full, unforgettable experience.
Getting there: It's in Lincoln Park, so a rideshare is the easiest way to go.
Price: $–$$
Why it's cool: This is the club founded by the blues icon himself! You’ll find incredible touring artists, local heroes, and a wall of music memorabilia that tells the story of the blues.
Heads up: Shows are often ticketed, so you'll want to reserve your spot ahead of time, especially for bigger acts.
When to go: Weeknight shows are great for a more relaxed, seated experience, while weekends are packed with high energy.
Getting there: It's in the South Loop, an easy trip from the city's museums and hotels.
Price: $$
Why it's cool: A family-run spot that’s as intimate as it is authentic. This place has a loyal following and some serious blues cred.
Heads up: They usually have tickets for shows, and the doors open early.
When to go: Thursday through Saturday evenings are the best time to catch a show.
Getting there: It's located in Logan Square, so you can easily get there by rideshare or the "L" train.
Price: $–$$
These spots are where the magic happens. They're all about next-level techniques, wild ingredients, and concepts that turn a simple drink into a full-on experience.
Why it's cool: This is a place for serious cocktail lovers. They serve up Japanese-inspired drinks with flawless presentation and hospitality that makes you feel instantly at home.
Heads up: Reservations are a good idea. The vibe is chill and slow-paced, so you can really savor the moment.
When to go: Early evening or late at night for a perfect, intimate experience.
Getting there: It's right in the West Loop, an easy rideshare away.
Price: $$$
Why it's cool: This is more than a bar—it’s a theatrical, bucket-list experience. Their progressive cocktails are served in curated courses, making every sip a show.
Heads up: Reservations are a must. If you want a taste of the action without the full commitment, try the lounge for a lighter menu.
When to go: Bookings for early evening slots go fast, so plan way ahead!
Getting there: Located in Fulton Market, it gets busy on weekends, so rideshare is your friend.
Price: $$$$
Why it's cool: A total gem in the neighborhood. They have an amaro-focused cocktail list and put their own thoughtful twist on all the classics you love.
Heads up: Walk-ins are welcome, but be prepared for a bit of a wait on a busy weekend night.
When to go: Late evening is the best time to soak up the local buzz.
Getting there: It's in Logan Square, so you're never far from other cool spots.
Price: $$
Why it's cool: This is a working distillery and a bar all in one. You can try their house-made spirits (including a certain famous Chicago bitter) and even take a tour to see how it all gets made.
Heads up: Check their tour times online, and be sure to try one of their tasting flights.
When to go: Perfect for a late afternoon visit before heading to dinner.
Getting there: It's in the West Loop, with plenty of rideshare options.
Price: $–$$
Why it's cool: They specialize in organic, grain-to-bottle spirits, and you can get a guided tasting or even take a class to learn all about them.
Heads up: Make a reservation for classes, and you can always pick up a bottle at their shop on your way out.
When to go: Weekend afternoons are the best time to visit.
Getting there: Located in Ravenswood, it's easily accessible by Metra or the "L."
Price: $–$$
To make sure your night is amazing, here are a few fun and practical tips to keep in mind.
What should I wear? For the most part, "smart casual" is a safe bet. Think neat layers and clean white sneakers. If you're heading to a fancy rooftop, you might want to dress it up a bit more. On weekends, it's a good idea to leave the jerseys and beachwear at home.
Do I need a reservation? It's a definite yes for those small, high-demand speakeasies and cocktail lounges. As for rooftops, you can usually walk right in, but just be ready for a line around sunset.
When do bars get busy? The real party time is Thursday from 8–11 pm and Friday/Saturday from 9 pm to 1 am. If you're looking for a chill spot to have a good conversation, the sweet spot is on a weeknight before 8 pm.
Where should I go bar-hopping? For total convenience, River North and the Loop can't be beat. If you want a great dinner with your drinks, check out the West Loop and Fulton Market. And for all kinds of nightlife fun, head to Wicker Park/Logan Square or Northalsted.
Start your adventure with us! Grab a drink with a view at CloudBar at 360 CHICAGO to get a feel for the city from 1,000 feet up. Once you're feeling oriented and inspired, you can dive headfirst into Chicago’s legendary nightlife scene.Check out our Plan Your Visit page for hours, parking, and ticket info. Or, if you need some inspiration, browse our Date Ideas in Chicago to create a perfect, unforgettable itinerary. And if you’re a rooftop fanatic, be sure to save our dedicated Rooftop Bars in Chicago guide for the next clear night.
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