The Best Bars in Chicago, Illinois

No list of best Chicago bars would be complete without this iconic institution. A former haunt of Al Capone and fellow gangsters in the 1920s, this storied spot has a long history with the city’s jazz scene and still retains its standing today, hosting some of the most eclectic in bebop, improvisational, modern and traditional arrangements. Playing strong to its down-to-earth ambience and charm, expect reasonably priced cocktails, beers and wine and a glittering line-up of jazz acts every night. If you love jazz bars, check out our list of the best jazz bars in Chicago.

Logan Square has a reputation for being home to some of the more hipster-approved hangouts in the city, and with its playful vibes and utterly Instagram-worthy decor and small plates (the goth bread is a must-try), Young American Bar is fast becoming a favorite on the scene. Offering an enticing mix of CBD-infused cocktails and nibbles, craft beers and “radical” wines, the bar also serves up a decent line-up of specialty non-alcoholic cocktails – with a restorative shot of turmeric and electrolyte powder on the side for the more discerning, health-conscious drinkers.

If you like your drinks served with a splash of intrigue and curiosity, The Darling has this down to an art. Enter through its Alice-in-Wonderland-style florist shop doors and prepare to be transported into an English-manor-style setting, complete with a giant Scrabble board, roaring fireplaces and a choice between seating in The Library or The Ballroom. Bespoke cocktails all have a distinctly British theme and come served with statement floral art centerpieces, while the fare takes on a more general European vibe. Reservations are strongly recommended.

If out of this world is what you’re after from your sips, then The Aviary is the place to go. In the spirit of the Alinea Group, cocktails are given the same treatment as the food, served with next level ingenuity and imagination. Think multi-sensory cocktail art, with feats of pure engineering to ensure a manhattan is served in a globe of ice, or a rooibos cocktail is served in a heated flask. An all-out feast for the senses, this is a one-of-a-kind experience for the bucket list. Bookings are a must.

If it’s all-out flamboyance with an edgy twist you’re seeking, Lost Lake’s tiki bar has all this and more. As it’s one of Chicago’s most-loved bars, a night here will not disappoint. A tropical adventure set in the heart of Logan Square, its selection of exotic specialty cocktails pushes the boundaries and defies all taste expectations thanks to its talented team of mixologists, offering a truly unique experience, right down to its eclectic glassware and, of course, those iconic banana dolphin garnishes.

Chicago loves to keep its top spots a bit more tucked away, so it’s no wonder that one of its best cocktail contenders, The Ladies’ Room, is hidden inside Fat Rice – a hugely popular Logan Square restaurant. Step inside The Ladies’ Room, and be treated to a unique and intimate setting in which to imbibe some of the most unusual infusions, elixirs and potions you’re ever likely to try – think reimagined classics, spirits and wines with unexpected global flavors.

One of Chicago’s most-buzzed-about openings in the Fulton Market area, The Hoxton plays host to several bars throughout the space, but Lazy Bird is its sweet spot, tucked away on the basement level. Positioning itself as a relaxed lounge for Chicagoans to hang – rather than exclusively for hotel guests only – the intimate and elegant space was designed by the Boka Restaurant Group, and features a tempting hand-drawn illustrated menu of specialty drinks and 52 classic cocktails. Perfect for drinks before or after dinner at one of The Hoxton’s two restaurants.

Taking the spirit of a neighborhood tavern and infusing it with the elegance of a cocktail bar, Spilt Milk has carved out a unique niche in Chicago’s busy nightlife scene. The carefully curated beer and wine lists are the highlights of this spot, alongside its cocktail line-up, with a lively ambience created in part by the sociable sweeping wooden bar just inviting a seat and a chat with the friendly bar staff.

If it’s a more authentic Chicago experience you’re after, you can’t go wrong with a visit to the historic Green Door Tavern. One of Chicago’s oldest drinking spots, it was originally an Italian restaurant with a speakeasy in the basement – it still has a massive bookshelf that moves to reveal a hole in the wall through which bootlegged kegs were smuggled. The bar retains plenty of its historic charm, mixed in with modern sports memorabilia, and is a great spot to sink a cold one and chat to the friendly bar staff. And, if it gives you a taste to discover a speakeasy experience too, pop downstairs to the cocktail bar, The Drifter.

Art Deco vibes, historic fixtures and an array of taxidermy all give the Sportsman’s Club its distinct traditional and cozy pub atmosphere. The venue takes its name from a bar once located at the same address, and some original features remain, adding to the character of the spot. Expect a rotation of daily cocktails, along with a solid line-up of draft and bottle selections.

One of Chicago’s most beloved cocktail spots, Cindy’s rooftop restaurant and bar at the Chicago Athletic Association Hotel has some of the best views of the city, sweeping across Millennium Park and out to Lake Michigan. A perfect pit stop for thirsty downtown explorers, Cindy’s has a menu of delicious craft and non-alcoholic cocktails, along with a great roster of beers and wines. Booking is advised during busy periods.

One of Chicago’s most anticipated West Loop openings, Japanese-inspired bar and restaurant Kumiko offers an intimate and exclusive experience quite unlike anything else in the city. It features an extensive à la carte cocktail list, infused with rare and usual Japanese ingredients, and a wide selection of alcohol-free infusions, too. Reservations are highly recommended. Check out the rest of Chicago’s cocktail scene with our list of the best cocktail bars in Chicago.

A speakeasy-style tiki bar, Three Dots and a Dash is a welcome oasis tucked away behind the streets of River North. It takes its tiki cocktails to the next level – each is meticulously crafted with exotic ingredients, spirits, elixirs and juices cold-pressed on-site and served in out-there tropical glassware, with extensively Instagram-worthy garnishes. The bar also hosts various events, which have included rum tastings.

For music fans, Delilah’s is the ultimate bar to just rock out in, featuring punk, metal, ska, reggae, garage and rockabilly music and DJs every night of the week. As the bar carries more than 1,000 spirit and beer options, it’s hard not to find your special sauce in the mix, but to offer some guidance, Delilah’s hosts regular whiskey and craft beer tasting events. Expect friendly bar service, nightly drink specials, and a whole lot of fun. Delve deeper into the city’s music scene with our list of the best bars with live music in Chicago.

Packing plenty of personality into a relatively small space, Fox Bar is a must-visit for those who enjoy the character and flair of Soho House spots, with a unique Chicago twist. More like a neighborhood bar than a fully fledged cocktail lounge, the bar has relaxed vibes and friendly service that will help you discover new tastes in spirits and cocktails, while its vinyl-centric DJs give a remix to nostalgic soundtracks, late into the night. If you enjoy craft beer, give our guide to the best craft breweries in Chicago a read.

If you’re looking to take the edge off Chicago’s cocktail focuses, then The Press Room could be just the place. A relaxing basement wine bar and restaurant, downstairs from The Publishing House B&B, it serves a stunning selection of wines from around the world, seasonally curated and available by glass or bottle. While away the hours in this cozy spot, and pair your wines with some of the tempting charcuterie and cheeses on offer to really get the most out of your evening. Also, check out our guide to the best wine bars in Chicago.

To really immerse yourself in the local neighborhood scene, a visit to The Whistler is your hot ticket to Chicago’s most eclectic and diverse creative communities. With its lively mix of well-crafted seasonally rotating cocktails, alongside showcasing the work of local artists and playing host to live music and DJ nights every night of the week, the fun never sleeps at this coveted spot.