Considered to be one of Chicago’s fastest-growing neighborhoods, the West Loop hosts some of the city’s hottest up-and-coming spots. Locals and tourists alike flock to experience the wide array of dining options: from Michelin-star restaurants to cozy bars on Randolph Street that were once historic meat and fish warehouses. 

The West Loop saw a huge surge in economic development with the addition of Google’s Chicago campus and the McDonald’s global headquarters. This recent advancement established West Loop as a hotspot for flourishing businesses and nightlife. 

Not to be confused with the South Loop, you’ll find some of the best West Loop bars here, and our team of locals has the inside scoop on where to go and what to drink. 

If you’d like your next home to be in this neighborhood, reach out to AptAmigo and we’ll help you find the perfect apartment! Still deciding on a neighborhood? Read our ULTIMATE Chicago neighborhood guide to find your ideal neck of the woods. 

The Best West Loop Bars

The Aviary

Located: 955 W Fulton Market, Chicago, IL 60607

From the creators of Alinea—quite possibly the most exclusive and highly esteemed Michelin-starred restaurant in Chicago— comes this incredible experimental cocktail experience. The Aviary’s mixologists take their beverage game to an entirely new level. With a focus on molecular gastronomy and other drinkable alchemies, every cocktail that you get from The Aviary is a work of art. Decorated with over 20 awards in the last ten years, The Aviary provides not just a cocktail, but an entire electrifying experience! With beverages ranging from $16-25 per drink to higher-priced pitchers for sharing, The Aviary is a worthwhile investment for your nightlife experience.

Our favorite drink: Their cocktail In the Rocks should be on the top of your list.  An interactive spin on a manhattan, a hollow ice sphere encases the beverage, and you crack it open with a mini slingshot to get the drink to spill out into your glass. Who says you can’t play with your food?

The Darling

Located: 905 W Randolph St, Chicago, IL 60607

Take a step back into an elegant, refined time period at The Darling. The British manor-style decor influences every element of your experience here— from the atmosphere to the menu, and even the glassware. You can enjoy your beverage in a number of aesthetically pleasing spaces within: The Library provides an intimate and moody space with comfy seating; The Rose Garden is a decadent open air patio; and The Ballroom supplies a bustling venue meant for socializing and small talk. Each distinct setting features a curated menu of cocktails, wines, and small bites that mimics the space’s mood.  

Our favorite drink: A perfect drink to enjoy during the colder months is The Dark Horse. Made with Rittenhouse rye whiskey, Averna, earl grey tea, and maple syrup, it will warm up any Chicagoan’s heart. 

The Press Room

Located: 1134 W Washington Blvd, Chicago, IL 60607

If you’re in the mood for a chic night out with friends at a trendy underground wine bar, look no further than The Press Room. Located in the basement of a very popular bed and breakfast, the Press Room’s historical roots in the West Loop neighborhood cannot be overlooked. What used to be a holography museum, then a casket factory, followed by the Free Methodist Publishing House, is now the best place in the neighborhood to grab a generous glass of wine and a sophisticated meal!

Our favorite drink: Obviously, since this is a wine bar, we suggest taking your server’s recommendation on a glass of vino— there are over 20 “by the glass” options, plus plenty more by the bottle. If you are holding out for a craft cocktail, we love the Jungle Bird, which is fashioned from Blackstrap rum, campari, and pineapple. 


Located: 660 W Lake St, Chicago, IL 60661

This hidden gem is located off the beaten path but is absolutely worth the detour. Moneygun serves all the standard beverages you would find at a Chicago bar but with original twists and an unbeatable ambiance. This is THE spot to be if you’re looking for classic dim lighting, old school hip hop, and an unmatched palpable energy. Moneygun is also popular for its humble drink prices, especially in comparison to other spots in this neighborhood.

Our favorite drink: Moneygun’s specialty is classics— and twists on classics, so we recommend going tried and true with your favorite cocktail. Don’t have a go-to? Give a new one a spin— we recommend the Pimm’s Cup or Last Word.

Booze Box

Located: 823 W Randolph St Downstairs, Chicago, IL 60607

Booze Box often gets overlooked because it can be found inside an already spectacular sushi restaurant, Sushi Dokku. It gives off speakeasy vibes due to it being hidden in an alleyway, but what it lacks in size it makes up for in flavor. You’ll find a bountiful selection of sake and adventurous cocktails that combine the incredible flavors of Japan— lychee, yuzu, ginger, wasabi, and more. Come in for a sushi roll, but stay for the sake!

Our favorite drink: If you’re not a sake kind of person, you’ve got to try the Atatamare Punch. Served hot and made with Hendrick’s gin, yuzu, and matcha— this drink is perfect for those harsh Chicago winter months!

Find your Dream Chicago Apartment

Now that you know the best West Loop bars, make this neighborhood your new home and become a regular! Just reach out to AptAmigo, and we’ll pair you with a dedicated apartment expert who will make your apartment hunt a breeze. With our team of Chicago locals, insider expertise, and access to the best deals, apartment hunting has never been easier. Our service is 100% free, and always will be!

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About the Author
Rebecca Denham

Rebecca is a freelance writer with eight years of journalism experience. She recently graduated with a BA in Communications and a minor in journalism. She currently bartends in downtown Chicago and spends her free time exploring the city and making connections.