Exploring Chicago: Best West Loop Bars

by | Feb 18, 2026 | Chicago, Exploring Chicago

As one of Chicago’s most popular dining destinations, the West Loop hosts some of the city’s hottest up-and-coming spots. Locals and tourists alike flock to this neighborhood for its world-class gustatory experiences, from Michelin-star restaurants to cozy bars on Randolph Street housed in 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 earlier this century. These additions established West Loop as a hotspot for flourishing businesses and nightlife, and our team of locals sought out 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. 

Related: South Loop Bars

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 order from The Aviary is a work of art. Decorated with numerous awards in the years since its inception, The Aviary provides not just a cocktail, but an entire electrifying experience. With beverages ranging from $16 to $25 per drink alongside higher-priced pitchers for sharing, The Aviary is a worthwhile investment for an elevated nightlife experience.

Our favorite drink:

Their cocktail In the Rocks should go 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 Press Room

Located: 1134 W Washington Blvd, Chicago, IL 60607

If the mood strikes you 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 popular bed and breakfast, the Press Room’s historical roots in the West Loop neighborhood stand out. What used to contain a holography museum, then a casket factory, followed by the Free Methodist Publishing House, now houses the best place in the neighborhood to grab a generous glass of wine and a sophisticated meal.

Our favorite drink:

Since this is a wine bar, we suggest taking your server’s recommendation on a glass of vino. They serve over 20 “by the glass” options, plus plenty more by the bottle. If you prefer a craft cocktail, we love the Andean Bird, fashioned from Zhumir Aguardiente, Campari, and pineapple. 

Moneygun

Located: 660 W Lake St, Chicago, IL 60661

Moneygun, nestled underneath the green and pink line train tracks, serves all the standard beverages you would expect at a Chicago bar, but with original twists and an unbeatable ambiance. This is THE spot to hit up 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 specializes in the classics (and twists on the classics), so we recommend going tried-and-true with your favorite cocktail. Don’t have a go-to? Give a new one a spin— perhaps start with a Pimm’s Cup or Last Word.

Booze Box

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

Booze Box often gets overlooked because it sits inside an already spectacular sushi restaurant, Sushi Dokku. It gives off speakeasy vibes due to its alleyway entrance and downstairs location, 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, such as lychee, yuzu, ginger, and wasabi. Come in for a sushi roll, but stay for the sake.

Our favorite drink:

If you’re not a sake kind of person and looking for an alcohol alternative, check out the impressive list of mocktails, NA wine and beer.

Find your Dream Chicago Apartment Near These West Loop Bars

Now that you know the best West Loop bars, make this neighborhood your new home and become a regular. 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.

Apartment Spotlight: Arthurs of Old Town

* The original version of this article was first published on January 4, 2021.

About the Author
Rebecca Denham

Rebecca is a freelance writer over a decade of journalism experience. She 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.

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