Top-tier Nightlife Destinations in Chicago

September 19, 2018 | EVENTS IN CHICAGO

During the day, the streets of Chicago act as a virtual haven for some of the best sights and sounds in all of Illinois. Locals and visitors alike sample world-class pizza, visit historic landmarks, and discover culture around each and every new corner. Come nighttime, the city transforms into a social epicenter, buzzing with diversified nightlife opportunities that impress even the strictest traveler. Take advantage of these fundamental nightlife attractions in Chicago, for a flavor of entertainment you’re not going to find anywhere else.


The Drop Lounge

Take life at a pace most conducive to your own enjoyment, at the Chicago nightlife staple that is The Drop Lounge. Featuring a young, busy vibe supported by a wide drink selection and buzzing conversation, The Drop Lounge easily delivers on the promise to elevate your evening. Welcome to an environment that resembles a cave, backed by a DJ for dynamic sound. One of the go-to locations in the neighborhood with regard to the local nightlife scene, it’s a lounge for anyone looking to capitalize on a laid-back, friendly nighttime experience.

You can even host your next party or social function at The Drop Lounge, everything from a bachelorette party to a get-together with friends. Their deep cocktail list actually changes as the seasons pass, providing you up-to-date, relevant drinks at industry-leading prices. Better yet, the friendly service on the premises makes for a well-spent night out. Check out their Drop shot list, available exclusively onsite, together with a host of locally-sourced craft brews entirely worth the investment. They’re open all the way until 4 a.m. each morning, so you have more than enough time to stop by until the sun rises!



With a name you’ll never forget and decor set to impress, Rebar is the true definition of a high-end nightlife experience in Chicago. The destination is actually located within the Trump Hotel in Chicago, so you can bet that each and every piece which furnishes the location’s interior is hand-selected. Specialty cocktails only add to the list of reasons why Rebar deserves to serve as one of your Chicago nightlife spots.

At Rebar, you’re also offered select views of the local skyline, widely recognized as one of the finest views in the entire continental United States. Known for its aggressive style to each dish placed in front of satisfied guests, Rebar functions not only as a nightlife destination in Chicago: it’s also one of the region’s top eateries. Asian-inspired cuisine and all well-respected spirits decorate the luxury nightlife location in the Windy City.


Jazz Showcase

Sometimes the name of the venue itself tells you everything you need to know. In the case of South Loop’s Jazz Showcase, this is indeed the case.  The Jazz Showcase readily puts some of the city’s finest musical talents on full display. Local acts, together with international entertainment, routinely take to their acclaimed stage.

Since 1947, the Jazz showcase has treated locals and visitors alike to world-class performances. For recognized saxophonists to jazz quartets to solo piano acts, this is your definitive opportunity to place yourself in the company of the nation’s finest music. And when you add high-quality drinks into the mix, you’re left with a Chicago nightlife location you can’t afford to pass up.



The Violet Hour

For all things sophisticated and hip, your best bet for enjoyment is to seek out Wicker Park’s own The Violet Hour. Sample delectable, bite-sized portions, paired well with some of your favorite beverage selections.

Located near the center of Wicker Park, it’s an award-winning venue set to impress. And with furnishings that include crystal chandeliers and elegant hardwood floors, you’re treated to a nightlife location that’s nothing like a traditional nightclub. Instead, it’s an upscale, luxurious vibe, exactly the type of respectable destination you’re looking for. World-class spaces are supplemented by readily affordable prices, at The Violet Hour.


No matter your mood on any given evening, there’s a nightlife location in Chicago that proves perfectly conducive to your immediate entertainment. From hopping clubs to sweeping to upscale eateries to destinations that offer sweeping, uninterrupted views of the city, Chicago is filled with a diversified nightlife portfolio, one that can easily define your stay in the Windy City as entirely unforgettable! For more destination guides and accommodation reviews, hotels and vacation rentals, check out Trip101.