Home #WHERETONEXT 5 Things to do on a Night Out in Chicago

5 Things to do on a Night Out in Chicago

Image by Jürgen Polle

Chicago, a vibrant city rich in history and cultural heritage, offers a dazzling array of attractions. By day, this world-class metropolis enthralls with its museums, skyscrapers, art institutes, and parks. As the sun sets across its stunning skyline, the Windy City transforms into a nightlife hub with a soaring atmosphere. From clandestine magic shows and al fresco movies to dinner cruises and scenic rooftop nightclubs, Chicago’s nightlife has something for everyone.

Here is a list of 5 things to do on a night out in Chicago:

Explore Underground Bars and Clubs

Explore the hidden layers of the city with a deep dive into Chicago’s underground nightclubs. A night out at star-studded clubs like Berlin and The Underground is an electrifying experience. With exceptionally talented DJs and booming new wave music, these nightclubs have great energy and incredible aesthetics. Not only that, but they offer some of the finest craft beer, wine, and a mix of eclectic drinks to ramp up the night.

Enjoy the Views from 360 Chicago

The 360 Chicago Observation Deck, formerly known as the John Hancock Observatory, offers breath-taking panoramic views of Chicago under the city’s twinkling night sky. Located on the 94th floor of the John Hancock Center, the observation deck offers views of up to four states and a distance of over 80 miles. It is also the home of TILT, Chicago’s classic thrill ride. TILT is an enclosed glass and steel movable platform that can hold up to 8 people. Gradually tilting outward to a thrilling angle, it generates a bird’s eye view of the city, giving you an adrenaline rush while offering stunning views from a never-before-seen angle.

Photo by Lance Anderson

Enjoy a River Cruise or take a Spin on a Riverboat Casino

One of the best ways to experience the sights of downtown Chicago is from the water. The city is adorned by two stunning waterfronts – the Chicago River and Lake Michigan, and each offers plenty of cruise options. Choose from a serene dining cruise, complete with delicious cuisine and the finest wine, or if you are in the mood for gaming and entertainment, riverboat casinos are a popular choice. One such great option is the Hollywood Casino Aurora. Established in 1993, it is one of the earliest riverboat casinos spanning over 53,000 square feet. It offers 1,000 slot machines and 26 table games ranging from Poker, Roulette to Mini-Baccarat. If you are looking for big entertainment and a night of gaming, Hollywood Casino Aurora will give you a memorable experience.

Explore the Flavors of West Loop

If food is the way to your heart, you will definitely enjoy a walk around West Loop. Once an industrial neighborhood, West Loop is now home to the French Market, which is peppered with Insta-worthy cafes and chic restaurants. Visit Restaurant Row on Randolph Street, where you will find the neighborhood’s most celebrated eateries, from fourth-generation sandwich shops to ramen joints and luxurious gourmet cuisine. Some of the most trending culinary hotspots include BomboBar, known for its exceptional desserts; Au Cheval, famous for its towering burgers; and Rose Mary, which combines Italian heritage with the bright flavors of Croatian cuisine. Indulge in some of the best flavors Chicago has to offer with a night out in West Loop.

Listen to Concerts Under the Stars

Experience stellar renditions of musical greats like Frank Sinatra, Ella Fitzgerald, Etta James, and Amy Winehouse, as well as iconic movie soundtracks presented by Chicago’s finest musicians. Be mesmerized by the swinging jazz-age vibe as you sip on some martinis or fine wine. The unique vintage sound, ambient atmosphere, and stunning views will transport you to another time as you take in the city lights for a night of pure indulgence. Swoon to jazz classics like ‘Fly Me to the Moon,’ ‘Valerie,’ ‘At Last, ’ and more as you go on a musical journey and relish the performances of iconic jazz numbers throughout the decades.