Chicago is an excellent place for having fun things at night. The Windy City presents unrivaled attractions. Whether you check out museums, iconic landmarks, or adventurous sites, you are free to explore Chicago offerings differently. Exploring the city after dark is the best opportunity to lose your day. During the summer, the warmer weather is conducive to exploring the outdoor attractions at night. Take joy in the late-night activities with unforgettable experiences.
During the winter, the temperature gets low. Don’t worry! The city also provides the perfect environment in frigid conditions. An array of indoor destinations is available to visit. You are free to listen to live music performances, see theater, or adore the museum collections. Are you getting complicated in finding the best fun things at night? Here are the top 20 fun things to do in Chicago at night. All you need is to relax and prepare your night activities to get kicked out of Chicago after dark.
1. Shop in Magnificent Mile
The Magnificent Mile, the Mag Mile, is one of the city’s most significant shopping spots you can visit after dark. The area stretches North Michigan Avenue one mile, where you’ll discover more than 450 retailers selling all your needs. Whether you want to pick brand-named outfits, classic bags, or signature foods, feel free to fulfill your demand.
With its boutiques, flagship stores, shops, malls, and restaurants, you will have more excitement along the Mag Mile. Most retailers are always available at night. Take an opportunity with your beloved peers to calm the sparkling night on the Magnificent Mile. A shopping area is the perfect place for an unforgettable shopping experience.
2. Dine-in at Portillo’s Restaurant
Your night trip to Chicago is incomplete without tasting the authentic menu at Portillo’s eatery. It is a well-known restaurant for teenagers, offering Italian beef and casual-style hot dogs. Get a taste of their unrivaled foods like plant-based cuisines, cheese fries, chopped salad, Italian beef sandwiches, and more irresistible dishes. If you want to promote your health, just order gluten-free menus, including delicious salads.
The best meal you should try is Italian beef. It offers thinly sliced, slow-roasted, and fresh-meat beef with selective seasonings. Don’t miss drinking their signature beverages, including chocolate shakes, vanilla shakes, and more. The Portillo’s provides a different atmosphere with a lively setting to gather with your friends.
3. Take a Chicago Ghost Tour
If you are looking for unusual things to do in Chicago at night, challenge yourself to the Chicago ghost tour. Whether you are willing to learn about the terrible crimes and mob in the Windy City or get up close to the city’s haunted history, don’t sleep on taking the craziest tour. You are free to have an opportunity to explore the different sides of Chicago.
By following this night tour, you will discover the dark sides of the city. The tours are available in some options. Whether you pick the free-admission ghost tour or the full-serviced tour, take the chance to pass your nights in the most notorious and haunted places in Chicago. Within 2-2.5 hours, revel in the different ambiance of the Windy City.
4. Join a Bus Panoramic Night Tour
One of the most recommended things to do in Chicago at night is a bus panoramic night tour. Get an experience of seeing the Chicago landscape at night. You can discover the dazzling skyscrapers and iconic landmarks in one package. The tours start from the Magnificent Mile to Michigan Avenue. During the 75-minute tour, you will experience the panoramic skyline of the Windy City in detail.
The bus also hop on and hops off at famous landmarks like the Museum Campus, the Wilis Tower, the John Hancock Center, the Millennium Park, and more. Take your beautiful photos with the great backgrounds of skyscrapers. You are also free to catch the fantastic cityscape on the big bus. Make sure to include this fascinating tour in your itinerary.
5. Freak Out on Romantic Sunset Cruise
When the sun goes down, it is a perfect chance to enjoy a romantic sunset cruise with your beloved ones. Toast your evening with a glass of authentic coffee or an icy cocktail. The tour lets you experience the city’s sparkling skyline from the vessels. Through the Michigan River, let’s admire the iconic buildings and skyscrapers from many angles, like the John Hancock building, Adler Planetarium, Shedd Aquarium, and other iconic venues.
While enjoying the beautiful scenery, grab your snack and try the unrivaled beverages. The full-service bar is always available. You can pick many of the Chicago signature products to accompany your journey. Don’t forget! Bring your best camera and capture the majestic venues during the trip. Invite your beloved partner to experience a lovely night with the romantic sunset tour.
6. Experience 90 Minute River and Lakefront Cruise
Your nightlife will be enriched by experiencing the Lakefront cruise. It is an alternative way to enjoy the city at night. Lose your night by watching Chicago’s historic buildings, glorious skyscrapers, and twinkling marvels. During the trip, you can lose the night on the cruise. Treat yourself as if you have the best opportunity in your life.
Throughout the journey, feel free to look eye-on at iconic venues like the Wilis Tower, Buckingham Fountain, John Hancock Building, Marina City, Wrigley Building, and others. For a more immersive experience, the tour guide brings a clear narration to enrich your knowledge about the city’s sights. Try a spectacular experience by gliding along the Chicago River and Lakefront.
7. Enjoy free live Music Performance
Are you bored at home? Let’s hang out and listen to the free live music at the Jay Pritzker Pavilion in Millennium Park. Feel free to attend an outdoor concert that showcases emerging and established musicians in the city. Whether you watch and listen to disco, pop, rock, hip-hop, R&B, or country music, the venue is a warm place for music across all genres. Grab your lawn spot and adore the live music performance, which will make your night.
Make sure to bring your picnic package during the show. You are free to savor your meals and beverages before and during the performance. Visiting to see the best musicians is a fun thing to do at night when you are flat broke. It is entirely free to have excitement at Millennium Park.
8. Watch outdoor movies
Chicago offers several places to have an outdoor movie the night. Head to Gallagher Way in Wrigleyville. You can watch the free movies on Wednesdays from May to September. See the best movies when you sit on the lawn or purchase VIP tickets. The gates open at 6 pm.
During summer, Millennium Park also offers outdoor movies from the middle of July to the end of August. The vast LED screen is available to provide high-rated movies. Just sit on the lawn and delight in the free movies. If you are staying near Navy Pier, thrill to the movies from July to August. You can discover new as well as old films based on your preference. Make sure you have the schedule.
9. Explore Chicago Jazz
Chicago comes with a spectacular jazz scene. Spend your night by getting a charge out of the live jazz music at contemporary clubs. You will find the spotlights delivering the new sounds of the next-level jazz. Your moods are gradually improving when you feel stuck. Just go to the Chicago jazz venues and release your boredom.
You are free to watch the jazz festival at Millennium Park. Notable jazz musicians like Ramsey Lewis, Dizzy Gillespie, Sarah Vaughan, Count Basie, and more will give you sophisticated performances. Discover live music in some jazz venues, including Andy’s Jazz Club, Benny’s Chop House, Constellations, and other venues. At the same time, be entertained by the jazz and taste the craft cocktails and delicious dishes.
10. Let’s laugh at the Second City
If you are crazy about comedy, let’s have fun at the Second City. It is an excellent place for extensive entertainment spots. Release your boredom and laugh freely with fresh comedy. The site offers sketch comedy and Chicago-style improvisations. You can keep on watching the stand-up comedy. It is an upscale comedy in that the comedians deliver unscripted, collaborative, and spontaneous stage performances.
Meet with the city’s notable comedians and get the opportunity to have a special night like no other. You can also have a good time with musical improvisation, which offers a fantastic experience. Book the signature cocktails and dishes before and during the comedy stage. Invite your peers to laugh together in the second city.
11. Overlook Fantastic Cityscape
One of the most exciting things in Chicago at night is seeing the sparkling cityscape from the observatory decks. Nighttime is a great chance to capture iconic Chicago landmarks from above. Get an experience of overlooking an eye-on-eye landscape. The two popular observatory decks, Skydeck Chicago and Chicago 360, are always available to provide a great night with your friends.
The Skydeck Chicago offers a glass tunnel to see the beautiful skyline. Located on the 103rd floor of the Wilis Tower, indulge in a great experience. Meanwhile, the Chicago 360 also provides spectacular views of the Magnificent Mile, Soldier Field, Navy Pier, and Lake Michigan. Don’t forget to bring your best camera to capture the sparkling skyline and cityscape. During the Chicago 360 trip, don’t miss stopping at the Signature Rooms on the 95th. You will find an irresistible place offering the best dining experience. Get high on the 360-degree scenery while tasting the best foods.
12. Watch Live Theater
Are you into Broadway productions, plays, and shows? Don’t sleep on seeing live theater. Chicago is home to many live theater venues that will make your night. Discover a great selection of top-notch theater performances across contemporary places. Head to the Goodman Theatre, known as the oldest and largest live performance in Chicago.
If you are willing to save the ticket cost, you can book mezzanine seats online. You can get a half price for each performance schedule. For an alternative option, check the other calendar events in Chicago, including Auditorium Theatre, Steppenwolf Theatre, Briar Street Theatre, or Cadillac Palace Theatre
Head to the Navy Pier to experience the spectacular views of Lake Michigan, Chicago parks, and the skyline. The summer night is perfect for exploring all the offerings at the Navy Pier. One of the best things to do in Chicago at night is delight in the fireworks. Keep your eyes on the fireworks shows.
The show runs on Wednesday and Saturday nights. It is a seasonal firework show from the weekends of Memorial Day to Labor Day. Relish another great activity after dark at the Navy Pier, Light up the lake! You get the great experience of kiddie train rides, an ice rink, a signature holiday Beer Park, light sculptures, and more.
Don’t sleep on trying the Ferris wheel, the most challenging attraction in the Windy City. You shouldn’t miss the beautiful view from above.
14. Get pleasure at Buckingham Fountain
Experience the fresh open air by visiting Grant Park. It belongs to a vast urban green park in the heart of downtown Chicago. One of the best offerings is the Buckingham Fountain. Invite your peers to luxuriate in the largest fountain in the world. Keep the schedule. The fountain show takes place from early May to the middle of October.
The attraction delivers the most excellent water display every 20 minutes up to 11 PM. With its powerful music, illuminating lights, and lively atmosphere, get pleasure from the inviting night at the Buckingham Fountain.
15. Try Escape Games
The popularity of escape games is booming these days. It’s one of the best things to do in Chicago at night. Known as the most-wanted indoor game, invite your friends to experience the next-level entertainment. The 60-minute live game offers adventurous themes ranging from a 1950 prison break to a classic art heist.
Call on your peers to find the clues, solve the puzzles, and complete the missions. Make sure to finish the task before the set amount of time. The escape game releases your boredom and elevates your mood after hectic daily activities. For more experience, let’s invite your beloved family members to live it up.
16. Go to a Magic Show
Get more experience with freaking out at a magic show. Chicago offers excellent magic show venues across the city. The place is dedicated to those who lose their nights with a lively ambiance. An array of the city’s top-notch magicians deliver new and impressive tricks to entertain the visitors.
Whether you look for fun card tricks, mind-reading, or hypnotizing, feel free in the inviting place to release your stress. Just head to the magic show lounge and get a good laugh. You will also be pleased to learn some basic tricks from the magicians. Come to see and get pleasure from the amazing magic show in Chicago.
17. Calm at the Rooftop Bars
Relaxing at the rooftop bars is one of the best things in Chicago. Get a memorable experience by overlooking the cityscape, tasting signature cocktails, and enjoying the fresh open air. All are available at a wide range of famous rooftop bars in Chicago.
Head to the local’s most-chosen rooftop bar, Cindy’s rooftop. With its unrivaled dining experience, the rooftop offers scenic views of Lake Michigan and Millennium Park. Relish your night with great pleasure with its flavored menus, sparkling lighting, and unrivaled atmosphere. Another famous rooftop you can visit is the Cerise Rooftop. Located on the 26th floor of the Virgin Hotel, savor various signature menus and live DJs. Of course, it will make your night unforgettable.
18. Support the Chicago Hockey Team
Come to see and support the Chicago hockey team, the Chicago Blackhawks. It is a perfect opportunity if you are into hockey. Go to the United Center, a home base of the Chicago Blackhawk. You will meet other hockey lovers who are in the same line.
The professional hockey players serve the best skills against the other team. Give a chant to Chicago’s famous team for winning every game. Attending the hockey match is a completely interesting way to pass your night. Invite your peers to watch and support the team.
19. Eat at the Signature Room
Enhance your night with dining on the 95th floor of the Signature Room. With its beautiful views, warm ambiance, and lively atmosphere, the restaurant offers an unrivaled dining experience. Don’t sleep on the best high-rise eatery with a shoreline and panoramic views.
Whether you taste local cuisine or world-class menus, try an array of signature offerings at the famous restaurant. Experience fine dining while you thrill to the sun going down. It is a perfect chance to create a warm and lively atmosphere. Discover the like-no-other dining experience in the Signature Room.
20. Stop at the Magnificent Mile
Known as Chicago’s finest shopping district, the Magnificent Mile offers the best dining and shopping experiences. Find more than 275 eateries that provide the city’s famous cuisines. You are free to taste authentic foods, from deep dishes to unique cocktails.
All foods are available at affordable prices. The street vendors provide five-star menus at competitive prices. Revel in your night by tasting the best selection of flavored foods at the Magnificent Mile. An array of famous retailers also stretches along the shopping area. Fulfill your needs with the best shopping experience.
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What is there to do in Chicago at night alone?
After dark, an array of fun activities in Chicago are always available. Watching free live music is perfect for getting rid of loneliness. Head to the contemporary pubs if you want to listen to tunable jazz music while tasting signature cocktails.
Where should you not stay in Chicago?
You should avoid visiting some dangerous neighborhoods in Chicago, including West Garfield Park, East Garfield Park, Englewood, Washington Park, North Lawndale, Grand Crossing, West Englewood, Riverdale, Chatham, and South Shore.
Is Chicago a happy city?
Of course. With its magnificent attractions, modern life, and friendly residents, Chicago made the list of “the happiest cities” in the country. It is worth spending your time in Chicago. You will find something fabulous that fits into your life.
Is Chicago cheaper than Los Angeles?
That is true. The cost of living in Chicago is lower, at around 18.5% than in Los Angeles. However, Chicago provides offerings that do not lose to Los Angeles.
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