14 Best Night Tours in Chicago To Book in 2023


You’ve made it to the right place! In this post, I’m going to break down the best night tours to experience in Chicago, whether it’s your first, second, or third time visiting the city, or even if you’re a local!

As an Illinois local who constantly visits Chicago, and has been visiting for over 10 years (I went to school there, too) I have been able to experience Chicago’s beautiful sites, day and night.

In this post, I want to share the best nighttime experiences in Chicago to help you experience Chicago in the night in a special way!

From sunset experiences in Chicago, to late night Chicago activities, there’s plenty to do when the sun begins to go down.

These tours are the best ways to close off a beautiful day exploring the city, even if you just have a night in Chicago! This list will help you make a solid plan!

So without further ado, let’s see the best night tours in Chicago to experience!

#1 Top Pick

Private Evening Sail in Chicago Ending with Navy Pier Fireworks

✔️ Private sailboat experience with fireworks

✔️ Bring up to 6 people

✔️ You get to choose the route and music


3-Hour Private Speakeasy Cocktail VIP Tour

✔️ Visit 3-4 Chicago active speakeasies

✔️ Hotel pick up and drop off

✔️ 3-hour guided tour with guide


45-Minute Private Helicopter Flight for 1-3 People

✔️ 45-minute long tour

✔️ Panoramic tour of Chicago’s main sites

✔️ Live commentary from your professional guide and pilot

14 Best Night Tours in Chicago in 2023

1. Gangsters and Ghosts Tour in Chicago

🌟Rating: 5/5 stars ⏰ Tour Length: 2 hours

ℹ️Check Rates and Availability

Step into the shadows of Chicago’s intriguing past when you book your spot on the Gangsters and Ghosts Tour!

This ever-popular night tour weaves together the tales of notorious gangsters who once ruled the city’s underworld during the Prohibition era, transporting you to the scenes of their illegal activities.

Through a blend of history and mystery, the Gangsters and Ghosts Tour offers a unique and chilling perspective on Chicago’s bygone era, making it a must for those seeking a thrilling exploration of its hidden past.

So if you’re looking to explore Chicago’s dark past, this tour is for you!

Walk through The Loop where many of Al Capone’s activities took place, explore the Chicago River Walk like it’s the 1920s and 30s, step through Al Capone’s favorite spots like the Palmer House, and many more sites!

Also a popular spooky Chicago night tour bus to consider is the Chicago Night Crimes Bus Tour also offering the same levels of spooky and history within the comfort of a bus!

“Great tour, especially if visiting Chicago for the first time and want to learn about the interesting history. Shout out to our tour guide Sarah!”

Jeff – read more reviews here


>> Read More: Weird Chicago Tours To Experience in 2023

2. Chicago Sunset Cruise

🌟Reviews: 4.5/5 stars Length of Tour: 1.5 hours

ℹ️Check Rates and Availability

Take in the breathtaking beauty of the city on the Chicago Sunset Cruise, one of the most popular Chicago night boat tours!

On this amazing Chicago by night 90 minute river and lakefront cruise, spot out some of the most famous skyscrapers Chicago is known for, from..

  • The John Hancock building
  • The Willis Tower
  • The Wrigley building

and much more as the sun dips below the city’s iconic skyline, and the city begins to sparkle!

Drift along Lake Michigan, with the city’s towering landmarks illuminated against the twilight backdrop.

Whether you’re seeking a romantic evening or a peaceful escape, the Chicago Sunset Cruise offers an unforgettable experience that captures the essence of the city’s charm and elegance during the evening.

“Our guide and the entire staff were excellent!! Throughly enjoyed every aspect and detail given on this cruise. Highly recommend!!”

Angela – read more reviews here


3. Chicago 3D Fireworks Cruise

🌟Rating: 4/5 stars ⏰ Length of Tour: 2 hours ℹ️Check Rates and Availability

Embark on an electrifying adventure with the Chicago 3D Fireworks Cruise, and set sail on Lake Michigan as the city’s skyline lights up with a mesmerizing fireworks spectacle!

Cross through the Chicago River, taking a look at the iconic architecture that the city is known for, and then make your way to Lake Michigan to get closer to the fireworks over the lake!

For this especially unique firework show, you’ll receive special 3D glasses, which will take the firework spectacle to a whole new level!

Pass through some of Chicago’s most iconic sights like the Buckingham Fountain from the water, and the John Hancock Center against the backdrop of Chicago’s illuminated landmarks and skyline.

Don’t miss it!

“Great experience entire family loved seeing fireworks up close & skyline at night. Chicago is fantastic!”

Sharon – read more reviews here


4. Big Bus Chicago Sunset Tour

🌟Rating: 4/5 stars ⏰Length of Tour: 1 hour and 15 minutes

ℹ️Check Availability and Rates

Relax on a 75-minute-long, open-top bus and soak in the panoramic views of illuminated landmarks like the Navy Pier, Magnificent Mile, and Millennium Park, when you book your night tour in Chicago with the Big Bus Chicago Sunset Tour.

As you pass these iconic landmarks on this memorable Big Bus Chicago night tour, including driving by the original Water Tower, the Bean, Wrigley building, and the Tribune building, you’ll listen to your guide who will enrich the journey with historical insights and fascinating anecdotes!

Whether you’re capturing stunning photos or simply savoring the city’s transformation into a twinkling metropolis, the Big Bus Chicago Sunset Tour promises a beautiful evening adventure that captures the essence of Chicago, with one of the best Chicago bus tours!

“The staff was really nice and the ride was amazing seen some amazing stuff sit back and enjoy 😊 when I come back to Chicago that’s one of my to do.”

Alice – read more reviews here


5. Chicago: Lake Michigan Gourmet Brunch/ Lunch/ Dinner Cruise

🌟Rating: 4/5 stars ⏰ Tour Length: 2 hours ℹ️Check Availability and Rates

Indulge in a culinary experience like no other on a Chicago night cruise dinner with the Lake Michigan Gourmet Cruise in Chicago!

Offering brunch, lunch, and dinner options, you’ll be treated to a delicious dinner experience against the backdrop of Chicago’s stunning skyline and the serene waters of Lake Michigan.

As you settle in for a memorable dinner, savoring local dishes created by the skilled chefs, you’ll glide past iconic landmarks, providing a unique and picturesque perspective of the city.

Enjoy from the live DJ, relish some games on board, or simply dance the night away, or make your way to the observation deck to view the Hancock Tower, Willis Tower, and Navy Pier!

There is a similar experience to this one called the Chicago Gourmet Brunch, Lunch or Dinner River Cruise, however this other option includes a Chicago night cruise with floor to ceiling windows and a glass roof to catch all the sights in one go!

“Really enjoyed this was a surprised gift from my family and my husband and I enjoyed it. The food was amazing.”

Read more reviews here


6. Chicago: Seadog Speedboat Fireworks Cruise on Lake Michigan

🌟Rating: 4.6/5 stars ⏰Tour Length: 1 hour ℹ️Check Availability and Rates

Dazzle your Chicago evening and prepare for a thrilling adventure under the night sky with the Seadog Speedboat Fireworks Cruise on Lake Michigan in Chicago!

For 60 minutes, you’ll enjoy this high-speed journey that not only offers a heart-pounding ride but also front-row views of the city’s fireworks display. Dash across the water for an exhilarating experience as you zoom past Chicago’s most famous landmarks!

While you look around Chicago’s iconic skyline, the sky will illuminate into a mesmerizing fireworks show, and you’ll witness the explosions of color from the perfect vantage point on the lake!

The tour also provides commentary throughout the experience, so you’ll learn important information about the city’s history, and more!

“The guide was great! He had a great sense of humor and kept us entertained! The fireworks were awesome!”

Connie – read more reviews here


7. Chicago: 45-Minute Private Helicopter Flight for 1-3 People

🌟Rating: 4.7/5 stars ⏰Tour Length: Customizable ℹ️Check Availability and Rates

Take your adventures to the sky, and elevate your Chicago adventure with a 45-Minute Private Helicopter Flight, perfect for 1-3 people!

This exclusive experience provides a bird’s-eye view of the Windy City’s iconic skyline, the famous Bean (Cloud Gate), Grant Park, and shimmering Lake Michigan, in a unique way!

From your experienced pilot, you’ll learn more about the city’s impressive history, including it’s architectural history and how the city pioneered the steel-frame construction, and more.

This private helicopter experience is not only a luxurious but unforgettable way to appreciate the grandeur of Chicago, and to capture stunning aerial memories with your loved ones.

“This experience was worth every penny! View beats any other way of taking in the city, especially at night and the pilot and co-pilot were very friendly and helped make our experience worth it! I highly suggest a night time flight, and also make sure you have a great camera too!”

Teshale – read more reviews here


8. Chicago: Small-Group Night Tour with Skydeck & Skyline Cruise

🌟Rating: 4.5/5 stars ⏰Tour Length: 3 hours ℹ️Check Availability and Rates

Combine two of the best night tours in Chicago, and look into the Small-Group Night Tour that includes the Skydeck and Skyline Cruise!

Begin your adventure at the Skydeck, where you’ll stand on The Ledge of the Willis Tower – a glass “box” balcony sticking out of the building’s 103rd floor!

Absorb the breathtaking 360-degree views of the city around, and below you from the top of the city, if you dare!

Afterward, embark on a night architecture tour of Chicago, and cruise along the Chicago River!

Take in the city’s architectural wonders illuminated against the night sky from all sides. Learn about the city’s history, including some fun facts you may have never heard before.

The great part about the small-group night tour with skydeck and and skyline cruise is the small setting, which ensures a personalized experience, rich with insights from your knowledgeable guide!

“We had a wonderful tour in Chicago with our guide Jake Edgar, we started with a river tour where we were informed from another guide about the architecture along the river, it was interesting to see the mix of old and new bulidings in chicago and to hear about the history behind it.”

Soren – read more reviews here


9. 2-Hour Pier Fireworks and Evening Segway Tour in Chicago

🌟Rating: 5/5 stars ⏰Tour Length: 2 hours ℹ️Check Availability and Rates

Roll around Chicago, and watch a beautiful fireworks spectacle when you book a fun Chicago lakeside magic with the 2-Hour Pier Fireworks and Evening Segway Tour.

As the sun sets over Lake Michigan, you’ll glide along the city’s lakefront on a Segway, enjoying the cool evening breeze and stunning views of Navy Pier and its iconic Ferris wheel!

Ride around the city’s sights like Buckingham Fountain, Millennium Park, the Bean, Maggie Dayley Park, and the beautiful gardens surrounding Chicago’s main parks!

Then as the night sky lights up, the tour will reach the best viewing point to admire the bright fireworks display over the pier.

Your expert guide will share intriguing stories about the city, making this tour not just a sightseeing adventure but an educational and thrilling evening in the heart of Chicago!

“Incredible experience! The tour very fun. The views are very nice. Our guide Sean spectacular! It was so worth it!”

Read more reviews here


10. Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

🌟Rating: 5/5 stars ⏰Tour Length: 3 hours ℹ️Check Availability and Rates

Add a little spice to your evening, and experience Chicago’s Prohibition-era allure with the 3-Hour Private Speakeasy Cocktail VIP Tour!

This private tour whisks you back in time to the era of hidden bars and secret cocktails, and is led by a knowledgeable guide.

On this unique and fun speakeasy tour, you’ll explore clandestine speakeasies that once flourished during Prohibition, and even get to learn about Al Capone’s favorite drink!

The unique and interesting information on this tour makes this one of the best and most immersive ways to learn about Chicago’s famous gangsters, and some of their leisure activities.

Find yourself in these retro-style bars, and with a VIP touch, you’ll enjoy priority seating and personalized attention, making this tour a blend of history, mixology, and upscale entertainment!

So if you’re ready to enter the Roaring Twenties, Chicago-style, this private speakeasy tour is for you!

“Would highly recommend this tour and Kai!”

Carol – read more reviews here


11. Private Evening Sail in Chicago Ending with Navy Pier Fireworks

🌟Rating:5/5 stars ⏰Tour Length: 2 hours ℹ️Check Availability and Rates

Have your own Chicago night boat party and sail into the enchanting Chicago evening on a Private Evening Sail culminating with Navy Pier Fireworks.

This exclusive experience offers a private boat charter on Lake Michigan, where you’ll bask in the serenity of the water and the romance of the twilight hour.

The beauty of this private boat sailing experience is that you’ll get the opportunity to select the music, route, and of course, guest list of up to 6 people, for 2 hours!

As the night unfolds, your journey will take you front-row to experience the dazzling Navy Pier fireworks display.

Whether you’re celebrating a special occasion or seeking a magical evening, this private sail guarantees an unforgettable adventure against the backdrop of Chicago’s sparkling skyline and the vibrant burst of fireworks over the lake!

“Captain Mike was amazing! The sail was incredible it was my fiance and I 3yr anniversary. We had an awesome time, Captain Mike had the perfect spot for fireworks. We will be doing this sail again.”

Christopher – read more reviews here


12. Chicago: 1.5-Hour Romantic Sunset Cruise

Looking for something romantic to do in Chicago? Consider the Chicago: 1.5-Hour Romantic Sunset Cruise for a captivating journey, setting the stage for a truly enchanting evening!

As the sun dips below the horizon, you and your significant other will embark on a serene cruise along Lake Michigan, with Chicago’s iconic skyline as your backdrop.

Enjoy your choice between wine, beer, a craft cocktail and snacks, as you look out towards the sunset views of Chicago!

Listen to your guide explaining the fascinating history of Chicago, get your perfect pictures taken for the perfect end to your evening, and admire the intimate atmosphere as you glide through the Chicago River and Lake Michigan.

The tour lasts 1.5 hours, and offers indoor and outdoor seating throughout the boat.

“A must do. Such breathtaking views and so fun. Our tour guide, Kay (my apologies if mis-spelled), was fantastic. Aside from the knowledge she shared, she made the experience personable by going around to everyone. My boyfriend and I had a great conversation with her. An absolute gem.”

Dee – read more reviews here


13. Chicago: Christmas Eve Gourmet Dinner Cruise Lake Michigan

🌟Rating: 5/5 stars ⏰Tour Length: 2.5 hours ℹ️Check Availability and Rates

Just because it’s Christmas, doesn’t mean you’ve run out of experiencing the best night tours in Chicago!

Check out the Chicago Christmas Eve Gourmet Dinner Cruise on Lake Michigan, and elevate your Christmas celebration, Chicago-style!

Hop aboard a luxurious cruise ship, and indulge in a delicious gourmet dinner prepared by skilled chefs while gliding along the tranquil waters of Lake Michigan.

Enjoy your 3-course meal, and then enjoy the live DJ and dancing, or look out the deck for incredible views of the Chicago skyline for a holiday night to remember!

It’s a delightful blend of culinary excellence and holiday spirit, creating a truly special evening in the heart of Chicago.

“Perfect sightseeing, music, service, and foods! I made a unforgettable memories though this trip!”

Read more reviews here


>> Read More: 5 Fun And Different Ways You Can Experience The Holidays In Chicago And Nearby Suburbs

14. Navy Pier Ferris Wheel at Night

Opt for one of the most wonderful scenic night tours in Chicago, and that is riding the Navy Pier Ferris Wheel at night for enchanting experience that brings Chicago’s skyline to life in a whole new way!

As the sun sets, hop on the city’s iconic Ferris wheel at Navy Pier, reaching almost 200 feet above Navy Pier, and get ready to enjoy the breathtaking panoramic views of the illuminated cityscape!

Each ride offers a unique perspective on Chicago’s glittering skyline, and the serene beauty of Lake Michigan at night adds to the charm.

Whether you’re on a romantic date or enjoying a family outing, the Navy Pier Ferris Wheel at night provides a memorable and magical journey above the city, making it a quintessential Chicago experience!

Because the Navy Pier Ferris Wheel is such an iconic activity in Chicago, make sure to pre-book your tickets (and look into skip-the-line tickets) to guarantee your spot and avoid long lines!


Best Night Tours in Chicago Questions and Answers

What are the best Night Tours in Chicago?

The best night tours will include a sightseeing experience that will allow you to see the city’s iconic skyline, learn about the city’s amazing architecture and history, while explore it’s hidden corners.

The beauty of Chicago is that there are tons of ways to experience the city’s sights in different ways, with plenty of night tour options!

Whether you want to experience the city’s skyline views from a bird’s eye view on a helicopter tour, or you want to hop on a night boat tour to see the sun set it’s light on the sparkling behind the the city.

Which experiences are best for night tours in Chicago?

You can never go wrong with a scenic sunset boat tour to enjoy Chicago’s famous waterways, get impressive views of the city’s world-class architecture, and of course, sail the famous Lake Michigan, which many tourists always get surprised with how big it actually is!

Aside from learning about Chicago on these epic sunset tours, you’ll also get to learn more about Lake Michigan!

You’ll learn how Lake Michigan is the 3rd largest Great Lake by volume, the 5th largest by surface area in the world, and much more!

What are the best places for night tours in Chicago?

The best places for night tours include the Chicago River, Lake Michigan, and exploring The Loop (the city’s central business district and heart of the city).

Is Chicago dangerous at night?

Like many other cities in the world, Chicago has it’s dangerous areas and other areas that are frequently visited, patrolled, and considered safe.

Sticking around Chicago’s famous sights is generally always safe, which is where all night tours take place.

Since these night tours are in groups, they take place in very touristic places, and you’ll be led by a local, you’ll have nothing to worry about when it comes to safety.

But as always, it’s important to keep a vigilant eye on your surroundings, here in Chicago, and any other huge city.

Concluding thoughts on the best night tours in Chicago

So, which night tour caught your eye the most? Which night tour will you include in your plans for a night in Chicago?

Will you take to the skies on an epic flying adventure on a helicopter tour, or will you sail Lake Michigan for those highly-coveted views of one of the greatest cities in the U.S?

Learn something new and have fun while you’re at it when you opt for a ghost tour, or a cool speakeasy tour!

Regardless of which night tour you go with, you’ll surely have fun exploring Chicago at night!

To more travel moments like this!

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