Chicago
Seasonal & Holiday Activities

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Our most recommended Chicago Seasonal & Holiday Activities

Chicago: 1.5-Hour Lake and River Architecture Cruise

1. Chicago: 1.5-Hour Lake and River Architecture Cruise

Experience an architecture cruise along the Chicago River and Lake Michigan, a family tradition since 1935. Admire Chicago’s historic and ever-changing skyline with a local expert guide as you cruise through the city. Choose between the open-air decks or the comfort of the climate-controlled interiors during the cruise. Start the cruise at Michigan Avenue (DuSable) bridge and go up the main branch of the Chicago River to Wolf Point before heading back past the Chicago Riverwalk towards Lake Michigan. Learn about historic skyscrapers like the Wrigley Building and the Tribune Tower, the deco Merchandise Mart, mid-century skyscrapers like the Mies Van der Rohe AMA Building, the circular Marina City Towers, the AON Center, and modernist structures like Aqua, Trump Tower, Nuveen, and the Vista Tower. After passing through the Chicago Lock and cruising past Navy Pier, admire the Chicago skyline from Lake Michigan, one of the largest bodies of fresh water in the world. Here you can also see the twin super-skyscrapers, the famous Willis (formerly Sears) Tower, and the John Hancock Building. See the majesty of Grant Park with its famous Buckingham Fountain, and iconic Chicago venues such as Soldier’s Field, Adler Planetarium, and the Shedd Aquarium. Enjoy several vantage points for memorable pictures throughout, and finally arrive back at Du Sable Bridge on Michigan Avenue.

Chicago: 360 Chicago Observation Deck Skip-the-Line Ticket

2. Chicago: 360 Chicago Observation Deck Skip-the-Line Ticket

Marvel at the views from 1,000 feet over Chicago’s legendary Michigan Avenue with this ticket to the 360 CHICAGO observation deck on the 94th floor of the John Hancock Center. Save time with skip-the-line access to this popular attraction. Head up to the 360 CHICAGO observation deck to take in breathtaking views of Chicago’s lakefront and view the city skyline from above. Take a peek at 4 neighboring states from this height. Feel the thrill of a 40-second ride in one of North America's fastest elevators to the observation deck to experience what 'Travel & Leisure Magazine' voted one of the best views in America. Get easy access to Chicago’s premier shopping and dining districts with 360 CHICAGO. Also, enjoy an interactive exhibit on the Ground Floor that highlights Chicago’s rich history and showcases 9 of the city’s culturally unique neighborhoods. Then, on the 94th floor, explore the history and architecture of the magnificent city stretched out before you with audio tours in 5 languages. If you wish, upgrade onsite to experience the Tilt. By purchasing this timed ticket, you get to skip the ticket desk and present your barcoded voucher to security to be scanned - you may have to wait in a short line at security, then head directly into the Ground Floor Exhibits, and then on to the Elevator Line.

Chicago: Fireworks Cruise with Lake or River Viewing Options

3. Chicago: Fireworks Cruise with Lake or River Viewing Options

Take in the amazing fireworks display off Navy Pier on a boat cruise. Briefly explore the architecture on Chicago River’s main branch before either heading out through the Chicago Locks onto Lake Michigan or staying inside the Locks to watch the fireworks. All cruises start by sailing inland up the Chicago River to Wolf Point, with some light narration provided focusing on history and architecture. Admire Chicago’s impressive architecture at twilight from either the indoor climate-controlled cabin or the airy outdoor deck. The cruise then heads back past the Chicago Riverwalk towards Lake Shore Drive, the Chicago Lock, and Lake Michigan for the spectacular fireworks show by Navy Pier. While on the boat, make sure to visit the full-service cash bar featuring authentic Chicago products, including local beer and spirits. Choose from the following options: River Fireworks Cruise from either Michigan Ave or the Riverwalk This shorter 45 to 60-minute River Fireworks Cruise option watches the fireworks display from the mouth of the Chicago River before returning to the dock. This cruise is perfect for families with children, couples, or groups of friends who are enjoying a night out on the town. Lake Michigan Fireworks Cruise from Michigan Ave This 2 to 2.5-hour Lake Michigan Fireworks Cruise goes through the Chicago Lock System, an American engineering marvel, and out onto Lake Michigan. The vessel will cruise along the shoreline with contemporary music and will ultimately stop on the lake and float alongside the fireworks display.

Chicago: 1.5-Hour Romantic Sunset Cruise

4. Chicago: 1.5-Hour Romantic Sunset Cruise

Relax as you glide over the Chicago River and into Lake Michigan on this cruise. Enjoy the glow of the sunset on Chicago's sparkling skyline. Have the option to purchase delectable drinks and snacks at the onboard bar as you sail. Start your sunset cruise on the Chicago River at Michigan Avenue. Make your way along the main branch of the river towards Lake Michigan before entering the Chicago Locks, a modern engineering marvel, that will transfer the vessel onto the great Lake Michigan. The vessel will cruise along Lake Michigan as the sun sets behind the wonderful skyline offering several amazing views. Your local tour guide will give a very brief commentary along the Chicago River and entrance to Lake Michigan, but most of the 1.5-hour cruise is spent without narration, leaving you to watch the sun put on a beautiful display with the City skyline. Admire the many angles of the Chicago skyline from Lake Michigan, one of the largest bodies of fresh water in the world. Capture magical views of Chicago's twin super-skyscrapers, the famous Willis (formerly Sears) Tower and the John Hancock Building. You'll also get to admire the majesty of Grant Park with its famous Buckingham Fountain, and iconic Chicago venues such as Soldier’s Field, Adler Planetarium, and the Shedd Aquarium. During your cruise, treat yourself at the full-service cash bar featuring authentic Chicago products. Try local beer and spirits and Garrett’s Popcorn. Choose between the fresh air of the open-air decks or enjoy the comfort of the climate-controlled interiors during your cruise. Don’t forget to take a selfie at the Grand Staircase at the front of the boat or pose for photos at the picturesque stern or bow of this classic vessel.

Chicago Seadog Speedboat Fireworks Cruise on Lake Michigan

5. Chicago Seadog Speedboat Fireworks Cruise on Lake Michigan

Enjoy a summer or autumn evening on this Chicago Seadog Speedboat Fireworks Cruise on Lake Michigan. This popular 60-minute narrated tour ensures you have the best views of this magnificent fireworks display. Every seat on the Seadog Speedboat Fireworks Cruise has amazing panoramic views of Chicago's historical skyline. Whether you are looking for a romantic evening, a night out with friends, or simply appreciate the art of pyrotechnics, this tour will have everyone of all ages leaving with a smile. Come and visit all of the possibilities that Chicago has to offer by enjoying a magical Fireworks Cruise on Lake Michigan. These memories are made to last a lifetime!

Chicago: Gangsters and Ghosts 2-Hour Walking Tour

6. Chicago: Gangsters and Ghosts 2-Hour Walking Tour

See a different side of Chicago on a family-friendly guided tour and hear the tales of the ghosts that haunt the city. Explore the famous Chicago Loop district with interesting stories hidden behind each turn. Embark along the Chicago Loop, known as the vice district during the 1920s and 30s. See the places where gangsters such as Al Capone used to party, make deals, and carry out business. Visit haunted locations and old crime scenes led by historians. Stop at the Congress Hotel, Death Alley, and the Palmer House. Enjoy a refreshment along with way, with frequent stops and a restroom break.

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

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

Enjoy spectacular views of Chicago from an MD500 helicopter. This helicopter flight over Chicago covers all the important highlights of the city from McCormick Place and Soldiers Field in the South to Wrigley Field in the North. Depart from Schaumburg Regional Airport and see some of Chicago's highlights including the Willis Tower, the John Hancock Building, Navy Pier, and Lake Michigan with its beaches and picturesque shoreline. Also see the Chicago River, Grant Park, Millennium Park, Buckingham Fountain, and Museum Campus. Make sure you also look out for Wrigley Field, home to the Chicago Cubs, and the United Center, where the Chicago Bulls and Blackhawks both play. This is a private helicopter experience for 1 to 3 passengers. Travel in complete safety with a professional pilot who will provide you with live commentary through noise-canceling headphones. In the summertime, have the added thrill of the doors being able to be off during the flight.

Chicago: Downtown Chicago Helicopter Sightseeing Tour

8. Chicago: Downtown Chicago Helicopter Sightseeing Tour

Discover Chicago from above on this 15-minute helicopter tour. Capture pictures of stunning city views as you fly over downtown Chicago. View sights like Willis Tower, Shedd Aquarium, and Soldier’s field (home of the Bears). Check in at the tour supplier's centrally-located office in Chicago and get ready to take off with a company that is committed to a safety-first policy. Hop aboard a spacious and comfortable helicopter and experience the excitement of lifting off. Feel the thrill of flying north over the Chicago River and past downtown, before looping over iconic Wrigley Field and flying back south along the famous Chicago beaches and Navy Pier. Snap pictures above the Willis Tower, the Chicago River, Wrigley Field (home of the Cubs), Lincoln Park Zoo, Navy Pier, Shedd Aquarium, and Soldier’s field (home of the Bears). End your tour with a smooth landing.

Chicago: Ghosts of Lincoln Park Walking Tour

9. Chicago: Ghosts of Lincoln Park Walking Tour

Meet your guide at the meeting point then set off on an unforgettable walking tour through Northside Chicago. Travel back in time as you visit some of the city’s most haunted locations in the mysterious Lincoln Park neighborhood. Learn about the forgotten burial ground that forms the foundation of this bustling district. Check out the bathroom mirrors at Lincoln Park Zoo, home to the ghost of a Victorian woman in white. And, hear about the spirit that haunted Al Capone in his final days.  Throughout the tour, you’ll listen to the strange and disturbing tales of each location. On the standard tour, visit eight historic sites, or opt for the extended tour which includes 12 ghoulish locations. By the end of the tour you’ll have learned about and experienced firsthand the alternative side of Chicago.

Chicago: Wind and Souls Adults Only Guided Ghost Tour

10. Chicago: Wind and Souls Adults Only Guided Ghost Tour

Enjoy a spine-tingling walking tour learning about Chicago's gruesome and haunting past with a local guide. Hear stories about paranormal activity in the Alley of Death, a librarian's spirit that haunts a local library, the ghost of Al Capone, and a hotel that is said to have inspired Steven King. Begin your tour at The Chicago Theater and hear the tragic story of how 602 people lost their lives at the Iroquois Theater in the 1903 fire. Continue walking to the nearby James M. Nederlander Theater and learn about the paranormal activity in the Alley of Death. Move on to the Chicago Cultural Center to hear about Frederick H. Hild, the second librarian in the history of Chicago's public library system, who is claimed to be haunting the local library.  Walk to nearby Lincoln Park and understand why it's considered to be more of a burial ground than an actual park. You will then stop by The Art Institute of Chicago and discuss how more than 300,000 items are considered to be haunted.  Then it's time to visit Congress Triangle Garden to view the Congress Plaza Hotel. Considered to be one of the most haunted hotels in the country, Congress Plaza Hotel is said to have served as a source of inspiration for a short story written by Stephen King. Complete your tour at the Exchequer Restaurant and Pub, where you will hear about Al Capone's dark past, and how people claim his ghost haunts the entirety of Chicago.

Frequently asked questions about Chicago Seasonal & Holiday Activities

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Other Sightseeing Options in Chicago

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What people are saying about Chicago

Overall rating

3.3 / 5

based on 11 reviews

The view is amazing. it wasn't too crowded but I didn't know the TILT wasn't included so I had to get it there, and I think we paid a lot more than it should be. Overall we had a great experience.

Great way to learn the history and some information about the amazing architecture of this beautiful city!

Sarah was an awesome guide! Very funny and knowledgeable! We really enjoyed our tour with her!

Very informative and relaxing to sit and see all of these incredible buildings.

Great tour about the history of gangsters and ghosts in Chicago!