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 the architecture cruise that started it all — a Chicago family tradition since 1935. View Chicago’s historic and ever-changing skyline on Chicago's only architecture tour with views from both directly from the Chicago River, and those only possible from Lake Michigan. During this comprehensive sightseeing tour, all of Chicago's architecture highlights will be viewed, discussed, and experienced. Choose between the fresh air of the open-air decks or enjoy the comfort of the climate-controlled interiors during your cruise. The tour starts at the Michigan Avenue (DuSable) bridge and goes up the main branch of the Chicago River to Wolf Point before heading back past the Chicago Riverwalk towards Lake Michigan. On the way, you will learn about ornate, historic early skyscrapers like the Wrigley Building and the Tribune Tower, the imposing art deco Merchandise Mart, mid-century sky...

    The police were chasing drunken boaters, so the locks were closed to all. We spent a long time in Lake Michigan and still continued the tour of the river after the locks opened again. I think it was more like a 3 hour tour and it was great fun.

  • Chicago: 1.5-Hour Romantic Sunset Cruise

    2. Chicago: 1.5-Hour Romantic Sunset Cruise

    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 ge...

    It was the best price for a river tour and I know sometimes if you pay less you get less but this star was outstanding. I would highly recommend

  • Chicago: Gangsters and Ghosts 2-Hour Walking Tour

    3. 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.

    We loved this tour, Stephan was very funny and knowledgeable. Will suggest to friends and family:)

  • Chicago: Ghosts of Lincoln Park Walking Tour

    4. 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.

    Tammie was an excellent guide, engaging and full of interesting stories. Other people on the tour squealed with delight as she told them tales of ghosts. Also some great history thrown in!!

  • 360 Chicago: Observation Deck Entry with a Drink at Bar 94

    5. 360 Chicago: Observation Deck Entry with a Drink at Bar 94

    Take your cocktail hour to a whole different level at Bar 94, 360 Chicago's own inviting bar located 1,000 feet over Chicago’s spectacular Magnificent Mile. Part observation deck, part cocktail and beer destination, Bar 94 combines breathtaking views and taste-tempting cocktail combinations. Featuring locally crafted beers from Revolution Brewing and locally inspired spirits from KOVAL Distillery, Bar 94 combines amazing 360-degree views with premium beer, wine, and spirits to give you a taste of Chicago you can’t find anywhere else. Your admission includes access to 360 Chicago, formerly The John Hancock Observatory, which combines superior lake views with close-ups of Chicago’s monumental landmarks. With views consistently rated as Chicago’s best, no other tower gets you closer to the heart of Chicago. Located on the Magnificent Mile and close to Navy Pier, 360 Chicago also provides...

    It was a great experience. The only suggestion I would say is to have a few more places to sit while drinking your cocktail. Otherwise, everything was fine.

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

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

    Enjoy spectacular views of Chicago from an MD500 helicopter. This 45-minute 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 headp...

    Was a very exciting and thrilled ride...Especially with the doors off. It was a sunny day with great views of the city

  • Chicago: Kayak or Paddleboard Rental with Optional Lesson

    7. Chicago: Kayak or Paddleboard Rental with Optional Lesson

    Rent a kayak or paddleboard and enjoy kayaking on either the Chicago River or Lake Michigan or paddleboarding on the calmer waters of Monroe Harbor on Lake Michigan. Choose to add on a paddleboard lesson. Take a skills assessment and watch a safety video upon arrival. If you don't pass the skills assessment, it is possible to partner with a more experienced friend. Enjoy on-site portable toilets and a changing room for your convenience. Single and tandem (2-person) kayaks are offered at both locations, while paddleboards are only available on Lake Michigan. Paddleboards are for 1-2 riders. The lakefront location in Monroe Harbor on Lake Michigan offers calmer conditions for both kayaking and paddleboarding and is perfect for beginners and families. More experienced kayakers can choose to kayak on the Chicago River, an amazing place to paddle, surrounded by spectacular architecture...

  • Chicago: Photo Shoot with a Private Vacation Photographer

    8. Chicago: Photo Shoot with a Private Vacation Photographer

    The tour provider will organize the locations for your photo shoot based on your own unique requirements, whether it be a family getaway, a romantic trip or a livelier one with friends.  Once the details are organized, you will receive confirmation of all the information you need, leaving you to simply meet the photographer on location in Chicago on the day and let them work their magic, capturing your travels in a contemporary and candid style of photography. Your Chicago vacation photographers are handpicked and highly experienced in addition to being local experts and will share their knowledge of the city with you like an old friend. Once your photo tour has finished, you will receive a link to your own personal online gallery (password protected) within 5 working days, containing your professionally edited images, all free to download. This photo tour will allow you to look back o...

  • Chicago: Holiday Lights Segway 2-Hour Tour

    9. Chicago: Holiday Lights Segway 2-Hour Tour

    Bundle up in your warm clothes and make your way to the starting point near Millennium Park in downtown Chicago to meet your guide for your Segway tour. Get started with a safety briefing and orientation to the Segway, then have time to become familiar with the controls and practice riding. Once you’re ready, set off with your expert guide through downtown Chicago.  Admire the holiday splendor of the Windy City as you watch ice skaters twirl around the Millennium Park Ice Rink, located below the city’s iconic silver ‘bean’ sculpture (officially named Cloud Gate). Then glide along Michigan Avenue under trees that glow with colorful lights and take in the fabulous holiday window displays at Macy's. Stop at Daley Plaza to check out the German-inspired Christkindlmarket, the city’s largest open-air Christmas festival. Made to resemble a European village in winter, the famous market feature...

  • Chicago Holiday Season: Guided Walking Tour and Samples

    10. Chicago Holiday Season: Guided Walking Tour and Samples

    From shimmering lights to decadent bites, Chicago puts its best foot forward for the holidays.   Experience the city come to life during this special time of year on a walking tour through the Loop’s iconic holiday destinations. Pass by Millennium Park's ice skating rink and massive Christmas tree, admire the shimmering holiday lights on State Street, and behold Macy's dazzling holiday decor and window displays. Treat yourself with some brownies at the historic Palmer House Hotel, where brownies were invented, taste the famous Chicago deep-dish pizza and hot dog, and tuck into the city's largest open-air Christmas festival, Christkindlemarket, for some seasonal shopping. For an additional fee you can also enjoy a VIP Christmas cocktail sampling package.

    Kevin was a fun, informative and all around great guide. Highly recommend the tour for some Chicago Holiday fun!

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 experience was out of this world! Highly recommend this activity & of course the Tilt! You will not be disappointed! It is VERY convenient to have the voucher ready to go within the app. The only downfall was the drink you receive with the purchase. The menu is very limited. Other then that, amazing experience.

Amazing and beautiful scenery while on the tour!! To see the beautiful Chicago Skyline as the sun set, was pleasing to my eyes. The tour guide was quite entertaining, which was an added bonus in the learning of Chicago's History. The tour was definitely worth taking!!

It was the best price for a river tour and I know sometimes if you pay less you get less but this star was outstanding. I would highly recommend

I had the best of Chicago experience. Higy recommended. Best crew and guide.

Wonderfully interesting, engaging guide who kept the group wanting more.