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Chicago Seasonal & holiday activities

Our most recommended Chicago Seasonal & holiday activities

Chicago: Gangsters and Ghosts 2-Hour Walking Tour

1. 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 your historian guide revealing the many interesting stories hidden behind each turn. Explore the Chicago Loop, known as the vice district during the 1920s and 30s, once the home of speakeasies, secret tunnels and bootleggers. 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 including Chicago Riverwalk, Death Alley, and the Chicago Theatre. Peak inside the haunted Palmer House. Finish up at the Congress Hotel, one of the most haunted places in Illinois. Enjoy frequent stops along the way, including a refreshment stop and a restroom break.

Chicago: Medieval Torture Museum Ticket with Ghost Hunting

2. Chicago: Medieval Torture Museum Ticket with Ghost Hunting

Gain entry into one of the largest interactive torture museums in the USA with this attraction ticket. Explore the museum with an audio guide and learn about the terrible history of punishment, torture, and executions from humanity's darkest times. Enter the 5,000 square foot exhibition and get your audio guide from the greeter. Follow the guide's instructions to learn about the hundreds of examples of torture, interrogation, restraint, and execution devices. Gain a greater understanding of how the devices worked by viewing the wax sculptures depicting executioners and victims. While you explore the museum, you can also participate in the thrilling Ghost Hunting Experience by downloading the app.

Chicago: Guided Walking Tour and Food Sampling

3. Chicago: Guided Walking Tour and Food Sampling

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. Upon arrival, for an additional fee you can also enjoy a VIP Christmas adult beverage sampling package.

Chicago: Christmas Eve Gourmet Dinner Cruise Lake Michigan

4. Chicago: Christmas Eve Gourmet Dinner Cruise Lake Michigan

Celebrate the magic of the season on the waters of Lake Michigan with a Christmas Eve gourmet Dinner Cruise in Chicago. You and your guests will enjoy a holiday 3-course, plated dinner freshly prepared by the chef, and full bar service. While onboard, experience exceptional views of Chicago’s iconic skyline and architecture, DJ entertainment, and festive décor. The crew will happily take care of the details, leaving you to celebrate the holidays on Lake Michigan with your friends and family. Sample Brunch Menu FOR THE TABLEASSORTED BREAD & BUTTER (V) STARTER (CHOICE OF ONE)BEET & BABY ARUGULA SALAD Feta Cheese | Cherry Tomatoes | Balsamic VinaigretteSIGNATURE SEAFOOD CHOWDER Clams | Flounder | Potatoes | Cream MAIN (CHOICE OF ONE)ROOT VEGETABLE FRICASSEEButternut Squash | Cauliflower | Zucchini | Grape Tomatoes | Gremolata | Cauliflower Coconut Cream SauceBROILED SALMON FILET WITH ROASTED TOMATO VINAIGRETTELemon Orzo | Farm Fresh Seasonal VegetablesOVEN-ROASTED CHICKEN BREAST WITH ROSEMARY & THYMERoasted New Red Potato Salad with Scallions | Haricot Verts | Creamy Mushroom SauceBRAISED BEEF SHORT RIBS WITH FRESNO PEPPER DEMI GLACE (G*)Garlic Mashed Potatoes | Baby Carrots | Broccoli DESSERT (CHOICE OF ONE)SIGNATURE CHOCOLATE CAKE Creme Anglaise | Raspberry Coulis | Candied Pecans MIXED FRUIT WITH STRAWBERRIES Madagascar Vanilla and Orange CreamNEW YORK STYLE CHEESECAKE Lemon Mascarpone Cream | Blueberry Compote **May contain Nuts

Chicago Outdoor Escape Game: Ghost Hunt

5. Chicago Outdoor Escape Game: Ghost Hunt

Discover Chicago’s famous haunted locations while playing the role of a lost soul wandering among the spirits of the city. As you solve challenges, the story unfolds and exact directions on your phone will guide you to the next location. Ready for an adventure? Head to the Chicago History Museum, where the game will start. It will take you between 1 to 1.5 hours to complete, but there’s no time limit so feel free to explore, and finish it at your own pace: pause the game and resume anytime from the location where you paused it. You will finish the game at the Alfred Caldwell Lily Pool. After your booking, you will receive an email with instructions on how to download and play the game on your phone. You can play on your own, in a large group or in several smaller groups that compete against each other and meet at the final stop of the game. We recommend that each user purchases a ticket for an optimal experience, although several people can share a phone.

Bobby's Fright Hike: Halloween Edition Chicago Bike Tour

6. Bobby's Fright Hike: Halloween Edition Chicago Bike Tour

Join Bobby’s Bike Hike as we unleash our Halloween "Fright" Hike bike tour through the city of Chicago! We’ll ride through a former cemetery where thousands of bodies are buried and visit the Chicago River site where 844 people drowned in the middle of broad daylight. It is believed that one man, Charley Porter, who was on the boat when it sunk, still haunts the area to this day. We’ll discuss Resurrection Mary, Chicago’s most infamous ghost, as well as explain some of Chicago’s most notoriously haunted locales from the Levee District to the Colombian Exposition and the exploits of the one and only H.H. Holmes.

Chicago River: Christmas Eve Gourmet Brunch River Cruise

7. Chicago River: Christmas Eve Gourmet Brunch River Cruise

Celebrate the magic of the season on a luxurious Christmas Eve gourmet brunch cruise aboard Chicago’s glass-enclosed Odyssey Chicago River – Chicago’s most premium experience on the water. You and your guests will enjoy a chef-prepared 3-course, plated holiday brunch, and full bar service. While onboard, experience exceptional views of Chicago’s iconic skyline and architecture from an incredibly unique perspective, DJ entertainment, and festive décor. The crew will happily take care of the details, leaving you to celebrate Christmas Eve on the Chicago River with your friends and family. Sample Brunch Menu STARTER (CHOICE OF ONE)BEET & BABY ARUGULA SALAD Feta Cheese | Cherry Tomatoes | Balsamic VinaigretteGREEK YOGURT & GRANOLA PARFAIT Chobani Non-Fat Greek Yogurt | Honey Granola | Fresh Blueberries and Strawberries MAIN (CHOICE OF ONE)SCRAMBLED EGGS Nueske's Applewood Triple-Thick Cut Bacon | New Red Potatoes & Cauliflower Hash | Arugula Salad with Champagne Vinaigrette & Red OnionsBRIOCHE FRENCH TOAST Stuffed with Nutella Cream | Fresh Strawberries | Maple Syrup (Contains Nuts)OVEN-ROASTED CHICKEN BREAST WITH ROSEMARY & THYMERoasted New Red Potato Salad with Scallions | Haricot Verts | Creamy Mushroom Sauce DESSERT (CHOICE OF ONE)SIGNATURE CHOCOLATE CAKE Creme Anglaise | Raspberry Coulis | Candied Pecans (Contains Nuts) MIXED FRUIT WITH STRAWBERRIES Madagascar Vanilla and Orange CreamNEW YORK STYLE CHEESECAKE (V)(N)Lemon Mascarpone Cream | Blueberry Compote **May contain Nuts Menu is subject to change.

Frequently asked questions about Chicago Seasonal & holiday activities

What are other things to do than Seasonal & holiday activities that are worth visiting in Chicago?

The other unmissable things to do in Chicago are:

Which Chicago Seasonal & holiday activities are taking additional COVID-19 precautions?

These Chicago Seasonal & holiday activities are taking additional COVID-19 precautions:

Other Sightseeing Options in Chicago

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What people are saying about Chicago

Overall rating

3.3 / 5

based on 11 reviews

First and foremost Nate our tour guide is why this tour was amazing! Within 5 minutes we were all family having a blast walking, eating, laughing and learning some cool things about Chicago. I've lived in the Chicago area for 40+ years and have taken a number of tours, and thought I knew it all, but Nate amazed me with new tales. Then there's the food. You can't go wrong with Chicago's iconic staples. Take the tour! You'll love it!!

Awesome tour with an awesome guide ! Baylor’s enthusiasm and friendliness really sold it and she even managed to give me goosebumps with the way she told some of the stories! :)

Our guide Ty was super cool and handled the whole tour well. I'll definitely tell all my friends who visit Chicago to take this tour.

It was a very fun tour and we learned a lot about the city that we didn't know before. Lizzie was an excellent guide!

Conor was very knowledgeable and the tour was a great pace with lots of info!