Top Illinois Holidays

Step into the shadows of Chicago’s past on this adults-only haunted pub crawl, where ghost stories, historic landmarks, and legendary nightlife collide. Beginning near the iconic Palmolive Building, this guided experience takes you through the city’s Gold Coast and beyond, uncovering the eerie aftermath of the Great Chicago Fire and the restless spirits it may have left behind. Along the way, you’ll visit a curated mix of historic sites and local bars, blending chilling storytelling with time to grab a drink and soak in the atmosphere. Adults 21+ only, must have valid I.D.

On this cheerful tour you’ll see Chicago’s most famous Christmas trees, as well as several under-the-radar ones you may not know about. Your guide will lead you around downtown, stopping at the Christkindlmarkt and the old Marshall Field’s, as well as hidden-gem spots with some of the city’s most impressive holiday decor. All the while, you’ll learn about some beloved Christmas stories and traditions from across the globe, and even get to stop for some holiday sweets.

Stroll through Chicago's winter streets, lit up for the holidays, without the hassle of navigating the city yourself on this gourmet walking tour. Learn about Chicago's celebrated holiday traditions like the European-inspired Christkindlmarket, the beautiful decor and windows on State Street, and ice skating at Millennium Park. Sample generous tastes of classic Chicago foods and holiday treats as you walk.

We invite you to join us on a holiday themed, festive and fun foodie adventure! This tour is just like our normal food tour, but with a holiday twist! Dig out those ugly Christmas sweaters and get ready to see the Hallmark of the Midwest in a new and foodie way. PLUS, rock out that ugly sweater and you will be in our contest to win a free tour! You will join your festive foodie guide down the famous Main Street of Galena enjoying some of the best food and drinks the town has to offer. Definitely bring an empty stomach and your holiday cheer!

Discover a dark, spooky side of Chicago that most tours miss on this adults-only ghost walking tour. Keep an eye out for sinister specters and ghastly ghouls as you explore abandoned buildings and shadowy alleyways near some of Chicago’s most popular landmarks, including the Chicago Theatre, Millennium Park, and the Art Institute of Chicago.

Discover many of Chicago’s best-known landmarks—and see the city dressed up in its festive best—on this holiday walking tour of the Windy City. Come bundled and join your guide and small group to explore the famous Christkindlmarket. Then continue to discover Millennium Park’s ice rink and Christmas tree, stroll the Magnificent Mile’s glowing lights, and more while you hear fun facts and cultural insights from your guide.

Maximize your Chicago sightseeing on a river cruise—and travel aboard a unique historical vessel, which other tours don’t offer—on this one-of-a-kind excursion. Pick from different departure times and board a classic Chicago fireboat, which served the city’s fire department from 1937 to 1981. As you sail Lake Michigan and the Chicago River, view architectural highlights including the Wrigley Building and Chicago Lighthouse, and chart the boat’s firefighting history via the on-board displays and commentary.

Get ready to unleash your creativity at the BYOB Candle-Making Class at Chicago Candle Co. This hands-on workshop invites you to craft stunning, personalized candles from upcycled wine bottles, all while enjoying your favorite drinks. Under the guidance of friendly instructors, you’ll learn the art of glass cutting and soy wax pouring, choosing from a variety of cocktail-inspired scents. Bond with friends or make new ones in a welcoming atmosphere as you create unique pieces that reflect your individual style and eco-friendly values. Perfect for a fun night out or a memorable group activity in the heart of Chicago.

Enjoy a food-focused cruise along the Chicago River and Lake Michigan, departing conveniently from Michigan Avenue. This experience combines city views with curated wine and cheese pairings in a relaxed, social setting. Choose between indoor and outdoor seating for comfort in a range of weather conditions, while the absence of narration allows for uninterrupted conversation. A full-service bar is also available for additional drinks throughout the cruise.

We'll explore five (5) of our favorite, Handcrafted Local Micro Breweries in two special locations of the historic, Chicago landmark district, Fulton Market; which used to be the meatpacking district, now becoming the Chicago Brewery District. Here you'll experience the fabulous, intricate world of the art of beer creation. We will all meet at the first one, introduce ourselves and try some delicious appetizers; where Carla will make a special Homemade Guacamole and Homemade Tortilla chips, and here, the first 3 handcrafted beers (3-5oz beers) are on us. Then we'll walk to the other breweries where you'll have a chance to order other beers and serve your own. Here you can stay as long as you want after the tour. During our expedition, we can all share our opinion about the flavors, the creation, etc... All the breweries are within walking distance.

Enjoy the city of Chicago during a magical time! This private experience takes you around Chicago in a private luxury vehicle with your own personal guide! Enjoy all the Holiday sites the city is known for including, Daley Plaza's Christkindl Market, Macy's Walnut Room and animated story windows, the Goodman Theatre, and marvel at the skaters under the iconic "Bean" of Millennium Park. This experience is the only way to see Chicago during the holidays!

This private Christmas walking tour in Chicago captures seasonal traditions within a historic urban setting. You will begin along Michigan Avenue, where architectural landmarks are illuminated with festive displays. How do European holiday customs shape winter traditions in American cities? Along State Street, seasonal décor reflects a long-standing retail heritage. The Christkindlmarket introduces a cultural tradition rooted in German history and craftsmanship. Wooden stalls and artisan goods echo centuries-old holiday markets of Europe. This experience blends festive atmosphere with cultural continuity in a refined city setting. Please note: The program and attractions may vary based on booking date/time and crowd conditions, ensuring each visit is a unique experience.

Escape Chicago for a day and experience Milwaukee’s culture, food, and legendary beer scene. This curated day trip includes highlights such as the Harley-Davidson Museum, free time at the Milwaukee Public Market, and an optional Miller Brewery tour and tasting. Enjoy scenic views along the lakefront and an outside visit to the Milwaukee Art Museum before returning to Chicago. Ideal for travelers looking for a relaxed, well-rounded introduction to Milwaukee.

Take an adventurous half-day journey through the most interesting Chicago neighborhoods with a friendly private guide and see the city from a new perspective riding a bike. Dive into the atmosphere of the city’s movement and combine it with tasting the most delicious and iconic treats of the Chi after whetting your appetite, absorbing the unique beauty of the city. Discover more sights in a shorter time using a bike Get a true taste of the City by the Lake following the tips of a local guide Discover iconic neighborhoods and be entertained with historical insights. Learn about the peculiarities of local cuisine and its origins.

"Dive into adventure with Let’s Roam, your go-to for the ultimate app-led adventure hunts! Step into a world where every landmark and hidden gem is waiting to be discovered. Challenge yourself with trivia, tackle brain-teasing puzzles, and embark on an epic journey of exploration! Whether you’re collaborating with your crew or turning up the competition, Let’s Roam Adventure Hunts guarantee a blast for all. Perfect for any occasion—whether it’s a spontaneous outing, a wild bachelorette bash, a festive birthday celebration, or a team-building extravaganza. Each player gets to dive into an interactive role, ensuring every challenge is as thrilling and unique as the next. So, gather your squad, choose your adventure, and let the good times roll! With Let’s Roam, every outing becomes a treasure trove of memories and excitement. Are you ready to conquer the city and create unforgettable experiences? Let’s Roam and make every day an adventure!"

Ready for a night that’s equal parts laughter, creativity and cocktails? Join this hands-on paint and sip class in Chicago hosted through!, and rediscover how fun it feels to just make something. Your local instructor keeps it light and easy while you sip, swirl and paint your way to a surprisingly awesome masterpiece — even if you swear you can’t draw a stick figure. Everything’s included (canvas, brushes, paint, apron), and every class takes place in a cool local spot like a brewery or bar. Whether it’s a casual date, a team hangout or your solo night of self-care, this experience guarantees good vibes, great drinks and a painting you’ll actually want to show off.

Enjoy a one-of-a-kind night at the theatre when you attend Chicago’s irreverent and comedic “Drunk Shakespeare” performance. Pick between two different start times, and choose a seating area that suits your budget and preferences. Then, sit back, relax, and prepare to laugh as an actor downs five shots of whiskey before attempting to perform in one of Shakespeare’s plays.