Top Illinois Holidays

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.

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.

Most people have to decide between a boozy Sunday and a river cruise. During this special boat ride in Chicago, you get the best of both worlds. Enjoy a range of mimosas and other brunch drinks for purchase as you cruise down the Chicago River. Enjoy front-row seats as you pass by iconic skyscrapers and other downtown landmarks, with staff available to answer your questions.

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.

Celebrate the magic of the season on the water with a Christmas Eve Premier Dinner Cruise in Washington DC. You and your guests will enjoy a holiday 3-course, plated dinner freshly prepared by our chef, full bar service, and City Cruises’ distinctive hospitality. While onboard, experience exceptional views of Washington DC’s iconic landmarks, DJ entertainment, and festive décor. Our team will happily take care of the details, leaving you to celebrate the holidays on the Potomac River with your friends and family. Happy Holidays Includes Three-hour Christmas Eve dinner cruise on the Potomac River Chef-prepared, three-course, plated holiday menu The most breathtaking views of the nation's greatest landmarks including the Washington Monument and Lincoln Memorial DJ entertainment Complimentary coffee, hot tea, and iced tea

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.

Our flagship vessel boasts a Tiki Chic vibe, two climate controlled decks, two bars, two bathrooms, premium sound system, outdoor and indoor viewing areas. Our upscale "Admirals Lounge" features top-shelf alcohol, including the captain's private reserve. Your adventure starts on the Chicago Riverwalk when you board a vessel. Enjoy a beverage as you complete the unique experience of transiting the Chicago Locks. Once on Lake Michigan take in the stunning views of Chicago's skyline.

Set sail for an unforgettable evening aboard one of our River star, Island Time, where the drinks are flowing and the views are unbeatable. Enjoy a refreshing beverage as you cruise along the Chicago River, taking in the breathtaking iconic skyscrapers. .

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.

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.

Enjoy a fun, festive, and one-of-a-kind way to admire the Chicago skyline and views over Lake Michigan aboard this tiki boat tour. Choose from several start times, meet your tiki-themed vessel right on the Chicago Riverwalk, and climb aboard. As you sail along the Chicago River and out onto Lake Michigan, you’ll enjoy a new perspective on the Windy City—and can purchase mimosas and other beverages at the on-board cash bar.

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.

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.

Admire up-close views of the Chicago skyline—and a fireworks show over the city—on this tiki bar boat tour. In the evening, make your own way to the departure point at the Chicago Riverwalk, hop aboard, and get comfortable in the air-conditioned seating area or on the deck. Purchase cocktails and food from the on-site tiki bar, watch the city float by, and then sit back and take in the show.

Chicago is well known for its architecture and many visitors admire the buildings on a cruise along the Chicago River. Take your river cruise to the next level aboard a floating tiki bar that allows you to take in all the sights with a drink in hand. Your captain also enhances the atmosphere with island tunes as you enjoy your leisurely sail.

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!

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.

Set sail on our flagship vessel, where style meets comfort in a Tiki Chic atmosphere. Your adventure begins on the iconic Chicago Riverwalk, where you’ll board a beautifully appointed boat featuring two climate-controlled decks, two full bars, two bathrooms, and both indoor and outdoor viewing areas—perfect for soaking in the sights no matter the weather. As you sip a refreshing beverage, enjoy the rare experience of transiting the historic Chicago Locks—a must-see for locals and visitors alike. Once you glide into the open waters of Lake Michigan, you’ll be treated to breathtaking views of Chicago’s world-famous skyline, framed by the gentle breeze and city lights. Looking to elevate your cruise? Upgrade to the exclusive Admiral’s Lounge, where you’ll enjoy top-shelf spirits, including selections from the Captain’s Private Reserve, all in a more intimate, upscale setting. This is more than just a boat ride—it’s a uniquely Chicago experience you won’t forget!

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.

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.

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!

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