Activities, Camps and After School Classes in Chicago, IL

This Chicago Food & Bike tour is perfect for the entire family, put on by Bobby’s Bike Hike, whose food tours in just the past year have ranked as Top 10 in America by USA Today and Top 20 in the world by Tripadvisor. Biking is easy in Chicago because of it's miles of bike trails, flat terrain and easy connections between attractions. We’ll be sampling from each of Chicago’s well known and unique foods -- deep dish pizza, a true Chicago hot dog, and a dessert for good measure. You’ll learn the history behind the foods and also get a taste for some of Chicago’s most popular downtown districts as we cruise through the Gold Coast, Chicago Riverwalk, Millennium Park, Buckingham Fountain, Museum Campus, Navy Pier and along the Lakefront. Whether day or night, you'll get fantastic views of the skyline and feel the city's vibrant energy. Veggie options available. Bikes, Helmets and all Child Equipment included on this engaging bicycle tour of Chicago.

Enjoy a private photoshoot in Chicago’s beautiful urban jungle at the Lincoln Park Conservatory. During this 40-minute session, I’ll help you feel confident and relaxed while taking high-quality photos using iPhone, optimized for social media. You’ll receive about 50 digital photos, including 5 professionally edited images, delivered via a private online gallery. Please download your photos within 14 days after receiving access, as the gallery link will expire.

Discover the elegance and beauty of Hanfu, the traditional 
clothing of ancient China, in this one-of-a-kind cultural experience here at our Chinatown Visitor Center! Step into Ancient Elegance in Authentic Hanfu Costumes! Take stunning photos & share with your friends Learn about the history and meaning of Hanfu Fun for families, friends, and culture lovers of all ages

⭐ Top-Rated Vacation Photoshoots 2025 We’re not just photographers, we’re storytellers capturing your holiday exactly as it feels. With over six years of experience photographing travellers around the world, our small team specialises in authentic, natural photography that truly reflects your trip. In Chicago, we combine creativity with local knowledge to show you hidden gems, secret angles, and the best light. You’ll not only get beautiful, professional photos but also insider tips to make the most of your time here. We’re proud to be recognised among the top-rated photography tours of 2025, trusted by travellers worldwide for our relaxed style and stunning results.

Experience the magic of Chicago at dusk on a live-guided panoramic adventure that captures the city in its most captivating light. Watch the entire skyline come to life, from Magnificent Mile to Museum Campus and beyond. From the top deck of an open-top double decker, you’ll have a perfect vantage point to see the best of Chicago. Witness the vibrant nightlife of River North brim with energy, trendy bars, and eclectic dining options. Your knowledgeable guide will provide fascinating insights and stories into the history and hidden stories of Chicago. Next, the journey takes you along the legendary Michigan Avenue. From the upscale shopping and historic architecture of The Magnificent Mile to the cultural treasures of State Street Theater District, you’ll experience the diverse facets of Chicago’s most famous avenues. See renowned attractions like the Wrigley Building, Tribune Tower, and the Art Institute of Chicago, all beautifully illuminated against the evening sky.

No visit to Navy Pier is complete without a ride on the Centennial Wheel, Navy Pier's iconic, 200-foot-tall Ferris wheel, promising unparalleled views of Lake Michigan and the Chicago skyline. Each gondola seats up to 8 guests and is fully enclosed for year-round comfort.

Discover the rich history and architecture of downtown Chicago with local expert Dave Lineal. Walking underneath the soaring buildings, we will learn how Chicago grew to become a global force in culture, commerce, and architecture. How did this roaring city come to be? We will hear the tales of Chicago history immersed in the places where it happened -- exploring historic building interiors like the world's oldest skyscrapers, City Hall, and the old library. This deep dive in city history and architecture aims to deepen our appreciation of what Chicago is today.

Get the best of both worlds: explore Chicago’s stunning architecture while uncovering its dark past. Inspired by Devil in the White City, this expert-led walking tour reveals the secrets of the city’s skyline and its shadowy history. If it’s raining the tour is almost all INDOOR. Led by a passionate local guide, you’ll visit architectural gems and hidden landmarks that BOAT TOURS MISS bringing Chicago’s rich and eerie past to life.

The Chicago Architecture Center River Cruise aboard Chicago's First Lady has long been the gold standard among all Chicago tour experiences, and is the only Chicago architecture boat tour led by highly trained expert docents. On this 90-minute cruise, you will enjoy an overview of historic and modern architectural styles including stories about the people who designed and built Chicago. As a certified nonprofit, all ticket purchases directly support education efforts and community engagement projects. No visit to Chicago is complete without experiencing this award winning tour, so accept no substitutes.

Six days to enjoy the beautiful scenery of the three major lakes in the Great Lakes region of the United States, all of which are located in Lake Michigan in the United States, Lake Superior, the largest freshwater lake in the world, and Lake Huron. Famous cities along the five great lakes: Chicago, Milwaukee and Traverse City along Lake Michigan, Green Bay along Green Bay, and Sault Ste. Mackinac Island, which was once selected as one of the top ten most beautiful islands in the world. Room Details All hotel rooms are based on two Full / Double beds or one King/Queen bed depends on what rooms are availiable at the hotel on the day. The maximum occupancy per room is four travelers. One Room Selection If you are a party of more than four guests or desire to have separate rooms, please create separate bookings. Avoid traveling in a different bus? If you have more than one booking, please provide all confirmation numbers once your bookings are complete.

Four days to enjoy the beautiful scenery of the three major lakes in the Great Lakes region of the US, all of which are located in Lake Michigan in the US. Four famous lakeside cities: Milwaukee and Traverse City along Lake Michigan, Green Bay along Green Bay, and Sault Ste. Mackinac Island, which was once selected as one of the top ten most beautiful islands in the world and known as the treasure of the Great Lakes in North America; Sleeping Bear Dunes National Lakeshore Scenic Area with beautiful beaches. Room Details All hotel rooms are based on two Full / Double beds or one King/Queen bed depends on what rooms are availiable at the hotel on the day. The maximum occupancy per room is four travelers. One Room Selection If you are a party of more than four guests or desire to have separate rooms, please create separate bookings. Avoid traveling in a different bus? If you have more than one booking, please provide all confirmation numbers once your bookings are complete.

Walk where a nation was born and experience the story behind America’s fight for independence. Join Rosotravel for a 2.5-hour guided walk along the Freedom Trail, crafted for travelers who want insight, emotion, and connection—not just photos. Starting at Boston Common, your Licensed Guide brings history to life at sites including the Massachusetts State House, Old South Meeting House, Old State House, Faneuil Hall, and Old North Church, ending near the Bunker Hill Monument. Through vivid storytelling and expert perspective, discover the people and events that shaped a nation. Don’t just visit Boston—understand it. Book your walking tour today. Discover Chicago’s dark past with a 5-Star Licensed Guide downtown Trace Al Capone’s rise from Riverwalk to Congress Plaza Hotel Learn how Prohibition gang wars shaped Michigan Avenue’s legacy See Chicago Theatre and Palmer House tied to crime lore Feel chills at Congress Plaza and Cloud Gate at night

The Chicago 3Quest Challenge is a scavenger hunt done on an app where players will find objects (given in the form of riddles) and complete fun challenges for points. The items & challenges are separated into 3 quests. Complete quest 1, then quest 2, then quest 3 in order to finish the game! Set a time limit for yourself to see if you can do all 3 quests in 2 hours! You'll have a remote host who will chat with you during the game if you need anything! The objective is to see if you can complete all 3 quests! Come play 3Quest Challenge in Chicago today!

Let’s Roam leads the way as the top app-led adventure hunt company! Explore the city’s top landmarks and uncover hidden gems while tackling trivia questions and overcoming challenges. Whether you're collaborating with your team or sparking friendly competition, you’ll discover new facts and forge unforgettable memories. Let’s Roam Adventure Hunts are perfect for any occasion—from everyday fun to bachelorette parties, birthdays, corporate team building events, and beyond! Each participant selects an interactive role, with challenges tailored to every adventurer's spirit.

Unleash your creativity at the Glow Workshop, a unique art experience where vibrant neon paints glow under blacklight. Guided by talented street art instructors, you’ll create a stunning 12x16" canvas masterpiece that comes to life in the dark. Perfect for a fun night out or a memorable date, this high-energy workshop offers an inviting atmosphere to connect with friends while enjoying your first craft brew on us. Bring your imagination and prepare for a night of painting, laughter, and glowing art.

Five days to enjoy the beautiful scenery of the three major lakes in the Great Lakes region of the United States, all of which are located in Lake Michigan in the United States, Lake Superior, the largest freshwater lake in the world, and Lake Huron. Famous cities along the five great lakes: Chicago, Milwaukee and Traverse City along Lake Michigan, Green Bay along Green Bay, and Sault Ste. Mackinac Island, which was once selected as one of the top ten most beautiful islands in the world. Room Details All hotel rooms are based on two Full / Double beds or one King/Queen bed depends on what rooms are availiable at the hotel on the day. The maximum occupancy per room is four travelers. One Room Selection If you are a party of more than four guests or desire to have separate rooms, please create separate bookings. Avoid traveling in a different bus? If you have more than one booking, please provide all confirmation numbers once your bookings are complete.

Chicago’s Loop is home to some of the city’s most perfectly preserved Art Deco architecture designed during the Roaring 20s. See 7 stunning Art Deco buildings, all masterpieces in their unique & individual ways, as well as 4-5 other notable properties and outdoor sculptures on this fun and fabulous walk of Chicago's Financial District and parts of the North Michigan Avenue corridor. Your tour guide, interior designer, and historical architecture guru Ronnie Frey will paint a picture you'll not soon forget of modern life in the New Machine Age.

This tour will show you many of these delightful cottages and the different styles they were designed and constructed in. You will also learn about their history and unique part of the growth of the city of Chicago. Plus you will hear about other fascinating Chicago history that dates back 150 years and beyond! The Oldtown Triangle is one of the oldest and most quaint areas of the city - an area that many Chicagoans love and cherish. You will feel like you have left the hustle and bustle of the city and will instantly be transported to another place, another time, specifically the late 1800's!

Our tours are not only personable (due to small group sizes), but also create an immersive experience with our knowledge and expertise in street art. What better way to explore a new neighborhood but with a local artist in tow to give expert commentary on the vibrant history and culture of the Chicago Art Scene.

Your private luxury tour experience begins with a prompt pickup in downtown Chicago. Step inside the climate-controlled cabin of a world-class Rolls-Royce. Your professional chauffeur will navigate the bustling streets of the Windy City. Glance through the panoramic windows at towering skyscrapers like the Willis Tower. Coast down Michigan Avenue to admire the luxury boutiques of the Magnificent Mile. Pass by the architectural marvels of the Loop and the lakefront beauty of Grant Park. This tour itinerary maximizes your time in the city. It is ideal for couples celebrating an anniversary, travelers on a tight schedule, or anyone seeking a VIP Chicago experience. Avoid the crowds of standard tour buses. Enjoy the privacy, comfort, and prestige of DS Luxury Rolls-Royce Tour.

The Blue-Collar side of Chicago many call it! This tour will show The Ford Factory, home of the steel mills, the blue-collar neighborhoods and many places on the South Side, home to the 44th President of The United States, Barack Obama. We tour Bronzeville! A historical African American neighborhood and early business district as well as Hyde Park, home of the World renowned University of Chicago (the spot where the atomic bomb was born and yes we show the spot!) We explore South Lake Drive and life along the lake. Chicago has a border with Indiana, we show how that special dynamic works. We visit Beverly Hills, Chinatown, and the large and highly populated Puerto Rican Neighborhood “Little Village”. We also pass through Pilsen, a proud Mexican community. Cook County jail, we pass by it too! We go thru Little Italy Greektown. It’s blue-collar! We visit a lime quarry in the Bridgeport neighborhood. After this tour you will know tons about The Southside of Chicago.