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Activities in Chicago

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$16* and up
Ranked #1 of 389 activities in Chicago
Category: Sightseeing Tours
Owner description: Bobby's Bike Hike is a great value - providing signature guided bicycle tours and year-round walking tours of Chicago's... more » Owner description: Bobby's Bike Hike is a great value - providing signature guided bicycle tours and year-round walking tours of Chicago's lakefront, iconic downtown loop, and neighborhood attractions, all appropriate for every age and fitness level. Check out our brand-new, season walking & food tours(Bobby's Hikes). Bobby tours Chicago in style with deluxe Schwinn Comfort bikes complete with cushy seats, fat tires, and annoying bells :). Our hand-selected guides are chock full of historical information which is sure to inform and entertain you on your journey. Our folks in the shop are friendly and helpful and they will take the time to teach you the ropes before sending you on your way. Tours include the Lakefront Neighborhoods Tour which was Voted Best Chicago Tour seven years in a row, the City Lights at Night Tour which is a healthy way to explore Chicago at night, Bobby's 'Tike' Hike for families with younger riders, and the Bikes, Bites, & Brews Tour which is a food sampling tour. If you want to learn about Chicago's seedier past, check out the Southside Chicago Gangster Tour. If you want the best views in Chicago, check out our brand-new Museums & Parks at Sunset Tour. We also offer year-round walking and food tours, including the Chicago Favorites Food Tour, Public Art & Architecture Tour, and the Holiday Hike - Season Sampling Tour. All walking tours make use of Chicago's elaborately unique indoor pedway system in inclement weather. « less
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$70* and up
Ranked #2 of 389 activities in Chicago
Category: Segway Tours; Sightseeing Tours
Owner description: For a great way to see Chicago’s top attractions in just 2 hours, try a Segway tour. If you’re wondering if they’re safe and... more » Owner description: For a great way to see Chicago’s top attractions in just 2 hours, try a Segway tour. If you’re wondering if they’re safe and easy to learn, the answer is YES! Sightseeing on a Segway is fun, unique, and exhilarating! Explore Chicago by day or night with our friendly tour guides. Whether you are visiting from out-of-town or a native of Chi-town, come join us on a tour to remember! « less
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Ranked #3 of 389 activities in Chicago
Category: Sightseeing Tours
Owner description: Chicago's Finest River Walk Tour is now Chicago's Finest Tours! We are Chicago’s most dynamic and fun entertainment activity... more » Owner description: Chicago's Finest River Walk Tour is now Chicago's Finest Tours! We are Chicago’s most dynamic and fun entertainment activity option! We offer our guests highly passionate and energy-packed activities ranging from walking tours, bus tours and highly advanced scavenger hunts. We distinguish ourselves by providing our guests captivating storytelling, keen visualizations and infectious enthusiasm! Our mission is to ensure each guest walks away with a smile on their face and better understanding of our amazing city! « less
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Ranked #4 of 389 activities in Chicago
Category: ; Walking tours; Sightseeing Tours
Owner description: Walking tours that delight visitors with the "second side of the Second City," with gorgeous, fascinating, and often hidden... more » Owner description: Walking tours that delight visitors with the "second side of the Second City," with gorgeous, fascinating, and often hidden details behind many doors. Get to know Chicago through its real-life stories: the explorers, settlers, architects, business people, laborers, immigrants, and revolutionaries who developed the area from its beginnings as a marshy outpost to the beating heart of America that it is today. Walk your walk through modern architectural history, all the way to plans for the future look of Chicago! Inside Chicago Walking Tours is a brand new walking tour company founded by Hillary Marzec, an experienced tour guide and product development director for a major sightseeing company in Chicago. Given the freedom to research and construct her own tours, she used her years of experience as a teacher, writer, improv comedian, and tour guide to create tours that tell the story of Chicago in an engaging, educational, and always entertaining way. We know that the best way to get information to "stick" with people -- and to be interesting to people -- is to convey it like a story, with a logical beginning, middle, and end. Most architecture tours of Chicago -- boats, walks, segways, etc. --present you the city like an overwhelming laundry list of information that you'll likely forget. For us, there is a reason we are exploring a certain area, or following a certain path: the architecture that we explore is like the vocabulary of the larger story we are telling. What makes us different? It's our ability to find the hidden and fascinating details of buildings and areas that people pass through or pass by every day. It's our passion for showing visitors, whether they be out-of-towners or Chicagoans, a side of Chicago that they haven't noticed before. We love to focus on the stunning interiors of buildings throughout downtown Chicago - including many of the buildings along the river - and we even provide you with an "insider's scoop" on lots of the exterior architectural elements that most guides won't show you. Your guide, Hillary, will delight you with a side of Chicago you've never seen. Take it from a past tour participant: "Imagine your favorite teacher when you were growing up - engaging, charismatic, and really made you love learning. That's Hillary. Don't miss her tours!" « less
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$50* and up
Ranked #5 of 389 activities in Chicago
Category: Sightseeing Tours
Owner description: Rated 'Best Chicago Tour' by Lonely Planet and featured on The Today Show (NBC), USA Today and Bon Appetit, Chicago Food... more » Owner description: Rated 'Best Chicago Tour' by Lonely Planet and featured on The Today Show (NBC), USA Today and Bon Appetit, Chicago Food Planet Food Tours offer delicious 3-hour food tasting events focused exclusively in Chicago's historic off-the-beaten-path neighborhoods near downtown including the Gold Coast, Chinatown, Bucktown, Lincoln Park, Old Town and Wicker Park. Suitable for all age groups and fitness levels, each walking tour provides a non-touristy, local experience so you feel like a native Chicagoan. The guided Food Tours include mouth-watering food samples, enough for a large lunch, from unique specialty food stores, local restaurants and ethnic eateries while providing a detailed insiders view of Chicago's most famous communities- their rich histories, treasured architecture, dazzling entertainment offerings and restaurant recommendations. Tours run 7 days a week between March and November. The earliest departure time leaves at 11am and depending on the tour will last between 2-3 hours. Tickets start at $35 adult with adolescent and child tickets available. « less
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Ranked #6 of 389 activities in Chicago
Category: Sightseeing Tours
Owner description: Chicago Greeter highlights more than 40 special interest areas and more than 25 neighborhoods for visitors to explore.... more » Owner description: Chicago Greeter highlights more than 40 special interest areas and more than 25 neighborhoods for visitors to explore. Chicago Greeter is designed to match a friendly, enthusiastic, and city knowledgeable local with a visitor for a two - four hour FREE informal, insider orientation to Chicago's sights. Through the Chicago Greeter service, visitors meet with a greeter who takes them around the city and demonstrates its walk-ability and the user-friendliness of its public transportation system. « less
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Ranked #7 of 389 activities in Chicago
Category: Sightseeing Tours
Chicago's Neighborhoods Food Tour.
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Ranked #8 of 389 activities in Chicago
Category: Sightseeing Tours
Owner description: Our PERSONALIZED RUNNING TOURS are completely customizable to the day, time, distance and sights you want to see. Your... more » Owner description: Our PERSONALIZED RUNNING TOURS are completely customizable to the day, time, distance and sights you want to see. Your personal running guide will pick you up from where you are staying, run at your pace, provide water and have a camera in case you feel like capturing the moment. At the completion of the run we will return you to where you are staying and you walk away with a souvenir goody bag. « less
Visitor photos (69)
Book a Tour
$65* and up
Ranked #9 of 389 activities in Chicago
Category: Segway Tours; Sightseeing Tours
Owner description: City Segway Tours of Chicago is the first Segway tour company in the world and in Chicago and we work hard to create... more » Owner description: City Segway Tours of Chicago is the first Segway tour company in the world and in Chicago and we work hard to create memorable experiences for our guests. From rolling smaller guest to guide ratios than the city requires to our experienced staff that comes back on a yearly basis, we realize that giving our guests the best tour possible starts before you step on the machine.Come join us for our tours that will take you through Grant Park, Museum Campus, Soldier Field and give you a great view of our hometown whether you've been in Chicago for 10 hours or 30 years.The Segway is a self-balancing, personal transporation device that requires no special skills to operate. Segways are designed to be used in any pedestrian enviornment and will carry you gracefully throughout the Windy City.City Segway Tours- Chicago uses the latest generation of Segways- the i2- that include the new lean Steer technology. « less
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Ranked #10 of 389 activities in Chicago
Category: Sightseeing Tours
Owner description: Only the Chicago Architecture Foundation and Chicago's First Lady Cruises can showcase Chicago's world renowned city... more » Owner description: Only the Chicago Architecture Foundation and Chicago's First Lady Cruises can showcase Chicago's world renowned city architecture with style, class and comfort. Open-air and air-conditioned seating is available. Learn about the architecture and design of over 50 buildings as described by CAF-Certified Volunteer Docents/Guides. Don't settle for imitations, look for the CAF logo. Full Service Bar onboard each vessel. 90-minute river architecture cruises depart daily. Cruising season May - November. All tours depart from Riverside Gardens, Michigan Ave. and Wacker Dr. (Southeast corner of the Michigan Avenue Bridge). Look for our blue awning. « less
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Book a Tour
$15* and up
Ranked #11 of 389 activities in Chicago
Category: Sightseeing Tours
Owner description: Touring with the Chicago Architecture Foundation (CAF) is the best way to explore Chicago. From our most popular tour, the... more » Owner description: Touring with the Chicago Architecture Foundation (CAF) is the best way to explore Chicago. From our most popular tour, the Architecture River Cruise to our more than 85 different walking, bus, bike, Segway and train tours you are sure to get a true Chicago experience. As a non-profit organization, our tours are led by highly-trained volunteer guides who are passionate about sharing the history of our beautiful city. Tours depart year-round. « less
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Ranked #12 of 389 activities in Chicago
Category: Sightseeing Tours
Owner description: Free Tours by Foot offers pay-what-you-like tours of Chicago, focusing on walking, but also food, bike and ghosts tours. Name... more » Owner description: Free Tours by Foot offers pay-what-you-like tours of Chicago, focusing on walking, but also food, bike and ghosts tours. Name your own price, including free. Pay-what-you-like tours are tours for every budget. « less
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Ranked #13 of 389 activities in Chicago
Category: Segway Tours; Sightseeing Tours
Map | Visitor photos (27)
Book a Tour
$20* and up
Ranked #14 of 389 activities in Chicago
Category: Sightseeing Tours
Owner description: Hello hello! I'm Margaret, tour guide, author and comedian. My tours are full of humor and fun and are definitely off the... more » Owner description: Hello hello! I'm Margaret, tour guide, author and comedian. My tours are full of humor and fun and are definitely off the beaten path. I'm a life-long Chicagoan and have been a tour guide for seven years. I love my job and my city and I'm all about showing it off to you. I'm an improviser and comedian from Second City, so expect some really hilarious (to me anyway?) impressions. We have a lot of fun on tours, you know, while we're learning. During the winter months I run the Pedway Tour (it's all indoors! We never go outside!) and in the summer I run The Disaster! Tour (best new tour!), the Loop Tour (highlights!) and the new Binoculars Tour! I am also available for private tours and group tours! Let's do this. « less
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Ranked #15 of 389 activities in Chicago
Category: Symphonies; Theater and Concerts
Map | Visitor photos (26)
Ranked #16 of 389 activities in Chicago
Category: Sightseeing Tours
Owner description: Chicago Beer Experience Beer Tours offer walkable beer tasting and bar tours in Chicago! Our initial tour takes place in the... more » Owner description: Chicago Beer Experience Beer Tours offer walkable beer tasting and bar tours in Chicago! Our initial tour takes place in the Lincoln Park/Lakeview Neighborhoods on Chicago's North Side. You'll taste several craft beers, learn about Chicago history from 1833 to the present, and even eat some bacon! Tours are led by a trained guide, who will weave Chicago history and beer together in a fun, informative way while visiting four establishments, some of which have been around since the days of Prohibition. Perfect for men and women ages 21 to 121, individuals and groups, from bachelor parties to corporate outings, we've got something for everyone. Book your beer tour today! « less
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Ranked #17 of 389 activities in Chicago
Category: Sightseeing Tours
Owner description: Interactive, Educational, and FUN! Chicago Private Tours invites you to discover Chicago, with the help of one of our expert... more » Owner description: Interactive, Educational, and FUN! Chicago Private Tours invites you to discover Chicago, with the help of one of our expert guides. Our tours cater to each group’s interests, including themes such as architecture, history, culture, sports, and shopping. Each outing is customized to fit your interests and includes an expert guide, luxury vehicle, and driver. Chicago Private Tours is for clients that are looking for more than the one-size-fits-all tour. See what you want to see, when you want to see it, and how you want to see it! “Customize your Chicago Experience!”Pick-up/Drop-offChicago Private Tours always accommodates its clients and will pick up anywhere in and around the city, including airports and train stations. This is ideal for individuals who do not have a lot of time, but want to see as many of the sites as possible on their busy schedule!TransportationAll of Chicago Private Tours’ vehicles are top of the line in luxury. Our fleet of vehicles can accommodate every group size, from 1 person to large groups- always in comfort and style.LanguageAll of our guides conduct tours in English, but if you desire the tour to be given in another language, we will gladly arrange a Guide who speaks the desired language at no additional cost.(Ex. Spanish, Italian, French, German, Mandarin, Russian, Japanese, and many more!) « less
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Ranked #18 of 389 activities in Chicago
Category: Sightseeing Tours
Owner description: Walk Chicago Tours is a privately owned walking tour service known for its personal amenities, experience and reasonable... more » Owner description: Walk Chicago Tours is a privately owned walking tour service known for its personal amenities, experience and reasonable rates. Its concierge-like treatment of all of its guests, and the ability of its experienced guides to engage visitors through skillful story-telling have set standards in Chicago. It offers a "no-gimmicks" product delivered in an engaging and professional style. Personal treatment for guests begins at the outset of their day. If you are staying at a Loop area hotel, your guide greets you in the lobby to begin your tour experience. If you are a disabled tourist or have special needs to be addressed, Walk Chicago Tours devises a completely accessible itinerary at no extra cost. There is also no combining of groups or joining groups with strangers. Each tour reservation is a private promise...only your group with your own private guide(see FAQ page of their website). Guides at Walk Chicago Tours have been carefully chosen based upon their natural ability to engage visitors and to narrate historical facts,culture and urban lore. The company motto, "A Story on Every Corner", is typical of the ownership's insistence that Chicago's history,its neighborhoods,its culture and urban lore be delivered to visitors in an entertaining and informative manner that appeals to a wide array of groups. In fact,several of the guides are former teachers with years of experience at engaging listeners. The result has been the reputation that Walk Chicago Tours is Chicago's most competent story telling ambassador. No service is more zealous about wanting you to leave Chicago loving Chicago as much as they do. And, they attempt to do this at a price that fits the budget of every visitor. Large groups are accomodated by the use of multiple guides. See their website and visit their FAQ page for answers to most of your questions. Email or call and they will respond immediately. . « less
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Ranked #19 of 389 activities in Chicago
Category: Performances; Theater and Concerts
Owner description: Chicago’s smash-hit musical inspired by the famed 1956 recording session that brought together rock 'n' roll icons Johnny... more » Owner description: Chicago’s smash-hit musical inspired by the famed 1956 recording session that brought together rock 'n' roll icons Johnny Cash, Jerry Lee Lewis, Carl Perkins and Elvis Presley for the first and only time. That legendary night is brought to life featuring a score of hits including "Blue Suede Shoes," "Great Balls of Fire," "Walk the Line," "Whole Lotta Shakin' Goin' On," "Hound Dog" and more.Don't miss your chance to be a fly on the wall of fame... Wed. 2pm & 7:30pm; Thurs. 7:30pm; Fri. 8pm; Sat. 5pm & 8pm; Sun. 3:30pm & 6:30pm. (Summer Sunday hours June through September - 2pm & 5pm) « less
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Ranked #20 of 389 activities in Chicago
Category: Segway Tours; Sightseeing Tours
Map | Visitor photos (74)
Book a Tour
$25* and up
Ranked #21 of 389 activities in Chicago
Category: Boat Tours; Boat tours & water sports
Owner description: Seadog Cruises offers the most fun and exciting ways to see the city. Choose from a 75-minute river and lake architectural... more » Owner description: Seadog Cruises offers the most fun and exciting ways to see the city. Choose from a 75-minute river and lake architectural tour, a 30-minute speedboat lake tour or Seadog's newest doggie, the Seadog Extreme which, at 30% faster than her doggie siblings features exhilarating high speeds and 180-360 degree spins. Seadog also offers Lakefront Firework Tours Memorial Day - Labor Day! We welcome day-of reservations. Please don't hesitate to call us if you are looking to cruise today! « less
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Ranked #22 of 389 activities in Chicago
Category: Performances; Operas; Theaters; Theater and Concerts
Map | Visitor photos (27)
Ranked #23 of 389 activities in Chicago
Category: Sightseeing Tours
Owner description: Experience Tastebud Tours, the #1 Food Tour in Chicago! Enjoy the best Deep Dish Pizza and Chicago-style Hot Dog. Savor the... more » Owner description: Experience Tastebud Tours, the #1 Food Tour in Chicago! Enjoy the best Deep Dish Pizza and Chicago-style Hot Dog. Savor the tastes of these iconic dishes and more! Walk through the heart of the city on a Tastebud adventure. Eat at five memorable restaurants and food specialty shops. Hear about Chicago's history, cultural fun facts and celebrated cuisine. Gift certificates available. Group Events & Customized Private Tours also available. Open year-round.The best deal in town! Advance ticket purchase is required. Tours sell out in advance. Come hungry! « less
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Ranked #24 of 389 activities in Chicago
Category: Performances; Theater and Concerts
Map | Visitor photos (55)
Ranked #25 of 389 activities in Chicago
Category: Walking tours; Sightseeing Tours
Owner description: Experience Chicago like a Chicagoan! Chicago is a city of unique neighborhoods. Let’s walk through some of them - Chinatown,... more » Owner description: Experience Chicago like a Chicagoan! Chicago is a city of unique neighborhoods. Let’s walk through some of them - Chinatown, the Gold Coast, Lincoln Park, Pilsen, OId Town, Kenwood, and more-interact with locals, see where people live, enjoy the local restaurants, and learn how each neighborhood’s unique history shaped its culture, art, and architecture. Walk with us and catch our passion for Chicago. « less
Visitor photos (43)
Book a Tour
$85* and up
Ranked #26 of 389 activities in Chicago
Category: Sightseeing Tours
Owner description: Embark on an adventure to Chicago's best restaurants aboard Chicago's premier Progressive Dining Tour. Guests are chauffeured... more » Owner description: Embark on an adventure to Chicago's best restaurants aboard Chicago's premier Progressive Dining Tour. Guests are chauffeured around Chicago in a stylish coach bus to enjoy Hors D'oeuvres served at the first restaurant, the Main Course at a second restaurant, and Dessert at a third restaurant. The tour offers a unique, fun and exciting way to experience different restaurants in Chicago, interact with others, and tour Chicago. Visit our website for details and sample menu. « less
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Book a Tour
$26* and up
Ranked #27 of 389 activities in Chicago
Category: Sightseeing Tours
Owner description: Guided tours of architecture, history and culture that bring people to explore stories and places locals don't even know.... more » Owner description: Guided tours of architecture, history and culture that bring people to explore stories and places locals don't even know. Tours include Good Times Historic Bar Tour, Inside the Loop Architectural Tour, and Jazz, Blues & Beyond Bus Tour. Guests get to share iPads with media while professional tour guides share forgotten stories from the past and create a fun, interactive dynamic. « less
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Ranked #28 of 389 activities in Chicago
Category: Theaters; Theater and Concerts
Owner description: The Lookingglass Theatre Company seeks to redefine the limits of theatrical experience and to make theatre exhilarating,... more » Owner description: The Lookingglass Theatre Company seeks to redefine the limits of theatrical experience and to make theatre exhilarating, inspirational, and accessible to all.Through theatre, which invites, even demands, interaction with its audience, the company's goal is to fire the imagination with love, to celebrate the human capacity to taste and smell, weep and laugh, create and destroy, and wake up where we first fell --- changed, charged and empowered. « less
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Ranked #29 of 389 activities in Chicago
Category: Performances; Theaters; Theater and Concerts
Owner description: Recipient of the Regional Theatre Tony Award, Chicago Shakespeare Theater offers a broad spectrum of theatrical experiences... more » Owner description: Recipient of the Regional Theatre Tony Award, Chicago Shakespeare Theater offers a broad spectrum of theatrical experiences year-round, engaging and entertaining audiences from all walks of life and from around the world. « less
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Ranked #30 of 389 activities in Chicago
Category: Theaters; Theater and Concerts
Owner description: Established in 1922, Goodman Theatre has been a part of life in Chicago for 90 years. Every season, the Goodman presents the... more » Owner description: Established in 1922, Goodman Theatre has been a part of life in Chicago for 90 years. Every season, the Goodman presents the work of an extraordinary group of local, national and international artists. « less
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