Top Chicago Outdoor Activities

An authentic Chicago tradition since 1935, this is the tour that started it all. This unique excursion tells the story of more than 200 years of fascinating social, cultural and political history, and explores more than a century of groundbreaking architecture. The journey begins with an up-close perspective of Chicago's internationally-known architecture as seen from the Chicago River. Then venture through the Chicago Lock on to the calm, cool waters of Lake Michigan for expansive views of Chicago's extraordinary 26-mile skyline. Take the selfie of a lifetime on this inspirational experience!

Experience one of the world’s most beautiful cities on a cruise down the historic Chicago River. On this architecture cruise, head down the main branch of the Chicago River, up the north branch to the East Bank Club, and then south past Willis Tower (Sears Tower) to the old Post Office Building. Take in magnificent city skyline views as you see more than 40 notable buildings, including the John Hancock Center and the Wrigley Building, and learn about their distinctive architecture from your onboard guide, an expert in architecture.

Marvel at the magnificent architecture on the Chicago River with expert tour guides! All ages welcome. Each architecture river tour is narrated by a professional guide which leads passengers down the Chicago River to discover the city’s most renowned landmarks. In addition to historical insight on well known structures such as the Civic Opera House, Trump Tower & the Merchandise Mart, passengers will also get a chance to learn about current and upcoming developments. The Chicago River Cruise navigates the three primary branches of the river including the main branch to Navy Pier, the north branch to Goose Island and the south branch to Chinatown.

No city embraces summer quite like Chicago. Join in the celebration with friends and family on this epic fireworks cruise. Get up-close and personal every Wednesday and Saturday night with an unobstructed 360-degree view of this exciting and thunderous spectacle.

The Lake Michigan Sunset Cruise departs near the DuSable (Michigan Avenue) Bridge on Wendella's world class tour boats. The Cruise will navigate from the Chicago River, through the Chicago Lock and out onto Lake Michigan. Watch the sun slowly set behind the city from the tranquil waters of Lake Michigan on this serene and romantic cruise.

The best views of Chicago can be yours at 360 Chicago Observation Deck! Perched 94 stories above the Windy City, the 360 Chicago provides commanding views of Lake Michigan and Chicago’s towering skyscrapers, including Willis (Sears) Tower. Located in the heart of downtown on Michigan Avenue, the observatory is steps away from other top Chicago attractions. It will be the high point (literally) of your Chicago trip! Upgrade your ticket onsite to include TILT, a thrill ride that offers visitors unique, downward facing views from 1,030 feet. Or grab refreshments at our newly CloudBar.

Gaze upon the city sights from the pinnacle of Chicago, the Skydeck. Located on the 103rd floor of Willis Tower, formerly Sears Tower -- the third-tallest building in the world -- the Skydeck offers spectacular sweeping views and is full of interactive exhibits. To complete your exciting Chicago experience, head to the Ledge, a glass balcony showcasing unbeatable views of Chicago’s top attractions like Wrigley Field and the Navy Pier. We added a brand new Chicago Experience that you start with by the box office prior taking the elevator trip to the 103rd floor. It is a 45,000 sq ft. museum of today. The New Experience is part Chicago History, part Architecural tour, part Selfie Museum and part Children's Museum. This is fun and interactive for all ages. Ride our "L" Train, see our infinity pizza bed, take pictures ontop of Willis Tower and so much more! This is the best way to see Chicago in one setting. With mobile tickets, simply scan your phone for direct entry into the SkyDeck

Interested in exploring Chicago from the perspective of ghosts and gangsters? Want to really immerse yourself in the history of this great American city, right from the locations that started it all? This tour visits the locations frequented by some of Chicago's most notorious gangsters along with many of the most haunted locations in Chicago! You can get the best of both worlds with this 2 in 1, history-based guided walking tour of Chicago’s gangsters and ghost stories, right from the famous Chicago Loop Vice District! Tour departs from 71 E Wacker Drive.

The lakeside metropolis of Chicago is famous for its striking skyscrapers, world-class museums and colorful history. Explore the “Windy City” at your own pace, with the choice of 24 Hour and 48 Hour tickets, all which include a hop-on, hop-off sightseeing bus tour with stops strategically located near the city’s top attractions. Hop on to experience sites like the Adler Planetarium and Navy Pier or hop off along the Magnificent Mile to shop, see the great city at heart-stopping heights from Willis Tower’s Skydeck.

Escape into Chicago's underworld on a crime and mob tour with stops on-and-off the luxury, climate-controlled bus. Walking tour paths explore historic crime scenes with great photo opportunities. True crime stories about Chicago Gangster Al Capone, The Untouchables, The Chicago Mob, Prohibition, John Dillinger, Frank “The Enforcer” Nitti, Cap George Streeter, Leopold & Loeb, H.H. Holmes and more. Visit historic landmark buildings like: The Biograph Theater, Holy Name Cathedral, Cook County Criminal Court House, Harry Caray’s Italian Steakhouse, etc. Tour famous Chicago neighborhoods: Streeterville, River North, Gold Coast, Lincoln Park, Old Town, Loop and Magnificent Mile. Locals and tourists agree that this educational and entertaining thing to do in Chicago is a unique cultural experience.

Create your own sightseeing itinerary with the Chicago Explorer Pass, saving up to 50%* off compared to buying individual attraction tickets. This multi-attraction pass, valid for 60 days after your first use, provides admission to your choice of up to seven attractions, tours or activities - all one one pass. Select from more than 25 top sites and things to do, including SkyDeck Chicago, Navy Pier and a Shoreline Architecture River Cruise. It's the easiest and most affordable way to explore the Windy City at your own pace. Simply save your pass on your mobile device (available as your 'ticket' after purchase) and go – no voucher redemption required! With Go City you can see more, do more, and save more. *Savings based on sample itineraries on the Go City website

Admire all of Chicago's fabulous lakefront sights and attractions on this Lake Michigan boat tour. Cruise along Lake Michigan and take in amazing views of the city’s famous skyscrapers from a great vantage point. Feel free to bring a lunch and enjoy drinks from the onboard bar as you relax on this sightseeing cruise.

Get acquainted with Chicago’s most iconic landmarks on this riotous guided bicycle tour! Join the expert guides of Bobby’s Bike Hike, America’s longest-running city bicycle tour company, on this exciting and informative adventure. Over the course of a 3-hour bike ride (traversed at a nice leisurely pace), you’ll get up close and personal with Chicago’s legendary Museum Campus, Grant Park, and Millennium Park. You’ll become intimately familiar with Soldier Field, The Adler Planetarium, Buckingham Fountain, The Pritzker Pavilion, and Cloud Gate (the formal name of Chicago’s dearly-beloved “Bean”). This tour is perfect for first time visitors looking to see all of the classic hotspots, and for returning guests looking to understand more about the landmarks they know and love. Hop on two wheels, and come make memories that are sure to last a lifetime!

Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire. This family-friendly introduction to the Windy City's rich history and architectural heritage features highlights from Wendella's full-length architecture tours. Hop aboard our world class vessels as our local authentic tour guides showcase our amazing city.

This tour is unique as it offers the ability for you and two of your friends or family (a total of 3 passengers) to experience what it is like to fly over the city of Chicago on a 45 minute thrill seeking guided tour. The price is the total for all 3 passengers (saving you money compared to other operators who charge per person.)

Chicago CityPASS® — Discover Chicago's best attractions at one great price with an easy to use mobile ticket. Spend less, experience more. Save 48% or more on prepaid admission to 5 must-see attractions: • Shedd Aquarium • Skydeck Chicago Plus your choice of admission to 3 of the following attractions: • Field Museum • Art Institute of Chicago • Museum of Science and Industry • 360 CHICAGO Observation Deck • Adler Planetarium • Shoreline Sightseeing Architecture River Tour

Experience the best of Chicago with a Premier Dinner Cruise and spend your evening on Lake Michigan with dining, picturesque views, DJ entertainment, and dancing. While onboard, you’ll enjoy our chef-prepared plated menus, creative cocktails, distinctive service, and breathtaking views of Chicago’s skyline and attractions from our climate-controlled interior and open-air rooftop decks. Whether for a romantic dinner for two or for a special evening with friends and family, our dinner cruises are the perfect way to elevate any occasion and see Chicago from the water! Includes - 3-course, chef-plated menu - Spectacular views of the Chicago skyline including the Willis Tower - and Adler Planetarium - DJ-curated music - Guaranteed table for your party size - Complimentary coffee, hot tea, and iced tea Extras & Upgrades: - Creative cocktails, wine, and beer are available for purchase from our fully stocked bar

Our Chicago Signature Lunch Cruise is an unforgettable way to experience the city from the water. Spend your afternoon on Lake Michigan with dining, picturesque views, DJ entertainment, and an assortment of games. While onboard, you’ll enjoy our chef-prepared lunch buffet, a fully stocked bar, and incredible views of Chicago’s skyline and attractions from our climate-controlled interior and open-air rooftop decks. Whether for a scenic lunch for two or for an unforgettable afternoon with friends and family, our Lunch Cruises are perfect for any occasion and serve as the best way to see Chicago from the water! 

Leave the hustle and bustle behind! Explore Chicago's shores with a leisurely trip around Lake Michigan. Take in the world-famous skyline, enjoy spectacular views, and discover the Windy City from the water. Windy is the Official Ship for the City of Chicago. At 148 feet long, she is one of only a few 4 masted Schooners built in the United States. You will enjoy a relaxing sail around aboard a truly historic vessel. Select from Pirates and Maritime Stories Sail at 1pm, Skyline/Architectural Theme at 3pm and 5pm, and Skyline Sunset Sail at 7pm. This sail is approximately 75 minutes. The ship leaves promptly at the scheduled time, please allow for time to park, off the pier if necessary.

This is the tour that made Bobby famous! Bobby’s Bike Hike is America’s longest-running city bicycle tour company, and has been repeatedly recognized for excellence by National Geographic, USA Today, The Associated Press, Conde Nast Traveler, and more! Bobby’s now offers over a dozen specialized tours, but The Lakefront Neighborhoods ride is what started it all. Join one of Bobby’s expert guides on this 3-hour romp through Chicago’s beautiful North Side neighborhoods. See the ever-rising skyscrapers of Streeterville, the luxe residential property of the Gold Coast, the cozy artists’ village of Old Town, and the rolling greenery of Lincoln Park. You’ll finish off with a cruise down the Lakefront Trail, one of the most popular waterfront bike paths in the nation. This leisure-paced journey is sure to make memories that’ll last a lifetime! Tour departs from 540 N. Lake Shore Drive, Chicago.

When you arrive at the Chicago Lincoln Park indoor skydiving location, get started by putting on your provided gear and going through a specialized training session from a flight instructor. Learn how to safely float in a 1,400-horsepower vertical wind tunnel that generates a wall-to-wall cushion of air, commonly used by professional skydivers. Experience the thrill of skydiving without having to hurl yourself from an airplane, and no experience is necessary. Once inside the enclosed space of the flight chamber, a tunnel operator slowly increases the wind speed until you and your instructor are airborne. Feel your adrenaline pumping as you 'free fall' at wind speeds reaching 180 mph (290 kph). The stable wind flow keeps you from falling off the column of air, and your instructor is on hand at all times to guide you. The first-time flyer experience takes about 75min. Each session includes up to 12 people, but fly one-on-one with your instructor in the wind tunnel twice for 60 seconds.

Feel the thrill of skydiving without jumping out of an airplane. It's true! Head to iFLY Chicago in Rosemont, a premier indoor skydiving facility powered by a state-of-the-art vertical wind tunnel. After a training session, you'll experience free-fall conditions with the help of an instructor. No experience is necessary, and afterward, you can take home a personalized flight certificate.

Located in River North, these adventures offer a one-of-a-kind premium experience. Follow clues and solve puzzles to complete your mission together. You might escape...You WILL have fun! Choose to play one of five uniquely immersive games: - Gold Rush: Find hidden gold in the California hills! - Prison Break: Complete a daring escape from the evil warden! - Special Ops: Mysterious Market: Uncover the truth as a secret agent! - The Heist: Recover a stolen masterpiece from an art thief! - Mission: Mars: Launch your spaceship from the Red Planet!