Top Illinois Outdoor Activities

Cruise down the Chicago River to see the city's famous architecture on this boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including more than 40 notable buildings like the Wrigley Building and the John Hancock Building. Cover all three branches of the Chicago River, passing the East Bank Club, the old Post Office Building and the Willis Tower (formerly known as the Sears Tower).

Get a front row perspective on the exquisite buildings that line the Chicago River during a 45-minute architecture cruise. Hear live commentary about the history and architectural heritage of Chicago on this family-friendly tour, which highlights landmarks such as the Chicago Riverwalk, Michigan Avenue Bridge, Wrigley Building, and Willis Tower. Sit on the open-air top deck or the sheltered bottom deck for the ultimate view of Chicago.

Step aboard a boat for a comprehensive cruise that details the history of Chicago's architecture. Enjoy views of the Chicago skyline accompanied by architecture-focused commentary that points out each of the landmark buildings. As you cruise through Lake Michigan, snap photos of you and your party against the stretch of Chicago's 26-mile shoreline.

Take in views of the Chicago skyline and its many landmarks during this Lake Michigan sightseeing boat cruise. Climb aboard your vessel for a laidback ride, enjoying panoramic views from a unique perspective. Along the way, you'll listen to informative audio commentary and take in views of the Navy Pier and the Willis Tower, along with many other landmarks. Plus, feel free to bring your own lunch or grab a drink at the onboard bar (own expense.)

Drink in a one-of-a-kind perspective on the Windy City when you go for an evening cruise, perfectly timed to coincide with the sunset. Hop aboard your open-top vessel in the heart of the Magnificent Mile, and cruise along the Chicago River, where your guide will point out architectural highlights. Then, see the skyline from a distance, and watch the skyscrapers light up, when you continue to Lake Michigan for a sunset viewing.

Experience a colorful side of Chicago history with this gangsters and ghosts tour. With a historian as your guide, you’ll step back to the Roaring Twenties, when the Chicago Loop was a hub for bootleggers, speakeasies, and gangsters like the infamous Al Capone. Visit onetime gangster hangouts and haunted sites like the Palmer House, Congress Hotel, and Death Alley.

Don’t spend time figuring out what to see in Chicago and how to get there—this hop-on hop-off tour provides a mapped-out itinerary of the city's top sights. With several strategically located stops, the tour allows you to explore the Windy City at your own pace. See the world-class Art Institute and landmark skyscrapers, while audio commentary onboard gives you insight into the city's colorful history.

Tower above the Windy City’s world-famous skyline with admission to 360 Chicago. Ascend one of the tallest buildings in North America aboard its lightning-fast elevator, and be rewarded with bird’s-eye views of Chicago and Lake Michigan. You can also upgrade to the Sip and View ticket, which includes one drink at the newly renovated CloudBar. Once onsite, you can purchase tickets to TILT, 360 Chicago's top attraction.

Enjoy a quintessential Chicago experience when you go on an architecture-themed river tour. Pick from multiple convenient start times, and board your vessel—the Lady Liberty—directly from the Chicago Riverwalk. Your trained docent guides will give you a rich introduction to the Windy City’s history, key landmarks, and architectural highlights—and you can spy landmarks like the Marina City towers and Navy Pier from the water’s edge.

Get the most out of your trip to Chicago as you enjoy discount access to five of the city’s top attractions with the CityPASS. This easy-to-use mobile ticket grants you free entry into top-tier sights including the Shedd Aquarium and Skydeck Chicago, plus your choice of admission to three of the following attractions: Field Museum, Art Institute of Chicago, Museum of Science and Industry, 360 CHICAGO Observation Deck, Adler Planetarium, or Shoreline Sightseeing Architecture River Tour.

Explore Chicago's gangster past on this mafia tour in a coach vehicle. Drive around the Windy City to see where Al Capone, The Untouchables, Hymie Weiss, and John Dillinger, among other thugs hung out. A history-savvy guide introduces you to some of the most storied locations of Chicago’s criminal past, including Holy Name Cathedral, Biography Theatre, and the site of the bloody St. Valentine’s Day Massacre. You'll be able to get out and pose for pictures in front of a historic courthouse, among other infamous sites.

Chicago is famous for its architecture, and the best way to see it is on a cruise down the Chicago River. Glide by historic and modern marvels like the Civic Opera House, Wrigley Building, and Willis Tower from the comfort of an open-deck boat. Live narration reveals each building’s fascinating history, so you'll learn more than you would just observing on your own.

The easiest and most affordable way to explore some of Chicago's top attractions, the Chicago Explorer Pass by Go City saves you up to 50 percent off compared to buying individual attraction tickets. Create your own sightseeing itinerary by choosing 2, 3, 4, 5, 6 or 7 attractions, tours, and activities from among more than 25 top sites, including the Skydeck Chicago, a sightseeing cruise, a hop-on hop-off Big Bus tour, Navy Pier, and more.

The Flyover experience takes 30 minutes from beginning to end. First, on-the-ground stories connect you with the spirit of the Windy City. Then, you’ll discover Chicago from a whole new perspective, as Flyover transports you over, around and through remarkable locations. You'll explore in motion with scenes captured by an award-winning creative team using custom-made drones and helicopter-mounted cameras, while scents, sounds and music deepen the immersion. It’ll take your breath away (we promise you’ll get it back).

Chicago is known internationally for its architectural diversity and dynamism—and this in-depth tour will introduce you to many of the city’s best-known and most influential landmarks. Meet at the pier right off Lake Shore Drive, hop aboard your boat, and set off. You’ll spy highlights ranging from Chicago’s skyscrapers and bustling Navy Pier to the famous “Bean” sculpture—and will learn about the different architectural movements that shaped the city. Upgrade your experience to a small boat with a maximum of 60 people.

Explore Chicago’s most iconic sites on a bike tour that explores Museum Campus, parks, and monuments. Follow your guide along the waterfront as you soak up the city skyline and enjoy the breeze along the easy-going route. Circle the Buckingham Fountain while you learn the history of the city’s public art, parks and museums, and capture unforgettable images of the Windy City.

Step on board a cruise boat bound for the waters of Lake Michigan, enjoying the sunset from the boat deck. Step up to the cash bar for drinks and snacks and find a place on board for a view of the epic fireworks display. A boat on the lake is the best place for catching the full fireworks spectacle and making great photos and videos.

Feel the rush of skydiving without going anywhere near a plane, with this indoor skydiving experience in Chicago. Start off with thorough training so you feel confident and know what to expect. Then, enjoy two 60-second ‘free fall’ experiences in a technologically advanced vertical wind tunnel, which feels much like real skydiving. No experience is necessary, and your instructor will give you hands-on assistance when you need.

Delve into the world of natural history with tickets to the Field Museum in Chicago. Choose general admission, or upgrade to visit one or several special exhibitions. Spend as long as you like exploring the museum's collection of more than 26 million artifacts. Get to know SUE, the world's largest T. Rex, or stroll through the sparkling Hall of Gems. You can also take advantage of free daily tours led by Field Museum docents.

Discover the ‘dark side’ of the Windy City thanks to this 2.5-hour, bus-based, nighttime crime history tour of Chicago. Explore the lives of notorious mobsters like Al Capone, Frank Nitti, Bugs Moran, and more as you explore infamous crime scenes like the St. Valentine’s Day Massacre, learn about ‘The Enforcer’s Safe,’ and stop by local watering holes.

An excellent choice for first-time visitors, this tour provides a comprehensive overview of the city and hits on both classic attractions and little-known sites. Beginning at the Chicago Theatre, work your way to the Chicago Pedway, an elaborate network of underground tunnels used by locals and commuters. Stroll the Chicago Riverwalk and see Millennium Park; then, embark on a food tour to taste some of the city’s famous foods.

Stroll through downtown Chicago on this walking food tour. Visit Millennium Park, the Palmer House Hotel and other city landmarks. Taste quintessential Chicago foods such as deep-dish pizza, hot dogs, plus chocolates and pastry. All food tastings are included, and the tour covers an easy 1.5 miles (2.4 km) suitable for most fitness levels. A bike or kayak rental is also included in the tour cost.

Explore Chicago's Chinese food scene on this walking tour in the Chinatown district. With a guide, learn about the cuisine of different regions of China and how Chinese culture has influenced Chicago and other areas. Enjoy included tastings from restaurants and other food venues in Chinatown—a great way to start a night out in the city.