Add dates
Chicago

For first-time visitors

Our most recommended Chicago For first-time visitors

Chicago River: 1.5-Hour Guided Architecture Cruise

1. Chicago River: 1.5-Hour Guided Architecture Cruise

Experience more of Chicago by boat than on any other architectural cruise. See architectural highlights and enjoy an open-air deck or climate-controlled interior as you travel the main River and its north and south branches. View all of Chicago's architectural highlights during this comprehensive sightseeing tour. Be entertained by the expert and friendly tour guides as they explain the 130 year-long history behind the skyline, while bartenders and staff keep you comfortable with refreshments.  Choose between the fresh air of the open-air decks or enjoy the comfort of the climate-controlled interiors during your cruise. The tour starts at the Michigan Avenue (DuSable) bridge and goes up the main branch of the Chicago River past Wolf Point. It then cruises along the north and south branches of the river, before heading back past the Chicago Riverwalk towards Lake Michigan. On the way, learn about ornate, historic early skyscrapers like the Wrigley Building and the Tribune Tower, the imposing art deco Merchandise Mart, mid-century skyscrapers like the Mies Van der Rohe AMA Building. Don't miss the circular Marina City Towers, the majestic Willis Tower (formerly the Sears Tower and the tallest building in Chicago) the soaring AON Center, and more modernist structures like Aqua, Trump Tower, Nuveen, and the new Vista Tower. During your cruise, have the opportunity to enjoy a full-service cash bar featuring authentic Chicago products, including local beer and spirits, and Garrett’s Popcorn. Don’t forget to take a selfie at the Grand Staircase at the front of the boat or pose for photos at the picturesque stern or bow of this classic vessel.

Chicago: Willis Tower Skydeck and The Ledge Ticket

2. Chicago: Willis Tower Skydeck and The Ledge Ticket

Enjoy an unrivaled view over the city of Chicago on a trip up the city's Willis Tower. This famous building, once known as the Sears Tower, is not only home to a Skydeck on the 103rd floor, but it also features The Ledge, a series of 4 glass-paneled boxes that extend out from the building's facade to give visitors a view straight down. As you wind through the ground levels of the Willis Tower, you will be surrounded by museum-quality exhibits highlighting the iconic tower. Learn about Chicago's rich history and culture through these informative visuals. Watch a video presentation, "Reaching for the Sky," where you will be briefed on the history of the building and of architecture in Chicago. Then step into your elevator and you will be amazed at how quickly it ascends. As you travel, your multimedia-equipped elevator will inform you about your vertical progress. Upon reaching the 103rd floor, step out onto the Skydeck, which offers views spanning over 50 miles and across 4 states. Then summon your courage to step out onto The Ledge, a glass balcony that hangs over the edge, for vertigo-inducing views 1,353 feet (about 412 meters) straight down to the city below! Download the Skydeck Mobile App for a free viewfinder which points out many of Chicago’s notable landmarks. Learn more about sights like Navy Pier, Wrigley Field, Grant Park, Art Institute of Chicago, Shedd Aquarium, and Field Museum of Natural History.

Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

3. Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Experience the views from the Centennial Wheel at the Historic Navy Pier in Chicago with this attraction ticket. Be suspended over Lake Michigan at the mouth of the Chicago River. Marvel at the Chicago skyline and gaze out over the sparkling waters of Lake Michigan. Choose between two options: With the Regular Barcoded ticket, skip the ticket line and enter the line to board the wheel. The Fastpass Express ticket allows you to skip both lines, and gives you VIP access. Both tickets allow you to visit within 7 days of your scheduled ticket date. Enjoy the Centennial Wheel, which was built in 2016 to celebrate the 100th anniversary of the Navy Pier opening. Featuring 42 gondolas, each holding 8 people, it operates year-round. They also feature LED lighting, padded seats, TV screens, and speakers, as well as panoramic windows on all 4 sides. A ride on the wheel gives you plenty of time to enjoy these panoramic views of Chicago as they unfold around you, and allows you to visit the top three times. Relax and take in the view, or get your camera out to snap pictures of the ever-changing Chicago landscape.

Chicago: 360 Chicago Observation Deck Skip-the-Line Ticket

4. Chicago: 360 Chicago Observation Deck Skip-the-Line Ticket

Marvel at the views from 1,000 feet over Chicago’s legendary Michigan Avenue with this ticket to the 360 CHICAGO observation deck on the 94th floor of the John Hancock Center. Save time with skip-the-line access to this popular attraction. Head up to the 360 CHICAGO observation deck to take in breathtaking views of Chicago’s lakefront and view the city skyline from above. Take a peek at 4 neighboring states from this height. Feel the thrill of a 40-second ride in one of North America's fastest elevators to the observation deck to experience what 'Travel & Leisure Magazine' voted one of the best views in America. Get easy access to Chicago’s premier shopping and dining districts with 360 CHICAGO. Also, enjoy an interactive exhibit on the Ground Floor that highlights Chicago’s rich history and showcases 9 of the city’s culturally unique neighborhoods. Then, on the 94th floor, explore the history and architecture of the magnificent city stretched out before you with audio tours in 5 languages. By purchasing this timed ticket, you get to skip the ticket desk and present your barcoded voucher to security to be scanned - you may have to wait in a short line at security, then head directly into the Ground Floor Exhibits, and then on to the Elevator Line.

Chicago Lakefront: Seadog Speedboat Ride

5. Chicago Lakefront: Seadog Speedboat Ride

This half-hour Seadog Speedboat ride along Chicago’s lakefront is one of the best ways to view the city’s skyline while learning about the city. Combine an exciting speedboat ride with informative and amusing stories about the world-famous Windy City. As you depart Chicago's Navy Pier, your captain will tell you interesting facts about the pier and the lakefront as he cranks up the music and races to key lakefront landmarks. Stop near the picturesque lakefront park of the Chicago Museum campus, where you’ll learn about the architecture and history of Chicago. Admire views of the Magnificent Mile neighborhood, including the Buckingham Fountain, Sears Tower, Grant Park, and Chicago's largest shopping district. Listen to the thrilling sound of the turbo engines as you race around the Lake Michigan waterfront and back to the Navy Pier. Upgrade to the Extreme Thrill Ride Option and experience exhilarating speeds and full 360° spins. This jet-propelled ride blasts off to start and splashes down to stop. Experience full-throttle slalom runs, sharp twists and turns, and the raw power of Seadog Extreme's 1400 HP engines.

Chicago: Field Museum of Natural History Ticket or VIP Tour

6. Chicago: Field Museum of Natural History Ticket or VIP Tour

Visit the Field Museum of Natural History, one of Chicago's great museums. With more than 35 world-renowned natural history exhibitions, there's something for everyone. Fuel your passion for discovery with dinosaurs, ancient artifacts, cultural insights, and groundbreaking science. Explore subterranean life in the Underground Adventure exhibit. Admire gemstones in the Hall of Gems and one of the largest collections of Chinese jade in North America in the Hall of Jades. Next, follow the stories of the Ice Age mammoth hunters and the temples of the Inca and Aztecs. Visit the Dinosaur Hall Evolving Planet exhibit to mingle with giant sloths, woolly mammoths, Sue, and Maximo. Upgrade to the All-Access Pass to see a 3-D movie and all 3 ticketed special exhibitions. Choose the Early Access VIP Tour option for a 1-hour VIP tour of the museum's dinosaurs before the museum opens to the general public. Take pictures with Sue or Maximo without the crowds. Then explore the rest of the museum with an all-access ticket including a 3D movie titled "Waking the T-Rex." If you want to see more, get a Discovery Pass to gain general admission to the museum as well as add one of their ticketed exhibitions or a 3D movie to your day. 

Chicago: Big Bus Hop-on Hop-off Sightseeing Tour

7. Chicago: Big Bus Hop-on Hop-off Sightseeing Tour

From your vantage point on the double-decker sightseeing bus, you'll enjoy panoramic views of Chicago’s finest skyscrapers, including the John Hancock Center, the Willis Tower, and the Wrigley Building. Take in the city's most impressive landmarks while listening to entertaining commentary and insight into Chicago's history. Explore this dynamic city with the freedom to hop on and hop off as many times as you wish to visit attractions such as the Shedd Aquarium and the Field Natural History Museum. You’ll travel along the famous Magnificent Mile, considered one of the great avenues of the world, and continue across the Michigan Avenue Bridge over the Chicago River. This hop-on, hop-off bus tour of Chicago makes it easy for you to explore the city's sights at your own pace. All stops are conveniently located to make navigating your way around the city easy, and with a choice of 24- or 48-hour tickets, you can take your time discovering Chicago. With the 48-hour ticket, enjoy a non-stop Panoramic Night Tour of the city included with your ticket! Admire the illuminated skyline from the Museum Campus and see River North's vibrant nightlife scene.

Chicago: Mob and Crime Bus Tour

8. Chicago: Mob and Crime Bus Tour

Experience Chicago’s underworld of criminals and gangsters on a luxury bus tour. Find out how some of the world’s most famous criminals, mobsters, and gangsters conned their way through the city. Ride comfortably in luxury, on a climate-controlled bus, as you see famous Chicago crime scenes that range from the 19th century through modern times. Unlike Chicago walking tours, this Mob and Crime Tour isn’t affected by the Windy City weather. Learn from a local expert tour guide giving interactive live commentary about Al Capone, the Untouchables, the Chicago Mob, John Dillinger, Terrible Tommy O'Connor, H. H. Holmes, the Chicago Black Sox, Leopold and Loeb, bank heists, Cap George Streeter, and more. Grab your camera for a drive-by shooting of the historic criminal courthouse, a Chicago architectural landmark where some of Chicago's most notorious cases were tried. You'll also view historic video footage, receive an informative pamphlet with photos, and can even take part in a crime quiz. Stake out crime scenes like the Biograph Theatre, Holy Name Cathedral, Clark Street Bridge, and other Chicago landmarks. See the site of the St. Valentine's Day Massacre, one of Chicago's most notorious murder scenes. Get off the bus and walk the path that notorious Chicago gangsters John Dillinger and Hymie Weiss followed just before their deaths. Travel into the criminal past of Chicago's River North, Gold Coast, Lincoln Park, Old Town, Loop, and Magnificent Mile neighborhoods.

Chicago: Gangsters and Ghosts 2-Hour Walking Tour

9. Chicago: Gangsters and Ghosts 2-Hour Walking Tour

See a different side of Chicago on a family-friendly guided tour and hear the tales of the ghosts that haunt the city. Explore the famous Chicago Loop district with interesting stories hidden behind each turn. Embark along the Chicago Loop, known as the vice district during the 1920s and 30s. See the places where gangsters such as Al Capone used to party, make deals, and carry out business. Visit haunted locations and old crime scenes led by historians. Stop at the Congress Hotel, Death Alley, and the Palmer House. Enjoy a refreshment along with way, with frequent stops and a restroom break.

Chicago: History Museum Admission Ticket

10. Chicago: History Museum Admission Ticket

Explore the history of Chicago and America through a collection of permanent and temporary exhibits drawn from approximately 22 million holdings. "Chicago: Crossroads of America" explores Chicago’s development and its influence on American history. Explore a treasure trove of historical artifacts, including a chunk of the original Fort Dearborn, a restored original L train car, a re-created jazz club, and the actual first locomotive to operate in Chicago. Use all five senses to discover Chicago’s history with the “Sensing Chicago” exhibit, riding a high-wheel bike, hearing the Great Chicago fire, and even enjoying a famous Chicago-style hot dog. Check out temporary exhibitions on everything from Chicago art to the history of lesbian, gay, bisexual, and transgender Chicagoans, to the city's fashion history. Feel the intensity of the Great Chicago Fire and splendor of the World’s Columbian Exposition, explore the sights of bustling Maxwell Street in the 1950s and peer down from an I-beam at the top of the Sears Tower in the 1970s.

  • Guided tours
  • Entry tickets
  • Water activities
16 activities found
Sort by:

Frequently asked questions about Chicago For first-time visitors

What are other things to do than For first-time visitors that are worth visiting in Chicago?

The other unmissable things to do in Chicago are:

Other Sightseeing Options in Chicago

Want to discover all there is to do in Chicago? Click here for a full list.

What people are saying about Chicago

Enjoyed the entire experience & certainly worth the time & money. Sat top deck even through the River's mist. Tour guide, Dave, was the highlight of the trip. Very knowledgeable about the artitecture of the buildings and history of the city along with some witty comedy.

skipped line, fast and reliable. but had to purchase tilt ticket at top. they sell out fast and may not be available when you are on top, but wait time is10-30 min to get tilt tickets. tilt is not for people with heights fear.

The only bad thing about this was that it didn’t last long enough. Loved it. Got soaked just what I expected and wanted, nearly lost my eyelashes due to the speed of the boat. Would defo recommend this.

We took the 18:45 and it was an excellent choice. We could see the buildings under dusk and with beautiful lights. The guide was very active and passionate with her description.

Our guide leader was very animated and seemed to love telling us about the history of the City.