Top 20 Things To Do In Chicago, USA 2023
Top Tours and Activities In Chicago, USA
Chicago Architecture River Cruise
2334 Reviews
$33.60
Experience one of the world’s most beautiful cities on a 75-minute cruise on 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.
Chicago City Hop-on Hop-off Tour
888 Reviews
$33.00
See all the sights of Chicago at your own pace! On a Chicago City Hop-on Hop-off Tour you can get off the bus at any scheduled stop to visit Chicago's most popular attractions, then pick up the tour where you left off or get on at any other regular stop on the route. For individuals and families, this is the best way to see the sites!
The tour includes the signature route which runs year round, while the seasonal neighborhoods routes and night tour operate May - September only. See itinerary below for specific stops.
Skydeck Chicago Admission
550 Reviews
$23.00
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.
With mobile tickets, simply scan your phone for direct entry into the SkyDeck
Chicago Grand Half-Day Tour
325 Reviews
$48.00
This comprehensive half-day tour of Chicago is the perfect introduction to the Windy City! Discover the highlights of Chicago’s North Side and South Side and enjoy a scenic drive along the Outer Drive. Pass by Chicago's beautiful Washington Park and Grant Park, and make a 20-minute stop at the fascinating Lincoln Park Conservatory. Stop for photo opportunity at the Adler Planetarium, see the impressive Wrigley Building and more. You'll come away with a fantastic overview of the best Chicago has to offer!
Chicago Crime and Mob Tour
280 Reviews
$35.95
Some of the world’s most notorious criminals, mobsters and gangsters bamboozled their way through Chicago. On this Chicago crime tour, escape into the city’s criminal underworld as you investigate stories about Al Capone, The Untouchables, the Chicago Mob and more. From a luxury coach, see the sites of storied crime scenes including Biograph Theatre, Holy Name Cathedral, Clark Street Bridge and the St Valentine's Day Massacre, one of Chicago's most notorious murders. Snap photos of the historic criminal courthouse, and hop off the coach to walk the path that Chicago gangsters John Dillinger and Hymie Weiss followed just before their deaths.
Chicago CityPASS
270 Reviews
$99.75
Chicago CityPASS is the best deal in the Windy City, giving you discounted admission to five of the city's premier attractions. The Chicago CityPASS ensures you'll get the most out of your vacation - yet it is so compact it will fit into your back pocket. It's all you need to see the best of Chicago!
Chicago Segway Tour
212 Reviews
$70.85
Hop on the most innovative tour to hit Chicago in years! Gliding around the Windy City on your very own Segway, you'll see all the famous sights - Buckingham Fountain, Navy Pier, Lake Michigan and more. Be one of the first to take part in this unique, unforgettable experience!
Chicago Explorer Pass
176 Reviews
$75.00
Create your own sightseeing itinerary with the Chicago Explorer Pass, saving up to 42% on ticket prices. This multi-attraction pass, valid for 30 days after your first use, provides admission to your choice of up to five attractions, tours or activities at one low price. Make your selections from more than 25 top sites and things to do, including Lincoln Park Zoo, Navy Pier and an Architecture River Cruise. It's the easiest and most affordable way to explore the Windy City at your own pace. Simply download your pass on your mobile device and go – no voucher redemption required!
Tommy Gun's Garage Dinner and Show
161 Reviews
$67.00
Welcome to the only speakeasy dinner show in Chicago Tommy Gun's Garage! Just say the password and you'll be transported back to the roaring twenties. You'll be entertained by gangsters and flappers, dancing the Charleston to the music of Cole Porter and George Gershwin. It's a night out in Chicago you'll never forget!
Lake Michigan and Chicago River Architecture Cruise by Speedboat
142 Reviews
$42.87
Chicago is renowned for its stunning and original architecture, and the most relaxing way to see it is on a cruise on the Chicago River! You'll learn all about Chicago's history and landmarks before the tour's grand finale, a thrilling speedboat ride on Lake Michigan.
Chicago Architectural River Cruise
128 Reviews
$48.16
Take in the views on this 90-minute Architectural Tour, a jaw-dropping excursion through a city that defied all expectations … even the laws of gravity.
Blue Man Group at the Briar Street Theater in Chicago
102 Reviews
$69.60
See the Blue Man Group, one of Chicago's longest running shows, at the Briar Street Theater in downtown Chicago. The phenomenon that has visited cities around the globe is integrating new technology into their shows with their 'GiPad,' a giant tablet. This family friendly show combines the traditional 'Blue Man' antics with 21st-century technology for an amazing visual experience.
Chicago Prohibition Tour
100 Reviews
$45.00
Discover the underground world of the Prohibition-era speakeasy on an entertaining adults-only tour that takes you to four historic Chicago bars. Learn why the sale of alcohol was banned for more than a decade in the United States, and the subsequent popularity of illicit establishments where liquor, jazz, and mobsters ruled. An air-conditioned coach shuffles you from bar to bar, so feel free to buy a drink or two. This small-group tour, limited to 20 people, ensures a more customized experience with your guide.
Chicago City Tour with Optional Architecture River Cruise
97 Reviews
$35.00
Don’t miss Chicago’s famous sights and fabulous views on this award-winning small-group sightseeing tour of the city. Travel through Chicago with an expert guide on a comfortable minibus, stopping at iconic locations like the Willis (Sears) Tower, The Rookery in downtown Chicago (Frank Lloyd Wright architecture), Museum Campus (for the BEST skyline view), The Magnificent Mile, Lincoln Park, Gold Coast, Lake Shore Drive and more! Along the way, your guide will provide historical and informational commentary about the area and its beautiful attractions. The small-group atmosphere with maximum of 12 people ensures a more personal experience.
You also have the option to upgrade to include a 75-minute Architecture Cruise down the Chicago River! This popular open-top boat tour offers the perfect vantage point to admire the city’s renowned buildings.
Chicago Walking Tour: Interior Architecture of the Loop and Pedway Tour
92 Reviews
$26.00
Get an in-depth look at Chicago Loop architecture on a walking tour that takes you inside landmark buildings in the design-rich city. Appreciate the interiors of the Marshall Fields Building, Chase Tower, Chicago Cultural Center and more, plus see public art by Chagall and Picasso. Stroll through elegant lobbies, under glittering domes and into the sprawling network of Chicago Pedway tunnels. Your expert guide shares insights about the city’s diverse architectural styles and history, bringing the details of the Windy City into vivid focus.
Chicago Pizza Tour
90 Reviews
$60.00
Enjoy Chicago’s only bus guided neighborhood pizza tour. Eat like a local as you travel off the beaten path into Chicago neighborhoods to savor the best pizza. Your local guide will teach you the science behind ingredient selection and baking as you sample slices from historic pizzerias. In just a few hours, you’ll leave stuffed, and with an understanding of why pizza is such an important part of Chicago’s culture.
360 Chicago Observation Deck (formerly John Hancock Observatory) Admission
89 Reviews
$18.45
The best views of Chicago can be yours at 360 Chicago (John Hancock Observatory)! 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, and with inclusions like panoramic touch-screens and interactive educational kiosks, it will be the high point (literally) of your Chicago trip!
With mobile tickets, simply scan your phone for direct entry into 360 Chicago.
If you want to extend your tour to day and night and observe Chicago at both times of day, upgrade to the Sun & Stars option, good for two visits.
Small-Group Chicago Food Tour: Gold Coast and Old Town
89 Reviews
$52.00
Discover Chicago's culinary side on this three-hour walking tour to taste the delicious flavors of the Gold Coast and Old Town. Along the way, your guide will show you the history and architecture in these culture-rich neighborhoods, just north of the downtown area. After stops at seven quintessential Chicago restaurants in these two neighborhoods, you'll feel like a real Chicagoan! The tour operates with a maximum of 18 people, ensuring you’ll receive personal attention from your expert guide. Tastings at 7 different locations is included.
Lake Michigan Sightseeing Cruise
86 Reviews
$19.60
Admire all of Chicago's fabulous lakefront sights and attractions on this 40-minute 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.
Big Bus Chicago Hop-On Hop-Off Tour
86 Reviews
$26.10
The lakeside metropolis of Chicago is famous for its striking skyscrapers, world-class museums and colorful political history. Explore the Windy City at your own pace during a hop-on hop-off bus tour with 14 stops strategically located near the city’s top attractions. Hop off along the Magnificent Mile to shop, see the great city at heart-stopping heights from Willis Tower’s Skydeck or '360 Chicago' at the John Hancock Center, visit the Art Institute or Shedd Aquarium, or snap a selfie in front of the shiny steel bean in Millennium Park. Live commentary on board the bus is provided.
Chicago City Tour and Chicago River Cruise
72 Reviews
$60.00
Discover Chicago from both land and water on this scenic half-day tour. Take a narrated coach tour through the city’s South Side and see highlights including Grant Park, the Loop, the Shedd Aquarium and exclusive shopping areas and neighborhoods. Then, experience Chicago from the water! Cruise along the Chicago River in a beautiful streamliner yacht and admire views of the stunning city skyline.
Famous Tastes of Chicago Food Tour
61 Reviews
$55.00
What should a visitor see and do while in Chicago? It goes without saying that the Windy City has it all; from food, history, architecture, culture and beyond that it can often be hard to decide where to start. Why not tantalize all of your desires and senses with a 3 hour small- group walking food excursion lead by a professional guide? You'll indulge in 5-6 of Chicago's quintessential staples while feeding your mind with intriguing and rememberable tidbits along the way. Before you know it, you'll feel like a local. Make sure to come hungry, this tour offers more than enough to be considered lunch.
Chicago Sunset Dinner Cruise with Buffet
60 Reviews
$89.66
Celebrate a night out in Chicago with dinner, dancing and sightseeing aboard a three-hour luxury cruise on Lake Michigan. Glimpse top Chicago attractions like Navy Pier, Soldier Field and more while you dine on a lavish, all-you-can-eat buffet! See spectacular views of the Chicago skyline while being entertained by a singing ship staff and a live DJ spinning your favorite songs.
Chicago Pedway Walking Tour
57 Reviews
$20.00
Explore Chicago by following the heated tunnels, walkways and passages that connect the city’s famous landmarks and buildings. Your comedic guide takes you on an interesting, informative and humorous walk while highlighting Chicago’s well-known and lesser-known landmarks from a different perspective.
Viator VIP: Willis Tower Skydeck Early Access, Trolley City Tour and Chicago River Cruise
57 Reviews
$124.00
See classic Chicago sights with this Viator VIP package that includes early entry to the Skydeck in Willis (formerly Sears) Tower where you'll be greeted and quickly escorted up to the 103rd floor. After a crowd-free morning looking over the Windy City, take a narrated tour on a classic Chicago trolley that passes John Hancock Center, Field Museum and Millennium Park. Finish your comprehensive Chicago tour — available only through Viator — with an afternoon cruise on the Chicago River with a complimentary drink in hand, learning about the city's many distinctive skyscrapers from an architecture-savvy guide.
Chicago Grand Tour and Admission to 360 Chicago (formerly John Hancock Observatory)
53 Reviews
$63.00
Take a tour of Chicago and visit the 360 Chicago (John Hancock Observatory)! This comprehensive half-day tour is the perfect introduction to the Windy City. Visit the highlights of the North Side and South Side and enjoy a scenic drive along the Outer Drive. Explore Chicago’s beautiful parks on this guided tour, including Lincoln Park, Washington Park and Grant Park. Stop at the fascinating Lincoln Park Conservatory and the Museum Campus, and enjoy admission to the skyscraping Hancock Center, one of Chicago's tallest landmarks. Climb to the top for spectacular city views!
Tastes of Chicago Bike Tour: Chicago-Style Pizza, Beer, Cupcakes, and Hot Dogs
53 Reviews
$75.42
Taste the flavors of Chicago, both edible and cultural, on a bike tour through the city. Sample four of Chicago’s favorite foods and drinks –pizza, cupcakes, hot dogs and beer – and experience the city as you make your way through the neighborhoods of Wrigleyville, the Gold Coast, Old Town, Lakeview and Lincoln Park with a local guide.
Chicago Food Tour: Chicago-Style Pizza, Beer, Brownies, and Hot Dogs
48 Reviews
$53.10
Sample your way through Chicago’s most iconic foods on this 2.5 hour walking tour of the Loop. Taste Chicago-style hot dogs, deep dish pizza, the original brownie, and locally crafted beer as you skip the waits at some of Chicago's most popular restaurants. Along the way, experience Millennium Park and its world-famous Bean, downtown Chicago's historic architecture and scintillating skyline, the Palmer House Hotel, and other surprises. By the end of the tour, your head will be full of fascinating knowledge and your stomach will be full of delicious food!
Chicago by Night Helicopter Tour
45 Reviews
$149.00
Watch the Chicago skyline sparkle from the air on this thrilling nighttime helicopter tour! Aboard a heated, state-of-the-art helicopter, soak in amazing views of Lake Michigan and fly past several Chicago landmarks like Willis Tower, Navy Pier, Millennium Park, the Shedd Aquarium and Lincoln Park. Your expert pilot will provide interesting commentary about the sights you see and can answer any questions you have. Tour route is subject to change.
Chicago Odyssey Dinner Cruise
43 Reviews
$88.26
Expect the exceptional on this 2.5-3 hour premier Chicago dinner cruise experience. Newly renovated, this luxury vessel features a newly furnished rooftop lounge, posh atmosphere and stylish interior. Relish a 3-course plated meal with celebrity-chef inspired dishes prepared from fresh ingredients right on-board. Dance the night away to DJ entertainment or simply relax in the elegant ambiance and admire unmatched views of the world-famous Chicago skyline as you glide along the shores of Lake Michigan.
Art Institute of Chicago Fast Pass Admission
42 Reviews
$35.00
Art lover or not, the Art Institute of Chicago – the second-largest art museum in America – is not to be missed. Located in Chicago’s Grant Park, this amazing museum features an extraordinary collection of Impressionist, post-Impressionist, modern and contemporary art from such masters as Monet, Renoir, van Gogh, Picasso and Pollock, as well as stunning new-age architectural, industrial and graphic design.
With mobile tickets, simply scan your phone for direct entry into the Art Institute.
Chicago Walking Tour: Art Deco Skyscrapers
41 Reviews
$18.00
Discover the opulent exteriors and interiors of the Roaring '20s Jazz Deco and the classic finishes of Art Moderne buildings in this 2 hour tour. Learn of Chicago's influence on the international Art Deco movement, and trace the history of lively architectural heritage.
Chicago Lakefront Neighborhoods Bicycle Tour
41 Reviews
$46.30
See Chicago off the tourist beat on this guided bicycle tour. Your expert local guide will lead you to Chicago’s best quiet neighborhood streets, city parks and scenic beaches on the North Side of Chicago. Catch a glimpse as to how Chicagoans live and enjoy their beautiful city on a mellow bike tour.
Chicago Style Food Tour
40 Reviews
$55.00
Confused on what to see and do while in Chicago? It goes without saying that the Windy City has it all; from food, history, architecture, culture and beyond. Combine them all by tantalizing all of your senses with a 3 hour small- group walking food excursion lead by a professional guide. You'll indulge in 5-6 of Chicago's quintessential staples while feeding your mind with intriguing and memorable tidbits along the way. Before you know it, you'll feel like a local. Make sure to come hungry, this tour offers more than enough to be considered lunch.
Chicago Film Tour
40 Reviews
$30.00
Movie buff or not, you’ll see the best of Chicago on this movie tour
of the city! Travel by luxury air-conditioned coach through 30 miles (48
km) of Chicago to see the exact locations where dozens of the greatest
movies and most popular blockbusters of the past 100 years were filmed!
Not only will you see the locations where the movies were shot, but you
will also get a tour of favorite Chicago neighborhoods like Gold Coast,
Wrigleyville, Old Town, Lincoln Park and more!
Chicago Walking Tour: Historic Skyscrapers
39 Reviews
$18.00
Perhaps Chicago's most identifiable claim to fame resides in its architecture. The prototype of the modern industrial metropolis arose from the charred landscape left by the Great Fire of 1871. Many of Chicago's surviving buildings are the forefathers of the great modern skyscrapers and on this walking tour you will discover the historic beginnings of the Chicago School of Architecture and the earliest skyscrapers, built between the 1870s and the 1930s.
Chicago Segway Night Tour
38 Reviews
$70.85
Hop on the most innovative tour to hit Chicago in years! Gliding through the Windy City on an eco-friendly Segway is the coolest ride of the 21st century! Far easier than walking, and more unique and personalized than a coach tour, riding a Segway personal transporter is a once-in-a-lifetime experience.
Chicago City Sights Helicopter Tour
34 Reviews
$149.00
Experience all of Chicago’s best sights from the air on this exciting helicopter tour! Aboard a state-of-the-art helicopter, you'll enjoy a magnificent view of Lake Michigan and fly past several top Chicago attractions like Willis Tower, Navy Pier, Millennium Park, the Shedd Aquarium and Lincoln Park. Your pilot will provide expert commentary about the sights you see and can answer any questions you have. Tour route is subject to change.
Small-Group Chicago Food Tour: Wicker Park and Bucktown
31 Reviews
$50.00
Let your local guide lead you through the streets of Wicker Park and Bucktown as you search for authentic and local cuisine at six different cafes and restaurants. You’ll taste the foods that have made Chicago famous, such as the classic Italian beef, as you tour a local brewpub, pastry shop and more! All tastings are included and the small-group atmosphere with maximum 16 people will ensure a more personal experience.
Chicago Walking Tour: Tiffany Treasures
29 Reviews
$29.99
This tour explores the art glass designed, crafted or installed by the Tiffany Glass and Decorating Company, Louis Comfort Tiffany and his contemporaries, in four late 19th Century Chicago landmarks: