Things to do in Chicago
60 bookable tours and activities in Chicago, USA: day trips, food tours, sightseeing and more, each with the price negotiated down for you.
- Chicago 3D Fireworks Cruise on Lake Michigan
This two-hour boat cruise departs from the Chicago Riverwalk on Wednesdays and Saturdays during the summer. The trip begins with live narration along the Chicago River as the boat…
- 360 Chicago Observation Deck Admission in Chicago
360 Chicago Observation Deck is located on the 94th floor of the former John Hancock Building at 875 North Michigan Avenue in downtown Chicago. Visitors reach the deck by a…
- Chicago 2-Hour Lakefront and Museum Campus Segway Tour
This 2-hour Segway tour begins at Absolutely Chicago Segway Tours, where participants should arrive 15 minutes early to check in and complete waivers. After receiving helmets,…
- Chicago River 90-Minute Architecture Boat Tour including Wrigley Building, Aqua Tower & Chinatown
This 90-minute guided boat tour follows the Chicago River through all three main branches: the main branch to Navy Pier, the north branch to Goose Island, and the south branch to…
- Chicago 45-Minute Private Helicopter Tour of Skyline with Live Commentary
This private helicopter tour takes up to three passengers for a 45-minute flight over Chicago’s skyline. The group flies together in a single helicopter, offering a shared…
- Private Skip-the-Line Guided Tour of the Art Institute of Chicago
This private guided tour of the Art Institute of Chicago lasts about two and a half hours and includes skip-the-line access. A professional guide leads the group, exclusively for…
- Art Institute of Chicago 2.5-Hour Skip-the-Line Semi-Private Guided Museum Tour
This semi-private guided tour offers early access to the Art Institute of Chicago, allowing visitors to avoid the crowds. An art historian leads a group of no more than 12 people…
- Private Arrival Transfer from Chicago Airports (ORD) (MDW)
This private transfer service provides one-way transportation from Chicago O'Hare International Airport (ORD) or Midway Airport (MDW) to downtown Chicago. The ride lasts about one…
- Chicago Lakefront Segway Tour with Local Guide and Helmet
This 90-minute Segway tour in Chicago covers the lakefront, parks, and skyline areas. Riders use Segways equipped with helmets and are accompanied by a local guide throughout. The…
- Chicago Walkin' History-Mystery-Comedy-Tragedy Tour with Colin
This two-hour walking tour covers about two miles through downtown Chicago’s Loop area. It begins at the Palmer House Hilton Historic Lobby, where participants spend 15 minutes…
- Chicago Bike & Classic Food Tour: Bikes, Bites & Views for Adults
This 4.5-hour guided bike and food tour in Chicago is for adults only and covers about 13 miles at a relaxed pace. Participants choose between two routes: a daytime route through…
- Chicago Walking Tour Through Time from Early Skyscrapers to Aqua Tower
Chicago is known for its varied architectural styles and significant contributions to skyscraper design. This 90-minute walking tour visits key buildings in the city, arranged in…
- Chicago Chinatown 3-Hour Walking Food Tour with Dim Sum, Szechuan, Xi’an Flatbread & Portuguese Egg Tarts
This walking food tour in Chicago’s Chinatown lasts about three hours and visits five top local eateries and cultural landmarks. The tour begins beneath the Chinatown Gateway,…
- Chicago 3-Hour Bike Tour of Lakefront Neighborhoods
This 3-hour guided bike tour covers several of Chicago’s North Side lakefront neighborhoods. The group rides at a relaxed pace with bikes and helmets provided. The tour begins by…
- Chicago 3-Hour Bike Tour of Downtown Attractions Including Millennium Park, Museum Campus, Riverwalk & Lakefront
Chicago’s downtown features a range of landmarks from modern parks to historic buildings along Lake Michigan’s shore. This guided bike tour covers Chicago’s key attractions over…
- Chicago Walking Tour: Art Deco Skyscrapers Loop in Downtown Chicago
This 90-minute walking tour follows a loop through downtown Chicago’s financial district, focusing on Art Deco skyscrapers built in the 1920s. The tour begins at 30 North LaSalle…
- Chicago Architectural River Cruise with Live Commentary and Beverages
This 90-minute Chicago Architectural River Cruise takes place on the Chicago River, where a certified docent provides live commentary throughout the trip. The guide presents more…
- Art Institute of Chicago 2.5-Hour Semi-Private Skip-the-Line Tour with 8 Guests Max
This is a 2.5-hour semi-private guided tour of the Art Institute of Chicago with a maximum of 8 guests per group. The tour includes skip-the-line entry and all entrance fees. An…
- Chicago Lake and River Architecture Tour
Passengers board a boat at Michigan Avenue to begin a 90-minute tour of Chicago's architecture along the Chicago River and Lake Michigan. The first half of the ride focuses on the…
- Chicago Night Cruise on River and Lake with Live Commentary
This 90-minute boat cruise moves along the Chicago River and Lake Michigan after dark, showing the city’s skyline lit up. The trip begins on the Chicago River, where guides share…
- Chicago Seadog River and Lake Architectural Tour with Speedboat Ride
The Chicago Seadog River and Lake Architectural Tour lasts 75 minutes and starts at Navy Pier. The tour begins by sailing through the Chicago Harbor Locks onto the Chicago River.…
- Chicago Architecture Tour: Underground Pedway and the Loop
This two-hour walking tour focuses on Chicago's architecture within the underground Pedway system and the Loop area. The tour begins with a 45-minute walk through the Pedway, a…
- Chicago Landmarks and Museum Campus Small-Group Segway Tour
This two-hour small-group Segway tour covers about 6 to 7 miles along Chicago’s lakefront and includes visits to several of the city’s landmarks and the Museum Campus. Guests…
- Chicago City Tour with Optional Architecture River Cruise
This Chicago tour focuses on the city’s architectural and urban highlights, tracing its development from the era of the first skyscrapers. The tour is conducted by an expert guide…
- Chicago Mobs and Haunts Walking Tour
The tour begins on foot through Chicago’s streets where guests encounter stories about mobsters and ghostly figures connected to the city’s past. This walking tour lasts between…
- Chicago Signature Lunch Cruise on Lake Michigan with Live DJ and Buffet
This two-hour lunch cruise on Lake Michigan offers views of Chicago landmarks like Adler Planetarium and Navy Pier. Guests board a boat with both open-air decks and…
- Chicago Fireboat Cruise on Lake Michigan and Chicago River with Historical and Architectural Narration
This two-hour boat cruise takes place aboard the retired Chicago fireboat Fred A Busse, Engine 41, which served from 1937 to 1981. Passengers travel on Lake Michigan and through…
- Chicago 2-Hour Murder Mystery Walking Tour with Souvenir Mugshot Photos
This outdoor walking tour in Chicago lasts about two hours and covers 1.2 miles. It combines a historical exploration with a murder mystery game. The tour starts in front of Water…
- Chicago River 45-Minute Architecture Boat Tour from Magnificent Mile
This 45-minute architecture boat tour departs from the Magnificent Mile area in Chicago. The boat follows the main and part of the south branch of the Chicago River. A guide…
- Field Museum of Natural History Admission Tickets in Chicago
The Field Museum of Natural History in Chicago offers admission tickets that include access to all general exhibits and ticketed exhibitions, as well as free daily docent-led…
- Chicago Night Crimes Bus Tour Including St Valentine's Day Massacre and Holy Name Cathedral
This bus tour in Chicago lasts about two to two and a half hours and focuses on the city’s crime history. The tour begins and ends outside 163 E. Pearson Street, near Michigan…
- Chicago Architecture and True Crime Walking Tour
This walking tour lasts about 90 to 105 minutes and covers Chicago’s architecture alongside stories of true crime. It begins at the historic Palmer House Hilton lobby, where the…
- Big Bus Chicago Hop-On Hop-Off Sightseeing Tour with 24/48/72-Hour Pass
The Big Bus Chicago Hop-On Hop-Off Sightseeing Tour operates on open-top, double-decker buses with both enclosed, climate-controlled lower decks and open upper decks offering…
- Museum of Ice Cream Chicago Admission Ticket
This ticket grants entry to the Museum of Ice Cream in Chicago, an indoor exhibit featuring 14 interactive installations themed around ice cream and creativity. Visitors can spend…
- Chicago Walking Tour: Historic Treasures of Michigan Avenue and State Street
This two-hour walking tour covers the historic architecture and treasures of Michigan Avenue and State Street in Chicago. The tour begins with a five-minute introduction at the…
- Skydeck Chicago Willis Tower Admission with The Ledge Glass Balcony
The Skydeck at Willis Tower, once called Sears Tower, offers views of Chicago from the 103rd floor, 1,353 feet above the ground. Visitors can step onto The Ledge, a glass balcony…
- Chicago Haunted Booze and Boos Ghost Walking Tour
This 2.5-hour Chicago Haunted Booze and Boos Ghost Walking Tour is a combination ghost tour and pub crawl led by a costumed local guide. The tour begins at Glascott's, a…
- Chicago River 90-Minute Architecture Tour
This 90-minute architecture tour explores Chicago’s history and development through its riverfront buildings. The tour follows all three branches of the Chicago River, beginning…
- Chicago Private Custom City Tour with Hotel Pickup
Chicago offers a private custom city tour lasting about three to four hours, starting with pickup from your downtown Chicago hotel. The tour takes place in a chauffeured vehicle…
- Chicago Food, History & Architecture Walking Tour in a Day
This walking tour in Chicago takes about four and a half hours and covers the city's architecture, history, and food. Starting beneath the Chicago Theater marquee, the guide…
- The Escape Game Chicago: 75-Minute Escape Room Adventures in River North
Chicago’s River North neighborhood is home to The Escape Game Chicago, located just off Michigan Avenue near many restaurants and entertainment options. This convenient location…
- Chicago Drunk Shakespeare 90-Minute Show Ticket with Special Treat
The Chicago Drunk Shakespeare 90-Minute Show takes place at The Lounge in Chicago's Loop district. The show features one classically trained actor who drinks five shots of whiskey…
- Chicago Architecture Interiors Tour: Dazzling Chicago Board of Trade, Cultural Center & Loop
This two-hour walking tour explores notable interior architectural spaces in Chicago’s Loop. A local guide leads the group first to the Chicago Board of Trade Building, where…
- Chicago Donut Walking Tour: Delicious Donuts & City Sights in The Loop
This two-hour walking tour takes place in Chicago’s Loop neighborhood and includes visits to four donut shops known for their delicious offerings. The tour begins at Doughnut…
- Lake Michigan Sunset Cruise in Chicago on Wendella Boats
This 90-minute boat cruise in Chicago begins near the DuSable (Michigan Avenue) Bridge aboard Wendella’s vessels. The tour travels along the Chicago River for about 15 minutes…
- BYOB Spray Paint and Sip Workshop at Studio W.I.P. in Chicago
The BYOB Spray Paint and Sip Workshop at Studio W.I.P. in Chicago lasts 90 minutes. Participants bring their own beverages to enjoy during the session. Local guest artists and…
- Chicago CityPASS® - Admission to 5 Top Attractions Including Aquarium and Skydeck Chicago
The Chicago CityPASS® offers admission to five major Chicago attractions over a period of nine consecutive days. This pass includes guaranteed entry to Shedd Aquarium and Skydeck…
- Chicago Architecture River Cruise on the Historic Chicago River
This guided boat cruise on the Chicago River lasts about one to one and a half hours. The route follows the main branch of the river, continues up the north branch to the East…
- Chicago 90-Minute River and Lake Sightseeing Cruise
This 90-minute boat tour travels along the Chicago River's main branch and Lake Michigan, offering views of the city's skyline and notable buildings. The guide provides live…
- Chicago City Minibus Tour with The Rookery, Museum Campus & Buckingham Fountain
Chicago is known for its impressive skyline and historic architecture. This small-group minibus tour covers the city's key sights over about two hours. The tour travels by…
- Lake Michigan 30-Minute Speedboat Ride in Chicago
This 30-minute speedboat ride departs from Navy Pier and travels along the Lake Michigan shoreline, offering clear views of Chicago’s skyline. The boat passes key landmarks…
- Chicago Architecture Center River Cruise aboard First Lady with Expert Docents
Chicago’s river has shaped the city’s growth through industry, transport, and recreation. This 90-minute boat tour aboard the First Lady offers a live guided commentary by trained…
- Chicago Loop District Food Tour with Deep Dish Pizza and Italian Beef Sandwich
Chicago’s Loop District features some of the city’s most notable architecture and public art alongside its famous food specialties. This walking food tour lasts about three hours…
- Chicago Neighborhood Pizza Bus Tour with Four Slices Included
This 3.5-hour bus tour in Chicago explores several neighborhoods known for their distinctive styles of pizza. A local guide leads the group through the city, explaining the…
- Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting in Chicago
This ticket grants entry to the Medieval Torture Museum in Chicago, one of the largest interactive torture museums in the United States. The museum covers 6,000 square feet and…
- Chicago Offbeat Street Art Tour: Urban Graffiti, Murals, and The 606
This two-hour walking tour focuses on Chicago's offbeat street art scene, highlighting urban graffiti, murals, and local artwork along The 606. The tour starts in an upstairs…
- Chicago Crime and Mob Bus Tour with Stops at Historic Landmarks
This 90-minute to 2-hour bus tour in Chicago covers key crime scenes and neighborhoods tied to the city’s mob history. The tour begins outside 163 E. Pearson Street, where a guide…
- Chicago Favorites Ultimate Food and Walking Tour with Deep-Dish Pizza, Hot Dog, and Italian Beef
This three-hour walking tour in downtown Chicago visits the city’s favorite foods and key landmarks. The tour covers about 1.25 miles at a comfortable pace, with some walking…
- Flyover Chicago 30-Minute Experience at Navy Pier
Visitors start by listening to on-the-ground stories that highlight Chicago’s character and history. The main part of the 30-minute Flyover experience simulates flying over,…
- Lake Michigan Skyline Cruise with Pre-Recorded Commentary in Chicago
This boat tour on Lake Michigan lasts between 30 and 45 minutes depending on the season and offers views of Chicago's lakefront and skyline. Passengers see major skyscrapers such…