Recent Searches
Clear

Top Chicago Half-day Tours

Saved to wishlist!
When are you traveling?
Select Dates
Popular
Search experiences that may have limited interaction with crowds.
Search experiences with increased health and safety practices.
Search tours and activities you can do from home.

You are viewing Virtual Experiences in Chicago. See more Virtual Experiences around the globe. 🌎

Price
$0
$500+
Duration
Time of Day
RatingClear
Specials
Select Dates
Dates
Sightseeing Tours
City Tours
Private and Luxury
Private Sightseeing Tours
Sightseeing Cruises
Cruises & Sailing
Culinary & Gourmet Tour
Historical Tours
Food Tours
Day Cruises
Dinner Cruises
Sunset Cruises
Cultural Tours
Architecture Tours
Markets
Coffee Cruises
Street Food Tours
Walking Tours
Crime Tours
Beer & Brewery Tours

45 results | All Chicago Tours

Sort by:Featured

Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour

Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour

star-5
268
Chicago dogs, deep-dish pizza, cupcakes and craft beer are all sampled on this half-day bike tour through the Windy City. Cover about 13 miles (21 km), following an informative guide at a moderate pace through the Chicago neighborhoods of Wrigleyville, the Gold Coast, Old Town, Lakeview and Lincoln Park. Stop along the way at a popular downtown bakery, pizza shop, hot dog stand and two breweries for a taste of local flavors.
More
  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$84.99
From
$84.99
Taking safety measures

Chicago Favorites Ultimate Food & Walking Tour

Chicago Favorites Ultimate Food & Walking Tour

star-5
175
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.
More
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$64.99
From
$64.99
Taking safety measures

Chicago Loop Secret Food Tour with Private Tour Option

Chicago Loop Secret Food Tour with Private Tour Option

star-5
248
Explore Chicago's buzzing food scene with a small group on this small group walking tour. Stroll around the 'Loop', stopping at hidden gems and hearing tales of the city from your guide. Taste classic Chicago foods, from deep-dish pizza to dipped Italian beef sandwiches.
More
  • 3 hours
  • Taking safety measures
From
$103.36
Price varies by group size
From
$103.36
Price varies by group size
Taking safety measures

Chicago in a Day: Food, History and Architecture Combo Tour

Chicago in a Day: Food, History and Architecture Combo Tour

star-5
83
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 the Magnificent Mile, then embark on a food tour to taste some of the city’s famous foods.
More
  • 5 hours
  • Free Cancellation
  • Taking safety measures
From
$102.30
From
$102.30
Taking safety measures

Chicago's West Side Foodie Ride Bike Tour

Chicago's West Side Foodie Ride Bike Tour

star-5
72
Taste food from around the world on this half-day cycling and tasting tour of Chicago. Follow your biking guide through the Chicago streets, stopping for views of Chicago’s famous architecture as well as bites like Polish pierogis, locally made chocolates, and Mexican tacos.
More
  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$79.99
From
$79.99
Taking safety measures

Bike Tour of Chicago's Lakefront Neighborhoods

Bike Tour of Chicago's Lakefront Neighborhoods

star-5
132
Pedal past the lakefront neighborhoods of Chicago's North Side on this bike tour of the Windy City. Follow a local guide along quiet streets, city parks and scenic beaches, starting at Lake Shore Drive and continuing along Rush Street and the Magnificent Mile. Catch a glimpse of the Playboy Mansion, Oprah’s penthouse and the Victorian houses of Old Town. Select from several departure times in the morning or afternoon.
More
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$49.99
From
$49.99
Taking safety measures

Chicago Pizza Tour
Likely to Sell OutLikely to Sell Out

Chicago Pizza Tour

star-5
212
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.
More
  • 3 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$60.00
From
$60.00
Taking safety measures

Chicago's Ultimate City Bike Tour

Chicago's Ultimate City Bike Tour

star-5
41
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.
More
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$49.99
From
$49.99
Taking safety measures

Chicago Family Food & Bike Tour with Top Attractions

Chicago Family Food & Bike Tour with Top Attractions

star-5
38
See Chicago light up with a 4-hour bicycle tour of the Windy City’s most iconic sights and neighborhoods. Follow your guide along a leisurely route, watch the Buckingham Fountain light show and take in daytime or evening views of Millennium Park and the Museum Campus. Sample culinary classics of Chicago, like deep-dish pizza, a true Chicago hot dog, Italian beef, and a tasty dessert for good measure. Upgrade your experience to enjoy a locally crafted beer pairing at three of the food stops. As you pedal through downtown streets, capture unforgettable images of Chicago’s magnificent skyline then finish your tour in the heart of the city.
More
  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$74.99
From
$74.99
Taking safety measures

Chicago Fireworks Dinner Cruise with Buffet
Likely to Sell OutLikely to Sell Out

Chicago Fireworks Dinner Cruise with Buffet

star-4
11
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 and a live DJ spinning your favorite songs. In the summer months, enjoy a breathtaking fireworks display.
More
  • 3 hours
  • Free Cancellation
From
$158.98
From
$158.98

Offbeat Chicago Food Tour: Go Deeper Than Deep Dish
Likely to Sell OutLikely to Sell Out

Offbeat Chicago Food Tour: Go Deeper Than Deep Dish

star-5
86
Savor the flavors of Chicago — the ‘City of Neighborhoods’ — on a guided, ethnic food tour. This 3.5-hour adventure explores two of Chicago's most diverse neighborhoods: Argyle and Andersonville on the city’s North Side. Sample seven distinctly different types of food, visit landmark locations and learn about the local history and culture.
More
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$70.00
From
$70.00
Taking safety measures

Chicago Craft Brewery Barrel Bus Tour

Chicago Craft Brewery Barrel Bus Tour

star-4.5
25
Learn about Chicago’s brewpub scene and taste different types of craft beer on this guided brewery tour. Visit unique breweries for craft beer samples plus an additional brewing production facility for an in-depth tour. Discover the science behind the brewing process, complete with step-by-step procedures, and enjoy plenty of beer samples throughout the tour. Round-trip transportation in a Prohibition-era-styled barrel bus is included.
More
  • 3 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$89.60
From
$89.60
Taking safety measures

Chicago Sunset Dinner Cruise on Lake Michigan
Likely to Sell OutLikely to Sell Out

Chicago Sunset Dinner Cruise on Lake Michigan

star-4.5
125
Make your evening in Chicago one to remember with this luxury sunset cruise featuring dinner, sightseeing and dancing along the shores of Lake Michigan. Feast your eyes on incredible views of iconic Windy City sights like Navy Pier, the Willis (Sears) Tower, Buckingham Fountain and Soldier Field, then fill your belly with a bountiful all-you-can-eat buffet. Continue the celebration with a live DJ who will mix up a selection of dance favorites.
More
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$115.46
From
$115.46
Taking safety measures

Chicago's Chinatown Food and Walking Tour

Chicago's Chinatown Food and Walking Tour

star-4.5
34
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.
More
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$64.99
From
$64.99
Taking safety measures

Premier Chicago River Dinner Cruise
Likely to Sell OutLikely to Sell Out

Premier Chicago River Dinner Cruise

star-3.5
6
Cruise down the Chicago River in style during this 3-hour dinner cruise aboard the Odyssey. Watch the beautiful city and its architecture pass by through the ship’s panoramic windows. Then sit down to delicious 3-course meal accompanied by DJ entertainment to set the mood for your journey. A full-service bar complete with microbrews, creative cocktails, and a wine list is also available for purchase.
More
  • 3 hours
  • Taking safety measures
From
$172.58
From
$172.58
Taking safety measures

Chicago Premier Fireworks Dinner Cruise on Lake Michigan
Likely to Sell OutLikely to Sell Out

Chicago Premier Fireworks Dinner Cruise on Lake Michigan

star-2.5
5
Set sail on Lake Michigan aboard a luxury yacht for a gourmet dinner cruise with views of the Chicago fireworks display. During the 3-hour cruise, the crew serves a 3-course plated meal with dishes prepared by your onboard chef. You can enjoy the stylish interior of the rooftop lounge, dance to DJ entertainment, or relax and soak in the views of the Chicago skyline.
More
  • 3 hours
  • Free Cancellation
From
$179.38
From
$179.38

Private Chicago Architecture Tour

Private Chicago Architecture Tour

star-5
4
Ever since Chicago became the birthplace of the modern skyscraper, the city has been renowned for its architectural creativity and ingenuity. Led by an expert guide, explore some of the city’s most iconic buildings such as Sears Tower, The John Hancock Building, historic brownstones, and the homes of Oak Park designed by beloved architect Frank Lloyd Wright. You will be able to explore the insides of some locations on this completely customizable tour.
More
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$660.00
per group
From
$660.00
per group
Taking safety measures

Chicago Lincoln Park Bike Adventure

Chicago Lincoln Park Bike Adventure

star-4
6
Experience Chicago like never before on this guided, 3-hour bicycle tour. Ride the walking- and cycling-only Chicago Lakefront Trail to and through the city’s beautiful beaches, parks and lagoons. See the coast of Lake Michigan and the breathtaking Chicago skyline, plus bustling Navy Pier, popular North Avenue Beach, the 35-acre Lincoln Park Zoo and Conservatory and much more. The use of a bike and helmet is included.
More
  • 3 hours
  • Free Cancellation
From
$42.50
From
$42.50

Private Al Capone Gangster Tour in Chicago

Private Al Capone Gangster Tour in Chicago

star-5
2
Chicago’s mob history has long been immortalized in popular media. Embark on this Chicago Gangster Tour to learn the true story. With an expert historian as your guide, you’ll visit notorious hangouts of John Dillinger, The Untouchables, and the legendary Al Capone. You’ll stop at former speakeasies, historic hotels, and epic crime sites like that of the Saint Valentine’s Day Massacre.
More
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$330.00
Price varies by group size
From
$330.00
Price varies by group size
Taking safety measures

Private Sightseeing Cruise in Chicago

Private Sightseeing Cruise in Chicago

star-5
1
What an amazing experience you will have on this One of a Kind Private Sightseeing tour! We will explore the wonders of Chicago from a 46-foot Private Yacht. Chicago's newest Harbor has been adorned with new playgrounds, swimming pools, food stands, and more. We will pick meet you here for the start of a wonderful day! After 31st harbor, we will board the amazing Italian Azimut Yacht for 4 hours of amazement. While others have ordinary boats and vessels, the Azimut is one of a kind. You won't find another in Chicago. Additionally, while others are sharing spaces with strangers, you have the luxury of your own Private Yacht for the day. We will cruise north and see the Planetarium, Shedd Aquarium, and Chicago's Skyline. Up the River, we will head to some of Chicago's finest restaurants and architecture for an hour of amazement. Only to end the day at one of Chicago's hot spots - The Chicago Play Pen. Swim, relax, listen to music and enjoy an hour together before we head back!
More
  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$1,750.00
per group
From
$1,750.00
per group
Taking safety measures

Holiday Hike Chicago-Style: Festive Food & Walking tour

Holiday Hike Chicago-Style: Festive Food & Walking tour

star-5
13
Stroll through Chicago's winter streets, lit up for the holidays, on this gourmet walking tour. Learn about Chicago's celebrated holiday traditions like the European-inspired Christkindlmarket, the beautiful decor and windows on State Street, and ice skating at Millennium Park. Sample generous tastes of classic Chicago foods and holiday treats as you walk. Seasonal craft beer tastings help you stay warm and toasty; please note this tour operates in all weather conditions, so dress appropriately.
More
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$69.99
From
$69.99
Taking safety measures

Private Chicago Highlights Driving Tour

Private Chicago Highlights Driving Tour

star-5
12
Get an insider’s look at the Windy City’s most iconic monuments during this 3-hour private tour. Travel through Chicago aboard a private vehicle as you discover some of the city’s top neighborhoods, including the Loop, River North, the Magnificent Mile (along Michigan Avenue), Streeterville, the Gold Coast and much more. Your private driver-guide and vehicle, bottled water and round-trip hotel transport are all included.
More
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$190.00
Price varies by group size
From
$190.00
Price varies by group size
Taking safety measures

Train & Walking Tour of Chicago Loop: Home of the Modern Skyscraper

Train & Walking Tour of Chicago Loop: Home of the Modern Skyscraper

star-5
2
We start our tour at one of the most interesting buildings in the Loop — the Fine Arts Building.  Built in 1884 as a showroom and office complex, the building was converted twelve years later into its present-day use. We then venture a few blocks to tour the Harold Washington Chicago Public Library, the design of which was the winner of a competition to design a new library for the City of Chicago.  Leaving the library, we'll view three Chicago landmarks built in the late 1800s, then we visit the beautiful Marquette Building, the Field Building (built on the site of the world's first modern skyscraper, the Home Insurance Building) and then see the amazing atrium lobby of the world-renowned Rookery Building. Next, we're off to the beautifully-restored Quincy L stop (authentic 1897 design) and take the train to our last stops.  We visit the iconic Macy's to see the beautiful Tiffany mosaic then we wrap up the tour at the Cultural Center to experience the world's largest Tiffany dome.
More
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$50.00
From
$50.00
Taking safety measures

Private Custom City Tour in Chicago

Private Custom City Tour in Chicago

star-4
1
See Chicago the way you want to see it. This private tour is fully customizable to your specifications. Whether you are interested in the architecture and history, the art, the cool neighborhoods, or peaceful parks and happening beaches, this tour will cater to your tastes. Work with a guide to discover Chicago your way.
More
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$330.00
Price varies by group size
From
$330.00
Price varies by group size
Taking safety measures

Filters

Frequently Asked Questions