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Top Chicago Half-day Tours

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

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

star-5
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.
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  • 4 hours
  • Taking safety measures
From
US$79.99
From
US$79.99
Taking safety measures

SO MUCH FUN

We had an absolute blast. James was incredibly knowledgeable and shared some really cool information along the way. My husband and I planned a weekend in Chicago and this light hearted fun kept us laughing and I’m so glad we did it. Absolutely recommend!

AmyB, Aug 2020

53 Chicago Half-day Tours | All Chicago Tours

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Chicago Grand Half-Day Bus Tour

Chicago Grand Half-Day Bus Tour

star-3.5
Get the perfect introduction to the wealth of sights in the Windy City during this 4-hour Chicago day tour. Discover the many landmarks spanning both the city's North Side and South Side, enjoying a scenic ride along Lake Michigan on Chicago's Outer Drive along the way. You'll also have the chance to admire the city's Washington and Grant Parks, explore inside the Lincoln Park Conservatory, see Adler Planetarium and visit the iconic Wrigley Building. This Chicago in a half day tour also includes transport between all sites and tour narration.
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  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
US$52.95
From
US$52.95
Taking safety measures

Chicago Loop Secret Food Tour w/ Private Tour Option

Chicago Loop Secret Food Tour w/ Private Tour Option

star-5
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.
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  • 3 hours
  • Taking safety measures
From
US$193.20
From
US$193.20
Taking safety measures

Spirit of Chicago Sunset Dinner Cruise with Buffet

Spirit of Chicago Sunset Dinner Cruise with Buffet

star-4.5
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.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
US$112.74
From
US$112.74
Taking safety measures

Famous Tastes of Chicago Food Tour

Famous Tastes of Chicago Food Tour

star-4.5
Discover Chicago’s food, history, architecture and culture on this 3-hour, small-group walking tour. Try six of the Windy City’s quintessential staples from local restaurants and specialty food shops like Pizano’s Pizza and the Berghoff, the oldest family run-establishment in Chicago. Taste local favorites including deep-dish pizza,  Chicago Italian Beef Sandwich and chocolates from Fannie May, just to name a few. Along the way, see and learn about the historical, cultural and architectural components that make up this legendary town.
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  • 3 hours
From
US$68.50
From
US$68.50

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

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

star-5
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.
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  • 5 hours
  • Free Cancellation
  • Taking safety measures
From
US$102.30
From
US$102.30
Taking safety measures

Chicago Prohibition Tour

Chicago Prohibition Tour

star-4.5
Visit four historic bars in operation since Prohibition in Chicago, and learn from a knowledgeable guide about the surreptitious world of the speakeasy. This adults-only tour takes you by coach to once-illicit establishments in Old Town, Wicker Park and the Chicago Loop where liquor, jazz and mobsters ruled. You’ll hear about Chicago gangsters like Al Capone and learn the historical context for the decade-long ban of alcohol. If you’d like, you can purchase recommended craft cocktails and signature drinks of the 1920s.
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  • 3 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
US$55.00
From
US$55.00
Taking safety measures

Small-Group Chicago Food Tour: Gold Coast and Old Town

Small-Group Chicago Food Tour: Gold Coast and Old Town

star-5
Savor the flavors of the Gold Coast and Old Town neighborhoods on this 3-hour Chicago food walking tour, led by an expert guide. You’ll stop at seven popular shops and eateries, including a specialty tea merchant, confectioner, European bakery and — of course — Chicago-style pizzeria. Explore these culture-rich neighborhoods just north of the downtown and learn about their architecture and history along the way. Numbers are limited to 18 participants for a small-group experience.
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  • 3 hours
  • Free Cancellation
From
US$74.67
From
US$74.67

Chicago Grand Tour and Admission to 360 Chicago (formerly John Hancock Observatory)

Chicago Grand Tour and Admission to 360 Chicago (formerly John Hancock Observatory)

star-3.5
This Chicago grand tour covers four hours of sightseeing with admission to 360 Chicago (John Hancock Observatory). Get oriented to the Windy City on a coach tour that takes you along a scenic route on Lake Shore Drive, and past North Side and South Side highlights including Museum Campus, Lincoln Park, Washington Park, Grant Park and Wrigley Field. Finish on the 94th floor of the Hancock Center, one of Chicago's tallest landmarks, for panoramic views of the Magnificent Mile from the open-air observation deck.
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  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
US$73.95
From
US$73.95
Taking safety measures

Chicago Style Food Tour

Chicago Style Food Tour

star-4.5
Discover Chicago’s food, history, architecture and culture on this small-group walking tour. Try the Windy City’s quintessential staples from local restaurants and specialty food shops like Downtown Dogs and the world-famous Billy Goat Tavern. Taste local favorites including deep-dish pizza, a Chicago-style hot dog, and chocolates from Fannie May, just to name a few. Along the way, see and learn about the historical, cultural, and architectural components that make up this legendary town.
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  • 3 hours
From
US$71.47
From
US$71.47

Chicago's Ultimate City Bike Tour

Chicago's Ultimate City Bike Tour

star-5
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.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
US$45.99
From
US$45.99
Taking safety measures

Half-Day Chicago City Sight Tour with Lunch and CTA Pass

Half-Day Chicago City Sight Tour with Lunch and CTA Pass

star-5
Discover some of Chicago’s top attractions—and step off the tourist trail when you visit several of its heritage, locals-frequented neighborhoods—on this introductory, small-group tour. Meet your guide in the Loop, and set off on foot. You’ll spy major landmarks like the Rookery Building, will head to Chinatown for a cultural immersion and delicious dumplings, will glimpse historical architecture in the Prairie District, will explore beautiful Grant Park, and more.
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  • 4 hours
  • Free Cancellation
From
US$99.00
From
US$99.00

Chicago Highlights Driving Tour: Covid-19 Safe and Private Tour

Chicago Highlights Driving Tour: Covid-19 Safe and Private Tour

star-5
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.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
US$190.00
Price varies by group size
From
US$190.00
Price varies by group size
Taking safety measures

Private Chicago Architecture Tour

Private Chicago Architecture Tour

star-5
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.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
US$660.00
per group
From
US$660.00
per group
Taking safety measures

Odyssey Chicago River Dinner Cruise

Odyssey Chicago River Dinner Cruise

star-3.5
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.
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  • 3 hours
  • Taking safety measures
From
US$169.86
From
US$169.86
Taking safety measures

Chicago Craft Brewery Barrel Bus Tour

Chicago Craft Brewery Barrel Bus Tour

star-4.5
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.
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  • 3 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
US$89.60
From
US$89.60
Taking safety measures

Land and River Architecture Tour of Chicago's Scenic North Side

Land and River Architecture Tour of Chicago's Scenic North Side

star-4.5
Discover Chicago’s iconic architectural gems from every angle on a 3.5-hour tour of the North Side. Divided between land and water, the comprehensive tour enables you to cover a huge area of the city without getting worn out. Travel comfortably by coach or trolley to Fort Dearborn, Wrigley Building, and more. Afterwards, see the Windy City's famous skyscrapers, bridges, and historical sites on a 90-minute cruise down Chicago River.
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  • 3 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
US$76.95
From
US$76.95
Taking safety measures

Private Al Capone Gangster Tour in Chicago

Private Al Capone Gangster Tour in Chicago

star-5
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.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
US$660.00
per group
From
US$660.00
per group
Taking safety measures

Bike Tour of Chicago's Lakefront Neighborhoods

Bike Tour of Chicago's Lakefront Neighborhoods

star-5
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.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
US$46.99
From
US$46.99
Taking safety measures

Chicago Odyssey Dinner Cruise

Chicago Odyssey Dinner Cruise

star-4
Take a gourmet dinner cruise on a high-end luxury yacht with the stunning skyline of Chicago serving as your backdrop. Climb aboard your recently renovated vessel, featuring a sumptuously-appointed rooftop lounge and stylish interior design, for your cruise along Lake Michigan. Then sit down for a 3-course dinner, informed by some of the world’s top celebrity chefs and composed of fresh ingredients cooked right on-board. After dinner, enjoy coffee and tea, captivating views of Chicago landmarks like the Willis (formerly Sears) Tower and Navy Pier, plus musical entertainment provided by the onboard DJ.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
US$108.66
From
US$108.66
Taking safety measures

Best of Chicago Tour Including a Deep-Dish Pizza

Best of Chicago Tour Including a Deep-Dish Pizza

star-2.5
Tour Chicago's sights aboard a luxury coach and enjoy some Chicago-style deep-dish pizza on this 5.5-hour guided tour. Visit sites like the Hancock Tower, the Lincoln Park Conservatory and the Loop. Pass through neighborhoods such as Wrigleyville, Lincoln Park and Gold Coast. Top off your tour with a visit to one of Chicago's most popular pizza restaurants to sample the famous Chicago-style deep dish pizza.
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  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
US$74.95
From
US$74.95
Taking safety measures

Bikes, Bites, and Brews: Chicago's West Side Foodie Ride

Bikes, Bites, and Brews: Chicago's West Side Foodie Ride

star-5
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.
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  • 4 hours
  • Taking safety measures
From
US$79.99
From
US$79.99
Taking safety measures

Chicago City Tour and Chicago River Cruise

Chicago City Tour and Chicago River Cruise

star-3.5
See Chicago from a new perspective during this 4-hour combined bus and boat excursion covering some of the city's most iconic sights. First discover Windy City landmarks such as the skyscrapers of the Loop, Grant Park, Shedd Aquarium, Soldier Field and the former stomping grounds of President Obama during a narrated coach tour. Then take a Chicago cruise aboard your state-of-the-art yacht, enjoying a cruise of the Chicago River that provides a unique look at the city's architecture from the water. This half-day Chicago exploration also includes hotel pickup.
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  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
US$76.95
From
US$76.95
Taking safety measures

Chicago Pizza and Cocktails Tour

Chicago Pizza and Cocktails Tour

star-5
Eat and drink your way through the famous food culture of the Windy City during this guided Chicago beer and pizza tour. Make your way by mini-coach to three local pizzerias to taste slices of the city's distinct pies, ranging from thin crust to deep dish, each of which is complemented by an included glass of beer or wine. During your ride between pizza stops, your guide will keep the fun going with facts and sights.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
US$80.00
From
US$80.00
Taking safety measures

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