Top Chicago Half-day Tours

When are you traveling?
Filter
Price Clear
$0 $500+
Popular Clear
Rating Clear
Duration Clear
Time of Day Clear

Chicago Tours

Attractions

Guides

Calendar

76 Results
Sort by:
Featured
  • Chicago Favorites Ultimate Food & Walking Tour
    Likely to Sell Out
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Chicago Favorites Ultimate Food & Walking Tour

    717

    The perfect tour for first timers to Chicago or those who want to explore Chicago's famous foods along with the city's top attractions ....all on...
    Read More

     3 hours  Free Cancellation  Instant Confirmation
    from
    $79.99
    Details
    from
    $79.99
    Details
  • Chicago in a Day: Food, History and Architecture Walking Tour
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

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

    518

    Ready to discover some of the best Chicago has to offer with a local by your side? Join us on an epic tour of some...
    Read More

     5 hours  Free Cancellation  Instant Confirmation
    from
    $108.08
    Details
    from
    $108.08
    Details
  • Chicago Pizza Tour
    Likely to Sell Out
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Chicago Pizza Tour

    220

    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...
    Read More

     3 hours 30 minutes  Free Cancellation
    from
    $75
    Details
    from
    $75
    Details
  • Chicago Craft Brewery Barrel Bus Tour
    Likely to Sell Out

    Chicago Craft Brewery Barrel Bus Tour

    149

    There’s never been a better time to be a beer drinker — and Chicago, with its thriving brewery scene and many destination-worthy beer bars, is...
    Read More

     3 hours 45 minutes  Free Cancellation  Instant Confirmation
    from
    $99.60
    Details
    from
    $99.60
    Details
  • Bike Tour of Chicago's Lakefront Neighborhoods
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Bike Tour of Chicago's Lakefront Neighborhoods

    103

    This is the tour that made Bobby famous! Bobby’s Bike Hike is America’s longest-running city bicycle tour company, and has been repeatedly recognized for excellence...
    Read More

     3 hours  Free Cancellation  Instant Confirmation
    from
    $54.99
    Details
    from
    $54.99
    Details
  • Private Speakeasy Pub Crawl in Chicago with Local Historian

    Private Speakeasy Pub Crawl in Chicago with Local Historian

    6

    Our Prohibition Era Speakeasy Pub Crawl is filled with cocktails and a perfect venue for bachelor or bachelorette parties, corporate events, or just a fun...
    Read More

     0  Hotel pickup offered  Free Cancellation  Instant Confirmation
    from
    $880
    Details
    from
    $880
    Details
  • Chicago's Ultimate City Bike Tour
    Likely to Sell Out
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Chicago's Ultimate City Bike Tour

    77

    Get acquainted with Chicago’s most iconic landmarks on this riotous guided bicycle tour! Join the expert guides of Bobby’s Bike Hike, America’s longest-running city bicycle...
    Read More

     3 hours  Free Cancellation  Instant Confirmation
    from
    $54.99
    Details
    from
    $54.99
    Details
  • Chicago Walking Food Tour With Secret Food Tours
    Likely to Sell Out
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Chicago Walking Food Tour With Secret Food Tours

    154

    Join this 3-hour tour of Chicago's food scene, and see what sets this friendly mid-western metropolis apart. On this 12 person maximum walking tour of...
    Read More

     3 hours  Free Cancellation
    from
    $87.87
    Details
    from
    $87.87
    Details
  • Best of Chicago Small Group Tour with Skydeck + Shoreline Cruise
    Likely to Sell Out
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Best of Chicago Small Group Tour with Skydeck + Shoreline Cruise

    125

    Explore the Windy City with See Sight Tours, Chicago’s best small group tours (max. 7 guests). Immerse yourself in Chicago’s distinct skyline with bold skyscrapers...
    Read More

     4 hours  Hotel pickup offered  Free Cancellation  Instant Confirmation
    from
    $215
    Details
    from
    $215
    Details
  • Chicago Family Food & Bike Tour with Top Attractions
    Likely to Sell Out
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Chicago Family Food & Bike Tour with Top Attractions

    43

    This could very well be the best food tour on the planet. Why? Nothing beats the freedom of a bicycle to explore so many unique...
    Read More

     4 hours  Free Cancellation  Instant Confirmation
    from
    $79.99
    Details
    from
    $79.99
    Details
  • Day in Chicago Food and Architecture
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Day in Chicago Food and Architecture

    26

    Get the whole Chicago experience combining our Chicago Architecture & Highlights Tour and Chicago Food Tour: Deep Roots to Deep Dish! Our two-part tour begins...
    Read More

     5 hours  Free Cancellation  Instant Confirmation
    from
    $99
    Details
    from
    $99
    Details
  • Day in Chicago Food and Architecture(Private)
    Likely to Sell Out

    Day in Chicago Food and Architecture(Private)

    1

    Get the whole Chicago experience combining our Chicago Architecture & Highlights Tour and Chicago Food Tour: Deep Roots to Deep Dish! Our two-part tour begins...
    Read More

     5 hours  Free Cancellation  Instant Confirmation
    from
    $298.50
    Details
    from
    $298.50
    Details
  • Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

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

    263

    Taste all of Chicago’s classic eats on this 4-hr guided bicycle tour! Join the expert tour guides of Bobby’s Bike Hike, America’s longest-running city bike...
    Read More

     4 hours  Free Cancellation  Instant Confirmation
    from
    $89.99
    Details
    from
    $89.99
    Details
  • Private Chicago Tour with Driver and tour Guide. Hotel pick up included
    Likely to Sell Out

    Private Chicago Tour with Driver and tour Guide. Hotel pick up included

    3

    One of the best ways to explore a city is with a private tour. This tour isn't any different. Have your driver and separate tour...
    Read More

     4 hours  Hotel pickup offered  Free Cancellation  Instant Confirmation
    from
    $483.70
    Details
    from
    $483.70
    Details
  • Walking Tour: Chicago Loop - Home of the Modern Skyscraper
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Walking Tour: Chicago Loop - Home of the Modern Skyscraper

    29

    We start our tour at one of the most interesting buildings in the Loop — the Fine Arts Building.  Built in 1884 as a showroom...
    Read More

     3 hours 30 minutes  Free Cancellation  Instant Confirmation
    from
    $60
    Details
    from
    $60
    Details
  • Holiday Hike Chicago-Style: Festive Food & Walking tour
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Holiday Hike Chicago-Style: Festive Food & Walking tour

    34

    There’s nothing more magical than downtown Chicago during the holiday season. Bobby’s Holiday Hike is a 3hr guided walking and food tour through the Chicago Loop,...
    Read More

     3 hours  Free Cancellation  Instant Confirmation
    from
    $79.99
    Details
    from
    $79.99
    Details
  • Chicago's Chinatown Food and Walking Tour
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Chicago's Chinatown Food and Walking Tour

    168

    Few neighborhoods in America combine such delicious cuisine with such fascinating history as Chicago’s Chinatown. Join Bobby’s Bike Hike, America’s longest running city bicycle tour...
    Read More

     3 hours  Free Cancellation  Instant Confirmation
    from
    $79.99
    Details
    from
    $79.99
    Details
  • Chicago's West Side Foodie Ride Bike Tour
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Chicago's West Side Foodie Ride Bike Tour

    17

    Take a detour off the beaten path, and explore the flavors of Chicago’s vibrant West Side with Bobbys's Bike Hike, America's longest running city bike...
    Read More

     4 hours  Free Cancellation  Instant Confirmation
    from
    $89.99
    Details
    from
    $89.99
    Details
  • Private Chicago Highlights Driving Tour
    Likely to Sell Out

    Private Chicago Highlights Driving Tour

    38

    See Chicago’s most essential landmarks from the comfort of a private vehicle on this 3-hour jaunt around town. Your guide will pick you up directly...
    Read More

     3 hours  Hotel pickup offered
    from
    $190
    Details
    from
    $190
    Details
  • Small-Group Tour of Chicago Neighborhoods - North and South Side
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Small-Group Tour of Chicago Neighborhoods - North and South Side

    34

    This unique tour of Chicago will allow for tourist to see most of Chicago’s 77 neighborhoods and city parks. There is no other tour that...
    Read More

     4 hours 30 minutes  Hotel pickup offered  Free Cancellation  Instant Confirmation
    from
    $125
    Details
    from
    $125
    Details
  • River North Food Walking Tour
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    River North Food Walking Tour

    70

    On our 3 hour food walking tour of Chicago, you will taste delectable foods from 5 different delicious places. Tease your tastebuds as you savor...
    Read More

     3 hours  Free Cancellation  Instant Confirmation
    from
    $89
    Details
    from
    $89
    Details
Filter

Frequently Asked Questions

The answers provided below are based on answers previously given to customers' questions.

Q: What are the best options for Chicago Half-day Tours?

A: According to verified reviews on Cool Destinations and TripAdvisor, the best Chicago Half-day Tours are:

Q: What are the best kid-friendly options for Chicago Half-day Tours Tours?

A: According to verified reviews on Cool Destinations and TripAdvisor, the best kid-friendly Chicago Half-day Tours are:

View all kid-friendly Tours →

Q: Which Chicago Half-day Tours have Instant Confirmation?

A: Chicago Half-day Tours with Instant Confirmation include:

View all Tours with Instant Confirmation →

Q: Which Chicago Half-day Tours have Free Cancellation?

A: Chicago Half-day Tours with Free Cancellation (in most cases up to 24 hours in advance of your tour date, check the specific tour page) include:

View all Tours with Free Cancellation →

Q: I need a ride! Which Chicago Half-day Tours include Hotel Pickup?

A: No problem. These Chicago Half-day Tours include Hotel Pickup:

View all Tours with Hotel Pickup →

Q: Got any more Chicago trip ideas?

A: We sure do. Check out our curated lists of hand-picked Chicago Tours.

View all Chicago Trip Ideas →

Q: What are the most popular styles of Tours and Activities in Chicago?

A: Based on our sales data over the past year, the most popular styles of tours and activities in Chicago are:

View all tour styles in Chicago →