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Top Illinois Half-day Tours

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Illinois Tours

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Chicago Favorites Ultimate Food and Walking Tour

The perfect Food Tour of Chicago for first timers or anyone eager to explore Chicago's famous foods & top attractions—all in one tour. Stroll the …More

Likely to Sell Out
Likely to Sell Out
Chicago, USA
4.9 (2,304)

Chicago Favorites Ultimate Food and Walking Tour

The perfect Food Tour of Chicago for first timers or anyone eager to explore Chicago's famous foods & top attractions—all in one tour. Stroll the...

3 hours • Free Cancellation
4.9 (2,304)
from
$85
Chicago Bike & Classic Food Tour: Bikes, Bites & Views - Adults

Taste all of Chicago’s classic eats on this 4 1/2 hr Adults-only guided food & bicycle tour! Join the expert guides of Bobby’s Bike Hike, …More

Chicago, USA
5.0 (756)

Chicago Bike & Classic Food Tour: Bikes, Bites & Views - Adults

Taste all of Chicago’s classic eats on this 4 1/2 hr Adults-only guided food & bicycle tour! Join the expert guides of Bobby’s Bike Hike,...

4 hours 30 minutes • Free Cancellation
5.0 (756)
from
$89
Chicago in a Day Walking Tour: Food, History & Architecture

Immerse yourself in Chicago's rich history and vibrant culinary scene on this captivating walking tour. Discover the city's iconic architecture and Prohibition-era charm while indulging …More

Chicago, USA
4.9 (1,363)

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

Immerse yourself in Chicago's rich history and vibrant culinary scene on this captivating walking tour. Discover the city's iconic architecture and Prohibition-era charm while indulging...

4 hours 30 minutes • Free Cancellation
4.9 (1,363)
from
$101
Bike Tour of Chicago's Lakefront Neighborhoods

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 …More

Likely to Sell Out
Likely to Sell Out
Chicago, USA
4.9 (243)

Bike Tour of Chicago's Lakefront Neighborhoods

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...

3 hours • Free Cancellation
4.9 (243)
from
$59
Chicago Food Tour: 6 Dishes with Deep Dish Pizza & Beef Sandwich

On our Secret Food Tour: Chicago, you'll enjoy a variety of foods with culinary influences from the people who built this city. You'll experience all …More

Likely to Sell Out
Likely to Sell Out
Chicago, USA
4.9 (1,011)

Chicago Food Tour: 6 Dishes with Deep Dish Pizza & Beef Sandwich

On our Secret Food Tour: Chicago, you'll enjoy a variety of foods with culinary influences from the people who built this city. You'll experience all...

3 hours • Free Cancellation
4.9 (1,011)
from
$85
Chicago Pizza Tour

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 …More

Chicago, USA
4.9 (483)

Chicago Pizza Tour

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...

3 hours 30 minutes • Free Cancellation
4.9 (483)
from
$89
Chicago Tour South Side

The Blue-Collar side of Chicago many call it! This tour will show The Ford Factory, home of the steel mills, the blue-collar neighborhoods and many …More

Chicago, USA
4.7 (46)

Chicago Tour South Side

The Blue-Collar side of Chicago many call it! This tour will show The Ford Factory, home of the steel mills, the blue-collar neighborhoods and many...

4 hours • Free Cancellation
4.7 (46)
from
$125
Chicago's Chinatown Food and Walking Tour

Chicago's Chinatown: Few neighborhoods in America combine such delicious cuisine with fascinating history. Join Bobby’s Bike Hike & Food Tours, whose food tours have ranked …More

Likely to Sell Out
Likely to Sell Out
Chicago, USA
4.9 (802)

Chicago's Chinatown Food and Walking Tour

Chicago's Chinatown: Few neighborhoods in America combine such delicious cuisine with fascinating history. Join Bobby’s Bike Hike & Food Tours, whose food tours have ranked...

3 hours • Free Cancellation
4.9 (802)
from
$80
Chicago's Ultimate City Bike Tour of Top Downtown Attractions

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

Chicago, USA
4.9 (267)

Chicago's Ultimate City Bike Tour of Top Downtown Attractions

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

3 hours • Free Cancellation
4.9 (267)
from
$59
Chicago Family Food and Bike Tour with Top Attractions

This Chicago Food & Bike tour is perfect for the entire family, put on by Bobby’s Bike Hike, whose food tours in just the past …More

Likely to Sell Out
Likely to Sell Out
Chicago, USA
4.9 (99)

Chicago Family Food and Bike Tour with Top Attractions

This Chicago Food & Bike tour is perfect for the entire family, put on by Bobby’s Bike Hike, whose food tours in just the past...

4 hours • Free Cancellation
4.9 (99)
from
$79
Private Chicago Food Tour with Deep Dish and Beef Sandwich

On our Secret Food Tour: Chicago, you'll enjoy a variety of foods with culinary influences from the people who built this city. You'll experience all …More

Likely to Sell Out
Likely to Sell Out
Chicago, USA
5.0 (87)

Private Chicago Food Tour with Deep Dish and Beef Sandwich

On our Secret Food Tour: Chicago, you'll enjoy a variety of foods with culinary influences from the people who built this city. You'll experience all...

3 hours • Free Cancellation
5.0 (87)
from
$160
Chicago's West Side Foodie Ride Bike Tour

Take a detour off the beaten path, and explore the flavors of Chicago’s delicious West Side with Bobbys's Bike Hike & Food Tours, America's longest …More

Chicago, USA
5.0 (113)

Chicago's West Side Foodie Ride Bike Tour

Take a detour off the beaten path, and explore the flavors of Chicago’s delicious West Side with Bobbys's Bike Hike & Food Tours, America's longest...

4 hours • Free Cancellation
5.0 (113)
from
$99
Small Group Tour of Chicago Neighborhoods: North and South Side

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 …More

Chicago, USA
4.8 (49)

Small Group Tour of Chicago Neighborhoods: North and South Side

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...

4 hours 30 minutes • Free Cancellation
4.8 (49)
from
$125
River North Food Walking Tour

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 …More

Chicago, USA
4.6 (94)

River North Food Walking Tour

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...

3 hours • Free Cancellation
4.6 (94)
from
$89
Chicago Private Custom City Tour with Hotel Pick Up

PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 5 PASSENGERS.  Thank you for contacting Chicago Private Tours! We would love to help your …More

Chicago, USA
5.0 (200)

Chicago Private Custom City Tour with Hotel Pick Up

PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 5 PASSENGERS.  Thank you for contacting Chicago Private Tours! We would love to help your...

3 to 4 hours • Hotel pickup offered • Free Cancellation
5.0 (200)
from
$539
Premium Chicago City Tour Small Group ICONIC Landmarks & Skyline

Discover the architectural soul of Chicago on a thoughtfully curated half-day city tour. Travel through the city’s most influential districts, from historic riverfront landmarks to …More

Chicago, USA
4.9 (34)

Premium Chicago City Tour Small Group ICONIC Landmarks & Skyline

Discover the architectural soul of Chicago on a thoughtfully curated half-day city tour. Travel through the city’s most influential districts, from historic riverfront landmarks to...

3 hours • Hotel pickup offered • Free Cancellation
4.9 (34)
from
$48
The Devil in the White City: A Haunting History Tour

We are Chicago's first and best Devil in the White City tour, offering the history, legends and lore surrounding H.H.Holmes, the World's Fair and Victorian …More

Chicago, USA
4.5 (17)

The Devil in the White City: A Haunting History Tour

We are Chicago's first and best Devil in the White City tour, offering the history, legends and lore surrounding H.H.Holmes, the World's Fair and Victorian...

3 hours • Free Cancellation
4.5 (17)
from
$75
Chicago Hauntings Original Ghost Bus Tour

Often imitated but never matched, this 3 hour ghost bus tour with stops remains the "Best of Chicago" since its founding 23 years ago by …More

Chicago, USA
4.1 (133)

Chicago Hauntings Original Ghost Bus Tour

Often imitated but never matched, this 3 hour ghost bus tour with stops remains the "Best of Chicago" since its founding 23 years ago by...

3 hours • Free Cancellation
4.1 (133)
from
$59
Chicago-Style Holiday Hike: Festive Food and Walking Tour

There’s nothing more magical than downtown Chicago during the holidays. Bobby’s Bike Hike & Food Tours—internationally recognized for quality—presents the Holiday Hike, a 3-hour guided …More

Chicago, USA
5.0 (77)

Chicago-Style Holiday Hike: Festive Food and Walking Tour

There’s nothing more magical than downtown Chicago during the holidays. Bobby’s Bike Hike & Food Tours—internationally recognized for quality—presents the Holiday Hike, a 3-hour guided...

3 hours • Free Cancellation
5.0 (77)
from
$85
Chicago Full-Day Walking Food Tour with Free Bike or Kayak Rental

Get ready for the most complete adventure the city has to offer—an immersive Full Day Chicago Food Tour and Walking Tour that blends Chicago’s legendary …More

Likely to Sell Out
Likely to Sell Out
Chicago, USA
5.0 (3)

Chicago Full-Day Walking Food Tour with Free Bike or Kayak Rental

Get ready for the most complete adventure the city has to offer—an immersive Full Day Chicago Food Tour and Walking Tour that blends Chicago’s legendary...

5 hours • Free Cancellation
5.0 (3)
from
$99

Frequently Asked Questions

These answers are based on answers previously given to Cool Destinations customers' questions.

Recent tour reviews
Chicago + Cool Destinations + Michael = ICONIC
New York City
Premium Chicago City Tour Small Group ICONIC Landmarks & Skyline
Girtha_B, Sep 2026
Chicago + Cool Destinations + Michael = ICONIC
This tour is labeled as ICONIC for a good reason as it was truly ICONIC. it was perfect for our small group of 6 people.! I loved the fact that they do direct hotel pickups! Michael was an extraordinary tour guide. Being a small group, he made many stops for us to get out, explore and experience sights we might not have had the option to do on a larger tour. He even let us go in to shop for Garretts popcorn and a Chicago Hot Dog! This is not to mention driving us up close to landmarks to cut down on some of the walking. I personally have mobility issues and use a walker. Michsel made sure I was safe and well taken care of. If I am ever in Chicago again or if I know of others going there and looking for a fabulous tour, I will be recommending this tour on Cool Destinations and most definitely requesting Michael as the tour guide. If I could give it 10 stars, I would in a heartbeat.
Read more
Wonderful way to learn about Chicago!
New York City
Chicago Favorites Ultimate Food and Walking Tour
danielbX4333MU, Sep 2026
Wonderful way to learn about Chicago!
Cassie was awesome! The food was only so-so, but that wasn’t the tour’s fault - New York Pizza is simply the best (and Colorado Rocky Mountain pizza is second). The Chicago dawg was very good, but the Palmer House brownie was my favorite. But the highlight of the tour was Cassie’s leadership and commentary. You can tell she really loves Chicago! And the city itself is a gem, of course. Whether you end up liking the food or not, a food tour is the best way to learn about a city.
Read more
Great Chicago Architecture Tour
New York City
Chicago in a Day Walking Tour: Food, History & Architecture
I3658GI_, Sep 2026
Great Chicago Architecture Tour
We had a great time on the Chicago architecture tour. Our guide Chad was very patient, knowledgeable, and took the time to explain the history and details behind the buildings. He was also happy to answer questions, which made the experience feel relaxed and informative. The food was really good as well and was a nice addition to the tour. Overall, it was a fun and enjoyable experience, and I would definitely recommend it.
Read more
Really great tour
New York City
Chicago in a Day Walking Tour: Food, History & Architecture
H8691CBryank, Sep 2026
Really great tour
I took a few coworkers on a tour today with Chad and it was an excellent experience. I’ve visited Chicago many times before but didn’t know some of the history until today. Visiting the Chicago Cultural Center and having a Chicago dog were the highlights of the tour. Would highly recommend.
Read more
Great value
New York City
Chicago Hauntings Original Ghost Bus Tour
Starr_1113, Sep 2026
Great value
Great tour, really appreciate the bus. Got to see more of the city during the drive. The price was great for the length of the tour.
Read more
Tasty food with an excellent tour guide!!
New York City
Chicago’s Chinatown Food and Walking Tour
Sara_M, Sep 2026
Tasty food with an excellent tour guide!!
The Chinatown food tour was the highlight of our trip! Hands down! York was a delight! His combination of city history and personal experiences was exactly what a tour like this needs. It could have been very bland. But York gave it heart. Also DELICIOUS!! Fantastic selection of area restaurants. I learned so much over that 3 hours. And had a full belly! Do yourself a favor and ask for York!!
Read more
Good Chicago history and delicious foood!
New York City
Chicago Favorites Ultimate Food and Walking Tour
Rodrigo_A, Sep 2026
Good Chicago history and delicious foood!
If you are interested in knowing some of the history of Chicago and enjoying some of Chicago’s best and classic food this is the tour to take. Plus our tour guys made the experience 10 times more worth it.
Read more
So much food and so...
New York City
Chicago’s Chinatown Food and Walking Tour
Hutch_Y, Sep 2026
So much food and so...
So much food and so little walking. We enjoyed this one immensely. Valerie was a wonderful tour guide.
Read more
Small Chicago city tour with Michael at the helm
New York City
Premium Chicago City Tour Small Group ICONIC Landmarks & Skyline
Jeanetta_A, Sep 2026
Small Chicago city tour with Michael at the helm
It was an excellent tour. Our driver and tour guide Michael was great; very kind and courteous He was knowledgeable and well spoken. His vehicle was clean and rode well
Read more
Great intro to the food and history of Chicago
New York City
Chicago Bike & Classic Food Tour: Bikes, Bites & Views – Adults
Jan_B, Sep 2026
Great intro to the food and history of Chicago
This was an easy biking 3 1/2 hour tour for the evening tour. Just a note the tour does go rain or shine, and we definitely got caught in the rain towards the end! Our guide, Nora, was a native of Chicago and gave us lots of fascinating history of both food and the city.
Read more
Different faces of Chicago
New York City
Bike Tour of Chicago’s Lakefront Neighborhoods
366krisztinab, Sep 2026
Different faces of Chicago
We had a great time despite the day starting with some rain. Our guide, Liam was fantastic, great energy and enthusiasm. He guided us through the different neighbourhoods making sure we were all safe, stopping regularly to share stories about the history of them. We also got to visit the zoo in Lincoln Park, and saw 4 lions among other animals. 3 hours just flew by.
Read more
Excellent Chicago food tour
New York City
Chicago Food Tour: 6 Dishes with Deep Dish Pizza & Beef Sandwich
Trail789249, Sep 2026
Excellent Chicago food tour
We went on a 3 hour food your which, not only allowed us to taste the foods Chicago is known for, but Sue Gould our tour guide, also showed an interesting architecture and provided a bit of Chicago history. The amount of food was right on and the pacing was excellent as well. The delivery of the tiur matched its description. Seeing the Rookery Building and hearing of its history gave us a deeper appreciation of the city.
Read more
Best food tour
New York City
Chicago Food Tour: 6 Dishes with Deep Dish Pizza & Beef Sandwich
P1479XSdeborahm, Sep 2026
Best food tour
I’ve done a few good food tours in Europe, but our food tour with Sue was by far the best. The food was great, but what made it exceptional was Sue’s knowledge of her city, and the way she presented it in a funny and engaging way. The time just flew by. If you want to find out a few (lots) of fun fact about Chicago and enjoy a great food experience as well, then I would highly recommend doing a food tour with Sue. Thanks Sue for an absolutely great day.
Read more
Great tour
New York City
Chicago Private Custom City Tour with Hotel Pick Up
elizabethmX9186LB, Sep 2026
Great tour
Matthew is a knowledgeable tour guide. I will definitely recommend this tour.
Read more
Pleased to be guided on US roads
New York City
Bike Tour of Chicago’s Lakefront Neighborhoods
alexo407, Sep 2026
Pleased to be guided on US roads
Craig gave us an informative and well paced tour of some Chicago neighbourhoods. Coming from the UK, I was a bit apprehensive about riding on US roads, but I felt comfortable and safe the whole time. For me, this was a highlight of my trip to Chicago.
Read more
Must do Pizza experience!
New York City
Chicago Pizza Tour
allanbulabula, Sep 2026
Must do Pizza experience!
Great Tour! James was a very knowledgeable guide and funny too! We learned about pizza and a lot of other Chicago facts. We had fun and would recommend this tour!!!!
Read more
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