Flights To Cook County - Cheap Flights Starting at CA $191

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Jet to one of Cook County's top cities

A river flowing through a forest with autumn-colored trees and fallen leaves.

Tinley Park

Flights
Tinley Park

How Much Does it Cost To Fly To Cook County?

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Mon, Sep 21 - Fri, Sep 25
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
CA $320 Roundtrip, just found
CA $320
Roundtrip
just found
Select Porter Airlines flight, departing Mon, Sep 21 from Billy Bishop Toronto City to Midway Intl., returning Fri, Sep 25, priced at CA $320 just found
Fri, Sep 25 - Wed, Sep 30
YTZ
Billy Bishop Toronto City
ORD
O'Hare Intl.
CA $321 Roundtrip, found 5 days ago
CA $321
Roundtrip
found 5 days ago
Select Air Canada flight, departing Fri, Sep 25 from Billy Bishop Toronto City to O'Hare Intl., returning Wed, Sep 30, priced at CA $321 found 5 days ago
Sat, Sep 19 - Wed, Sep 23
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $332 Roundtrip, found 4 hours ago
CA $332
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Sat, Sep 19 from Pearson Intl. to O'Hare Intl., returning Wed, Sep 23, priced at CA $332 found 4 hours ago
Sun, Sep 20 - Sun, Sep 27
YYZ
Pearson Intl.
MDW
Midway Intl.
CA $340 Roundtrip, found 4 hours ago
CA $340
Roundtrip
found 4 hours ago
Select Delta flight, departing Sun, Sep 20 from Pearson Intl. to Midway Intl., returning Sun, Sep 27, priced at CA $340 found 4 hours ago
Sat, Sep 19 - Wed, Sep 23
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $340 Roundtrip, found 4 hours ago
CA $340
Roundtrip
found 4 hours ago
Select Delta flight, departing Sat, Sep 19 from Pearson Intl. to O'Hare Intl., returning Wed, Sep 23, priced at CA $340 found 4 hours ago
Mon, Sep 21 - Fri, Sep 25
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
CA $351 Roundtrip, just found
CA $351
Roundtrip
just found
Select Air Transat flight, departing Mon, Sep 21 from Billy Bishop Toronto City to Midway Intl., returning Fri, Sep 25, priced at CA $351 just found
Fri, Oct 2 - Sun, Oct 4
YXX
Abbotsford Intl.
ORD
O'Hare Intl.
CA $405 Roundtrip, found 1 hour ago
CA $405
Roundtrip
found 1 hour ago
Select WestJet flight, departing Fri, Oct 2 from Abbotsford Intl. to O'Hare Intl., returning Sun, Oct 4, priced at CA $405 found 1 hour ago
Sun, Sep 6 - Tue, Sep 22
YVR
Vancouver Intl.
ORD
O'Hare Intl.
CA $410 Roundtrip, found 7 hours ago
CA $410
Roundtrip
found 7 hours ago
Select WestJet flight, departing Sun, Sep 6 from Vancouver Intl. to O'Hare Intl., returning Tue, Sep 22, priced at CA $410 found 7 hours ago
OriginDestinationTravel datesFlights from*
LAXChicagoOctober 19 to October 24CA $275
FCOChicagoOctober 14 to October 18CA $792
HKGChicagoSeptember 16 to September 20CA $1,222
PVGChicagoOctober 26 to November 4CA $1,492
PEKChicagoSeptember 22 to September 28CA $1,731
CANChicagoSeptember 19 to October 3CA $1,869
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
LAXChicagoAugust 30 to September 5CA $520
FCOChicagoAugust 30 to September 8CA $1,110
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
4.0-star property

Level Chicago Fulton Market

Nov 18 - Nov 22

4 night stay

Toronto (YYZ) to Chicago (ORD)

United • Roundtrip • Coach
Price was CA $1,687, price is now CA $1,141 per person
CA $1,141
per person
found 1 day ago
Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

Sep 14 - Sep 17

3 night stay

Hamilton (YHM) to Chicago (ORD)

Air Canada • Non-stop roundtrip • Coach
Price was CA $2,991, price is now CA $2,090 per person
CA $2,090
per person
found 14 hours ago
Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

Nov 5 - Nov 9

4 night stay

Regina (YQR) to Chicago (ORD)

United • Non-stop roundtrip • Coach
Price was CA $2,774, price is now CA $1,939 per person
CA $1,939
per person
found 5 hours ago
Don't see what you're looking for?
See all available trips from Toronto to Cook County
View all trips

Travelers ❤️ These Cook County 🏨

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
8/10 Very good! (10,288 reviews)
"Convenient to many attractions. Comfortable room. Fastest elevators! Favorite place to stay in Chicago!"

Reviewed on Aug 23, 2026

Opens in a new windowCongress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Opens in a new windowThe Chicago Hotel Collection Ambassador Gold Coast
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4 out of 5
One Superior Place Chicago IL
Stay at this aparthotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
9.4/10 Exceptional! (865 reviews)
"Awesome stay. I love the property. Staff comfort me when I found out that my dad passed away. This is/was going beyond the call of duty and doing an extra great job so 10 stars. You are greatly appreciated. Primetime location downtown near magnificent mile and Navy Pier,"

Reviewed on Aug 21, 2026

Opens in a new windowKasa Magnificent Mile Chicago
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
171 W Randolph St Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Opens in a new windowThe Allegro Royal Sonesta Hotel Chicago Loop
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much is the cheapest flight to Cook County?
During the last seven days, the cheapest roundtrip flight to Cook County cost CA $275 on our site. Search through our fabulous deals, make your booking and get ready for your next trip. This price was available on Travelocity for flights to Cook County departing within the next year. Prices and availability are subject to change. Additional terms apply.
Which airlines fly to Cook County?
There are 15 airline companies flying to Cook County. If you're thinking about a break in Steger, go for Southwest Airlines. This popular carrier operates 5,737 services a month to Cook County's gateway city.
What is the cheapest month to fly to Cook County?
Based on Travelocity's direct return flight demand from January to December last year, September is the cheapest time to fly to Cook County. Keep an eye out for flights across this month and lock in a great deal today.
How can I check my flight status to Cook County?
Go to our customer portal, Trips. You'll find everything related to your flight to Cook County here, including information about gate changes, flight status and more. Trips is located at the top right of the Travelocity homepage. Simply sign up, log in and find the answers you're after. Or you can access your itinerary while you're on the go and get trip updates through the Travelocity app. All your itineraries are in one convenient place, making it a breeze to share details with any members of your family flying with you.
How do I find the best deals on flights to Cook County?
A simple way to snag a bargain is to be flexible with your dates. Begin by searching for your flight to Cook County, then click on "Flexible dates" above your results. It will reveal prices for nearby days. Like more advice? Book early. To give you an idea of airfares, CA $275 was the best price for a roundtrip flight to Cook County in the last seven days on our site. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Cook County with Travelocity?
If you're chasing cheap flights to Cook County, you'll discover some top deals with Travelocity. From cheap family flights with low-cost airlines to flexible fares, we can help with your journey. Experience a worry-free vacation with our 24/7 social media customer support, Price Match Guarantee and free cancellations with most hotels. Start packing your bags and get ready to fly out to this vibrant destination.
What are the most popular flight routes to Cook County?
To help you in your search for flights to Cook County, check out our list of some of the major routes:

  • Denver, CO (DEN-Denver Intl.) to O'Hare Intl. Airport (ORD) - 4,203 flights a month.
  • Minneapolis, MN (MSP-Minneapolis - St. Paul Intl.) to O'Hare Intl. Airport (ORD) - 4,155 flights a month.
  • New York, NY (LGA-LaGuardia) to O'Hare Intl. Airport (ORD) - 4,138 flights a month.

How much is a flight to Cook County on average?
Get your next big adventure off to a great start by grabbing an awesome deal with Travelocity. In the last seven days, roundtrip flights to Cook County cost between CA $275 and CA $1,869. Look through our site and secure an airfare that's within your budget. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.