Flights To Cook County - Cheap Flights Starting at CA $248

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A wooden boardwalk over a river, surrounded by trees and greenery.

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.

Tue, Dec 1 - Tue, Dec 1
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $405 Roundtrip, found 2 days ago
CA $405
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Dec 1 from Pearson Intl. to O'Hare Intl., returning Tue, Dec 1, priced at CA $405 found 2 days ago
Sat, Dec 5 - Mon, Dec 7
YYZ
Pearson Intl.
MDW
Midway Intl.
CA $413 Roundtrip, just found
CA $413
Roundtrip
just found
Select Delta flight, departing Sat, Dec 5 from Pearson Intl. to Midway Intl., returning Mon, Dec 7, priced at CA $413 just found
Wed, Nov 4 - Wed, Nov 11
YUL
Pierre Elliott Trudeau Intl.
MDW
Midway Intl.
CA $422 Roundtrip, found 2 days ago
CA $422
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Nov 4 from Pierre Elliott Trudeau Intl. to Midway Intl., returning Wed, Nov 11, priced at CA $422 found 2 days ago
Fri, Dec 11 - Sun, Dec 13
YUL
Pierre Elliott Trudeau Intl.
ORD
O'Hare Intl.
CA $422 Roundtrip, found 2 hours ago
CA $422
Roundtrip
found 2 hours ago
Select Delta flight, departing Fri, Dec 11 from Pierre Elliott Trudeau Intl. to O'Hare Intl., returning Sun, Dec 13, priced at CA $422 found 2 hours ago
Fri, Nov 20 - Mon, Nov 23
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $464 Roundtrip, found 1 hour ago
CA $464
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Fri, Nov 20 from Pearson Intl. to O'Hare Intl., returning Mon, Nov 23, priced at CA $464 found 1 hour ago
Sat, Dec 5 - Mon, Dec 7
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $464 Roundtrip, just found
CA $464
Roundtrip
just found
Select American Airlines flight, departing Sat, Dec 5 from Pearson Intl. to O'Hare Intl., returning Mon, Dec 7, priced at CA $464 just found
Sun, Nov 22 - Sat, Nov 28
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $464 Roundtrip, found 8 hours ago
CA $464
Roundtrip
found 8 hours ago
Select United flight, departing Sun, Nov 22 from Pearson Intl. to O'Hare Intl., returning Sat, Nov 28, priced at CA $464 found 8 hours ago
Sun, Nov 22 - Sat, Nov 28
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $469 Roundtrip, found 8 hours ago
CA $469
Roundtrip
found 8 hours ago
Select Air Canada flight, departing Sun, Nov 22 from Pearson Intl. to O'Hare Intl., returning Sat, Nov 28, priced at CA $469 found 8 hours ago
OriginDestinationTravel datesFlights from*
LAXChicagoDecember 2 to December 7CA $253
LAXChicagoOctober 29 to November 2CA $274
FCOChicagoNovember 20 to November 26CA $944
XIYChicagoNovember 8 to November 12CA $1,467
PVGChicagoNovember 12 to November 22CA $1,588
PEKChicagoDecember 20 to February 20CA $1,698
TFUChicagoDecember 19 to January 3CA $1,735
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
LAXChicagoOctober 11 to October 16CA $540
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination
3.5-star property

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Dec 24 - Dec 31

7 night stay

Toronto (YTO) to Chicago (ORD)

Porter Airlines • Roundtrip • Coach
Save 100% on your flight
Price was CA $2,241, price is now CA $1,441 per person
CA $1,441
per person
found 17 hours ago
Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

Nov 19 - Nov 24

5 night stay

Toronto (YTO) to Chicago (ORD)

Delta • Non-stop roundtrip • Coach
Save 100% on your flight
Price was CA $3,247, price is now CA $2,124 per person
CA $2,124
per person
found 1 day ago
Four Seasons Hotel Chicago
5.0-star property

Four Seasons Hotel Chicago

Nov 18 - Nov 21

3 night stay

Toronto (YTO) to Chicago (ORD)

Delta • Non-stop roundtrip • Coach
Save 100% on your flight
Price was CA $3,062, price is now CA $2,064 per person
CA $2,064
per person
found 1 day ago
Don't see what you're looking for?
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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.
Opens in a new windowCongress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
8.8/10 Excellent! (5,499 reviews)
"My hotel room door was left open and unlatched the entire day. I came back to see my door unlocked, and open for anyone to go in. This was a huge safety issue, thankfully it doesn’t seem like anything was stolen. However I am hesitant to stay here again. Also, the air conditioner was very loud, and ..."

Reviewed on Oct 8, 2026

Opens in a new windowRiver 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.
8/10 Very good! (2,436 reviews)
"The hotel is in a nice neighborhood and the room was clean. The bed and toilet were both very low to the ground, and there were very few electrical outlets, but otherwise it was a pleasant stay."

Reviewed on Oct 8, 2026

Opens in a new windowThe Chicago Hotel Collection Ambassador Gold Coast
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The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. 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 - Magnificent Mile
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 $253 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, December 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 $253 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 $253 and CA $1,735. 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.