Flights To Cook County - Cheap Flights Starting at CA $185

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649-36 Hammel Creek Dusted in Snow

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.

Sat, Jun 13 - Sun, Jun 14
YYZ
Pearson Intl.
MDW
Midway Intl.
CA $329 Roundtrip, found 1 day ago
CA $329
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Jun 13 from Pearson Intl. to Midway Intl., returning Sun, Jun 14, priced at CA $329 found 1 day ago
Tue, Sep 8 - Tue, Sep 8
YTZ
Billy Bishop Toronto City
ORD
O'Hare Intl.
CA $338 Roundtrip, found 2 days ago
CA $338
Roundtrip
found 2 days ago
Select Porter Airlines flight, departing Tue, Sep 8 from Billy Bishop Toronto City to O'Hare Intl., returning Tue, Sep 8, priced at CA $338 found 2 days ago
Fri, Sep 4 - Tue, Sep 8
YTZ
Billy Bishop Toronto City
ORD
O'Hare Intl.
CA $340 Roundtrip, found 3 hours ago
CA $340
Roundtrip
found 3 hours ago
Select Porter Airlines flight, departing Fri, Sep 4 from Billy Bishop Toronto City to O'Hare Intl., returning Tue, Sep 8, priced at CA $340 found 3 hours ago
Mon, Jun 22 - Tue, Jun 23
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
CA $343 Roundtrip, just found
CA $343
Roundtrip
just found
Select Porter Airlines flight, departing Mon, Jun 22 from Billy Bishop Toronto City to Midway Intl., returning Tue, Jun 23, priced at CA $343 just found
Fri, Jun 12 - Sat, Jun 20
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $355 Roundtrip, found 1 hour ago
CA $355
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Fri, Jun 12 from Pearson Intl. to O'Hare Intl., returning Sat, Jun 20, priced at CA $355 found 1 hour ago
Wed, Jun 24 - Fri, Jul 3
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $375 Roundtrip, found 1 day ago
CA $375
Roundtrip
found 1 day ago
Select Air Canada flight, departing Wed, Jun 24 from Pearson Intl. to O'Hare Intl., returning Fri, Jul 3, priced at CA $375 found 1 day ago
Fri, Aug 14 - Tue, Aug 25
YYC
Calgary Intl.
ORD
O'Hare Intl.
CA $380 Roundtrip, found 5 days ago
CA $380
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Aug 14 from Calgary Intl. to O'Hare Intl., returning Tue, Aug 25, priced at CA $380 found 5 days ago
Tue, Sep 1 - Tue, Sep 8
YTZ
Billy Bishop Toronto City
ORD
O'Hare Intl.
CA $381 Roundtrip, found 3 days ago
CA $381
Roundtrip
found 3 days ago
Select Air Transat flight, departing Tue, Sep 1 from Billy Bishop Toronto City to O'Hare Intl., returning Tue, Sep 8, priced at CA $381 found 3 days ago
OriginDestinationTravel datesFlights from*
LAXChicagoAugust 17 to August 26CA $457
LAXChicagoAugust 14 to August 16CA $654
FCOChicagoAugust 3 to November 4CA $1,238
HKGChicagoJune 14 to September 4CA $1,507
PEKChicagoJune 18 to July 1CA $1,635
PVGChicagoJuly 1 to July 15CA $1,897
XIYChicagoJuly 25 to August 15CA $2,555
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
LAXChicagoMay 29 to June 1CA $725
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
4.5-star property

Swissotel - Chicago

Aug 20 - Aug 25

5 night stay

Toronto (YTO) to Chicago (ORD)

Porter Airlines • Roundtrip • Coach
Price was CA $1,916, price is now CA $1,274 per person
CA $1,274
per person
found 1 day ago
Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

Aug 2 - Aug 7

5 night stay

Toronto (YTO) to Chicago (ORD)

Air Canada • Non-stop roundtrip • Coach
Price was CA $2,231, price is now CA $1,411 per person
CA $1,411
per person
found 18 hours ago
Level Chicago Fulton Market
4.0-star property

Level Chicago Fulton Market

Aug 20 - Aug 25

5 night stay

Toronto (YTO) to Chicago (ORD)

Porter Airlines • Roundtrip • Coach
Price was CA $2,401, price is now CA $1,567 per person
CA $1,567
per person
found 1 day ago
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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.
8/10 Very Good! (10,134 reviews)
"Great location. Walkable to all the downtown attractions. Historical hotel with updated rooms. Highly recommend."

Reviewed on May 23, 2026

Opens in a new windowCongress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
9.4/10 Exceptional! (4,221 reviews)
"The room is clean. The location is great with many nice shops nearby, including the Starbucks Reserve Roastery. It’s within walking distance to Navy Pier, Willis Tower, boat ride and many other architectural marvels. The breakfast is good with some variations each day. The staff are generally friendly ..."

Reviewed on May 24, 2026

Opens in a new windowHotel Riu Plaza Chicago
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, 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.
8.2/10 Very Good! (2,717 reviews)
"Too small room no refrigerator no microwave over prized vallet parking when they park in open public parking space which cost less."

Reviewed on May 23, 2026

Opens in a new windowHotel Felix River North/Magnificent Mile
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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.
7.8/10 Good! (1,464 reviews)
"There're bed bugs. Be careful"

Reviewed on May 24, 2026

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 $329 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, June 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 $329 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 $329 and CA $2,555. 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.