Flights To Illinois - Cheap Flights Starting at CA $186

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Chicago

Flights
Chicago

How Much Does it Cost To Fly To Illinois?

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

Wed, Feb 4 - Tue, Feb 17
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $257 Roundtrip, found 6 days ago
CA $257
Roundtrip
found 6 days ago
Select United flight, departing Wed, Feb 4 from Pearson Intl. to O'Hare Intl., returning Tue, Feb 17, priced at CA $257 found 6 days ago
Sat, Feb 7 - Tue, Feb 17
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $257 Roundtrip, found 6 days ago
CA $257
Roundtrip
found 6 days ago
Select Air Canada flight, departing Sat, Feb 7 from Pearson Intl. to O'Hare Intl., returning Tue, Feb 17, priced at CA $257 found 6 days ago
Mon, Feb 23 - Wed, Feb 25
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $263 Roundtrip, found 10 hours ago
CA $263
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Mon, Feb 23 from Pearson Intl. to O'Hare Intl., returning Wed, Feb 25, priced at CA $263 found 10 hours ago
Fri, Feb 20 - Tue, Feb 24
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $264 Roundtrip, found 1 day ago
CA $264
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Feb 20 from Pearson Intl. to O'Hare Intl., returning Tue, Feb 24, priced at CA $264 found 1 day ago
Mon, Feb 23 - Wed, Feb 25
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $270 Roundtrip, found 10 hours ago
CA $270
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Mon, Feb 23 from Pearson Intl. to O'Hare Intl., returning Wed, Feb 25, priced at CA $270 found 10 hours ago
Fri, Feb 20 - Tue, Feb 24
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $271 Roundtrip, found 1 day ago
CA $271
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Feb 20 from Pearson Intl. to O'Hare Intl., returning Tue, Feb 24, priced at CA $271 found 1 day ago
Mon, Feb 23 - Wed, Feb 25
YYZ
Pearson Intl.
MDW
Midway Intl.
CA $293 Roundtrip, found 10 hours ago
CA $293
Roundtrip
found 10 hours ago
Select Delta flight, departing Mon, Feb 23 from Pearson Intl. to Midway Intl., returning Wed, Feb 25, priced at CA $293 found 10 hours ago
Mon, Feb 23 - Wed, Feb 25
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $293 Roundtrip, found 10 hours ago
CA $293
Roundtrip
found 10 hours ago
Select Delta flight, departing Mon, Feb 23 from Pearson Intl. to O'Hare Intl., returning Wed, Feb 25, priced at CA $293 found 10 hours ago
OriginDestinationTravel datesFlights from*
EWRChicagoJanuary 8 to January 11CA $100
ATLChicagoJanuary 24 to January 25CA $155
DFWChicagoJanuary 8 to January 15CA $197
LAXChicagoDecember 25 to January 2CA $308
LAXSt. LouisJanuary 16 to January 18CA $597
HKGChicagoJanuary 22 to January 28CA $1,193
PVGChicagoDecember 27 to January 11CA $1,380
CANChicagoFebruary 1 to February 16CA $1,590
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
EWRChicagoDecember 14 to December 18CA $251
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

Mar 6 - Mar 8

2 night stay

Toronto (YYZ) to Chicago (ORD)

WestJet • Non-stop roundtrip • Coach
Price was CA $1,177, price is now CA $861 per person
CA $861
per person
found 6 hours ago
Chicago luxury home suites
2.0-star property

Chicago luxury home suites

Feb 25 - Mar 1

4 night stay

St. John's (YYT) to Chicago (ORD)

Air Canada • Non-stop roundtrip • Coach
Price was CA $3,751, price is now CA $2,782 per person
CA $2,782
per person
found 1 day ago
theWit Chicago, a Hilton Hotel
4.5-star property

theWit Chicago, a Hilton Hotel

Feb 25 - Mar 1

4 night stay

St. John's (YYT) to Chicago (ORD)

Air Canada • Non-stop roundtrip • Coach
Price was CA $1,227, price is now CA $920 per person
CA $920
per person
found 1 day ago
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Travelers ❤️ These Illinois 🏨

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
8.4/10 Very Good! (5,354 reviews)
Amendities and location is great, but the facility needs fresh coat of paint

Reviewed on Dec 5, 2025

Opens in a new windowEmbassy Suites by Hilton Chicago Downtown River North
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
8.8/10 Excellent! (3,453 reviews)
Pleasant staff, clean and spacious rooms. Excellent centralized location to many restaurants and things to do in Chicago that are both accessible by train and on foot. Definitely one of my new go to stays in the city.

Reviewed on Dec 9, 2025

Opens in a new windowHilton Chicago/Magnificent Mile Suites
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
10 S Wabash Ave 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 Millennium Park and Chicago Riverwalk are located nearby.
9.2/10 Wonderful! (2,099 reviews)
Staff was AMAZING... rooms very clean

Reviewed on Dec 5, 2025

Opens in a new windowSilversmith Hotel Chicago Downtown
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Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
8.4/10 Very Good! (2,115 reviews)
great stay

Reviewed on Dec 5, 2025

Opens in a new windowPalmer House a Hilton Hotel
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 Illinois?
A roundtrip flight to Illinois cost as little as CA $100 within the last seven days. When you're ready to make a booking, we'll help you find a top deal. This price was available on Travelocity for flights to Illinois departing within the next year. Prices and availability are subject to change. Additional terms apply.
Which airlines fly to Illinois?
You'll have a choice of 15 airlines when you want to organize your flight to Illinois. Let Southwest Airlines take you there. This top carrier offers 5,737 services a month to Chicago, Illinois's premier city.
What is the cheapest month to fly to Illinois?
Splash out more money on epic experiences and less on airfares by visiting Illinois in February. This is the most affordable time to set off to this destination based on Travelocity's direct return flight demand between January and December last year. Take a peek at our list of flights and get away from it all without draining your bank account.
How can I check my flight status to Illinois?
Visit the Travelocity customer portal, Trips. You'll find almost everything related to your flight to Illinois here, including valuable information about any gate changes, flight delays and more. Keep an eye out for Trips at the top right of the Travelocity homepage. Simply sign up, log in and discover what you need. Or you can access your itinerary on the go and get real-time travel updates with the Travelocity app. You'll find all your itineraries in one convenient place, so you can quickly share details with any members of your family flying with you.
How do I find the best deals on flights to Illinois?
Being flexible with your travel dates is one of the best ways to score a fantastic deal. Travelocity makes it a snap to find your perfect fare through the "Flexible dates" feature. First, search for your flight to Illinois, then compare prices for surrounding days by clicking the Flexible dates box above. Booking ahead of time and traveling outside of peak periods will also help you save. In the last seven days, the cheapest price for a return flight to Illinois was CA $100 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 Illinois with Travelocity?
Look for cheap flights to Illinois with Travelocity and start arranging your next adventure. With 24/7 customer assistance during every step of your trip and a Price Match Guarantee, we take the difficulty out of reserving cheap family flights, places to stay and more. Bag a top deal today and prepare for an amazing adventure.
What are the most popular flight routes to Illinois?
To help you in your search for flights to Illinois, browse our list of some of the preferred 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 Illinois on average?
Airfares for roundtrip flights to Illinois cost between CA $100 and CA $1,590 in the last seven days. The moment you see a fabulous deal, snap it up and get ready to set off on your next wonderful adventure with Travelocity. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

Destinations in Illinois

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.