Flights To Illinois - Cheap Flights Starting at CA $181

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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.

Sat, May 23 - Mon, May 25
YYC
Calgary Intl.
ORD
O'Hare Intl.
CA $296 Roundtrip, just found
CA $296
Roundtrip
just found
Select WestJet flight, departing Sat, May 23 from Calgary Intl. to O'Hare Intl., returning Mon, May 25, priced at CA $296 just found
Thu, Jun 4 - Fri, Jun 5
YTZ
Billy Bishop Toronto City
ORD
O'Hare Intl.
CA $300 Roundtrip, found 5 days ago
CA $300
Roundtrip
found 5 days ago
Select Air Canada flight, departing Thu, Jun 4 from Billy Bishop Toronto City to O'Hare Intl., returning Fri, Jun 5, priced at CA $300 found 5 days ago
Thu, Jun 4 - Fri, Jun 5
YTZ
Billy Bishop Toronto City
ORD
O'Hare Intl.
CA $308 Roundtrip, found 1 day ago
CA $308
Roundtrip
found 1 day ago
Select Air Canada flight, departing Thu, Jun 4 from Billy Bishop Toronto City to O'Hare Intl., returning Fri, Jun 5, priced at CA $308 found 1 day ago
Sat, Jun 6 - Thu, Jun 11
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
CA $308 Roundtrip, just found
CA $308
Roundtrip
just found
Select Porter Airlines flight, departing Sat, Jun 6 from Billy Bishop Toronto City to Midway Intl., returning Thu, Jun 11, priced at CA $308 just found
Tue, Jun 9 - Sat, Jun 13
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $312 Roundtrip, found 6 days ago
CA $312
Roundtrip
found 6 days ago
Select Air Canada flight, departing Tue, Jun 9 from Pearson Intl. to O'Hare Intl., returning Sat, Jun 13, priced at CA $312 found 6 days ago
Sat, Jun 13 - Sat, Jun 13
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $312 Roundtrip, found 6 days ago
CA $312
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Jun 13 from Pearson Intl. to O'Hare Intl., returning Sat, Jun 13, priced at CA $312 found 6 days ago
Wed, May 13 - Sat, May 16
YYC
Calgary Intl.
MDW
Midway Intl.
CA $315 Roundtrip, found 3 days ago
CA $315
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, May 13 from Calgary Intl. to Midway Intl., returning Sat, May 16, priced at CA $315 found 3 days ago
Wed, May 13 - Sat, May 16
YYZ
Pearson Intl.
MDW
Midway Intl.
CA $320 Roundtrip, found 6 days ago
CA $320
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, May 13 from Pearson Intl. to Midway Intl., returning Sat, May 16, priced at CA $320 found 6 days ago
Thu, May 28 - Sat, Jun 6
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $320 Roundtrip, found 1 day ago
CA $320
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, May 28 from Pearson Intl. to O'Hare Intl., returning Sat, Jun 6, priced at CA $320 found 1 day ago
Sat, Jun 6 - Thu, Jun 11
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
CA $350 Roundtrip, just found
CA $350
Roundtrip
just found
Select Air Transat flight, departing Sat, Jun 6 from Billy Bishop Toronto City to Midway Intl., returning Thu, Jun 11, priced at CA $350 just found
OriginDestinationTravel datesFlights from*
LGAChicagoJune 8 to June 16CA $160
DFWChicagoMay 14 to May 19CA $182
ATLChicagoJune 23 to June 25CA $234
LAXChicagoMay 23 to May 29CA $325
DFWChicagoJune 20 to June 23CA $371
LAXChicagoMay 22 to May 29CA $579
LAXSt. LouisMay 16 to May 18CA $649
EWRChicagoMay 15 to May 19CA $738
HKGChicagoJune 18 to July 2CA $1,559
PVGChicagoJuly 12 to August 24CA $2,052
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
EWRChicagoMay 2 to May 3CA $406
ATLChicagoMay 2 to May 3CA $462
LAXChicagoMay 3 to May 7CA $689
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile
4.0-star property

Hotel Saint Clair- Magnificent Mile

Jul 2 - Jul 5

3 night stay

Toronto (YYZ) to Chicago (ORD)

Air Canada • Roundtrip • Coach
Price was CA $1,326, price is now CA $840 per person
CA $840
per person
found 1 day ago
The Wade
4.5-star property

The Wade

Jun 3 - Jun 8

5 night stay

Vancouver (YVR) to Chicago (ORD)

WestJet • Non-stop roundtrip • Coach
Price was CA $2,400, price is now CA $1,405 per person
CA $1,405
per person
found 1 day ago
Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0-star property

Sable at Navy Pier Chicago, Curio Collection by Hilton

May 20 - May 27

7 night stay

Detroit (DTW) to Chicago (ORD)

American Airlines • Coach

Chicago (ORD) to Detroit (DTW)

Delta • Coach
Price was CA $2,159, price is now CA $1,415 per person
CA $1,415
per person
found 17 hours ago
Don't see what you're looking for?
See all available trips from Toronto to Illinois
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Travelers ❤️ These Illinois 🏨

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! (2,648 reviews)
Clean room

Reviewed on Apr 30, 2026

Opens in a new windowHotel Felix River North/Magnificent Mile
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! (5,137 reviews)
Beautiful, clean room with an incredible downtown Chicago view. Totally worth it

Reviewed on Apr 29, 2026

Opens in a new windowRiver Hotel
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
8.8/10 Excellent! (3,462 reviews)
Great check in and check out experience

Reviewed on Apr 29, 2026

Opens in a new windowClub Quarters Hotel, Central Loop, Chicago
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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! (4,001 reviews)
The best breakfast buffet I’ve ever had!

Reviewed on Apr 29, 2026

Opens in a new windowHotel Riu Plaza Chicago
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 $160 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 19 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 May. 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 $160 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 $160 and CA $2,052 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.

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