Flights To Illinois - Cheap Flights Starting at CA $224

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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.

Thu, Dec 3 - Tue, Dec 8
YYZ
Pearson Intl.
MDW
Midway Intl.
CA $402 Roundtrip, found 2 days ago
CA $402
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Dec 3 from Pearson Intl. to Midway Intl., returning Tue, Dec 8, priced at CA $402 found 2 days ago
Sun, Nov 15 - Thu, Nov 19
YYZ
Pearson Intl.
MDW
Midway Intl.
CA $413 Roundtrip, found 3 days ago
CA $413
Roundtrip
found 3 days ago
Select Delta flight, departing Sun, Nov 15 from Pearson Intl. to Midway Intl., returning Thu, Nov 19, priced at CA $413 found 3 days ago
Tue, Jan 5 - Sat, Jan 9
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $415 Roundtrip, found 2 days ago
CA $415
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Jan 5 from Pearson Intl. to O'Hare Intl., returning Sat, Jan 9, priced at CA $415 found 2 days ago
Wed, Nov 18 - Mon, Nov 23
YYZ
Pearson Intl.
MDW
Midway Intl.
CA $423 Roundtrip, found 6 days ago
CA $423
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Nov 18 from Pearson Intl. to Midway Intl., returning Mon, Nov 23, priced at CA $423 found 6 days ago
Thu, Jan 21 - Sun, Jan 24
YYC
Calgary Intl.
MDW
Midway Intl.
CA $425 Roundtrip, found 17 hours ago
CA $425
Roundtrip
found 17 hours ago
Select Delta flight, departing Thu, Jan 21 from Calgary Intl. to Midway Intl., returning Sun, Jan 24, priced at CA $425 found 17 hours ago
Sat, Nov 28 - Mon, Nov 30
YYZ
Pearson Intl.
MDW
Midway Intl.
CA $434 Roundtrip, found 3 days ago
CA $434
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Nov 28 from Pearson Intl. to Midway Intl., returning Mon, Nov 30, priced at CA $434 found 3 days ago
Fri, Nov 20 - Sat, Nov 28
YTZ
Billy Bishop Toronto City
ORD
O'Hare Intl.
CA $465 Roundtrip, found 1 day ago
CA $465
Roundtrip
found 1 day ago
Select Air Canada flight, departing Fri, Nov 20 from Billy Bishop Toronto City to O'Hare Intl., returning Sat, Nov 28, priced at CA $465 found 1 day ago
Sat, Dec 26 - Sat, Jan 9
YTZ
Billy Bishop Toronto City
ORD
O'Hare Intl.
CA $467 Roundtrip, found 2 days ago
CA $467
Roundtrip
found 2 days ago
Select Air Transat flight, departing Sat, Dec 26 from Billy Bishop Toronto City to O'Hare Intl., returning Sat, Jan 9, priced at CA $467 found 2 days ago
Fri, Feb 26 - Tue, Mar 9
YYC
Calgary Intl.
ORD
O'Hare Intl.
CA $472 Roundtrip, found 2 days ago
CA $472
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Feb 26 from Calgary Intl. to O'Hare Intl., returning Tue, Mar 9, priced at CA $472 found 2 days ago
Tue, Nov 24 - Sun, Nov 29
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $473 Roundtrip, found 12 hours ago
CA $473
Roundtrip
found 12 hours ago
Select United flight, departing Tue, Nov 24 from Pearson Intl. to O'Hare Intl., returning Sun, Nov 29, priced at CA $473 found 12 hours ago
Tue, Apr 20 - Tue, Apr 27
YYC
Calgary Intl.
ORD
O'Hare Intl.
CA $514 Roundtrip, found 2 days ago
CA $514
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Apr 20 from Calgary Intl. to O'Hare Intl., returning Tue, Apr 27, priced at CA $514 found 2 days ago
OriginDestinationTravel datesFlights from*
ATLSt. LouisDecember 2 to December 7CA $72
ATLChicagoNovember 18 to November 26CA $82
DFWChicagoDecember 2 to December 9CA $113
ATLChicagoDecember 24 to December 29CA $152
DFWChicagoDecember 2 to December 9CA $154
DFWSt. LouisNovember 13 to November 15CA $194
LAXChicagoDecember 8 to December 9CA $195
LAXSt. LouisDecember 4 to December 9CA $200
LGAChicagoFebruary 3 to February 10CA $280
EWRChicagoJanuary 21 to January 23CA $314
LAXChicagoNovember 24 to December 1CA $484
LGASt. LouisDecember 31 to January 3CA $610
HKGChicagoNovember 16 to December 1CA $1,265
PVGChicagoNovember 19 to December 2CA $1,599
PEKChicagoDecember 20 to February 20CA $1,667
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
DFWChicagoNovember 7 to November 7CA $407
DFWChicagoNovember 7 to November 7CA $407
ATLChicagoNovember 6 to November 8CA $476
ATLChicagoNovember 8 to November 11CA $509
LAXChicagoNovember 8 to November 11CA $668
DFWSpringfieldNovember 7 to November 10CA $720
LAXSt. LouisNovember 6 to November 8CA $1,047
HKGChicagoNovember 8 to November 12CA $1,319
XIYChicagoNovember 8 to November 12CA $1,777
ATLSt. LouisNovember 6 to November 8CA $2,115
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
4.5-star property

Pendry Chicago

Jan 2 - Jan 7

5 night stay

Toronto (YYZ) to Chicago (ORD)

American Airlines • Roundtrip • Coach
Price was CA $1,637, price is now CA $1,188 per person
CA $1,188
per person
found 11 hours ago
The Wildwood Hotel
3.5-star property

The Wildwood Hotel

Nov 12 - Nov 19

7 night stay

Toronto (YYZ) to St. Louis (STL)

American Airlines • Non-stop roundtrip • Coach
Price was CA $2,238, price is now CA $1,430 per person
CA $1,430
per person
found 11 hours ago
The Peninsula Chicago
5.0-star property

The Peninsula Chicago

Jan 2 - Jan 7

5 night stay

Toronto (YYZ) to Chicago (ORD)

American Airlines • Roundtrip • Coach
Price was CA $3,080, price is now CA $2,027 per person
CA $2,027
per person
found 11 hours ago
Don't see what you're looking for?
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Travelers ❤️ These Illinois 🏨

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
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! (2,619 reviews)
"This hotel is awful. Check in person was unfriendly and uncommunicative. Room Is, quite frankly, scary. Down a dilapidated hallway with padlocks on the fuse boxes. The room itself is dingy, dreary and needs updates. Has three pictures on the walls the sizes of postcards. Carpet is so filthy I didn’t ..."

Reviewed on Oct 30, 2026

Opens in a new windowThe Chicago Hotel Collection Ambassador Gold Coast
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.
Opens in a new windowRiver Hotel
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The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Navy Pier are located nearby.
Opens in a new windowThe Wade
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 $72 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 20 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 December. 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 $72 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 $72 and CA $2,115 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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