Flights To Illinois - Cheap Flights Starting at CA $155

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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, Mar 19 - Wed, Mar 25
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
CA $249 Roundtrip, found 1 day ago
CA $249
Roundtrip
found 1 day ago
Select Air Transat flight, departing Thu, Mar 19 from Billy Bishop Toronto City to Midway Intl., returning Wed, Mar 25, priced at CA $249 found 1 day ago
Fri, Jan 16 - Sun, Jan 25
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $264 Roundtrip, found 10 hours ago
CA $264
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Fri, Jan 16 from Pearson Intl. to O'Hare Intl., returning Sun, Jan 25, priced at CA $264 found 10 hours ago
Sat, Jan 17 - Wed, Jan 21
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $266 Roundtrip, found 2 days ago
CA $266
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Jan 17 from Pearson Intl. to O'Hare Intl., returning Wed, Jan 21, priced at CA $266 found 2 days ago
Fri, Jan 16 - Sun, Jan 25
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $272 Roundtrip, found 10 hours ago
CA $272
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Fri, Jan 16 from Pearson Intl. to O'Hare Intl., returning Sun, Jan 25, priced at CA $272 found 10 hours ago
Sat, Nov 22 - Sat, Nov 22
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $287 Roundtrip, found 2 days ago
CA $287
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Nov 22 from Pearson Intl. to O'Hare Intl., returning Sat, Nov 22, priced at CA $287 found 2 days ago
Tue, Nov 18 - Mon, Nov 24
YYZ
Pearson Intl.
MDW
Midway Intl.
CA $295 Roundtrip, found 2 days ago
CA $295
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Nov 18 from Pearson Intl. to Midway Intl., returning Mon, Nov 24, priced at CA $295 found 2 days ago
Tue, Nov 25 - Mon, Jan 5
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $325 Roundtrip, found 1 day ago
CA $325
Roundtrip
found 1 day ago
Select Air Canada flight, departing Tue, Nov 25 from Pearson Intl. to O'Hare Intl., returning Mon, Jan 5, priced at CA $325 found 1 day ago
Sun, Dec 7 - Fri, Jan 2
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $325 Roundtrip, found 1 day ago
CA $325
Roundtrip
found 1 day ago
Select United flight, departing Sun, Dec 7 from Pearson Intl. to O'Hare Intl., returning Fri, Jan 2, priced at CA $325 found 1 day ago
Fri, Nov 21 - Fri, Nov 21
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $403 Roundtrip, found 10 hours ago
CA $403
Roundtrip
found 10 hours ago
Select WestJet flight, departing Fri, Nov 21 from Pearson Intl. to O'Hare Intl., returning Fri, Nov 21, priced at CA $403 found 10 hours ago
OriginDestinationTravel datesFlights from*
LGAChicagoNovember 8 to November 15CA $77
DFWChicagoNovember 11 to November 17CA $85
ATLChicagoNovember 12 to November 15CA $121
LAXChicagoNovember 8 to November 14CA $154
LGASt. LouisDecember 4 to December 11CA $264
DFWSt. LouisNovember 13 to November 16CA $461
LAXSt. LouisNovember 6 to November 9CA $698
HKGChicagoJanuary 17 to April 15CA $1,227
EWRChicagoNovember 27 to November 30CA $1,303
PVGChicagoNovember 24 to December 8CA $1,329
PEKChicagoNovember 28 to December 5CA $1,794
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
LGAChicagoOctober 25 to October 27CA $210
ATLChicagoOctober 26 to November 1CA $450
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Art Villa
5.0-star property

Art Villa

Nov 24 - Nov 28

4 night stay

Calgary (YYC) to Chicago (ORD)

United • Roundtrip • Coach
Price was CA $2,042, price is now CA $1,107 per person
CA $1,107
per person
found 1 day ago
Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

Nov 24 - Nov 28

4 night stay

Calgary (YYC) to Chicago (ORD)

United • Roundtrip • Coach
Price was CA $2,229, price is now CA $1,332 per person
CA $1,332
per person
found 1 day ago
The Wildwood Hotel
3.5-star property

The Wildwood Hotel

Oct 30 - Nov 5

6 night stay

Toronto (YYZ) to St. Louis (STL)

Delta • Non-stop roundtrip • Coach
Price was CA $1,973, price is now CA $1,202 per person
CA $1,202
per person
found 1 day ago
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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 free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
7.8/10 Good! (9,469 reviews)
Nice location.

Reviewed on Oct 18, 2025

Opens in a new windowCongress Plaza Hotel
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! (3,128 reviews)
Very nice clean and spacious room. All of the staff were very pleasant and helpful. I had no issues at all. Easy check-in/out. The Chapel Restaurant was delicious! Definitely will stay again!

Reviewed on Oct 17, 2025

Opens in a new windowHilton Chicago/Magnificent Mile Suites
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
7.8/10 Good! (2,494 reviews)
Bathroom recently redone and was fabulous, but room was old and tattered. Bed was nice and comfy. Nice crisp sheets.

Reviewed on Oct 18, 2025

Opens in a new windowFreehand Chicago
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citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the bar in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
9.2/10 Wonderful! (3,963 reviews)
Great spot next to the pendry

Reviewed on Oct 18, 2025

Opens in a new windowcitizenM Chicago Downtown
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 $77 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 17 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 March. 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 $77 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 $77 and CA $1,794 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.