Flights To Illinois - Cheap Flights Starting at CA $151

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Jet to one of Illinois's top cities

Chicago showing a high-rise building and a city as well as a family

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.

Fri, Feb 6 - Fri, Feb 27
YYC
Calgary Intl.
ORD
O'Hare Intl.
CA $237 Roundtrip, found 4 days ago
CA $237
Roundtrip
found 4 days ago
Select WestJet flight, departing Fri, Feb 6 from Calgary Intl. to O'Hare Intl., returning Fri, Feb 27, priced at CA $237 found 4 days ago
Thu, Sep 25 - Tue, Oct 7
YYC
Calgary Intl.
ORD
O'Hare Intl.
CA $254 Roundtrip, found 3 days ago
CA $254
Roundtrip
found 3 days ago
Select Air Canada flight, departing Thu, Sep 25 from Calgary Intl. to O'Hare Intl., returning Tue, Oct 7, priced at CA $254 found 3 days ago
Mon, Oct 27 - Thu, Oct 30
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
CA $286 Roundtrip, found 1 day ago
CA $286
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Mon, Oct 27 from Billy Bishop Toronto City to Midway Intl., returning Thu, Oct 30, priced at CA $286 found 1 day ago
Tue, Nov 11 - Thu, Nov 13
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
CA $288 Roundtrip, found 4 days ago
CA $288
Roundtrip
found 4 days ago
Select Porter Airlines flight, departing Tue, Nov 11 from Billy Bishop Toronto City to Midway Intl., returning Thu, Nov 13, priced at CA $288 found 4 days ago
Tue, Oct 28 - Sat, Nov 8
YYC
Calgary Intl.
MDW
Midway Intl.
CA $308 Roundtrip, found 6 days ago
CA $308
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Oct 28 from Calgary Intl. to Midway Intl., returning Sat, Nov 8, priced at CA $308 found 6 days ago
Thu, Nov 6 - Sun, Nov 9
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
CA $329 Roundtrip, just found
CA $329
Roundtrip
just found
Select Air Transat flight, departing Thu, Nov 6 from Billy Bishop Toronto City to Midway Intl., returning Sun, Nov 9, priced at CA $329 just found
Tue, Nov 11 - Thu, Nov 13
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
CA $330 Roundtrip, found 4 days ago
CA $330
Roundtrip
found 4 days ago
Select Air Transat flight, departing Tue, Nov 11 from Billy Bishop Toronto City to Midway Intl., returning Thu, Nov 13, priced at CA $330 found 4 days ago
Thu, Nov 6 - Sun, Nov 9
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
CA $332 Roundtrip, just found
CA $332
Roundtrip
just found
Select Air Transat flight, departing Thu, Nov 6 from Billy Bishop Toronto City to Midway Intl., returning Sun, Nov 9, priced at CA $332 just found
Thu, Nov 6 - Sun, Nov 9
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
CA $332 Roundtrip, just found
CA $332
Roundtrip
just found
Select Porter Airlines flight, departing Thu, Nov 6 from Billy Bishop Toronto City to Midway Intl., returning Sun, Nov 9, priced at CA $332 just found
Mon, Oct 6 - Sun, Oct 12
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
CA $344 Roundtrip, found 1 hour ago
CA $344
Roundtrip
found 1 hour ago
Select Porter Airlines flight, departing Mon, Oct 6 from Billy Bishop Toronto City to Midway Intl., returning Sun, Oct 12, priced at CA $344 found 1 hour ago
Sat, Sep 27 - Sun, Sep 28
YTZ
Billy Bishop Toronto City
ORD
O'Hare Intl.
CA $360 Roundtrip, found 4 days ago
CA $360
Roundtrip
found 4 days ago
Select Air Canada flight, departing Sat, Sep 27 from Billy Bishop Toronto City to O'Hare Intl., returning Sun, Sep 28, priced at CA $360 found 4 days ago
OriginDestinationTravel datesFlights from*
LGAChicagoSeptember 23 to September 30CA $78
DFWChicagoNovember 6 to November 12CA $125
LAXChicagoSeptember 27 to October 4CA $189
ATLChicagoOctober 25 to October 27CA $216
ATLChicagoOctober 11 to October 12CA $276
DFWSt. LouisOctober 16 to October 19CA $340
LGASt. LouisOctober 3 to October 9CA $392
LAXSt. LouisSeptember 26 to September 28CA $688
HKGChicagoNovember 29 to December 15CA $1,790
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
ATLChicagoSeptember 13 to September 15CA $250
LGAChicagoSeptember 12 to September 14CA $267
DFWChicagoSeptember 12 to September 13CA $307
ATLChicagoSeptember 12 to October 5CA $416
LAXChicagoSeptember 13 to September 23CA $482
DFWSt. LouisSeptember 12 to September 14CA $841
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Arlo Chicago
4.0-star property

Arlo Chicago

Oct 20 - Oct 24

4 night stay

Toronto (YTO) to Chicago (ORD)

Air Canada • Non-stop • Coach

Chicago (ORD) to Toronto (YTO)

United • Non-stop • Coach
Price was CA $1,302, price is now CA $820 per person
CA $820
per person
found 1 day ago
Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

Oct 23 - Oct 26

3 night stay

Toronto (YTO) to Chicago (ORD)

Porter Airlines • Roundtrip • Coach
Price was CA $1,903, price is now CA $1,148 per person
CA $1,148
per person
found 24 hours ago
The Allegro Royal Sonesta Hotel Chicago Loop
4.0-star property

The Allegro Royal Sonesta Hotel Chicago Loop

Oct 20 - Oct 24

4 night stay

Toronto (YTO) to Chicago (ORD)

Air Canada • Non-stop • Coach

Chicago (ORD) to Toronto (YTO)

United • Non-stop • Coach
Price was CA $1,352, price is now CA $827 per person
CA $827
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Toronto to Illinois
View all trips

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.
Congress Plaza Hotel
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 4-star 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.
Embassy Suites by Hilton Chicago Downtown River North
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Stay at this 3-star 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 Michigan Avenue and Chicago Riverwalk are located nearby.
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
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.
citizenM 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 $78 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 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 $78 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 $78 and CA $1,790 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.