Flights To Illinois - Cheap Flights Starting at CA $192

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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, Sep 19 - Wed, Sep 23
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
CA $322 Roundtrip, just found
CA $322
Roundtrip
just found
Select Porter Airlines flight, departing Sat, Sep 19 from Billy Bishop Toronto City to Midway Intl., returning Wed, Sep 23, priced at CA $322 just found
Fri, Sep 25 - Sat, Oct 3
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
CA $331 Roundtrip, found 4 days ago
CA $331
Roundtrip
found 4 days ago
Select Porter Airlines flight, departing Fri, Sep 25 from Billy Bishop Toronto City to Midway Intl., returning Sat, Oct 3, priced at CA $331 found 4 days ago
Fri, Sep 4 - Sun, Sep 6
YTZ
Billy Bishop Toronto City
ORD
O'Hare Intl.
CA $332 Roundtrip, found 2 days ago
CA $332
Roundtrip
found 2 days ago
Select Air Canada flight, departing Fri, Sep 4 from Billy Bishop Toronto City to O'Hare Intl., returning Sun, Sep 6, priced at CA $332 found 2 days ago
Fri, Nov 6 - Sun, Nov 8
YTZ
Billy Bishop Toronto City
ORD
O'Hare Intl.
CA $341 Roundtrip, found 4 days ago
CA $341
Roundtrip
found 4 days ago
Select Porter Airlines flight, departing Fri, Nov 6 from Billy Bishop Toronto City to O'Hare Intl., returning Sun, Nov 8, priced at CA $341 found 4 days ago
Sat, Sep 19 - Tue, Sep 22
YYZ
Pearson Intl.
MDW
Midway Intl.
CA $342 Roundtrip, found 1 day ago
CA $342
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Sep 19 from Pearson Intl. to Midway Intl., returning Tue, Sep 22, priced at CA $342 found 1 day ago
Sun, Sep 20 - Mon, Sep 21
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $345 Roundtrip, found 1 day ago
CA $345
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sun, Sep 20 from Pearson Intl. to O'Hare Intl., returning Mon, Sep 21, priced at CA $345 found 1 day ago
Sat, Sep 19 - Wed, Sep 23
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
CA $353 Roundtrip, just found
CA $353
Roundtrip
just found
Select Air Transat flight, departing Sat, Sep 19 from Billy Bishop Toronto City to Midway Intl., returning Wed, Sep 23, priced at CA $353 just found
Wed, Dec 23 - Sat, Dec 26
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $456 Roundtrip, found 1 day ago
CA $456
Roundtrip
found 1 day ago
Select United flight, departing Wed, Dec 23 from Pearson Intl. to O'Hare Intl., returning Sat, Dec 26, priced at CA $456 found 1 day ago
OriginDestinationTravel datesFlights from*
EWRChicagoSeptember 27 to September 30CA $305
DFWSt. LouisAugust 15 to August 18CA $323
ATLChicagoSeptember 24 to September 28CA $407
LAXChicagoAugust 29 to September 2CA $450
JFKSt. LouisAugust 11 to August 18CA $484
DFWChicagoOctober 29 to November 1CA $556
LAXSt. LouisSeptember 24 to September 28CA $615
ATLChicagoAugust 7 to August 10CA $636
ATLSt. LouisSeptember 11 to September 13CA $1,193
HKGChicagoSeptember 10 to September 17CA $1,275
PVGChicagoAugust 18 to October 31CA $2,190
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
JFKChicagoJuly 31 to August 4CA $483
LAXChicagoJuly 31 to August 4CA $730
ATLChicagoAugust 2 to August 6CA $876
LAXSt. LouisJuly 31 to August 4CA $881
DFWChicagoAugust 1 to August 5CA $1,196
PEKChicagoAugust 1 to August 5CA $2,447
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

Aug 18 - Aug 22

4 night stay

Montreal (YUL) to Chicago (ORD)

Air Canada • Roundtrip • Coach
Price was CA $2,087, price is now CA $1,330 per person
CA $1,330
per person
found 1 day ago
Four Seasons Hotel Chicago
5.0-star property

Four Seasons Hotel Chicago

Oct 9 - Oct 16

7 night stay

Montreal (YUL) to Chicago (ORD)

American Airlines • Non-stop • Coach

Chicago (ORD) to Montreal (YUL)

Air Canada • Non-stop • Coach
Price was CA $6,383, price is now CA $3,985 per person
CA $3,985
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

Oct 9 - Oct 16

7 night stay

Montreal (YUL) to Chicago (ORD)

American Airlines • Non-stop • Coach

Chicago (ORD) to Montreal (YUL)

Air Canada • Non-stop • Coach
Price was CA $4,438, price is now CA $2,835 per person
CA $2,835
per person
found 1 day ago
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Travelers ❤️ These Illinois 🏨

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.
Opens in a new windowThe Chicago Hotel Collection Ambassador Gold Coast
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rosemont Theatre and Fashion Outlets of Chicago are located nearby.
8.8/10 Excellent! (2,892 reviews)
"We stayed here for 1 night and checked out the following day. The hotel has onsite parking available, door man to assist with luggage (he was super friendly and welcoming). We were able to check-in early, had our luggage brought up to our room. We used the onsite gym, which was clean, had a variety ..."

Reviewed on Jul 24, 2026

Opens in a new windowHyatt Regency O'Hare Chicago
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
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Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
9.2/10 Wonderful! (1,946 reviews)
"Perfect location and overall an excellent experience!"

Reviewed on Jul 24, 2026

Opens in a new windowOmni Chicago 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 $305 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 September. 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 $305 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 $305 and CA $2,447 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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