Flights To Illinois - Cheap Flights Starting at CA $190

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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, Sep 24 - Mon, Sep 28
YTZ
Billy Bishop Toronto City
ORD
O'Hare Intl.
CA $314 Roundtrip, found 4 hours ago
CA $314
Roundtrip
found 4 hours ago
Select Air Canada flight, departing Thu, Sep 24 from Billy Bishop Toronto City to O'Hare Intl., returning Mon, Sep 28, priced at CA $314 found 4 hours ago
Thu, Sep 24 - Mon, Sep 28
YTZ
Billy Bishop Toronto City
ORD
O'Hare Intl.
CA $319 Roundtrip, found 4 hours ago
CA $319
Roundtrip
found 4 hours ago
Select Air Canada flight, departing Thu, Sep 24 from Billy Bishop Toronto City to O'Hare Intl., returning Mon, Sep 28, priced at CA $319 found 4 hours ago
Wed, Sep 23 - Sat, Sep 26
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $322 Roundtrip, just found
CA $322
Roundtrip
just found
Select Air Canada flight, departing Wed, Sep 23 from Pearson Intl. to O'Hare Intl., returning Sat, Sep 26, priced at CA $322 just found
Fri, Oct 2 - Mon, Oct 5
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $322 Roundtrip, just found
CA $322
Roundtrip
just found
Select American Airlines flight, departing Fri, Oct 2 from Pearson Intl. to O'Hare Intl., returning Mon, Oct 5, priced at CA $322 just found
Wed, Sep 23 - Thu, Sep 24
YYZ
Pearson Intl.
MDW
Midway Intl.
CA $330 Roundtrip, just found
CA $330
Roundtrip
just found
Select Delta flight, departing Wed, Sep 23 from Pearson Intl. to Midway Intl., returning Thu, Sep 24, priced at CA $330 just found
Tue, Sep 29 - Wed, Sep 30
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
CA $335 Roundtrip, just found
CA $335
Roundtrip
just found
Select Porter Airlines flight, departing Tue, Sep 29 from Billy Bishop Toronto City to Midway Intl., returning Wed, Sep 30, priced at CA $335 just found
Thu, Nov 26 - Sun, Nov 29
YTZ
Billy Bishop Toronto City
ORD
O'Hare Intl.
CA $335 Roundtrip, just found
CA $335
Roundtrip
just found
Select Porter Airlines flight, departing Thu, Nov 26 from Billy Bishop Toronto City to O'Hare Intl., returning Sun, Nov 29, priced at CA $335 just found
Thu, Nov 26 - Sun, Nov 29
YTZ
Billy Bishop Toronto City
ORD
O'Hare Intl.
CA $377 Roundtrip, just found
CA $377
Roundtrip
just found
Select Air Transat flight, departing Thu, Nov 26 from Billy Bishop Toronto City to O'Hare Intl., returning Sun, Nov 29, priced at CA $377 just found
OriginDestinationTravel datesFlights from*
ATLSt. LouisNovember 7 to November 10CA $161
LAXChicagoOctober 10 to October 17CA $303
JFKChicagoSeptember 26 to September 28CA $374
DFWChicagoOctober 5 to October 10CA $387
ATLChicagoOctober 21 to October 24CA $401
LAXChicagoOctober 10 to October 17CA $457
DFWSt. LouisSeptember 28 to September 30CA $462
DALChicagoOctober 6 to November 14CA $474
ATLChicagoOctober 4 to October 7CA $478
EWRChicagoOctober 2 to October 3CA $487
LAXSt. LouisOctober 23 to October 24CA $489
DFWSavoyOctober 27 to October 31CA $719
HKGChicagoNovember 23 to December 1CA $1,215
PVGChicagoOctober 26 to November 4CA $1,471
PEKChicagoSeptember 23 to September 29CA $1,601
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
JFKChicagoSeptember 11 to September 28CA $427
LAXChicagoSeptember 12 to September 23CA $512
ATLChicagoSeptember 12 to September 15CA $587
ATLChicagoSeptember 13 to September 19CA $600
DFWChicagoSeptember 12 to September 13CA $732
DFWSt. LouisSeptember 12 to September 13CA $737
LAXSt. LouisSeptember 11 to September 18CA $943
EWRSt. LouisSeptember 13 to September 18CA $2,193
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

Nov 11 - Nov 16

5 night stay

Vancouver (YVR) to Chicago (ORD)

United • Roundtrip • Coach
Price was CA $3,172, price is now CA $1,966 per person
CA $1,966
per person
found 1 day ago
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

Sep 17 - Sep 20

3 night stay

Ottawa (YOW) to Chicago (ORD)

American Airlines • Non-stop roundtrip • Coach
Price was CA $3,260, price is now CA $2,206 per person
CA $2,206
per person
found 1 day ago
Four Seasons Hotel Chicago
5.0-star property

Four Seasons Hotel Chicago

Oct 11 - Oct 14

3 night stay

Québec (YQB) to Chicago (ORD)

Air Canada • Non-stop roundtrip • Coach
Price was CA $3,343, price is now CA $2,349 per person
CA $2,349
per person
found 14 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.
8/10 Very good! (10,318 reviews)
"I loved the location. It was perfect for seeing the city sights and getting to them on public transit.. I thought the front desk was unwelcoming and acted I different to concerns. Other staff were appropriately accommodating and helpful."

Reviewed on Sep 8, 2026

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! (2,184 reviews)
"I liked the Ambassador, it was a great! location. but, no coffee in the room and no maid service, We stayed 2 nights, but didn't get our room touched up. thus the 4 stars"

Reviewed on Sep 8, 2026

Opens in a new windowThe Chicago Hotel Collection Ambassador Gold Coast
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4 out of 5
One Superior Place Chicago IL
Stay at this aparthotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
9.4/10 Exceptional! (890 reviews)
"Great spot!"

Reviewed on Sep 7, 2026

Opens in a new windowKasa Magnificent Mile Chicago
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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! (5,429 reviews)
"Very convenient to all the Chicago things to do!"

Reviewed on Sep 8, 2026

Opens in a new windowRiver 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 $161 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 $161 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 $161 and CA $2,193 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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