Flights To Illinois - Cheap Flights Starting at CA $177

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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.

Fri, Oct. 24 - Mon, Nov. 3
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $269 Roundtrip, found 6 days ago
CA $269
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, Oct. 24 from Pearson Intl. to O'Hare Intl., returning Mon, Nov. 3, priced at CA $269 found 6 days ago
Mon, Nov. 3 - Tue, Nov. 4
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $269 Roundtrip, found 4 days ago
CA $269
Roundtrip
found 4 days ago
Select American Airlines flight, departing Mon, Nov. 3 from Pearson Intl. to O'Hare Intl., returning Tue, Nov. 4, priced at CA $269 found 4 days ago
Fri, Sep. 5 - Sun, Sep. 7
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $276 Roundtrip, found 8 hours ago
CA $276
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Fri, Sep. 5 from Pearson Intl. to O'Hare Intl., returning Sun, Sep. 7, priced at CA $276 found 8 hours ago
Thu, Sep. 4 - Sat, Sep. 13
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $292 Roundtrip, just found
CA $292
Roundtrip
just found
Select Delta flight, departing Thu, Sep. 4 from Pearson Intl. to O'Hare Intl., returning Sat, Sep. 13, priced at CA $292 just found
Fri, Sep. 26 - Wed, Oct. 1
YYZ
Pearson Intl.
MDW
Midway Intl.
CA $292 Roundtrip, found 15 hours ago
CA $292
Roundtrip
found 15 hours ago
Select Delta flight, departing Fri, Sep. 26 from Pearson Intl. to Midway Intl., returning Wed, Oct. 1, priced at CA $292 found 15 hours ago
Sun, Sep. 14 - Sat, Sep. 20
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
CA $294 Roundtrip, just found
CA $294
Roundtrip
just found
Select Porter Airlines flight, departing Sun, Sep. 14 from Billy Bishop Toronto City to Midway Intl., returning Sat, Sep. 20, priced at CA $294 just found
Wed, Sep. 10 - Wed, Sep. 17
YUL
Pierre Elliott Trudeau Intl.
ORD
O'Hare Intl.
CA $296 Roundtrip, found 5 hours ago
CA $296
Roundtrip
found 5 hours ago
Select Delta flight, departing Wed, Sep. 10 from Pierre Elliott Trudeau Intl. to O'Hare Intl., returning Wed, Sep. 17, priced at CA $296 found 5 hours ago
Sun, Sep. 14 - Sat, Sep. 20
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
CA $336 Roundtrip, just found
CA $336
Roundtrip
just found
Select Air Transat flight, departing Sun, Sep. 14 from Billy Bishop Toronto City to Midway Intl., returning Sat, Sep. 20, priced at CA $336 just found
Mon, Sep. 1 - Fri, Sep. 5
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $337 Roundtrip, found 2 days ago
CA $337
Roundtrip
found 2 days ago
Select United flight, departing Mon, Sep. 1 from Pearson Intl. to O'Hare Intl., returning Fri, Sep. 5, priced at CA $337 found 2 days ago
OriginDestinationTravel datesFlights from*
ATLChicagoAugust 9 to August 16CA $99
LGAChicagoSeptember 6 to September 13CA $124
LAXChicagoAugust 8 to August 16CA $149
EWRSt. LouisAugust 14 to August 18CA $172
DFWChicagoAugust 7 to August 10CA $226
ATLChicagoAugust 7 to August 11CA $278
LAXSt. LouisAugust 23 to August 30CA $302
EWRChicagoOctober 4 to October 6CA $353
JFKSavoyAugust 16 to August 23CA $561
HKGChicagoOctober 17 to October 19CA $1,166
PEKChicagoSeptember 22 to November 30CA $1,356
SHAChicagoSeptember 25 to October 2CA $1,551
PVGSt. LouisSeptember 2 to October 2CA $1,738
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
DFWChicagoJuly 26 to July 28CA $455
LAXSt. LouisJuly 26 to July 27CA $708
DFWChicagoJuly 26 to July 28CA $881
HKGChicagoJuly 27 to September 17CA $1,645
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Arlo Chicago
4.0-star property

Arlo Chicago

Sep 10 - Sep 14

4 night stay

Edmonton (YEG) to Chicago (ORD)

United • Roundtrip • Coach
per person
found 1 day ago
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

Sep 10 - Sep 14

4 night stay

Edmonton (YEG) to Chicago (ORD)

United • Roundtrip • Coach
per person
found 1 day ago
Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

Sep 10 - Sep 14

4 night stay

Edmonton (YEG) to Chicago (ORD)

United • Roundtrip • Coach
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 Art Institute of Chicago are located nearby.
7.8/10 Good! (8,945 reviews)
"Room was extremely warm and air conditioner did not make much difference"

Reviewed on Jul. 23, 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave, Chicago, IL
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
9/10 Wonderful! (2,086 reviews)
"Walking distance to a lot of great spots."

Reviewed on Jul. 21, 2025

InterContinental Chicago Magnificent Mile by IHG
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! (2,512 reviews)
"Great spacious suites for hubby & I. Clean hotel. Walking distance to mostly everywhere downtown. Kind & helpful staff. Would definitely stay here again."

Reviewed on Jul. 22, 2025

Hilton Chicago/Magnificent Mile Suites
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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.
8.4/10 Very Good! (4,520 reviews)
"Property had some minor things needed fixing, cracks on the bathroom ceiling and door of the bathroom had a crack and dirty. One of the staff members when asking for transportation direction and other area question, seemed not to be aware of the area and was unable to help, had no recommendations. ..."

Reviewed on Jul. 23, 2025

Embassy Suites by Hilton Chicago Downtown River North
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 $99 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 16 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 October. 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 $99 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 $99 and CA $1,738 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.