Flights To Illinois - Cheap Flights Starting at CA $165

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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. 4 - Fri., Sep. 5
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $261 Roundtrip, found 7 hours ago
CA $261
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Thu., Sep. 4 from Pearson Intl. to O'Hare Intl., returning Fri., Sep. 5, priced at CA $261 found 7 hours ago
Thu., Oct. 23 - Sat., Oct. 25
YYC
Calgary Intl.
ORD
O'Hare Intl.
CA $267 Roundtrip, found 4 days ago
CA $267
Roundtrip
found 4 days ago
Select American Airlines flight, departing Thu., Oct. 23 from Calgary Intl. to O'Hare Intl., returning Sat., Oct. 25, priced at CA $267 found 4 days ago
Thu., Oct. 23 - Fri., Oct. 24
YYC
Calgary Intl.
ORD
O'Hare Intl.
CA $267 Roundtrip, found 4 days ago
CA $267
Roundtrip
found 4 days ago
Select WestJet flight, departing Thu., Oct. 23 from Calgary Intl. to O'Hare Intl., returning Fri., Oct. 24, priced at CA $267 found 4 days ago
Fri., Oct. 24 - Fri., Oct. 24
YYC
Calgary Intl.
ORD
O'Hare Intl.
CA $267 Roundtrip, found 4 days ago
CA $267
Roundtrip
found 4 days ago
Select Air Canada flight, departing Fri., Oct. 24 from Calgary Intl. to O'Hare Intl., returning Fri., Oct. 24, priced at CA $267 found 4 days ago
Thu., Sep. 4 - Fri., Sep. 5
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $269 Roundtrip, found 7 hours ago
CA $269
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Thu., Sep. 4 from Pearson Intl. to O'Hare Intl., returning Fri., Sep. 5, priced at CA $269 found 7 hours ago
Thu., Sep. 4 - Fri., Sep. 5
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $292 Roundtrip, found 7 hours ago
CA $292
Roundtrip
found 7 hours ago
Select Delta flight, departing Thu., Sep. 4 from Pearson Intl. to O'Hare Intl., returning Fri., Sep. 5, priced at CA $292 found 7 hours ago
Sat., Sep. 6 - Tue., Sep. 9
YYZ
Pearson Intl.
MDW
Midway Intl.
CA $292 Roundtrip, found 2 days ago
CA $292
Roundtrip
found 2 days ago
Select Delta flight, departing Sat., Sep. 6 from Pearson Intl. to Midway Intl., returning Tue., Sep. 9, priced at CA $292 found 2 days ago
Sat., Aug. 9 - Mon., Aug. 11
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $292 Roundtrip, found 8 hours ago
CA $292
Roundtrip
found 8 hours ago
Select United flight, departing Sat., Aug. 9 from Pearson Intl. to O'Hare Intl., returning Mon., Aug. 11, priced at CA $292 found 8 hours ago
OriginDestinationTravel datesFlights from*
EWRChicagoJune 25 to June 27CA $137
DFWChicagoAugust 22 to August 25CA $144
ATLChicagoAugust 16 to August 23CA $151
LAXChicagoJune 26 to July 4CA $194
ATLSt. LouisAugust 30 to September 5CA $234
LAXChicagoSeptember 10 to September 10CA $345
EWRSt. LouisJuly 10 to July 13CA $353
EWRChicagoAugust 16 to August 22CA $429
HKGChicagoJuly 17 to July 20CA $1,568
PVGChicagoJuly 15 to July 24CA $1,623
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
LAXChicagoJune 14 to June 16CA $309
DFWChicagoJune 14 to June 18CA $392
LGAChicagoJune 13 to June 15CA $478
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Congress Plaza Hotel
3.5-star property

Congress Plaza Hotel

Jul 19 - Jul 26

7 night stay

Montreal (YMQ) to Chicago (ORD)

Air Canada • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Chicago River Side Suites
2.0-star property

Chicago River Side Suites

Jul 19 - Jul 26

7 night stay

Montreal (YMQ) to Chicago (ORD)

Air Canada • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

Aug 24 - Aug 31

7 night stay

Montreal (YMQ) to Chicago (ORD)

Air Canada • Roundtrip • Coach
Save 100% on your flight
per person
found 17 hours ago
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Travelers ❤️ These Illinois 🏨

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! (4,170 reviews)
"You can’t go wrong with Embassy Suites. They never disappoint."

Reviewed on Jun. 6, 2025

Embassy Suites by Hilton Chicago Downtown River North
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! (1,857 reviews)
"Great. I got room early at 10:30am and was able to do a conference call. Towles were soft. Shower head pressure was a bit off - adjustable bit didnt work well."

Reviewed on Jun. 6, 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! (2,286 reviews)
"My family thoroughly enjoyed our stay here! Staff was extremely helpful and the room was spacious and clean! Highly recommend!"

Reviewed on Jun. 8, 2025

Hilton Chicago/Magnificent Mile Suites
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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! (8,849 reviews)
"Very good"

Reviewed on Jun. 7, 2025

Congress Plaza 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.

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.