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.

Sat., Sep. 20 - Tue., Sep. 23
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $261 Roundtrip, found 4 days ago
CA $261
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat., Sep. 20 from Pearson Intl. to O'Hare Intl., returning Tue., Sep. 23, priced at CA $261 found 4 days ago
Wed., Sep. 10 - Sun., Sep. 14
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $265 Roundtrip, found 2 days ago
CA $265
Roundtrip
found 2 days ago
Select Air Canada flight, departing Wed., Sep. 10 from Pearson Intl. to O'Hare Intl., returning Sun., Sep. 14, priced at CA $265 found 2 days ago
Thu., Jul. 17 - Wed., Jul. 30
YYC
Calgary Intl.
ORD
O'Hare Intl.
CA $266 Roundtrip, just found
CA $266
Roundtrip
just found
Select WestJet flight, departing Thu., Jul. 17 from Calgary Intl. to O'Hare Intl., returning Wed., Jul. 30, priced at CA $266 just found
Tue., Sep. 30 - Tue., Oct. 7
YYC
Calgary Intl.
ORD
O'Hare Intl.
CA $266 Roundtrip, found 17 hours ago
CA $266
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Tue., Sep. 30 from Calgary Intl. to O'Hare Intl., returning Tue., Oct. 7, priced at CA $266 found 17 hours ago
Sat., Sep. 20 - Tue., Sep. 23
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 Sat., Sep. 20 from Pearson Intl. to O'Hare Intl., returning Tue., Sep. 23, priced at CA $269 found 4 days ago
Sat., Sep. 6 - Sun., Sep. 7
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $291 Roundtrip, found 1 hour ago
CA $291
Roundtrip
found 1 hour ago
Select Delta flight, departing Sat., Sep. 6 from Pearson Intl. to O'Hare Intl., returning Sun., Sep. 7, priced at CA $291 found 1 hour ago
Sun., Oct. 26 - Mon., Oct. 27
YYZ
Pearson Intl.
MDW
Midway Intl.
CA $292 Roundtrip, found 15 hours ago
CA $292
Roundtrip
found 15 hours ago
Select Delta flight, departing Sun., Oct. 26 from Pearson Intl. to Midway Intl., returning Mon., Oct. 27, priced at CA $292 found 15 hours ago
Wed., Jun. 18 - Tue., Jun. 24
YYC
Calgary Intl.
MDW
Midway Intl.
CA $329 Roundtrip, found 2 days ago
CA $329
Roundtrip
found 2 days ago
Select Delta flight, departing Wed., Jun. 18 from Calgary Intl. to Midway Intl., returning Tue., Jun. 24, priced at CA $329 found 2 days ago
OriginDestinationTravel datesFlights from*
ATLChicagoJuly 5 to July 9CA $118
JFKChicagoSeptember 6 to September 13CA $133
DFWChicagoJuly 17 to July 21CA $144
LAXChicagoJuly 9 to July 14CA $182
EWRChicagoSeptember 13 to September 22CA $324
LGASt. LouisJuly 20 to July 27CA $366
DFWSt. LouisJuly 24 to July 27CA $477
PVGChicagoAugust 19 to August 27CA $1,623
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
LGAChicagoJune 20 to June 29CA $240
LAXChicagoJune 22 to June 24CA $295
DFWChicagoJune 22 to June 25CA $301
LAXSt. LouisJune 20 to June 22CA $597
LAXChicagoJune 21 to June 22CA $1,046
HKGChicagoJune 22 to July 6CA $1,499
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
4.5-star property

Swissotel - Chicago

Sep 4 - Sep 7

3 night stay

Toronto (YTO) to Chicago (ORD)

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

Trump International Hotel & Tower Chicago

Sep 4 - Sep 7

3 night stay

Toronto (YTO) to Chicago (ORD)

Air Canada • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

Aug 29 - Sep 1

3 night stay

Montreal (YUL) to Chicago (ORD)

Air Canada • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day 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! (4,202 reviews)
"Convenient location"

Reviewed on Jun. 12, 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! (1,865 reviews)
"Exceptional stay"

Reviewed on Jun. 13, 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! (2,289 reviews)
"My check-in was not so pleasant. I did arrive early and knew I would need to wait which was no problem. I was told I could check my bags at the bell desk but no one was there after standing for a bit finally some out it the 3 people at the front desk asked if I needed help. When I checked in about ..."

Reviewed on Jun. 11, 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! (8,868 reviews)
"Would definitely do this place again. Short 20min walk to union station"

Reviewed on Jun. 14, 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.