Flights To Illinois - Cheap Flights Starting at CA $166

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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., Nov. 21 - Fri., Dec. 12
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $236 Roundtrip, found 5 days ago
CA $236
Roundtrip
found 5 days ago
Select Air Canada flight, departing Fri., Nov. 21 from Pearson Intl. to O'Hare Intl., returning Fri., Dec. 12, priced at CA $236 found 5 days ago
Fri., Oct. 10 - Sat., Oct. 25
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $240 Roundtrip, found 5 days ago
CA $240
Roundtrip
found 5 days ago
Select Air Canada flight, departing Fri., Oct. 10 from Pearson Intl. to O'Hare Intl., returning Sat., Oct. 25, priced at CA $240 found 5 days ago
Thu., Jun. 19 - Fri., Oct. 3
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
CA $244 Roundtrip, found 2 days ago
CA $244
Roundtrip
found 2 days ago
Select Porter Airlines flight, departing Thu., Jun. 19 from Billy Bishop Toronto City to Midway Intl., returning Fri., Oct. 3, priced at CA $244 found 2 days ago
Tue., Oct. 28 - Tue., Oct. 28
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $246 Roundtrip, found 6 days ago
CA $246
Roundtrip
found 6 days ago
Select Air Canada flight, departing Tue., Oct. 28 from Pearson Intl. to O'Hare Intl., returning Tue., Oct. 28, priced at CA $246 found 6 days ago
Thu., Sep. 4 - Tue., Sep. 9
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 Thu., Sep. 4 from Pearson Intl. to O'Hare Intl., returning Tue., Sep. 9, priced at CA $261 found 4 days ago
Tue., Jun. 24 - Mon., Jun. 30
YTZ
Billy Bishop Toronto City
ORD
O'Hare Intl.
CA $292 Roundtrip, found 5 days ago
CA $292
Roundtrip
found 5 days ago
Select Air Canada flight, departing Tue., Jun. 24 from Billy Bishop Toronto City to O'Hare Intl., returning Mon., Jun. 30, priced at CA $292 found 5 days ago
Thu., Oct. 16 - Sun., Oct. 19
YYZ
Pearson Intl.
MDW
Midway Intl.
CA $292 Roundtrip, found 4 days ago
CA $292
Roundtrip
found 4 days ago
Select Delta flight, departing Thu., Oct. 16 from Pearson Intl. to Midway Intl., returning Sun., Oct. 19, priced at CA $292 found 4 days ago
Sat., Aug. 30 - Tue., Sep. 2
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
CA $293 Roundtrip, found 3 days ago
CA $293
Roundtrip
found 3 days ago
Select Air Transat flight, departing Sat., Aug. 30 from Billy Bishop Toronto City to Midway Intl., returning Tue., Sep. 2, priced at CA $293 found 3 days ago
OriginDestinationTravel datesFlights from*
EWRChicagoJuly 10 to July 14CA $126
ATLChicagoAugust 16 to August 23CA $139
LAXChicagoJune 30 to July 8CA $152
DFWChicagoSeptember 11 to September 14CA $163
EWRChicagoJuly 9 to July 12CA $285
ATLSt. LouisAugust 8 to August 10CA $326
DALChicagoSeptember 11 to September 14CA $558
HKGChicagoJuly 17 to July 20CA $1,652
PEKChicagoJuly 7 to July 22CA $1,937
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
LAXChicagoJune 6 to June 8CA $296
ATLChicagoJune 6 to June 10CA $296
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Chicago River Side Suites
2.0-star property

Chicago River Side Suites

Aug 11 - Aug 16

5 night stay

Hamilton (YHM) to Chicago (ORD)

Air Canada • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
The Wildwood Hotel
3.5-star property

The Wildwood Hotel

Jul 4 - Jul 8

4 night stay

Toronto (YTO) to St. Louis (STL)

Air Canada • 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 11 - Aug 16

5 night stay

Hamilton (YHM) to Chicago (ORD)

Air Canada • Non-stop roundtrip • Coach
Save 100% on your flight
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! (8,786 reviews)
"Very nice place"

Reviewed on May 28, 2025

Congress Plaza Hotel
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the bar in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
9.2/10 Wonderful! (3,122 reviews)
"Excellent experience! Centrally located and clean"

Reviewed on May 31, 2025

citizenM Chicago Downtown
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
909 North Michigan Ave, Chicago, IL
Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour fitness center. 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! (1,007 reviews)
"Absolutely top tier!! Definitely a whole vibe."

Reviewed on May 30, 2025

The Westin Michigan Avenue Chicago
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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! (2,270 reviews)
"We stayed one night however all of the employees we had an interaction with were all very pleasant. The room was nice and comfortable. Desk staff were all very kind and helpful. The staff working outside by the door were very kind and helpful with questions we had about directions and ..."

Reviewed on May 30, 2025

Hilton Chicago/Magnificent Mile Suites
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.