Flights To Illinois - Cheap Flights Starting at CA $194

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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.

Tue, Jun 2 - Wed, Jun 3
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
CA $288 Roundtrip, found 3 days ago
CA $288
Roundtrip
found 3 days ago
Select Porter Airlines flight, departing Tue, Jun 2 from Billy Bishop Toronto City to Midway Intl., returning Wed, Jun 3, priced at CA $288 found 3 days ago
Sat, May 9 - Thu, May 14
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $300 Roundtrip, found 6 days ago
CA $300
Roundtrip
found 6 days ago
Select Air Canada flight, departing Sat, May 9 from Pearson Intl. to O'Hare Intl., returning Thu, May 14, priced at CA $300 found 6 days ago
Wed, May 13 - Fri, May 15
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
CA $305 Roundtrip, found 3 days ago
CA $305
Roundtrip
found 3 days ago
Select Porter Airlines flight, departing Wed, May 13 from Billy Bishop Toronto City to Midway Intl., returning Fri, May 15, priced at CA $305 found 3 days ago
Sat, Aug 22 - Wed, Sep 2
YYZ
Pearson Intl.
MDW
Midway Intl.
CA $307 Roundtrip, found 4 days ago
CA $307
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Aug 22 from Pearson Intl. to Midway Intl., returning Wed, Sep 2, priced at CA $307 found 4 days ago
Mon, Jun 1 - Wed, Jun 3
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
CA $320 Roundtrip, found 5 days ago
CA $320
Roundtrip
found 5 days ago
Select Porter Airlines flight, departing Mon, Jun 1 from Billy Bishop Toronto City to Midway Intl., returning Wed, Jun 3, priced at CA $320 found 5 days ago
Mon, May 11 - Sun, May 17
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $320 Roundtrip, found 6 days ago
CA $320
Roundtrip
found 6 days ago
Select United flight, departing Mon, May 11 from Pearson Intl. to O'Hare Intl., returning Sun, May 17, priced at CA $320 found 6 days ago
Fri, Mar 20 - Sat, Apr 4
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $327 Roundtrip, found 6 days ago
CA $327
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, Mar 20 from Pearson Intl. to O'Hare Intl., returning Sat, Apr 4, priced at CA $327 found 6 days ago
Tue, Jun 2 - Wed, Jun 3
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
CA $362 Roundtrip, found 3 days ago
CA $362
Roundtrip
found 3 days ago
Select Air Transat flight, departing Tue, Jun 2 from Billy Bishop Toronto City to Midway Intl., returning Wed, Jun 3, priced at CA $362 found 3 days ago
OriginDestinationTravel datesFlights from*
EWRChicagoMarch 25 to March 30CA $80
ATLChicagoApril 18 to April 20CA $109
DFWChicagoMay 7 to May 13CA $128
LAXChicagoApril 23 to April 28CA $158
LGASt. LouisJune 2 to June 5CA $438
LAXSt. LouisApril 3 to April 6CA $752
DFWChicagoApril 5 to April 12CA $860
HKGChicagoApril 9 to April 22CA $1,522
CANChicagoApril 5 to April 9CA $1,637
PEKChicagoMay 30 to June 3CA $1,799
PVGChicagoMarch 24 to March 28CA $1,997
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
EWRChicagoMarch 14 to March 16CA $201
ATLChicagoMarch 14 to March 16CA $287
LAXChicagoMarch 13 to March 16CA $658
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Four Points by Sheraton Chicago Westchester/Oak Brook
3.0-star property

Four Points by Sheraton Chicago Westchester/Oak Brook

Jun 6 - Jun 11

5 night stay

Kelowna (YLW) to Chicago (ORD)

WestJet • Non-stop roundtrip • Coach
Price was CA $1,140, price is now CA $864 per person
CA $864
per person
found 13 hours ago
Waldorf Astoria Chicago
5.0-star property

Waldorf Astoria Chicago

Apr 15 - Apr 20

5 night stay

Vancouver (YVR) to Chicago (ORD)

Delta • Non-stop roundtrip • Coach
Price was CA $2,941, price is now CA $2,099 per person
CA $2,099
per person
found 24 hours ago
Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

Mar 21 - Mar 28

7 night stay

Vancouver (YVR) to Chicago (ORD)

Air Canada • Non-stop roundtrip • Coach
Price was CA $3,722, price is now CA $2,711 per person
CA $2,711
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Kelowna to Illinois
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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! (9,933 reviews)
Great historic vibe, but feels old.

Reviewed on Mar 9, 2026

Opens in a new windowCongress Plaza Hotel
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 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.
8.6/10 Excellent! (5,741 reviews)
Nice

Reviewed on Mar 9, 2026

Opens in a new windowEmbassy Suites by Hilton Chicago Downtown River North
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
9.4/10 Exceptional! (3,495 reviews)
Plenty of stores and restaurants around. Great location downtown. Short walk to the river. Very clean and new.

Reviewed on Mar 9, 2026

Opens in a new windowHotel Riu Plaza 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.
9/10 Wonderful! (3,893 reviews)
Our room was very warm despite turning the thermostat down to a more comfortable temperature.

Reviewed on Mar 9, 2026

Opens in a new windowHilton 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.

Frequently asked questions

How much is the cheapest flight to Illinois?
A roundtrip flight to Illinois cost as little as CA $80 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 June. 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 $80 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 $80 and CA $1,997 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.