Flights To Illinois - Cheap Flights Starting at CA $164

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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, Mar 26 - Sun, Mar 29
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $257 Roundtrip, found 1 day ago
CA $257
Roundtrip
found 1 day ago
Select Air Canada flight, departing Thu, Mar 26 from Pearson Intl. to O'Hare Intl., returning Sun, Mar 29, priced at CA $257 found 1 day ago
Sat, Jan 24 - Sun, Jan 25
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $264 Roundtrip, found 14 hours ago
CA $264
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Sat, Jan 24 from Pearson Intl. to O'Hare Intl., returning Sun, Jan 25, priced at CA $264 found 14 hours ago
Fri, Jan 16 - Sun, Jan 25
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $264 Roundtrip, found 6 days ago
CA $264
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, Jan 16 from Pearson Intl. to O'Hare Intl., returning Sun, Jan 25, priced at CA $264 found 6 days ago
Sat, Nov 22 - Tue, Nov 25
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $272 Roundtrip, found 4 hours ago
CA $272
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Sat, Nov 22 from Pearson Intl. to O'Hare Intl., returning Tue, Nov 25, priced at CA $272 found 4 hours ago
Thu, Mar 26 - Sun, Mar 29
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $275 Roundtrip, found 1 day ago
CA $275
Roundtrip
found 1 day ago
Select United flight, departing Thu, Mar 26 from Pearson Intl. to O'Hare Intl., returning Sun, Mar 29, priced at CA $275 found 1 day ago
Fri, Feb 27 - Mon, Mar 2
YYC
Calgary Intl.
ORD
O'Hare Intl.
CA $290 Roundtrip, found 12 hours ago
CA $290
Roundtrip
found 12 hours ago
Select WestJet flight, departing Fri, Feb 27 from Calgary Intl. to O'Hare Intl., returning Mon, Mar 2, priced at CA $290 found 12 hours ago
Mon, Nov 17 - Mon, Nov 24
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $292 Roundtrip, found 9 hours ago
CA $292
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Mon, Nov 17 from Pearson Intl. to O'Hare Intl., returning Mon, Nov 24, priced at CA $292 found 9 hours ago
Fri, Nov 21 - Fri, Nov 28
YYZ
Pearson Intl.
MDW
Midway Intl.
CA $294 Roundtrip, found 13 hours ago
CA $294
Roundtrip
found 13 hours ago
Select Delta flight, departing Fri, Nov 21 from Pearson Intl. to Midway Intl., returning Fri, Nov 28, priced at CA $294 found 13 hours ago
Thu, Mar 26 - Sun, Mar 29
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $330 Roundtrip, found 1 day ago
CA $330
Roundtrip
found 1 day ago
Select United flight, departing Thu, Mar 26 from Pearson Intl. to O'Hare Intl., returning Sun, Mar 29, priced at CA $330 found 1 day ago
OriginDestinationTravel datesFlights from*
LGAChicagoNovember 12 to November 15CA $69
DFWChicagoNovember 13 to November 17CA $86
ATLChicagoNovember 17 to November 19CA $131
LAXChicagoDecember 4 to December 11CA $187
ATLChicagoNovember 18 to November 24CA $296
EWRSt. LouisDecember 4 to December 8CA $491
HKGChicagoNovember 13 to November 17CA $1,212
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
LGAChicagoNovember 1 to November 8CA $103
ATLChicagoNovember 1 to November 4CA $319
LAXChicagoNovember 1 to November 5CA $402
PVGChicagoNovember 2 to November 17CA $1,719
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
The Wildwood Hotel
3.5-star property

The Wildwood Hotel

Nov 14 - Nov 17

3 night stay

Calgary (YYC) to St. Louis (STL)

Delta • Non-stop roundtrip • Coach
Price was CA $1,281, price is now CA $888 per person
CA $888
per person
found 1 day ago
Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

Oct 30 - Nov 2

3 night stay

Calgary (YYC) to Chicago (ORD)

Delta • Non-stop roundtrip • Coach
Price was CA $2,432, price is now CA $1,603 per person
CA $1,603
per person
found 11 hours ago
Park Hyatt Chicago
5.0-star property

Park Hyatt Chicago

Dec 16 - Dec 20

4 night stay

Calgary (YYC) to Chicago (ORD)

Air Canada • Non-stop • Coach

Chicago (ORD) to Calgary (YYC)

Delta • Non-stop • Coach
Price was CA $2,015, price is now CA $1,390 per person
CA $1,390
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! (5,145 reviews)
This was my first time visiting Chicago. The stay far exceeded my expectations. The staff were so friendly my favorite was Arnold. The evening reception was a nice little addition to a wonderful stay. I did observe a guest lick the spoon and put it back in the hummus, zero stars gor him that was ...

Reviewed on Oct 24, 2025

Opens in a new windowEmbassy Suites by Hilton Chicago Downtown River North
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! (9,611 reviews)
Great

Reviewed on Oct 28, 2025

Opens in a new windowCongress Plaza Hotel
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! (3,191 reviews)
i have been visiting chicago frequently over the last few months and this hotel thus far has exceeded any hotel stay that ive had. the staff was amazing and the location and room was great for the money spent. i will return

Reviewed on Oct 28, 2025

Opens in a new windowHilton Chicago/Magnificent Mile Suites
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Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
7.8/10 Good! (2,533 reviews)
Excellent location close to everything. Room with a double bed was small but had a nice bathroom. Nice and friendly staff.

Reviewed on Oct 27, 2025

Opens in a new windowFreehand Chicago
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 $69 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 17 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 March. 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 $69 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 $69 and CA $1,719 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.