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.

Mon, Aug. 25 - Sat, Sep. 6
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
CA $226 Roundtrip, found 4 days ago
CA $226
Roundtrip
found 4 days ago
Select Porter Airlines flight, departing Mon, Aug. 25 from Billy Bishop Toronto City to Midway Intl., returning Sat, Sep. 6, priced at CA $226 found 4 days ago
Sun, Oct. 12 - Tue, Oct. 14
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $235 Roundtrip, found 2 days ago
CA $235
Roundtrip
found 2 days ago
Select United flight, departing Sun, Oct. 12 from Pearson Intl. to O'Hare Intl., returning Tue, Oct. 14, priced at CA $235 found 2 days ago
Sun, Oct. 12 - Tue, Oct. 14
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $248 Roundtrip, found 2 days ago
CA $248
Roundtrip
found 2 days ago
Select Air Canada flight, departing Sun, Oct. 12 from Pearson Intl. to O'Hare Intl., returning Tue, Oct. 14, priced at CA $248 found 2 days ago
Fri, Nov. 14 - Wed, Nov. 19
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $261 Roundtrip, found 3 days ago
CA $261
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, Nov. 14 from Pearson Intl. to O'Hare Intl., returning Wed, Nov. 19, priced at CA $261 found 3 days ago
Sat, Dec. 20 - Wed, Dec. 31
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $276 Roundtrip, found 2 days ago
CA $276
Roundtrip
found 2 days ago
Select Air Canada flight, departing Sat, Dec. 20 from Pearson Intl. to O'Hare Intl., returning Wed, Dec. 31, priced at CA $276 found 2 days ago
Sat, Aug. 23 - Sun, Sep. 28
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $281 Roundtrip, found 4 days ago
CA $281
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Aug. 23 from Pearson Intl. to O'Hare Intl., returning Sun, Sep. 28, priced at CA $281 found 4 days ago
Thu, Sep. 4 - Sat, Sep. 13
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $291 Roundtrip, found 4 days ago
CA $291
Roundtrip
found 4 days ago
Select Delta flight, departing Thu, Sep. 4 from Pearson Intl. to O'Hare Intl., returning Sat, Sep. 13, priced at CA $291 found 4 days ago
Wed, Feb. 11 - Wed, Feb. 18
YYZ
Pearson Intl.
MDW
Midway Intl.
CA $292 Roundtrip, found 5 hours ago
CA $292
Roundtrip
found 5 hours ago
Select Delta flight, departing Wed, Feb. 11 from Pearson Intl. to Midway Intl., returning Wed, Feb. 18, priced at CA $292 found 5 hours ago
OriginDestinationTravel datesFlights from*
ATLChicagoAugust 16 to August 23CA $99
LGAChicagoSeptember 6 to September 13CA $124
LAXChicagoSeptember 16 to September 17CA $191
DFWSt. LouisAugust 21 to August 28CA $206
DFWChicagoOctober 16 to October 22CA $217
ATLSt. LouisAugust 15 to August 17CA $229
LAXChicagoSeptember 10 to September 12CA $386
EWRSt. LouisSeptember 11 to September 14CA $515
PEKChicagoSeptember 22 to November 30CA $1,356
PVGChicagoNovember 6 to November 12CA $1,357
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
LGAChicagoAugust 1 to August 7CA $369
DFWChicagoAugust 3 to August 8CA $382
LAXChicagoAugust 1 to August 11CA $409
ATLChicagoAugust 1 to August 3CA $458
ATLChicagoAugust 1 to August 3CA $750
EWRChicagoAugust 2 to August 3CA $908
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

Sep 23 - Sep 26

3 night stay

Toronto (YTO) to Chicago (ORD)

Porter Airlines • Roundtrip • Coach
per person
found 1 day ago
Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

Oct 5 - Oct 11

6 night stay

Toronto (YTO) to Chicago (ORD)

Air Canada • Non-stop • Coach

Chicago (ORD) to Toronto (YTO)

United • Non-stop • Coach
per person
found 1 day ago
Park Hyatt Chicago
5.0-star property

Park Hyatt Chicago

Oct 5 - Oct 11

6 night stay

Toronto (YTO) to Chicago (ORD)

Air Canada • Non-stop • Coach

Chicago (ORD) to Toronto (YTO)

United • Non-stop • Coach
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! (9,033 reviews)
"There are areas of the property outside that need some tlc. The hallways are outdated in decor but the room was clean and comfortable. The reception area was very pretty. The staff was courteous and friendly. The hotel itself has a good location walkable to the Soldier Field which we were in town ..."

Reviewed on Jul. 29, 2025

Congress Plaza Hotel
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! (2,129 reviews)
Overall a great family hotel
"Great time in Chicago and the hotel made it phenomenal! It’s in a very central location and allows access to all the major tourist attractions within walking distance. We really enjoyed Saturday movie night at the pool!"

Reviewed on Jul. 28, 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! (2,558 reviews)
"Had a wonderful stay. Walking distance to all fine dining and shopping. Will be staying here again."

Reviewed on Jul. 28, 2025

Hilton Chicago/Magnificent Mile Suites
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Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
8.8/10 Excellent! (1,311 reviews)
Comfy stay.
"Me & my family really enjoyed staying here. Stylish, clean & comfortable. Guest service associates were very welcoming. Would most certainly recommend & stay again when in town."

Reviewed on Jul. 27, 2025

Crowne Plaza Chicago West Loop by IHG
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 $99 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 August. 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 $99 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 $99 and CA $1,357 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.