Flights To Illinois - Cheap Flights Starting at CA $181

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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, May 12 - Sun, May 17
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
CA $300 Roundtrip, just found
CA $300
Roundtrip
just found
Select Porter Airlines flight, departing Tue, May 12 from Billy Bishop Toronto City to Midway Intl., returning Sun, May 17, priced at CA $300 just found
Tue, Jun 9 - Sat, Jun 13
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $312 Roundtrip, found 12 hours ago
CA $312
Roundtrip
found 12 hours ago
Select Air Canada flight, departing Tue, Jun 9 from Pearson Intl. to O'Hare Intl., returning Sat, Jun 13, priced at CA $312 found 12 hours ago
Sat, Jun 13 - Sat, Jun 13
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $312 Roundtrip, found 12 hours ago
CA $312
Roundtrip
found 12 hours ago
Select Delta flight, departing Sat, Jun 13 from Pearson Intl. to O'Hare Intl., returning Sat, Jun 13, priced at CA $312 found 12 hours ago
Wed, Jun 10 - Sun, Jun 14
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $312 Roundtrip, found 12 hours ago
CA $312
Roundtrip
found 12 hours ago
Select United flight, departing Wed, Jun 10 from Pearson Intl. to O'Hare Intl., returning Sun, Jun 14, priced at CA $312 found 12 hours ago
Wed, May 13 - Sat, May 16
YYZ
Pearson Intl.
MDW
Midway Intl.
CA $320 Roundtrip, found 8 hours ago
CA $320
Roundtrip
found 8 hours ago
Select Delta flight, departing Wed, May 13 from Pearson Intl. to Midway Intl., returning Sat, May 16, priced at CA $320 found 8 hours ago
Thu, Sep 17 - Wed, Sep 23
YTZ
Billy Bishop Toronto City
ORD
O'Hare Intl.
CA $340 Roundtrip, found 8 hours ago
CA $340
Roundtrip
found 8 hours ago
Select Porter Airlines flight, departing Thu, Sep 17 from Billy Bishop Toronto City to O'Hare Intl., returning Wed, Sep 23, priced at CA $340 found 8 hours ago
Tue, May 12 - Sun, May 17
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
CA $342 Roundtrip, just found
CA $342
Roundtrip
just found
Select Air Transat flight, departing Tue, May 12 from Billy Bishop Toronto City to Midway Intl., returning Sun, May 17, priced at CA $342 just found
Tue, Sep 15 - Tue, Oct 20
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $361 Roundtrip, found 6 days ago
CA $361
Roundtrip
found 6 days ago
Select American Airlines flight, departing Tue, Sep 15 from Pearson Intl. to O'Hare Intl., returning Tue, Oct 20, priced at CA $361 found 6 days ago
OriginDestinationTravel datesFlights from*
EWRChicagoMay 24 to May 29CA $149
DFWChicagoMay 24 to May 30CA $201
LAXChicagoMay 9 to May 15CA $218
ATLChicagoMay 15 to May 19CA $244
LAXChicagoMay 20 to May 27CA $415
DFWChicagoJune 11 to June 14CA $422
EWRChicagoMay 13 to May 15CA $558
LAXSt. LouisMay 16 to May 18CA $649
PVGChicagoJune 26 to September 1CA $1,452
HKGChicagoMay 18 to June 1CA $1,566
PEKChicagoMay 11 to May 24CA $1,820
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
ATLChicagoMay 1 to May 4CA $183
DFWChicagoMay 2 to May 5CA $202
LGAChicagoMay 1 to May 6CA $331
DFWChicagoMay 1 to May 8CA $536
LAXChicagoMay 1 to May 8CA $562
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0-star property

Sable at Navy Pier Chicago, Curio Collection by Hilton

Jun 1 - Jun 4

3 night stay

Toronto (YTO) to Chicago (ORD)

Air Canada • Roundtrip • Coach
Price was CA $1,601, price is now CA $1,042 per person
CA $1,042
per person
found 24 hours ago
Level Chicago Fulton Market
4.0-star property

Level Chicago Fulton Market

Jun 9 - Jun 14

5 night stay

Toronto (YTO) to Chicago (ORD)

Air Canada • Roundtrip • Coach
Price was CA $2,237, price is now CA $1,387 per person
CA $1,387
per person
found 1 day ago
Swissotel - Chicago
4.5-star property

Swissotel - Chicago

May 15 - May 18

3 night stay

Detroit (DTW) to Chicago (ORD)

American Airlines • Coach

Chicago (ORD) to Detroit (DTW)

Delta • Coach
Price was CA $2,223, price is now CA $1,472 per person
CA $1,472
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 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! (10,127 reviews)
Great price for the location. Common areas are beautiful. The rooms are ok. One of the staff members was great. She went out of her way to help and offer suggestions. The rest of the staff we encountered were hard to find and not particularly motivated to be helpful. It took 30 minutes to get someone ...

Reviewed on Apr 24, 2026

Opens in a new windowCongress Plaza Hotel
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
8.2/10 Very Good! (2,633 reviews)
Great location, staff and value for money

Reviewed on Apr 24, 2026

Opens in a new windowHotel Felix River North/Magnificent Mile
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
8.8/10 Excellent! (5,119 reviews)
This property is in an excellent location. Can walk anywhere downtown. When our first room had a broken air conditioner, within minutes we were moved to another floor with working air. Nice having a good restaurant right next door and a Starbucks around the corner. The building is old but cleaning ...

Reviewed on Apr 24, 2026

Opens in a new windowRiver Hotel
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Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
8.8/10 Excellent! (3,451 reviews)
The facility is not kept up well. Sofa has a vinyl covering which was peeling badly and should be thrown out.

Reviewed on Apr 24, 2026

Opens in a new windowClub Quarters Hotel, Central Loop, 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 $149 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 May. 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 $149 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 $149 and CA $1,820 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.

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