Flights To Illinois - Cheap Flights Starting at CA $207

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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., Apr. 18 - Sat., Apr. 19
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $301 Roundtrip, found 1 day ago
CA $301
Roundtrip
found 1 day ago
Select United flight, departing Fri., Apr. 18 from Pearson Intl. to O'Hare Intl., returning Sat., Apr. 19, priced at CA $301 found 1 day ago
Thu., Apr. 24 - Thu., May 1
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
CA $316 Roundtrip, found 2 days ago
CA $316
Roundtrip
found 2 days ago
Select Porter Airlines flight, departing Thu., Apr. 24 from Billy Bishop Toronto City to Midway Intl., returning Thu., May 1, priced at CA $316 found 2 days ago
Thu., May 8 - Mon., May 12
YYZ
Pearson Intl.
MDW
Midway Intl.
CA $331 Roundtrip, found 4 days ago
CA $331
Roundtrip
found 4 days ago
Select Delta flight, departing Thu., May 8 from Pearson Intl. to Midway Intl., returning Mon., May 12, priced at CA $331 found 4 days ago
Tue., Apr. 29 - Tue., May 6
YYZ
Pearson Intl.
MDW
Midway Intl.
CA $332 Roundtrip, found 5 days ago
CA $332
Roundtrip
found 5 days ago
Select Delta flight, departing Tue., Apr. 29 from Pearson Intl. to Midway Intl., returning Tue., May 6, priced at CA $332 found 5 days ago
Tue., Apr. 22 - Tue., Apr. 29
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $344 Roundtrip, found 4 days ago
CA $344
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue., Apr. 22 from Pearson Intl. to O'Hare Intl., returning Tue., Apr. 29, priced at CA $344 found 4 days ago
Fri., Oct. 17 - Sat., Oct. 18
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $349 Roundtrip, found 5 days ago
CA $349
Roundtrip
found 5 days ago
Select Delta flight, departing Fri., Oct. 17 from Pearson Intl. to O'Hare Intl., returning Sat., Oct. 18, priced at CA $349 found 5 days ago
Fri., May 2 - Mon., May 5
YTZ
Billy Bishop Toronto City
ORD
O'Hare Intl.
CA $352 Roundtrip, found 3 hours ago
CA $352
Roundtrip
found 3 hours ago
Select Air Canada flight, departing Fri., May 2 from Billy Bishop Toronto City to O'Hare Intl., returning Mon., May 5, priced at CA $352 found 3 hours ago
Wed., Apr. 30 - Sun., May 4
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
CA $394 Roundtrip, just found
CA $394
Roundtrip
just found
Select Air Transat flight, departing Wed., Apr. 30 from Billy Bishop Toronto City to Midway Intl., returning Sun., May 4, priced at CA $394 just found
OriginDestinationTravel datesFlights from*
ATLChicagoJune 13 to June 20CA $136
DFWChicagoMay 3 to May 4CA $141
EWRChicagoApril 28 to April 30CA $362
EWRSt. LouisMay 24 to May 29CA $369
ATLChicagoJuly 3 to July 6CA $670
CANChicagoMay 7 to July 24CA $1,315
HKGChicagoJuly 12 to July 31CA $1,734
PVGSt. LouisApril 27 to May 9CA $3,115
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

Jun. 25 - Jun. 29

4 night stay

Edmonton (YEG) to Chicago (ORD)

WestJet • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

Jun. 18 - Jun. 22

4 night stay

Toronto (YYZ) to Chicago (ORD)

Air Canada • Roundtrip • Coach
Save 100% on your flight
per person
found 20 hours ago
Urban Chicago Oasis
2.0-star property

Urban Chicago Oasis

Jun. 4 - Jun. 8

4 night stay

Toronto (YYZ) to Chicago (ORD)

Delta • Non-stop roundtrip • Coach
Save 100% on your flight
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.
8.2/10 Very Good! (3,843 reviews)
"Very nice stay. Breakfast was good options for the buffet also the afternoon reception was a nice bonus. The staff were pleasant and helpful. Would recommend."

Reviewed on Apr. 4, 2025

Embassy Suites by Hilton Chicago Downtown River North
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
323 E Wacker Dr, Chicago, IL
Book a stay at this eco-certified hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
8.8/10 Excellent! (2,036 reviews)
"View n clean"

Reviewed on Apr. 6, 2025

Swissotel - Chicago
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.
8.6/10 Excellent! (1,007 reviews)
"Good"

Reviewed on Apr. 2, 2025

Crowne Plaza Chicago West Loop by IHG
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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! (2,107 reviews)
"Hotel was clean and great staff. Unfortunately we booked this trip for my daughter to swim at but the pool will be closed for another month. Wish i would have known prior to booking"

Reviewed on Apr. 6, 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.

Frequently asked questions

How much is the cheapest flight to Illinois?
A roundtrip flight to Illinois cost as little as CA $136 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 April. 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 $136 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 $136 and CA $3,115 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.