Flights To Illinois - Cheap Flights Starting at CA $208

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Jet to one of Illinois's top cities

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, Oct 5 - Fri, Oct 9
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $327 Roundtrip, found 2 days ago
CA $327
Roundtrip
found 2 days ago
Select Air Canada flight, departing Mon, Oct 5 from Pearson Intl. to O'Hare Intl., returning Fri, Oct 9, priced at CA $327 found 2 days ago
Wed, Oct 14 - Sat, Oct 17
YYZ
Pearson Intl.
MDW
Midway Intl.
CA $335 Roundtrip, found 2 days ago
CA $335
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Oct 14 from Pearson Intl. to Midway Intl., returning Sat, Oct 17, priced at CA $335 found 2 days ago
Wed, Oct 14 - Sat, Oct 17
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $335 Roundtrip, found 2 days ago
CA $335
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Oct 14 from Pearson Intl. to O'Hare Intl., returning Sat, Oct 17, priced at CA $335 found 2 days ago
Thu, Oct 15 - Sat, Oct 24
YYC
Calgary Intl.
ORD
O'Hare Intl.
CA $404 Roundtrip, found 4 days ago
CA $404
Roundtrip
found 4 days ago
Select American Airlines flight, departing Thu, Oct 15 from Calgary Intl. to O'Hare Intl., returning Sat, Oct 24, priced at CA $404 found 4 days ago
Wed, Sep 9 - Wed, Sep 30
YYC
Calgary Intl.
MDW
Midway Intl.
CA $412 Roundtrip, found 1 day ago
CA $412
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Sep 9 from Calgary Intl. to Midway Intl., returning Wed, Sep 30, priced at CA $412 found 1 day ago
Tue, Oct 13 - Tue, Oct 20
YYZ
Pearson Intl.
STL
Lambert-St. Louis Intl.
CA $439 Roundtrip, found 1 day ago
CA $439
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Oct 13 from Pearson Intl. to Lambert-St. Louis Intl., returning Tue, Oct 20, priced at CA $439 found 1 day ago
Wed, Sep 9 - Tue, Sep 15
YYC
Calgary Intl.
STL
Lambert-St. Louis Intl.
CA $493 Roundtrip, found 4 days ago
CA $493
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Sep 9 from Calgary Intl. to Lambert-St. Louis Intl., returning Tue, Sep 15, priced at CA $493 found 4 days ago
Sat, Jun 27 - Fri, Jul 3
YYZ
Pearson Intl.
CMI
University Of Illinois Urbana-Champaign Williard
CA $746 Roundtrip, found 2 days ago
CA $746
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Jun 27 from Pearson Intl. to University Of Illinois Urbana-Champaign Williard, returning Fri, Jul 3, priced at CA $746 found 2 days ago
OriginDestinationTravel datesFlights from*
ATLSt. LouisJuly 7 to July 15CA $168
JFKChicagoAugust 17 to August 18CA $209
LAXChicagoJuly 28 to August 5CA $340
DFWChicagoJuly 4 to July 8CA $413
LAXChicagoAugust 19 to August 26CA $440
ATLChicagoAugust 12 to August 18CA $458
LAXSt. LouisSeptember 9 to September 14CA $487
LGAChicagoJuly 9 to July 12CA $936
DFWSt. LouisAugust 6 to August 10CA $1,138
EWRSt. LouisJuly 7 to July 15CA $1,181
HKGChicagoJuly 15 to July 19CA $1,897
PEKChicagoJuly 18 to July 31CA $2,171
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
EWRChicagoJune 19 to June 24CA $455
LAXSt. LouisJune 19 to June 23CA $795
LAXChicagoJune 21 to June 28CA $1,077
ATLChicagoJune 19 to June 24CA $1,215
PEKChicagoJune 19 to June 28CA $2,272
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Motel 6 Elk Grove Village, IL - O'Hare
2.0-star property

Motel 6 Elk Grove Village, IL - O'Hare

Aug 25 - Aug 28

3 night stay

Winnipeg (YWG) to Chicago (ORD)

Air Canada • Non-stop roundtrip • Coach
Price was CA $1,185, price is now CA $779 per person
CA $779
per person
found 8 hours ago
Holiday Inn Express Rolling Meadows - Schaumburg Area by IHG
2.5-star property

Holiday Inn Express Rolling Meadows - Schaumburg Area by IHG

Aug 25 - Aug 28

3 night stay

Winnipeg (YWG) to Chicago (ORD)

Air Canada • Non-stop roundtrip • Coach
Price was CA $1,345, price is now CA $884 per person
CA $884
per person
found 8 hours ago
Motel 6 Villa Park, IL - Chicago West
2.0-star property

Motel 6 Villa Park, IL - Chicago West

Aug 25 - Aug 28

3 night stay

Winnipeg (YWG) to Chicago (ORD)

Air Canada • Non-stop roundtrip • Coach
Price was CA $1,201, price is now CA $790 per person
CA $790
per person
found 8 hours ago
Don't see what you're looking for?
See all available trips from Winnipeg to Illinois
View all trips

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 Art Institute of Chicago are located nearby.
8/10 Very Good! (10,281 reviews)
"Wish had one more full size towel."

Reviewed on Jun 15, 2026

Opens in a new windowCongress Plaza Hotel
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rosemont Theatre and Allstate Arena are located nearby.
8.8/10 Excellent! (2,670 reviews)
"The hotel itself is nice staff friendly but beware of parking costs and expensive breakfast buffet. Would stay again."

Reviewed on Jun 14, 2026

Opens in a new windowHyatt Regency O'Hare Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Book a stay at this boutique 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 Michigan Avenue and Chicago Riverwalk are located nearby.
7.8/10 Good! (1,588 reviews)
"Older property but locations is great! One block from miracle mile. Rooftop bar was great. Staff wonderful! Had a fitness center that I didn’t use but it was quite large with lots of equipment. The breakfast buffet was adequate but not spectacular. The bus stop is one block from hotel and runs frequently ..."

Reviewed on Jun 15, 2026

Opens in a new windowThe Chicago Hotel Collection - Magnificent Mile
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, 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! (1,607 reviews)
"Easy check-in with friendly and helpful staff. Perfect location, would definitely stay again."

Reviewed on Jun 14, 2026

Opens in a new windowThe Chicago Hotel Collection Ambassador Gold Coast
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 $168 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 October. 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 $168 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 $168 and CA $2,272 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.

Explore More Ways to Travel with Travelocity