Flights To Illinois - Cheap Flights Starting at CA $200

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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, Sep 24 - Mon, Sep 28
YTZ
Billy Bishop Toronto City
ORD
O'Hare Intl.
CA $339 Roundtrip, found 1 day ago
CA $339
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Thu, Sep 24 from Billy Bishop Toronto City to O'Hare Intl., returning Mon, Sep 28, priced at CA $339 found 1 day ago
Sun, May 24 - Fri, May 29
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
CA $342 Roundtrip, found 4 days ago
CA $342
Roundtrip
found 4 days ago
Select Porter Airlines flight, departing Sun, May 24 from Billy Bishop Toronto City to Midway Intl., returning Fri, May 29, priced at CA $342 found 4 days ago
Fri, Sep 4 - Mon, Sep 7
YTZ
Billy Bishop Toronto City
ORD
O'Hare Intl.
CA $343 Roundtrip, just found
CA $343
Roundtrip
just found
Select Porter Airlines flight, departing Fri, Sep 4 from Billy Bishop Toronto City to O'Hare Intl., returning Mon, Sep 7, priced at CA $343 just found
Mon, Jun 1 - Tue, Jun 2
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $345 Roundtrip, found 6 days ago
CA $345
Roundtrip
found 6 days ago
Select Air Canada flight, departing Mon, Jun 1 from Pearson Intl. to O'Hare Intl., returning Tue, Jun 2, priced at CA $345 found 6 days ago
Sun, May 24 - Sat, May 30
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $345 Roundtrip, found 5 days ago
CA $345
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sun, May 24 from Pearson Intl. to O'Hare Intl., returning Sat, May 30, priced at CA $345 found 5 days ago
Sun, May 24 - Fri, May 29
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
CA $348 Roundtrip, found 4 days ago
CA $348
Roundtrip
found 4 days ago
Select Porter Airlines flight, departing Sun, May 24 from Billy Bishop Toronto City to Midway Intl., returning Fri, May 29, priced at CA $348 found 4 days ago
Sun, May 31 - Sun, Jun 7
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $351 Roundtrip, found 6 days ago
CA $351
Roundtrip
found 6 days ago
Select Delta flight, departing Sun, May 31 from Pearson Intl. to O'Hare Intl., returning Sun, Jun 7, priced at CA $351 found 6 days ago
Mon, May 4 - Mon, May 11
YYZ
Pearson Intl.
MDW
Midway Intl.
CA $372 Roundtrip, found 3 days ago
CA $372
Roundtrip
found 3 days ago
Select Delta flight, departing Mon, May 4 from Pearson Intl. to Midway Intl., returning Mon, May 11, priced at CA $372 found 3 days ago
OriginDestinationTravel datesFlights from*
EWRChicagoApril 9 to April 14CA $108
ATLChicagoMay 3 to May 12CA $108
DFWChicagoMay 7 to May 13CA $128
LAXChicagoApril 15 to April 19CA $198
DFWSt. LouisApril 11 to April 18CA $384
DFWChicagoJune 27 to July 1CA $653
EWRChicagoMarch 31 to April 12CA $994
HKGChicagoApril 24 to November 17CA $1,273
PVGChicagoApril 4 to April 6CA $1,809
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
EWRChicagoMarch 21 to March 28CA $239
ATLChicagoMarch 20 to March 23CA $301
DFWChicagoMarch 20 to March 22CA $642
LAXChicagoMarch 21 to March 27CA $962
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
La Banque Hotel
4.0-star property

La Banque Hotel

May 25 - May 29

4 night stay

Toronto (YTO) to Chicago (ORD)

Porter Airlines • Roundtrip • Coach
Price was CA $1,259, price is now CA $829 per person
CA $829
per person
found 1 hour ago
Level Chicago Fulton Market
4.0-star property

Level Chicago Fulton Market

May 18 - May 22

4 night stay

Toronto (YTO) to Chicago (ORD)

American Airlines • Coach

Chicago (ORD) to Toronto (YTO)

Delta • Coach
Price was CA $1,878, price is now CA $1,207 per person
CA $1,207
per person
found 21 hours ago
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

Jun 4 - Jun 7

3 night stay

Toronto (YTO) to Chicago (ORD)

Air Canada • Roundtrip • Coach
Price was CA $1,855, price is now CA $1,226 per person
CA $1,226
per person
found 1 day ago
Don't see what you're looking for?
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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! (9,934 reviews)
It was everything we needed it to be but the bed felt like laying on soft carpet. Why is it so firm that it didn’t even mold to my body?

Reviewed on Mar 15, 2026

Opens in a new windowCongress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
9.4/10 Exceptional! (3,536 reviews)
Staff was really nice and polite, Portuguese and Spanish speakers which was a must and breakfast buffet was amazing, highly recommended!

Reviewed on Mar 15, 2026

Opens in a new windowHotel Riu Plaza Chicago
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 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.
8.6/10 Excellent! (5,743 reviews)
Yes great

Reviewed on Mar 15, 2026

Opens in a new windowEmbassy Suites by Hilton Chicago Downtown River North
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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.
9/10 Wonderful! (3,920 reviews)
Good place

Reviewed on Mar 15, 2026

Opens in a new windowHilton 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 $108 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 September. 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 $108 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 $108 and CA $1,809 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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