Flights To Illinois - Cheap Flights Starting at CA $190

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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.

Wed, Nov 18 - Thu, Nov 26
YTZ
Billy Bishop Toronto City
ORD
O'Hare Intl.
CA $314 Roundtrip, found 4 hours ago
CA $314
Roundtrip
found 4 hours ago
Select Air Canada flight, departing Wed, Nov 18 from Billy Bishop Toronto City to O'Hare Intl., returning Thu, Nov 26, priced at CA $314 found 4 hours ago
Wed, Nov 18 - Thu, Nov 26
YTZ
Billy Bishop Toronto City
ORD
O'Hare Intl.
CA $319 Roundtrip, found 4 hours ago
CA $319
Roundtrip
found 4 hours ago
Select Air Canada flight, departing Wed, Nov 18 from Billy Bishop Toronto City to O'Hare Intl., returning Thu, Nov 26, priced at CA $319 found 4 hours ago
Sat, Nov 28 - Tue, Dec 1
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $322 Roundtrip, found 5 hours ago
CA $322
Roundtrip
found 5 hours ago
Select United flight, departing Sat, Nov 28 from Pearson Intl. to O'Hare Intl., returning Tue, Dec 1, priced at CA $322 found 5 hours ago
Fri, Sep 25 - Sun, Sep 27
YYZ
Pearson Intl.
MDW
Midway Intl.
CA $330 Roundtrip, found 2 hours ago
CA $330
Roundtrip
found 2 hours ago
Select Delta flight, departing Fri, Sep 25 from Pearson Intl. to Midway Intl., returning Sun, Sep 27, priced at CA $330 found 2 hours ago
Tue, Oct 13 - Thu, Oct 15
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $330 Roundtrip, just found
CA $330
Roundtrip
just found
Select Delta flight, departing Tue, Oct 13 from Pearson Intl. to O'Hare Intl., returning Thu, Oct 15, priced at CA $330 just found
Wed, Sep 23 - Sat, Sep 26
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
CA $335 Roundtrip, just found
CA $335
Roundtrip
just found
Select Porter Airlines flight, departing Wed, Sep 23 from Billy Bishop Toronto City to Midway Intl., returning Sat, Sep 26, priced at CA $335 just found
Thu, Oct 29 - Sat, Oct 31
YTZ
Billy Bishop Toronto City
ORD
O'Hare Intl.
CA $335 Roundtrip, just found
CA $335
Roundtrip
just found
Select Porter Airlines flight, departing Thu, Oct 29 from Billy Bishop Toronto City to O'Hare Intl., returning Sat, Oct 31, priced at CA $335 just found
Thu, Oct 29 - Sat, Oct 31
YTZ
Billy Bishop Toronto City
ORD
O'Hare Intl.
CA $377 Roundtrip, just found
CA $377
Roundtrip
just found
Select Air Transat flight, departing Thu, Oct 29 from Billy Bishop Toronto City to O'Hare Intl., returning Sat, Oct 31, priced at CA $377 just found
OriginDestinationTravel datesFlights from*
ATLSt. LouisNovember 7 to November 10CA $161
LAXChicagoOctober 16 to October 20CA $301
ATLChicagoOctober 21 to October 24CA $329
ATLChicagoSeptember 29 to October 3CA $332
JFKChicagoOctober 20 to October 21CA $374
DFWChicagoOctober 5 to October 10CA $387
DALChicagoOctober 6 to November 14CA $387
LAXChicagoOctober 10 to October 17CA $452
DFWSt. LouisSeptember 28 to September 30CA $462
EWRChicagoOctober 2 to October 3CA $487
LAXSt. LouisOctober 23 to October 24CA $489
DFWSavoyOctober 27 to October 31CA $719
HKGChicagoNovember 23 to December 1CA $1,217
PVGChicagoOctober 26 to November 4CA $1,476
PEKChicagoSeptember 23 to September 29CA $1,565
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
JFKChicagoSeptember 11 to September 14CA $426
ATLChicagoSeptember 12 to September 15CA $561
LAXChicagoSeptember 12 to September 23CA $562
ATLChicagoSeptember 13 to September 19CA $600
JFKSt. LouisSeptember 12 to September 13CA $729
DFWSt. LouisSeptember 12 to September 13CA $737
DALChicagoSeptember 12 to September 13CA $763
LAXSt. LouisSeptember 11 to September 18CA $943
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection
4.5-star property

The Talbott, Autograph Collection

Nov 12 - Nov 16

4 night stay

Detroit (DTW) to Chicago (ORD)

American Airlines • Coach

Chicago (ORD) to Detroit (DTW)

Delta • Coach
Price was CA $1,321, price is now CA $904 per person
CA $904
per person
found 8 hours ago
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

Nov 12 - Nov 16

4 night stay

Detroit (DTW) to Chicago (ORD)

American Airlines • Coach

Chicago (ORD) to Detroit (DTW)

Delta • Coach
Price was CA $1,605, price is now CA $996 per person
CA $996
per person
found 8 hours ago
Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

Nov 12 - Nov 16

4 night stay

Detroit (DTW) to Chicago (ORD)

American Airlines • Coach

Chicago (ORD) to Detroit (DTW)

Delta • Coach
Price was CA $2,355, price is now CA $1,541 per person
CA $1,541
per person
found 8 hours 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! (10,333 reviews)
"Excellent location, very clean and comfortable room."

Reviewed on Sep 9, 2026

Opens in a new windowCongress Plaza Hotel
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.
Opens in a new windowThe Chicago Hotel Collection Ambassador Gold Coast
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4 out of 5
One Superior Place Chicago IL
Stay at this aparthotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
9.4/10 Exceptional! (890 reviews)
"Great spot!"

Reviewed on Sep 7, 2026

Opens in a new windowKasa Magnificent Mile Chicago
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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! (5,434 reviews)
"Great area and view but unfortunately no fridge so we couldn’t keep any food leftovers"

Reviewed on Sep 8, 2026

Opens in a new windowRiver Hotel
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 $161 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 November. 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 $161 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 $161 and CA $1,565 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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