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C$ 172+ Direct flights to Chicago

This is the cheapest price on a non-stop flight to Chicago found by a Cheapflights user in the last 72 hours by searching for a flight departing on 15/12. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
24 Dec — 31 Dec1
1 adult
1 adult, Economy, 0 bags

Find flight deals to Chicago

Enter your travel dates to find the best prices.

Cheapest flights to Chicago
Explore the most affordable flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on 24 November 2025.

Fri 5/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 8/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 21/11C$ 254
Mon 5/12:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 6/111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 22/11C$ 255
Wed 7/19:00 p.m.YYZ - ORD
Nonstop2h 05mAir Canada
Wed 14/18:00 a.m.ORD - YYZ
Nonstop1h 40mAir Canada
Deal found 23/11C$ 257
Mon 29/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 6/111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 22/11C$ 257
Thu 26/23:30 p.m.YYZ - ORD
Nonstop2h 09mUnited Airlines
Sun 8/37:10 a.m.ORD - YYZ
Nonstop1h 48mUnited Airlines
Deal found 22/11C$ 258
Thu 8/19:00 p.m.YYZ - ORD
Nonstop2h 05mUnited Airlines
Sun 11/111:15 a.m.ORD - YYZ
Nonstop1h 46mUnited Airlines
Deal found 23/11C$ 259
Thu 1/12:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 20/111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 23/11C$ 261
Wed 31/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 6/111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 22/11C$ 262
Thu 8/19:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 11/111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 23/11C$ 265
Thu 1/12:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 18/111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 22/11C$ 266
Tue 30/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 6/111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 22/11C$ 268
Sat 3/19:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 6/111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 22/11C$ 272

Best time to book a flight to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Fare Finder

 
Use the slider to find non-stop flights to Chicago within your budget. Price data is based on user searches made on Cheapflights. Over the past seven days, Cheapflights users made 629,999 searches and data was last updated on 24 November 2025.
Use the filters below to find and compare direct flights to Chicago that are best for you.

Fly from

Toronto

Route

Depart

Return

Price

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 7/1

9:00 p.m.-10:05 p.m.

Nonstop2h 05m

Chicago O'Hare Intl

Wed 14/1

8:00 a.m.-10:40 a.m.

Nonstop1h 40m

C$ 257

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 24/1

5:30 p.m.-6:50 p.m.

Nonstop2h 20m

Chicago O'Hare Intl

Mon 26/1

1:13 p.m.-4:02 p.m.

Nonstop1h 49m

C$ 258

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 12/1

6:45 p.m.-7:45 p.m.

Nonstop2h 00m

Chicago O'Hare Intl

Thu 15/1

8:00 a.m.-10:40 a.m.

Nonstop1h 40m

C$ 258

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 1/2

9:00 a.m.-10:06 a.m.

Nonstop2h 06m

Chicago O'Hare Intl

Thu 5/2

7:10 a.m.-9:58 a.m.

Nonstop1h 48m

C$ 258

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 13/2

6:45 p.m.-7:45 p.m.

Nonstop2h 00m

Chicago O'Hare Intl

Mon 16/2

8:40 p.m.-11:19 p.m.

Nonstop1h 39m

C$ 258

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 25/1

3:30 p.m.-4:40 p.m.

Nonstop2h 10m

Chicago O'Hare Intl

Thu 29/1

11:15 a.m.-2:01 p.m.

Nonstop1h 46m

C$ 258

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 13/2

9:00 a.m.-10:07 a.m.

Nonstop2h 07m

Chicago O'Hare Intl

Mon 16/2

7:07 a.m.-9:58 a.m.

Nonstop1h 51m

C$ 258

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 8/1

9:00 p.m.-10:05 p.m.

Nonstop2h 05m

Chicago O'Hare Intl

Sat 10/1

1:13 p.m.-4:02 p.m.

Nonstop1h 49m

C$ 258

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 6/1

9:00 a.m.-10:05 a.m.

Nonstop2h 05m

Chicago O'Hare Intl

Tue 13/1

4:50 p.m.-7:45 p.m.

Nonstop1h 55m

C$ 258

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 8/1

5:30 p.m.-6:50 p.m.

Nonstop2h 20m

Chicago O'Hare Intl

Sun 11/1

9:15 p.m.-11:59 p.m.

Nonstop1h 44m

C$ 259

Flights are sorted by cheapest round-trip flights first.

Deals found on 22/11

Showing 1-10 of 41 results
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Reviews of airlines flying non-stop to Chicago

Get insights into the airlines that provide direct flights to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 24 November 2025.
Read through reviews of airlines serving the United States, such as Porter Airlines,Air Transat, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
393 reviews
Check prices

Crew

8.6

Boarding

8.2

Food

7.6

Entertainment

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Porter Airlines
8.0
Very good
393 reviews
Porter Airlines
8.0
Very good
393 reviews
Check prices

Crew

8.6

Boarding

8.2

Food

7.6

Entertainment

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Air Transat
7.8
Good
478 reviews
Porter Airlines
8.0
Very good
393 reviews
Check prices

Crew

8.6

Boarding

8.2

Food

7.6

Entertainment

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
United Airlines
7.4
Good
9,036 reviews
Porter Airlines
8.0
Very good
393 reviews
Check prices

Crew

8.6

Boarding

8.2

Food

7.6

Entertainment

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
American Airlines
7.2
Good
11,045 reviews
Porter Airlines
8.0
Very good
393 reviews
Check prices

Crew

8.6

Boarding

8.2

Food

7.6

Entertainment

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Air Canada
7.1
Good
10,466 reviews
Porter Airlines
8.0
Very good
393 reviews
Check prices

Crew

8.6

Boarding

8.2

Food

7.6

Entertainment

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out

Temperature and rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average temperature and rainfall totals by month.

CHI

Temperature

-5 - 23 °C

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

FAQ about direct flights to Chicago

Find answers to frequently asked questions about direct flights to Chicago to unlock the best deals on Cheapflights.

  • How much are direct flights to Chicago?

    On average, a one-way direct flight to Chicago will cost users approximately C$ 471. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 1,552.

  • Which airlines fly direct to Chicago?

    At the moment, Air Canada, United Airlines, Porter Airlines, WestJet, American Airlines, Delta, Air Transat offer direct flights to Chicago. Air Canada is currently the most popular airline that flies direct to Chicago.

  • What is the best time of year to fly direct to Chicago?

    If you're seeking the lowest price on a direct flight to Chicago, April is worth consideration, as prices are usually at their lowest, on average. January may be most appealing to users looking for the quietest time to visit Chicago, when demand is typically at its lowest.

  • What is the most popular direct flight origin to Chicago?

    Currently, the most popular direct flight origin to Chicago is Toronto Pearson Intl Airport. A round-trip direct flight from Toronto Pearson Intl Airport to Chicago typically costs around C$ 2,158.

See more FAQs

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