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C$ 178+ 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 20/1. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
19 Nov — 26 Nov1
1 adult
1 adult, Economy

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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 20 October 2025.

Fri 9/19:15 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Mon 12/111:00 a.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 19/10C$ 242
Fri 16/19:15 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Mon 19/111:00 a.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 18/10C$ 245
Mon 12/12:15 p.m.YYZ - ORD
Nonstop1h 55mAir Canada
Wed 14/18:15 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 19/10C$ 250
Sat 17/111:00 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Wed 21/111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 20/10C$ 255
Fri 16/19:00 p.m.YYZ - ORD
Nonstop2h 05mUnited Airlines
Mon 19/16:28 p.m.ORD - YYZ
Nonstop1h 53mUnited Airlines
Deal found 18/10C$ 258
Thu 11/126:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Sun 14/122:55 p.m.ORD - YYZ
Nonstop1h 49mAmerican Airlines
Deal found 18/10C$ 264
Thu 4/121:10 p.m.YYZ - ORD
Nonstop2h 00mAmerican Airlines
Mon 8/128:10 a.m.ORD - YYZ
Nonstop1h 46mAmerican Airlines
Deal found 19/10C$ 265
Sat 17/111:00 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 19/111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 19/10C$ 272
Thu 4/121:10 p.m.YYZ - ORD
Nonstop2h 00mBritish Airways
Thu 11/128:10 a.m.ORD - YYZ
Nonstop1h 46mBritish Airways
Deal found 19/10C$ 285
Thu 18/129:00 a.m.YYZ - ORD
Nonstop2h 05mUnited Airlines
Wed 7/111:15 a.m.ORD - YYZ
Nonstop1h 46mUnited Airlines
Deal found 19/10C$ 287
Wed 24/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Thu 1/14:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/10C$ 293
Sun 21/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Thu 1/14:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/10C$ 297

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 20 October 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

YTZ - MDW

YTZMDW

Toronto Island

Wed 8/4

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Sat 11/4

12:45 p.m.-3:27 p.m.

Nonstop1h 42m

C$ 250

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 2/3

9:00 p.m.-10:04 p.m.

Nonstop2h 04m

Chicago O'Hare Intl

Mon 9/3

3:55 p.m.-6:34 p.m.

Nonstop1h 39m

C$ 258

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 1/2

12:05 p.m.-1:01 p.m.

Nonstop1h 56m

Chicago O'Hare Intl

Wed 25/2

10:00 a.m.-12:40 p.m.

Nonstop1h 40m

C$ 258

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 4/12

11:36 a.m.-12:31 p.m.

Nonstop1h 55m

Chicago O'Hare Intl

Mon 8/12

8:10 a.m.-10:56 a.m.

Nonstop1h 46m

C$ 265

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 18/12

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

Nonstop2h 05m

Chicago O'Hare Intl

Wed 7/1

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

Nonstop1h 46m

C$ 287

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 31/12

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

Nonstop2h 05m

Chicago O'Hare Intl

Mon 5/1

8:15 p.m.-10:54 p.m.

Nonstop1h 39m

C$ 287

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 4/12

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Thu 11/12

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

C$ 317

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 14/1

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Thu 15/1

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 329

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 4/12

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Mon 8/12

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

C$ 342

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 28/11

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Tue 2/12

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 353

Flights are sorted by cheapest round-trip flights first.

Deals found on 19/10

Showing 1-10 of 42 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 20 October 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
381 reviews
Check prices

Comfort

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.0

Food

7.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Porter Airlines
8.0
Very good
381 reviews
Porter Airlines
8.0
Very good
381 reviews
Check prices

Comfort

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.0

Food

7.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Air Transat
7.8
Good
466 reviews
Porter Airlines
8.0
Very good
381 reviews
Check prices

Comfort

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.0

Food

7.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
United Airlines
7.4
Good
8,991 reviews
Porter Airlines
8.0
Very good
381 reviews
Check prices

Comfort

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.0

Food

7.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
American Airlines
7.2
Good
11,026 reviews
Porter Airlines
8.0
Very good
381 reviews
Check prices

Comfort

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.0

Food

7.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Air Canada
7.1
Good
10,334 reviews
Porter Airlines
8.0
Very good
381 reviews
Check prices

Comfort

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.0

Food

7.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.

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$ 697. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 1,486.

  • Which airlines fly direct to Chicago?

    At the moment, Air Canada, United Airlines, WestJet, Porter Airlines, 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$ 1,555.

See more FAQs

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