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C$ 188+ 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 20/10. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
16 oct. — 23 oct.1
1 adult
1 adult, Economy

Find flight deals to Chicago

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 16 septiembre 2025.

sáb. 18/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
sáb. 25/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 14/9C$ 332
jue. 16/103:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
dom. 19/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 15/9C$ 333
sáb. 18/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
lun. 20/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 14/9C$ 336
jue. 6/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
dom. 9/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 14/9C$ 337
jue. 16/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
lun. 20/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 14/9C$ 338
mié. 15/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
jue. 16/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 15/9C$ 340
lun. 6/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
jue. 9/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 14/9C$ 341
vie. 17/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
dom. 26/104:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 14/9C$ 343
vie. 17/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
vie. 31/1011:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 14/9C$ 344
dom. 12/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
jue. 16/105:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 14/9C$ 345
mié. 15/103:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
vie. 17/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 15/9C$ 347
dom. 12/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
lun. 20/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 15/9C$ 348

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 16 septiembre 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

dom. 12/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

lun. 20/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 332

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

lun. 13/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

mar. 21/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 332

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

sáb. 18/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

sáb. 25/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 332

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

mié. 15/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

mar. 21/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 332

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

mié. 15/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

vie. 17/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 332

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

dom. 12/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

jue. 23/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 332

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

mar. 14/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

lun. 20/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 332

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

vie. 14/11

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

Nonstop1h 50m

Chicago Midway

dom. 16/11

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

Nonstop1h 42m

C$ 338

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

jue. 16/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

lun. 20/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 338

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

vie. 17/10

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

Chicago Midway

lun. 20/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 338

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/9

Showing 1-10 of 46 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 16 septiembre 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
7.9
Good
363 reviews
Check prices

Entertainment

7.0

Overall

7.9

Food

7.6

Crew

8.6

Comfort

7.9

Boarding

8.1

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
7.9
Good
363 reviews
Porter Airlines
7.9
Good
363 reviews
Check prices

Entertainment

7.0

Overall

7.9

Food

7.6

Crew

8.6

Comfort

7.9

Boarding

8.1

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
7.7
Good
438 reviews
Porter Airlines
7.9
Good
363 reviews
Check prices

Entertainment

7.0

Overall

7.9

Food

7.6

Crew

8.6

Comfort

7.9

Boarding

8.1

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
8,924 reviews
Porter Airlines
7.9
Good
363 reviews
Check prices

Entertainment

7.0

Overall

7.9

Food

7.6

Crew

8.6

Comfort

7.9

Boarding

8.1

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
10,000 reviews
Porter Airlines
7.9
Good
363 reviews
Check prices

Entertainment

7.0

Overall

7.9

Food

7.6

Crew

8.6

Comfort

7.9

Boarding

8.1

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
10,000 reviews
Porter Airlines
7.9
Good
363 reviews
Check prices

Entertainment

7.0

Overall

7.9

Food

7.6

Crew

8.6

Comfort

7.9

Boarding

8.1

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$ 556. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 771.

  • 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$ 1,098.

See more FAQs

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