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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 22/4. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
26 Mar — 2 Apr1
1 adult

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 21 March 2025.

Sun 27/43:50 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 6/59:40 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 20/3C$ 277
Wed 16/49:00 p.m.YYZ - ORD
Nonstop2h 06mAir Canada
Wed 23/412:59 p.m.ORD - YYZ
Nonstop1h 47mAir Canada
Deal found 20/3C$ 278
Fri 2/57:55 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Sat 3/59:40 a.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 20/3C$ 283
Sun 25/51:00 p.m.YYZ - ORD
Nonstop2h 01mMultiple Airlines
Fri 30/59:35 a.m.ORD - YYZ
Nonstop1h 40mMultiple Airlines
Deal found 20/3C$ 285
Thu 1/53:35 p.m.YTZ - MDW
Nonstop1h 49mMultiple Airlines
Sat 10/59:40 a.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 21/3C$ 294
Tue 29/41:00 p.m.YYZ - ORD
Nonstop2h 05mUnited Airlines
Wed 14/59:35 a.m.ORD - YYZ
Nonstop1h 40mUnited Airlines
Deal found 20/3C$ 324
Wed 9/411:35 a.m.YYZ - ORD
Nonstop1h 55mAmerican Airlines
Sun 13/49:55 a.m.ORD - YYZ
Nonstop1h 40mAmerican Airlines
Deal found 20/3C$ 346

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 21 March 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

Sun 27/4

3:50 p.m.-4:40 p.m.

Nonstop1h 50m

Chicago Midway

Tue 6/5

9:40 a.m.-12:22 p.m.

Nonstop1h 42m

C$ 277

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 16/4

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

Nonstop2h 06m

Chicago O'Hare Intl

Wed 23/4

12:59 p.m.-3:46 p.m.

Nonstop1h 47m

C$ 278

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 2/5

7:55 a.m.-8:45 a.m.

Nonstop1h 50m

Chicago Midway

Sat 3/5

9:40 a.m.-12:22 p.m.

Nonstop1h 42m

C$ 283

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 25/5

1:00 p.m.-2:01 p.m.

Nonstop2h 01m

Chicago O'Hare Intl

Fri 30/5

9:35 a.m.-12:15 p.m.

Nonstop1h 40m

C$ 285

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 1/5

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

Nonstop1h 49m

Chicago Midway

Sat 10/5

9:40 a.m.-12:22 p.m.

Nonstop1h 42m

C$ 294

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 29/4

1:00 p.m.-2:05 p.m.

Nonstop2h 05m

Chicago O'Hare Intl

Wed 14/5

9:35 a.m.-12:15 p.m.

Nonstop1h 40m

C$ 324

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 9/4

11:35 a.m.-12:30 p.m.

Nonstop1h 55m

Chicago O'Hare Intl

Sun 13/4

9:55 a.m.-12:35 p.m.

Nonstop1h 40m

C$ 346

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 22/4

11:00 a.m.-12:03 p.m.

Nonstop2h 03m

C$ 178

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 21/4

9:30 a.m.-10:20 a.m.

Nonstop1h 50m

C$ 178

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 21/5

7:55 a.m.-8:45 a.m.

Nonstop1h 50m

C$ 179

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/3

Showing 1-10 of 12 results
1
2

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 21 March 2025.
Delta
8.0
Very good
7,895 reviews
Check prices

Entertainment

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,895 reviews
Delta
8.0
Very good
7,895 reviews
Check prices

Entertainment

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Porter Airlines
7.9
Good
275 reviews
Delta
8.0
Very good
7,895 reviews
Check prices

Entertainment

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Air Transat
7.8
Good
380 reviews
Delta
8.0
Very good
7,895 reviews
Check prices

Entertainment

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
United Airlines
7.4
Good
8,605 reviews
Delta
8.0
Very good
7,895 reviews
Check prices

Entertainment

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,895 reviews
Check prices

Entertainment

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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$ 538. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 2,440.

  • Which airlines fly direct to Chicago?

    At the moment, Air Canada, United Airlines, Porter Airlines, WestJet, American Airlines, Delta, Alaska Airlines, Air Transat, WestJet Encore 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, February 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 Calgary. A round-trip direct flight from Calgary to Chicago typically costs around C$ 921.

See more FAQs

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