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C$ 166+ 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 25/6. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
4 May — 11 May1
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 29 April 2025.

Sat 12/77:55 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Wed 16/79:40 a.m.MDW - YTZ
Nonstop1h 40mPorter Airlines
Deal found 28/4C$ 245
Sat 31/57:55 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Mon 2/69:40 a.m.MDW - YTZ
Nonstop1h 40mMultiple Airlines
Deal found 27/4C$ 249
Fri 6/611:00 a.m.YYZ - ORD
Nonstop2h 01mAir Canada
Sun 8/67:04 a.m.ORD - YYZ
Nonstop1h 54mAir Canada
Deal found 28/4C$ 252
Thu 10/73:35 p.m.YTZ - MDW
Nonstop1h 49mAir Transat
Sun 13/75:20 p.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 28/4C$ 310
Mon 21/72:10 p.m.YYZ - ORD
Nonstop1h 54mMultiple Airlines
Fri 25/78:25 p.m.ORD - YYZ
Nonstop1h 45mMultiple Airlines
Deal found 28/4C$ 358
Thu 22/51:00 p.m.YYZ - ORD
Nonstop2h 01mUnited Airlines
Wed 28/55:55 p.m.ORD - YYZ
Nonstop1h 49mUnited Airlines
Deal found 28/4C$ 359
Fri 30/51:15 p.m.YYZ - ORD
Nonstop1h 55mAmerican Airlines
Sun 1/68:11 a.m.ORD - YYZ
Nonstop1h 40mAmerican Airlines
Deal found 28/4C$ 399
Sat 17/56:30 a.m.YYZ - ORD
Nonstop1h 55mWestJet Encore
Sat 17/59:50 a.m.ORD - YYZ
Nonstop1h 40mWestJet Encore
Deal found 27/4C$ 402
Thu 22/52:10 p.m.YYZ - ORD
Nonstop1h 55mLufthansa
Sun 25/58:25 p.m.ORD - YYZ
Nonstop1h 42mLufthansa
Deal found 28/4C$ 414

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 29 April 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

Fri 6/6

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

Nonstop1h 49m

Chicago Midway

Mon 9/6

5:50 p.m.-8:32 p.m.

Nonstop1h 42m

C$ 245

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 28/8

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

Nonstop1h 50m

Chicago Midway

Mon 1/9

9:15 a.m.-11:57 a.m.

Nonstop1h 42m

C$ 249

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 6/6

11:00 a.m.-12:01 p.m.

Nonstop2h 01m

Chicago O'Hare Intl

Sun 8/6

7:04 a.m.-9:58 a.m.

Nonstop1h 54m

C$ 252

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 10/7

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

Nonstop1h 49m

Chicago Midway

Sun 13/7

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

C$ 310

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 21/7

2:10 p.m.-3:04 p.m.

Nonstop1h 54m

Chicago O'Hare Intl

Fri 25/7

8:25 p.m.-11:10 p.m.

Nonstop1h 45m

C$ 358

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 22/5

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

Nonstop2h 01m

Chicago O'Hare Intl

Wed 28/5

5:55 p.m.-8:44 p.m.

Nonstop1h 49m

C$ 359

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 27/5

3:10 p.m.-4:05 p.m.

Nonstop1h 55m

Chicago O'Hare Intl

Tue 3/6

8:11 a.m.-10:51 a.m.

Nonstop1h 40m

C$ 380

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 30/5

1:15 p.m.-2:10 p.m.

Nonstop1h 55m

Chicago O'Hare Intl

Sun 1/6

8:11 a.m.-10:51 a.m.

Nonstop1h 40m

C$ 399

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 22/5

2:10 p.m.-3:05 p.m.

Nonstop1h 55m

Chicago O'Hare Intl

Sun 25/5

8:25 p.m.-11:07 p.m.

Nonstop1h 42m

C$ 414

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 25/6

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

Nonstop1h 49m

C$ 166

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/4

Showing 1-10 of 15 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 29 April 2025.
Porter Airlines
8.0
Very good
285 reviews
Check prices

Overall

8.0

Crew

8.8

Entertainment

7.0

Boarding

8.2

Food

7.6

Comfort

8.1

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Porter Airlines
8.0
Very good
285 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Overall

8.0

Crew

8.8

Entertainment

7.0

Boarding

8.2

Food

7.6

Comfort

8.1

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Delta
8.0
Very good
7,929 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Overall

8.0

Crew

8.8

Entertainment

7.0

Boarding

8.2

Food

7.6

Comfort

8.1

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Air Transat
7.8
Good
385 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Overall

8.0

Crew

8.8

Entertainment

7.0

Boarding

8.2

Food

7.6

Comfort

8.1

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Aeromexico
7.5
Good
1,697 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Overall

8.0

Crew

8.8

Entertainment

7.0

Boarding

8.2

Food

7.6

Comfort

8.1

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
United Airlines
7.4
Good
8,696 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Overall

8.0

Crew

8.8

Entertainment

7.0

Boarding

8.2

Food

7.6

Comfort

8.1

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you

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$ 633. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 1,349.

  • Which airlines fly direct to Chicago?

    At the moment, Air Canada, United Airlines, Porter Airlines, WestJet, American Airlines, Delta, Alaska Airlines, 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, 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 Vancouver Intl Airport. A round-trip direct flight from Vancouver Intl Airport to Chicago typically costs around C$ 611.

See more FAQs

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