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C$ 147+ 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 15/9. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
21 Jun — 28 Jun1
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 16 June 2025.

Wed 16/73:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Wed 23/75:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 15/6C$ 219
Fri 19/92:10 p.m.YYZ - ORD
Nonstop1h 54mAir Canada
Mon 22/92:00 p.m.ORD - YYZ
Nonstop1h 43mAir Canada
Deal found 14/6C$ 223
Tue 8/72:45 p.m.YYZ - ORD
Nonstop2h 05mUnited Airlines
Wed 16/79:14 p.m.ORD - YYZ
Nonstop1h 44mUnited Airlines
Deal found 15/6C$ 251
Sat 12/77:55 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Sat 19/79:40 a.m.MDW - YTZ
Nonstop1h 40mAir Transat
Deal found 14/6C$ 254
Fri 4/77:00 a.m.YYZ - ORD
Nonstop1h 59mLufthansa
Mon 7/75:55 p.m.ORD - YYZ
Nonstop1h 49mLufthansa
Deal found 13/6C$ 262
Tue 29/77:55 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Tue 5/89:40 a.m.MDW - YTZ
Nonstop1h 40mMultiple Airlines
Deal found 14/6C$ 274
Sat 5/76:30 a.m.YYZ - ORD
Nonstop1h 55mMultiple Airlines
Mon 7/75:55 p.m.ORD - YYZ
Nonstop1h 49mMultiple Airlines
Deal found 14/6C$ 329
Sat 2/86:24 p.m.YYZ - ORD
Nonstop2h 00mAmerican Airlines
Sat 9/88:15 a.m.ORD - YYZ
Nonstop1h 44mAmerican Airlines
Deal found 15/6C$ 340

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 June 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 16/7

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

Nonstop1h 49m

Chicago Midway

Wed 23/7

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

Nonstop1h 42m

C$ 219

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 19/9

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

Nonstop1h 54m

Chicago O'Hare Intl

Mon 22/9

2:00 p.m.-4:43 p.m.

Nonstop1h 43m

C$ 223

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 8/7

2:45 p.m.-3:50 p.m.

Nonstop2h 05m

Chicago O'Hare Intl

Wed 16/7

9:14 p.m.-11:58 p.m.

Nonstop1h 44m

C$ 251

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 12/7

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

Nonstop1h 50m

Chicago Midway

Sat 19/7

9:40 a.m.-12:20 p.m.

Nonstop1h 40m

C$ 254

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 4/7

7:00 a.m.-7:59 a.m.

Nonstop1h 59m

Chicago O'Hare Intl

Mon 7/7

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

Nonstop1h 49m

C$ 262

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 29/7

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

Nonstop1h 50m

Chicago Midway

Tue 5/8

9:40 a.m.-12:20 p.m.

Nonstop1h 40m

C$ 274

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 5/7

6:30 a.m.-7:25 a.m.

Nonstop1h 55m

Chicago O'Hare Intl

Mon 7/7

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

Nonstop1h 49m

C$ 329

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 2/8

6:24 p.m.-7:24 p.m.

Nonstop2h 00m

Chicago O'Hare Intl

Sat 9/8

8:15 a.m.-10:59 a.m.

Nonstop1h 44m

C$ 340

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 15/9

4:40 p.m.-5:33 p.m.

Nonstop1h 53m

C$ 147

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 21/7

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

Nonstop1h 50m

C$ 147

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/6

Showing 1-10 of 14 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 16 June 2025.
Porter Airlines
8.0
Very good
289 reviews
Check prices

Entertainment

7.0

Comfort

8.1

Food

7.6

Crew

8.7

Boarding

8.2

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Porter Airlines
8.0
Very good
289 reviews
Porter Airlines
8.0
Very good
289 reviews
Check prices

Entertainment

7.0

Comfort

8.1

Food

7.6

Crew

8.7

Boarding

8.2

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Delta
8.0
Very good
7,963 reviews
Porter Airlines
8.0
Very good
289 reviews
Check prices

Entertainment

7.0

Comfort

8.1

Food

7.6

Crew

8.7

Boarding

8.2

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
KLM
7.8
Good
1,361 reviews
Porter Airlines
8.0
Very good
289 reviews
Check prices

Entertainment

7.0

Comfort

8.1

Food

7.6

Crew

8.7

Boarding

8.2

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Air Transat
7.8
Good
398 reviews
Porter Airlines
8.0
Very good
289 reviews
Check prices

Entertainment

7.0

Comfort

8.1

Food

7.6

Crew

8.7

Boarding

8.2

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
United Airlines
7.4
Good
8,797 reviews
Porter Airlines
8.0
Very good
289 reviews
Check prices

Entertainment

7.0

Comfort

8.1

Food

7.6

Crew

8.7

Boarding

8.2

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

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$ 436. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 1,109.

  • 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, May 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$ 1,034.

See more FAQs

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