Find flights
Deals
When to book
Airlines

C$ 149+ 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 21/7. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
1 Jul — 8 Jul1
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 26 June 2025.

Thu 7/87:55 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 10/89:40 a.m.MDW - YTZ
Nonstop1h 40mPorter Airlines
Deal found 25/6C$ 220
Thu 7/88:15 a.m.YYZ - ORD
Nonstop1h 54mAir Canada
Sun 10/88:25 p.m.ORD - YYZ
Nonstop1h 45mAir Canada
Deal found 24/6C$ 232
Fri 12/91:00 p.m.YYZ - ORD
Nonstop2h 01mUnited Airlines
Tue 16/98:55 a.m.ORD - YYZ
Nonstop1h 54mUnited Airlines
Deal found 25/6C$ 234
Sat 19/77:55 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Sat 26/79:40 a.m.MDW - YTZ
Nonstop1h 40mAir Transat
Deal found 25/6C$ 260
Fri 8/87:25 p.m.YYZ - ORD
Nonstop2h 01mAmerican Airlines
Fri 15/84:04 p.m.ORD - YYZ
Nonstop1h 41mAmerican Airlines
Deal found 23/6C$ 267
Sat 9/87:55 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Sat 16/89:40 a.m.MDW - YTZ
Nonstop1h 40mMultiple Airlines
Deal found 26/6C$ 275
Fri 8/87:25 p.m.YYZ - ORD
Nonstop2h 01mBritish Airways
Fri 15/84:04 p.m.ORD - YYZ
Nonstop1h 41mBritish Airways
Deal found 24/6C$ 293
Fri 18/79:00 p.m.YYZ - ORD
Nonstop2h 05mLufthansa
Mon 21/79:14 p.m.ORD - YYZ
Nonstop1h 44mLufthansa
Deal found 25/6C$ 301
Thu 7/89:00 a.m.YYZ - ORD
Nonstop1h 55mMultiple Airlines
Sun 10/88:25 p.m.ORD - YYZ
Nonstop1h 45mMultiple Airlines
Deal found 26/6C$ 308

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 26 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

Thu 7/8

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

Nonstop1h 50m

Chicago Midway

Sun 10/8

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

Nonstop1h 40m

C$ 220

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 7/8

8:15 a.m.-9:09 a.m.

Nonstop1h 54m

Chicago O'Hare Intl

Sun 10/8

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

Nonstop1h 45m

C$ 232

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 12/9

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

Nonstop2h 01m

Chicago O'Hare Intl

Tue 16/9

8:55 a.m.-11:49 a.m.

Nonstop1h 54m

C$ 234

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 21/7

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

Nonstop1h 50m

Chicago Midway

Sun 27/7

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

Nonstop1h 40m

C$ 258

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 8/8

7:25 p.m.-8:26 p.m.

Nonstop2h 01m

Chicago O'Hare Intl

Fri 15/8

4:04 p.m.-6:45 p.m.

Nonstop1h 41m

C$ 267

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 9/8

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

Nonstop1h 50m

Chicago Midway

Sat 16/8

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

Nonstop1h 40m

C$ 275

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 8/8

7:25 p.m.-8:26 p.m.

Nonstop2h 01m

Chicago O'Hare Intl

Fri 15/8

4:04 p.m.-6:45 p.m.

Nonstop1h 41m

C$ 293

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 18/7

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

Nonstop2h 05m

Chicago O'Hare Intl

Mon 21/7

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

Nonstop1h 44m

C$ 301

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 7/8

9:00 a.m.-9:55 a.m.

Nonstop1h 55m

Chicago O'Hare Intl

Sun 10/8

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

Nonstop1h 45m

C$ 308

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 21/7

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

Nonstop1h 50m

C$ 149

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/6

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 26 June 2025.
Read through reviews of airlines serving the United States, such as Porter Airlines,Delta, andAir Transat. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
293 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Comfort

8.1

Food

7.6

Crew

8.7

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
293 reviews
Porter Airlines
8.0
Very good
293 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Comfort

8.1

Food

7.6

Crew

8.7

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
7,964 reviews
Porter Airlines
8.0
Very good
293 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Comfort

8.1

Food

7.6

Crew

8.7

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
401 reviews
Porter Airlines
8.0
Very good
293 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Comfort

8.1

Food

7.6

Crew

8.7

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
8,838 reviews
Porter Airlines
8.0
Very good
293 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Comfort

8.1

Food

7.6

Crew

8.7

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!!!
Virgin Atlantic
7.4
Good
654 reviews
Porter Airlines
8.0
Very good
293 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Comfort

8.1

Food

7.6

Crew

8.7

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$ 440. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 929.

  • Which airlines fly direct to Chicago?

    At the moment, Air Canada, United Airlines, WestJet, Porter Airlines, American Airlines, Delta, Air Transat, Alaska Airlines 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$ 627.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Direct flights to Illinois

Book a non-stop flight to one of these other cities located in Illinois.
Direct flights to St. Louis

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.