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C$ 152+ 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 15/6. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
4 Jun — 11 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 30 May 2025.

Mon 23/67:55 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 30/69:40 a.m.MDW - YTZ
Nonstop1h 40mPorter Airlines
Deal found 29/5C$ 225
Fri 3/106:35 p.m.YYZ - ORD
Nonstop1h 54mAir Canada
Mon 6/108:25 p.m.ORD - YYZ
Nonstop1h 43mAir Canada
Deal found 29/5C$ 227
Thu 4/91:00 p.m.YYZ - ORD
Nonstop2h 01mUnited Airlines
Mon 8/99:12 p.m.ORD - YYZ
Nonstop1h 46mUnited Airlines
Deal found 29/5C$ 228
Wed 23/77:00 a.m.YYZ - ORD
Nonstop1h 59mLufthansa
Tue 29/75:55 p.m.ORD - YYZ
Nonstop1h 49mLufthansa
Deal found 29/5C$ 258
Mon 21/73:35 p.m.YTZ - MDW
Nonstop1h 49mAir Transat
Sat 26/79:40 a.m.MDW - YTZ
Nonstop1h 40mAir Transat
Deal found 29/5C$ 263
Fri 4/77:55 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Sat 5/79:40 a.m.MDW - YTZ
Nonstop1h 40mMultiple Airlines
Deal found 29/5C$ 271
Thu 19/66:30 a.m.YYZ - ORD
Nonstop1h 55mAmerican Airlines
Sun 22/69:55 a.m.ORD - YYZ
Nonstop1h 45mAmerican Airlines
Deal found 29/5C$ 358

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 30 May 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

Mon 23/6

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

Nonstop1h 50m

Chicago Midway

Mon 30/6

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

Nonstop1h 40m

C$ 225

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 11/7

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

Nonstop1h 54m

Chicago O'Hare Intl

Fri 18/7

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

Nonstop1h 45m

C$ 235

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 20/6

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

Nonstop1h 59m

Chicago O'Hare Intl

Mon 23/6

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

Nonstop1h 44m

C$ 240

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 23/7

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

Nonstop1h 59m

Chicago O'Hare Intl

Tue 29/7

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

Nonstop1h 49m

C$ 258

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 16/6

4:05 p.m.-4:54 p.m.

Nonstop1h 49m

Chicago Midway

Wed 18/6

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

Nonstop1h 42m

C$ 276

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 26/6

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

Nonstop1h 50m

Chicago Midway

Sun 29/6

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

Nonstop1h 42m

C$ 287

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 19/6

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

Nonstop2h 05m

Chicago O'Hare Intl

Sun 22/6

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

Nonstop1h 44m

C$ 341

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 18/6

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

Nonstop1h 55m

Chicago O'Hare Intl

Sun 22/6

9:55 a.m.-12:40 p.m.

Nonstop1h 45m

C$ 358

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 30/6

9:00 a.m.-9:59 a.m.

Nonstop1h 59m

Chicago O'Hare Intl

Thu 10/7

10:00 a.m.-12:45 p.m.

Nonstop1h 45m

C$ 362

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 15/6

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

Nonstop1h 50m

C$ 152

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/5

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 30 May 2025.
Porter Airlines
8.0
Very good
286 reviews
Check prices

Food

7.6

Comfort

8.1

Crew

8.7

Overall

8.0

Entertainment

7.0

Boarding

8.2

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
286 reviews
Porter Airlines
8.0
Very good
286 reviews
Check prices

Food

7.6

Comfort

8.1

Crew

8.7

Overall

8.0

Entertainment

7.0

Boarding

8.2

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
7,954 reviews
Porter Airlines
8.0
Very good
286 reviews
Check prices

Food

7.6

Comfort

8.1

Crew

8.7

Overall

8.0

Entertainment

7.0

Boarding

8.2

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
389 reviews
Porter Airlines
8.0
Very good
286 reviews
Check prices

Food

7.6

Comfort

8.1

Crew

8.7

Overall

8.0

Entertainment

7.0

Boarding

8.2

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
8,756 reviews
Porter Airlines
8.0
Very good
286 reviews
Check prices

Food

7.6

Comfort

8.1

Crew

8.7

Overall

8.0

Entertainment

7.0

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
American Airlines
7.2
Good
10,000 reviews
Porter Airlines
8.0
Very good
286 reviews
Check prices

Food

7.6

Comfort

8.1

Crew

8.7

Overall

8.0

Entertainment

7.0

Boarding

8.2

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$ 392. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 1,179.

  • 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, 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$ 1,094.

See more FAQs

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