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C$ 133+ Cheap flights from Chicago

CHI — YYZ
23 Nov — 30 Nov1
1 adult
1 adult, Economy, 0 bags

Find flights from Chicago within your budget

 

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoToronto

ORD Chicago O'Hare Intl - YTZ Toronto Island

ORDYTZ

Chicago O'Hare Intl

Sat 13/2

1:55 p.m.-7:56 p.m.

1 stop5h 01m

Toronto Island

Wed 31/12

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

Nonstop0h 00m

C$ 143

ChicagoToronto

ORD Chicago O'Hare Intl - YTZ Toronto Island

ORDYTZ

Chicago O'Hare Intl

Fri 27/11

6:20 p.m.-9:05 p.m.

Nonstop1h 45m

Toronto Island

Wed 31/12

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

Nonstop0h 00m

C$ 154

ChicagoToronto

ORD Chicago O'Hare Intl - YTZ Toronto Island

ORDYTZ

Chicago O'Hare Intl

Sun 6/12

7:05 a.m.-2:21 p.m.

1 stop6h 16m

Toronto Island

Wed 31/12

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

Nonstop0h 00m

C$ 155

ChicagoToronto

ORD Chicago O'Hare Intl - YYZ Toronto Pearson Intl

ORDYYZ

Chicago O'Hare Intl

Sat 2/1

6:54 a.m.-9:47 a.m.

Nonstop1h 53m

Toronto Pearson Intl

Wed 31/12

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

Nonstop0h 00m

C$ 158

ChicagoToronto

ORD Chicago O'Hare Intl - YYZ Toronto Pearson Intl

ORDYYZ

Chicago O'Hare Intl

Mon 14/12

10:57 a.m.-5:49 p.m.

1 stop5h 52m

Toronto Pearson Intl

Wed 31/12

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

Nonstop0h 00m

C$ 171

ChicagoToronto

ORD Chicago O'Hare Intl - YYZ Toronto Pearson Intl

ORDYYZ

Chicago O'Hare Intl

Thu 3/12

2:30 p.m.-11:26 p.m.

1 stop7h 56m

Toronto Pearson Intl

Wed 31/12

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

Nonstop0h 00m

C$ 171

ChicagoToronto

ORD Chicago O'Hare Intl - YYZ Toronto Pearson Intl

ORDYYZ

Chicago O'Hare Intl

Mon 29/3

4:40 p.m.-7:34 p.m.

Nonstop1h 54m

Toronto Pearson Intl

Wed 31/12

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

Nonstop0h 00m

C$ 172

ChicagoToronto

ORD Chicago O'Hare Intl - YYZ Toronto Pearson Intl

ORDYYZ

Chicago O'Hare Intl

Fri 12/2

7:05 a.m.-9:47 a.m.

Nonstop1h 42m

Toronto Pearson Intl

Wed 31/12

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

Nonstop0h 00m

C$ 172

ChicagoToronto

MDW Chicago Midway - YTZ Toronto Island

MDWYTZ

Chicago Midway

Mon 16/11

6:08 a.m.-12:50 p.m.

2 stops29h 42m

Toronto Island

Wed 31/12

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

Nonstop0h 00m

C$ 185

ChicagoToronto

ORD Chicago O'Hare Intl - YYZ Toronto Pearson Intl

ORDYYZ

Chicago O'Hare Intl

Sun 22/11

5:55 a.m.-2:25 p.m.

1 stop7h 30m

Toronto Pearson Intl

Wed 31/12

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

Nonstop0h 00m

C$ 186

Flights are sorted by cheapest round-trip flights first.

Deals found on 23/10

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Chicago

Have a flexible travel schedule? Discover the best time to fly from Chicago with our price prediction graph.
Estimated round-trip price

Travel insights for flights from Chicago

Get recent, data-driven insights about flights from Chicago including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Chicago?

Currently, February is the cheapest month in which you can book a flight from Chicago (average of C$ 403). Flying from Chicago in August will prove the most costly (average of C$ 576). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

Which airlines fly from Chicago?

For flights departing from Chicago check dates and pricing for the following: United Airlines, Air Canada, American Airlines. These airlines depart to the following popular destinations: Toronto.

Etihad Airways
Etihad Airways
From C$ 965
Emirates
Emirates
From C$ 930
Air Canada
Air Canada
From C$ 236
Qatar Airways
Qatar Airways
From C$ 987

What are popular destinations to fly to from Chicago?

From Chicago you can expect to find greater availability for the following destinations: New York (1,180 flights per day), Detroit (838 flights per day) and Los Angeles (667 flights per day).

Toronto
Toronto
From C$ 113
Abu Dhabi Zayed Intl
Abu Dhabi Zayed Intl
From C$ 499
Doha Hamad Intl
Doha Hamad Intl
From C$ 986
Dubai Intl
Dubai Intl
From C$ 1,411

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Toronto, with prices starting at C$ 113. Explore other affordable destinations below.

Toronto
Toronto
From C$ 113
New York
New York
From C$ 136
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From C$ 139
Denver Intl
Denver Intl
From C$ 170

When is the best time to book a flight from Chicago?

The price you pay for your flight from Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 71 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

When is the cheapest time to fly from Chicago?

Those who are seeking the cheapest fare on flights departing from Chicago would be wise to consider leaving during Sunday at noon when prices are typically at their lowest. When considering other options, price-conscious travelers should avoid Monday mornings when fares are usually the most expensive.

Airline reviews for flights from Chicago

Check out reviews from past customers who have flown United Airlines from Chicago to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.3
Good
10,432 reviews
Check prices

Overall

7.3

Food

6.7

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Dawn,Aug 2026

ORD - DEN

I missed my connecting flight because our plane took off ten minutes late and then when we got to the airport another plane was in our shoot waiting to get fueled up and that took 30 minutes so I missed my connecting flight. I asked if I could get off and they assured me the plane would most likely wait for me since they know what time the planes get in because of an app. I was not happy. I had to wait till 7:25 to board the next flight and then that was delayed. Gates changed till 9:20. Terrible
United Airlines
7.3
Good
10,432 reviews
United Airlines
7.3
Good
10,432 reviews
Check prices

Overall

7.3

Food

6.7

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Dawn,Aug 2026

ORD - DEN

I missed my connecting flight because our plane took off ten minutes late and then when we got to the airport another plane was in our shoot waiting to get fueled up and that took 30 minutes so I missed my connecting flight. I asked if I could get off and they assured me the plane would most likely wait for me since they know what time the planes get in because of an app. I was not happy. I had to wait till 7:25 to board the next flight and then that was delayed. Gates changed till 9:20. Terrible

Browse thousands of different options on Cheapflights for your next trip

Popular international destinations from Chicago

Flights from O'Hare Intl to Dubai
Flights from O'Hare Intl to Calgary
Flights from O'Hare Intl to Hong Kong

Related info for your journey

  • What are the most popular destinations to fly to from Chicago?

    This month, the top selected destinations from Chicago are Atlanta, Boston, Ahmedabad. Throughout the year, Atlanta, Boston, Mumbai are some of the top choices made by users flying from Chicago.

  • Which is the cheapest airport to catch a flight from Chicago?

    The cheapest routes to Québec City can be found at Chicago O'Hare Intl airport from C$ 291. While Chicago Midway airport is usually cheaper if your destination is Montreal with prices starting at C$ 415. Reference our flight search to find the best deals in real time.

  • What are the cheapest airlines flying from Chicago to anywhere?

    According to our data, users have found Frontier, Air Canada, and WestJet to have the cheapest round-trip prices from Chicago. Some of the destinations and prices are as follows: Frontier flights from Chicago to Atlanta Hartsfield-Jackson (C$ 62). Air Canada flights from Chicago to Montreal (C$ 137). WestJet flights from Chicago to Calgary (C$ 190).

  • What is the cheapest month to fly from Chicago?

    At the present moment the cheapest month to fly from Chicago is currently February; with August being the most expensive. Prices will vary depending on multiple factors such as booking in advance, airline and departure airports and times.

  • Where are the cheapest places to fly to from Chicago?

    Check out the cheapest flights from Chicago to embark to:
    Travel from Chicago to Toronto from C$ 291 round trip
    Travel from Chicago to Montreal from C$ 356 round trip
    Travel from Chicago to Vancouver from C$ 391 round trip
    Travel from Chicago to Calgary from C$ 479 round trip
    Travel from Chicago to Québec City from C$ 710 round trip

  • How does Cheapflights help users find flights from Chicago?

    Cheapflights helps you search for flights from Chicago via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

  • Why should you use Cheapflights to find cheap flight tickets from Chicago?

    By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights from Chicago.

  • Can Cheapflights find flights from Chicago with no change fees?

    Cheapflights does show flights with no change fees to all users. To see these options for flights from Chicago, users can toggle the no change fees filter when performing a flight search.

  • Can Cheapflights notify me if prices for flights from Chicago become cheaper?

    Of course! You can now track prices for flights from Chicago and get an alert from Cheapflights when they change. Click the bell icon next to the flight deals above and provide your email address to set up price alerts.

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How does Cheapflights help users find flights from Chicago?

Cheapflights helps you search for flights from Chicago via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

Why should you use Cheapflights to find cheap flight tickets from Chicago?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights from Chicago.

Can Cheapflights find flights from Chicago with no change fees?

Cheapflights does show flights with no change fees to all users. To see these options for flights from Chicago, users can toggle the no change fees filter when performing a flight search.

Can Cheapflights notify me if prices for flights from Chicago become cheaper?

Of course! You can now track prices for flights from Chicago and get an alert from Cheapflights when they change. Click the bell icon next to the flight deals above and provide your email address to set up price alerts.

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