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C$ 140+ Cheap flights from Chicago

CHI — YYZ
11 Oct — 18 Oct1
1 adult
1 adult, Economy, 0 bags

Find flights from Chicago within your budget

 

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoToronto

MDW Chicago Midway - YTZ Toronto Island

MDWYTZ

Chicago Midway

Wed 30/9

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

Toronto Island

Wed 31/12

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

Nonstop0h 00m

C$ 140

ChicagoToronto

ORD Chicago O'Hare Intl - YYZ Toronto Pearson Intl

ORDYYZ

Chicago O'Hare Intl

Fri 4/12

8:55 a.m.-11:28 p.m.

1 stop13h 33m

Toronto Pearson Intl

Wed 31/12

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

Nonstop0h 00m

C$ 144

ChicagoToronto

ORD Chicago O'Hare Intl - YYZ Toronto Pearson Intl

ORDYYZ

Chicago O'Hare Intl

Tue 6/10

7:30 a.m.-1:47 p.m.

1 stop5h 17m

Toronto Pearson Intl

Wed 31/12

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

Nonstop0h 00m

C$ 144

ChicagoToronto

ORD Chicago O'Hare Intl - YYZ Toronto Pearson Intl

ORDYYZ

Chicago O'Hare Intl

Sun 6/12

9:34 p.m.-11:48 a.m.

1 stop13h 14m

Toronto Pearson Intl

Wed 31/12

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

Nonstop0h 00m

C$ 144

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Wed 28/10

9:29 a.m.-5:19 p.m.

1 stop6h 50m

Toronto Pearson Intl

Wed 31/12

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

Nonstop0h 00m

C$ 145

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Tue 20/10

1:27 p.m.-10:56 p.m.

1 stop8h 29m

Toronto Pearson Intl

Wed 31/12

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

Nonstop0h 00m

C$ 145

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Sat 26/9

6:40 p.m.-10:59 p.m.

1 stop3h 19m

Toronto Pearson Intl

Wed 31/12

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

Nonstop0h 00m

C$ 145

ChicagoToronto

ORD Chicago O'Hare Intl - YYZ Toronto Pearson Intl

ORDYYZ

Chicago O'Hare Intl

Sat 5/12

10:25 a.m.-6:43 p.m.

1 stop7h 18m

Toronto Pearson Intl

Wed 31/12

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

Nonstop0h 00m

C$ 145

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Sun 22/11

1:31 p.m.-10:57 p.m.

1 stop8h 26m

Toronto Pearson Intl

Wed 31/12

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

Nonstop0h 00m

C$ 145

ChicagoToronto

ORD Chicago O'Hare Intl - YYZ Toronto Pearson Intl

ORDYYZ

Chicago O'Hare Intl

Thu 10/12

8:55 a.m.-11:28 p.m.

1 stop13h 33m

Toronto Pearson Intl

Wed 31/12

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

Nonstop0h 00m

C$ 145

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/9

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$ 398). Flying from Chicago in August will prove the most costly (average of C$ 568). 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$ 990
Emirates
Emirates
From C$ 889
Air Canada
Air Canada
From C$ 233
United Airlines
United Airlines
From C$ 141

What are popular destinations to fly to from Chicago?

From Chicago you can expect to find greater availability for the following destinations: New York (713 flights per day), Orlando (435 flights per day) and Los Angeles (325 flights per day).

Toronto
Toronto
From C$ 134
Abu Dhabi Zayed Intl
Abu Dhabi Zayed Intl
From C$ 464
Dubai Intl
Dubai Intl
From C$ 1,101
Montreal
Montreal
From C$ 193

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Dallas/Fort Worth, with prices starting at C$ 65. Explore other affordable destinations below.

Dallas/Fort Worth
Dallas/Fort Worth
From C$ 65
New York
New York
From C$ 134
Toronto
Toronto
From C$ 134
Boston Logan Intl
Boston Logan Intl
From C$ 150

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 65 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 Friday evenings when prices are typically at their lowest. When considering other options, price-conscious travelers should avoid Saturday 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
7.4
Good
10,202 reviews
Check prices

Overall

7.4

Crew

8.1

Entertainment

7.1

Food

6.7

Comfort

7.3

Boarding

7.7

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
7.4
Good
10,202 reviews
United Airlines
7.4
Good
10,202 reviews
Check prices

Overall

7.4

Crew

8.1

Entertainment

7.1

Food

6.7

Comfort

7.3

Boarding

7.7

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 Cairo
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 Boston, Atlanta, Athens. 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 Ottawa can be found at Chicago O'Hare Intl airport from C$ 282. While Chicago Midway airport is usually cheaper if your destination is Toronto with prices starting at C$ 285. 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$ 61). Air Canada flights from Chicago to Montreal (C$ 135). WestJet flights from Chicago to Calgary (C$ 188).

  • 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$ 282 round trip
    Travel from Chicago to Calgary from C$ 343 round trip
    Travel from Chicago to Montreal from C$ 419 round trip
    Travel from Chicago to Vancouver from C$ 478 round trip
    Travel from Chicago to Québec City from C$ 517 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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