C$ 83+ Cheap flights from Chicago

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/11. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
CHI — YUL
11 Oct — 18 Oct1
1 adult
1 adult, Economy

What to know about flights from Chicago

Discover essential information about flights departing from Chicago, including flight schedules, destinations, airlines operating at the Chicago airport, and any specific guidelines or requirements for travellers. Please note that the information is based on the most recent updates available. Data last updated 11 September 2025.

Cheapest airline

Air Canada

Good round-trip deal

C$ 88 or less

Good one-way deal

C$ 79 or less
On average, Air Canada currently has the cheapest one-way flight from Chicago (avg. price of C$ 508).
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Price to beat on a round-trip flight from Chicago.
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Price to beat on a one-way flight from Chicago.
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Find flights from Chicago

Cheapest flights from Chicago
Explore the most affordable flight options available from Chicago. Find the lowest fares based on data from user searches, with prices last updated on 11 September 2025.

Fri 10/105:30 p.m.ORD - YYC
Nonstop3h 49mWestJet
Fri 17/1012:15 p.m.YYC - ORD
Nonstop3h 28mWestJet
Deal found 10/9C$ 193
Sat 11/105:30 p.m.ORD - YYC
Nonstop3h 49mWestJet
Sat 18/1012:15 p.m.YYC - ORD
Nonstop3h 28mWestJet
Deal found 9/9C$ 194
Fri 10/105:30 p.m.ORD - YYC
Nonstop3h 49mWestJet
Thu 16/1012:15 p.m.YYC - ORD
Nonstop3h 28mWestJet
Deal found 9/9C$ 197
Sun 12/105:30 p.m.ORD - YYC
Nonstop3h 49mWestJet
Sat 18/1012:15 p.m.YYC - ORD
Nonstop3h 28mWestJet
Deal found 9/9C$ 198
Sat 18/105:30 p.m.ORD - YVR
1 stop7h 06mWestJet
Fri 24/107:00 a.m.YVR - ORD
1 stop7h 43mWestJet
Deal found 9/9C$ 200
Thu 16/105:30 p.m.ORD - YVR
1 stop7h 06mWestJet
Sun 19/107:00 a.m.YVR - ORD
1 stop7h 43mWestJet
Deal found 9/9C$ 201
Sat 11/105:30 p.m.ORD - YYC
Nonstop3h 49mWestJet
Sun 12/1012:15 p.m.YYC - ORD
Nonstop3h 28mWestJet
Deal found 9/9C$ 202
Fri 31/102:20 p.m.ORD - YYC
Nonstop3h 55mWestJet
Mon 3/119:00 a.m.YYC - ORD
Nonstop3h 35mWestJet
Deal found 9/9C$ 204
Mon 6/105:30 p.m.ORD - YYC
Nonstop3h 49mWestJet
Thu 16/1012:15 p.m.YYC - ORD
Nonstop3h 28mWestJet
Deal found 9/9C$ 205
Sun 26/102:20 p.m.ORD - YYC
Nonstop3h 55mWestJet
Sun 2/119:00 a.m.YYC - ORD
Nonstop3h 35mWestJet
Deal found 11/9C$ 206
Sat 18/105:30 p.m.ORD - YVR
1 stop7h 06mWestJet
Sat 25/107:00 a.m.YVR - ORD
1 stop7h 43mWestJet
Deal found 9/9C$ 208
Thu 9/105:30 p.m.ORD - YYC
Nonstop3h 49mWestJet
Sat 18/1012:15 p.m.YYC - ORD
Nonstop3h 28mWestJet
Deal found 9/9C$ 208

Find flights from Chicago within your budget

 
Find flights departing from Chicago that match your specified budget. Filter results by price range, allowing you to narrow down options and find flights that fit within your financial constraints. Please note that the search results are based on data from user searches, with fares last updated on 11 September 2025. In the last 7 days, Cheapflights users made a total of 629,999 searches

Fly to

Pierre Elliott Trudeau Intl

Route

Depart

Return

Price

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 4/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

Toronto Island

Wed 8/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

C$ 237

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 15/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

Toronto Island

Wed 22/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

C$ 240

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 2/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

Toronto Island

Sun 5/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

C$ 240

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Wed 5/11

8:45 a.m.-11:35 a.m.

Nonstop3h 50m

Calgary

Tue 11/11

12:37 p.m.-5:10 p.m.

Nonstop3h 33m

C$ 256

ChicagoQuébec City

ORD - YQB

ORDYQB

Chicago O'Hare Intl

Mon 27/10

10:46 a.m.-2:13 p.m.

Nonstop2h 27m

Québec City

Thu 30/10

6:00 a.m.-11:18 a.m.

1 stop6h 18m

C$ 256

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Thu 6/11

8:45 a.m.-11:35 a.m.

Nonstop3h 50m

Calgary

Tue 11/11

12:37 p.m.-5:10 p.m.

Nonstop3h 33m

C$ 256

ChicagoQuébec City

ORD - YQB

ORDYQB

Chicago O'Hare Intl

Sun 2/11

10:46 a.m.-2:13 p.m.

Nonstop2h 27m

Québec City

Mon 17/11

6:00 a.m.-11:18 a.m.

1 stop6h 18m

C$ 256

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Fri 31/10

8:45 a.m.-11:35 a.m.

Nonstop3h 50m

Calgary

Mon 3/11

12:37 p.m.-5:10 p.m.

Nonstop3h 33m

C$ 256

ChicagoQuébec City

ORD - YQB

ORDYQB

Chicago O'Hare Intl

Mon 27/10

9:56 a.m.-1:36 p.m.

Nonstop2h 40m

Québec City

Fri 31/10

4:14 p.m.-6:04 p.m.

Nonstop2h 50m

C$ 261

ChicagoQuébec City

ORD - YQB

ORDYQB

Chicago O'Hare Intl

Mon 27/10

9:56 a.m.-1:36 p.m.

Nonstop2h 40m

Québec City

Thu 30/10

4:14 p.m.-6:04 p.m.

Nonstop2h 50m

C$ 261

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

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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
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.

Travel insights for flights from Chicago

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

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

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Pierre Elliott Trudeau Intl. Price data was last updated on 29 August 2025.

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 51 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, November is the cheapest month in which you can book a flight from Chicago (average of C$ 157). Flying from Chicago in July will prove the most costly (average of C$ 373). 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: Air Canada. This airline departs to the following popular destinations: Montreal.

Etihad Airways
Etihad Airways
From C$ 707
Air India
Air India
From C$ 733
Air Canada
Air Canada
From C$ 147
United Airlines
United Airlines
From C$ 123

What are popular destinations to fly to from Chicago?

From Chicago you can expect to find greater availability for the following destinations: New York (1,401 flights per day), Detroit (894 flights per day) and Los Angeles (736 flights per day).

Toronto
Toronto
From C$ 57
Abu Dhabi Zayed Intl
Abu Dhabi Zayed Intl
From C$ 338
Calgary
Calgary
From C$ 29
Istanbul
Istanbul
From C$ 369

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Calgary, with prices starting at C$ 40. Explore other affordable destinations below.

Calgary
Calgary
From C$ 29
New York
New York
From C$ 33
Vancouver Intl
Vancouver Intl
From C$ 42
Detroit
Detroit
From C$ 46

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.

Popular international destinations from Chicago

The most popular international flight routes departing from Chicago we’ve come across at this time.
Flights from O'Hare Intl to New Delhi
Flights from O'Hare Intl to Dubai
Flights from O'Hare Intl to Hong Kong
Flights from O'Hare Intl to Calgary
Flights from O'Hare Intl to Cancún
Flights from O'Hare Intl to Lisbon

Related info for your journey

Access useful and relevant information related to your journey from Chicago. This can include details such as airport transportation, visa requirements, travel insurance, luggage regulations, and any other information that can ensure a smooth and hassle-free travel experience. Please note that the information is based on general guidance and may need to be verified with official sources. Data last updated 11 September 2025.

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

    This month, the top selected destinations from Chicago are Athens, Boston, Atlanta. 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 Toronto can be found at Chicago Midway airport from C$ 237. While Chicago O'Hare Intl airport is usually cheaper if your destination is Ottawa with prices starting at C$ 240. 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 Spirit Airlines, Frontier, and WestJet to have the cheapest round-trip prices from Chicago. Some of the destinations and prices are as follows: Spirit Airlines flights from Chicago to Fort Lauderdale (C$ 57). Frontier flights from Chicago to Nashville Intl (C$ 71). WestJet flights from Chicago to Calgary (C$ 94).

  • What is the cheapest month to fly from Chicago?

    At the present moment the cheapest month to fly from Chicago is currently November; with July 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$ 237 round trip
    Travel from Chicago to Québec City from C$ 240 round trip
    Travel from Chicago to Calgary from C$ 244 round trip
    Travel from Chicago to Vancouver from C$ 247 round trip
    Travel from Chicago to Montreal from C$ 333 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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