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C$ 97+ 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 18/3. 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 — YYZ
26 Nov — 3 Dec1
1 adult
1 adult, Economy, 0 bags

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 27 October 2025.

Cheapest airline

WestJet

Good round-trip deal

C$ 64 or less

Good one-way deal

C$ 110 or less
On average, WestJet currently has the cheapest one-way flight from Chicago (avg. price of C$ 316).
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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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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 27 October 2025.

Fri 20/22:20 p.m.ORD - YYC
Nonstop3h 55mWestJet
Mon 23/29:00 a.m.YYC - ORD
Nonstop3h 35mWestJet
Deal found 26/10C$ 235
Tue 9/127:05 a.m.ORD - YQB
1 stop6h 14mAir Canada
Tue 16/1210:55 a.m.YQB - ORD
1 stop5h 15mAir Canada
Deal found 25/10C$ 253
Sat 15/1112:45 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Mon 17/112:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 25/10C$ 267
Fri 14/114:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 16/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 27/10C$ 269
Wed 3/124:01 p.m.ORD - YVR
1 stop21h 11mMultiple Airlines
Sun 7/1211:00 p.m.YVR - ORD
1 stop16h 27mMultiple Airlines
Deal found 25/10C$ 271
Fri 5/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 7/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 26/10C$ 271
Tue 2/125:00 a.m.ORD - YYZ
1 stop5h 14mAmerican Airlines
Fri 5/126:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Deal found 26/10C$ 271
Mon 8/1212:59 p.m.ORD - YVR
1 stop11h 21mMultiple Airlines
Mon 15/129:15 p.m.YVR - ORD
2 stops19h 31mMultiple Airlines
Deal found 25/10C$ 274
Fri 9/12:20 p.m.ORD - YYC
Nonstop3h 55mWestJet
Fri 16/19:00 a.m.YYC - ORD
Nonstop3h 35mWestJet
Deal found 26/10C$ 274
Wed 12/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sat 22/1111:00 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 26/10C$ 276
Mon 10/114:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Tue 11/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 26/10C$ 277
Tue 11/1110:46 a.m.ORD - YQB
Nonstop2h 27mUnited Airlines
Sat 15/112:55 p.m.YQB - ORD
Nonstop3h 02mUnited Airlines
Deal found 27/10C$ 277

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 27 October 2025. In the last 7 days, Cheapflights users made a total of 629,999 searches

Fly to

Pearson Intl

Route

Depart

Return

Price

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 13/11

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

Toronto Island

Sun 16/11

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

C$ 269

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 5/12

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

Toronto Island

Sun 7/12

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

C$ 276

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 15/11

12:45 p.m.-3:27 p.m.

Nonstop1h 42m

Toronto Island

Mon 17/11

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

C$ 276

ChicagoQuébec City

ORD - YQB

ORDYQB

Chicago O'Hare Intl

Tue 11/11

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

Nonstop2h 27m

Québec City

Sat 15/11

2:55 p.m.-4:57 p.m.

Nonstop3h 02m

C$ 277

ChicagoQuébec City

ORD - YQB

ORDYQB

Chicago O'Hare Intl

Wed 12/11

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

Nonstop2h 27m

Québec City

Sat 15/11

2:55 p.m.-4:57 p.m.

Nonstop3h 02m

C$ 277

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 20/2

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

Toronto Island

Wed 25/2

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

C$ 284

ChicagoQuébec City

ORD - YQB

ORDYQB

Chicago O'Hare Intl

Thu 19/3

7:15 a.m.-2:29 p.m.

1 stop6h 14m

Québec City

Mon 23/3

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

1 stop6h 18m

C$ 292

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Wed 17/12

9:10 p.m.-11:59 p.m.

Nonstop1h 49m

Toronto Pearson Intl

Mon 5/1

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

Nonstop2h 05m

C$ 294

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 21/3

12:45 p.m.-3:27 p.m.

Nonstop1h 42m

Toronto Island

Sun 22/3

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

C$ 295

ChicagoQuébec City

ORD - YQB

ORDYQB

Chicago O'Hare Intl

Sat 4/4

9:00 a.m.-3:59 p.m.

1 stop5h 59m

Québec City

Mon 6/4

6:05 a.m.-10:57 a.m.

1 stop5h 52m

C$ 298

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/10

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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 Pearson Intl. Price data was last updated on 24 October 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 68 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, March is the cheapest month in which you can book a flight from Chicago (average of C$ 148). Flying from Chicago in July will prove the most costly (average of C$ 262). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

When is the cheapest time to fly from Chicago?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Pearson Intl. Price data was last updated on 16 December 2024.

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

Which airlines fly from Chicago?

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

Air India
Air India
From C$ 999
Etihad Airways
Etihad Airways
From C$ 1,016
United Airlines
United Airlines
From C$ 172
Air Canada
Air Canada
From C$ 206

What are popular destinations to fly to from Chicago?

From Chicago you can expect to find greater availability for the following destinations: Detroit (500 flights per day), New York (431 flights per day) and Orlando (396 flights per day).

Istanbul
Istanbul
From C$ 523
Toronto
Toronto
From C$ 113
Montreal
Montreal
From C$ 170
Vancouver Intl
Vancouver Intl
From C$ 113

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$ 64. Explore other affordable destinations below.

Dallas/Fort Worth
Dallas/Fort Worth
From C$ 64
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From C$ 109
New York
New York
From C$ 110
Vancouver Intl
Vancouver Intl
From C$ 113

Airline reviews for flights from Chicago

Get insights into the airlines that provide service from Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing airline for your flight from Chicago. In the last 7 days, Cheapflights users made a total of 629,999 searches.
Check out reviews from past customers who have flown United Airlines and Air Canada 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
8,997 reviews
Check prices

Food

6.6

Crew

8.1

Boarding

7.7

Overall

7.4

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
8,997 reviews
United Airlines
7.4
Good
8,997 reviews
Check prices

Food

6.6

Crew

8.1

Boarding

7.7

Overall

7.4

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
Air Canada
7.1
Good
10,370 reviews
United Airlines
7.4
Good
8,997 reviews
Check prices

Food

6.6

Crew

8.1

Boarding

7.7

Overall

7.4

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

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

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 27 October 2025.

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

    This month, the top selected destinations from Chicago are Boston, Atlanta, Ahmedabad. Throughout the year, Atlanta, Boston, Ahmedabad 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$ 197. While Chicago O'Hare Intl airport is usually cheaper if your destination is Québec City with prices starting at C$ 232. 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 Dallas/Fort Worth (C$ 71). WestJet flights from Chicago to Calgary (C$ 95).

  • What is the cheapest month to fly from Chicago?

    At the present moment the cheapest month to fly from Chicago is currently March; 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$ 197 round trip
    Travel from Chicago to Montreal from C$ 236 round trip
    Travel from Chicago to Calgary from C$ 257 round trip
    Travel from Chicago to Vancouver from C$ 271 round trip
    Travel from Chicago to Québec City from C$ 277 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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