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C$ 84+ 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 23/2. 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 — YVR
25 Feb — 4 Mar1
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 26 January 2026.

Cheapest airline

WestJet

Good round-trip deal

C$ 170 or less

Good one-way deal

C$ 87 or less
On average, WestJet currently has the cheapest one-way flight from Chicago (avg. price of C$ 306).
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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 26 January 2026.

Fri 24/42:20 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Mon 27/412:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Deal found 26/1C$ 225
Wed 15/48:42 a.m.
ORD
-
YYC
Nonstop3h 50m
United Airlines
Wed 22/412:34 p.m.
YYC
-
ORD
Nonstop3h 27m
United Airlines
Deal found 25/1C$ 253
Mon 20/411:00 a.m.
MDW
-
YUL
1 stop5h 45m
Porter Airlines
Thu 30/410:15 a.m.
YUL
-
MDW
1 stop6h 05m
Porter Airlines
Deal found 26/1C$ 255
Wed 6/53:50 p.m.
ORD
-
YYC
1 stop8h 08m
Air Canada
Wed 13/56:30 a.m.
YYC
-
ORD
1 stop7h 25m
Air Canada
Deal found 26/1C$ 256
Mon 25/510:25 a.m.
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Tue 2/66:30 a.m.
YUL
-
MDW
1 stop4h 10m
Porter Airlines
Deal found 24/1C$ 257
Tue 2/65:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Thu 11/612:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Deal found 25/1C$ 257
Thu 19/210:00 a.m.
ORD
-
YYZ
Nonstop1h 40m
Air Canada
Mon 23/22:15 p.m.
YYZ
-
ORD
Nonstop1h 55m
Air Canada
Deal found 26/1C$ 259
Tue 19/55:30 p.m.
ORD
-
YYC
Nonstop3h 49m
WestJet
Wed 27/512:15 p.m.
YYC
-
ORD
Nonstop3h 28m
WestJet
Deal found 24/1C$ 260
Thu 9/44:15 p.m.
MDW
-
YUL
1 stop5h 30m
Porter Airlines
Mon 13/46:45 a.m.
YUL
-
MDW
1 stop4h 20m
Porter Airlines
Deal found 24/1C$ 262
Fri 3/42:20 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Mon 13/49:00 a.m.
YYC
-
ORD
Nonstop3h 35m
WestJet
Deal found 24/1C$ 262
Fri 24/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Sun 26/49:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 24/1C$ 263
Thu 4/65:35 p.m.
MDW
-
YTZ
Nonstop1h 40m
Multiple Airlines
Sun 7/64:00 p.m.
YTZ
-
MDW
Nonstop1h 50m
Multiple Airlines
Deal found 25/1C$ 266

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 26 January 2026. In the last 7 days, Cheapflights users made a total of 629,999 searches

Fly to

Vancouver Intl

Route

Depart

Return

Price

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Wed 15/4

8:42 a.m.-11:32 a.m.

Nonstop3h 50m

Calgary

Wed 22/4

12:34 p.m.-5:01 p.m.

Nonstop3h 27m

C$ 253

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Mon 25/5

10:25 a.m.-5:15 p.m.

1 stop5h 50m

Montreal Pierre Elliott Trudeau Intl

Fri 5/6

6:30 a.m.-9:40 a.m.

1 stop4h 10m

C$ 255

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Mon 20/4

11:00 a.m.-4:30 p.m.

1 stop4h 30m

Montreal Pierre Elliott Trudeau Intl

Thu 30/4

11:25 a.m.-3:20 p.m.

1 stop4h 55m

C$ 257

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 4/6

5:35 p.m.-8:15 p.m.

Nonstop1h 40m

Toronto Island

Sun 7/6

4:00 p.m.-4:50 p.m.

Nonstop1h 50m

C$ 266

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Fri 1/5

10:25 a.m.-5:15 p.m.

1 stop5h 50m

Montreal Pierre Elliott Trudeau Intl

Tue 5/5

12:25 p.m.-4:50 p.m.

1 stop5h 25m

C$ 267

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Fri 10/4

4:15 p.m.-10:45 p.m.

1 stop5h 30m

Montreal Pierre Elliott Trudeau Intl

Sun 12/4

10:15 a.m.-3:20 p.m.

1 stop6h 05m

C$ 267

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Wed 1/4

11:00 a.m.-6:15 p.m.

1 stop6h 15m

Montreal Pierre Elliott Trudeau Intl

Tue 14/4

12:05 p.m.-3:20 p.m.

1 stop4h 15m

C$ 267

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Thu 23/4

11:00 a.m.-5:45 p.m.

1 stop5h 45m

Montreal Pierre Elliott Trudeau Intl

Mon 27/4

11:25 a.m.-3:20 p.m.

1 stop4h 55m

C$ 267

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 12/3

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

Nonstop1h 42m

Toronto Island

Thu 19/3

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

C$ 268

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 29/5

5:35 p.m.-8:15 p.m.

Nonstop1h 40m

Toronto Island

Sun 31/5

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

C$ 268

Flights are sorted by cheapest round-trip flights first.

Deals found on 25/1

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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 Vancouver Intl. Price data was last updated on 23 January 2026.

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 74 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, February is the cheapest month in which you can book a flight from Chicago (average of C$ 144). Flying from Chicago in August will prove the most costly (average of C$ 412). 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. This airline departs to the following popular destinations: Vancouver.

Air India
Air India
From C$ 844
Etihad Airways
Etihad Airways
From C$ 955
Air Canada
Air Canada
From C$ 148
United Airlines
United Airlines
From C$ 169

What are popular destinations to fly to from Chicago?

From Chicago you can expect to find greater availability for the following destinations: New York (1,444 flights per day), Detroit (956 flights per day) and Toronto (796 flights per day).

Abu Dhabi Zayed Intl
Abu Dhabi Zayed Intl
From C$ 437
Toronto
Toronto
From C$ 87
New Delhi Indira Gandhi Intl
New Delhi Indira Gandhi Intl
From C$ 379
Istanbul
Istanbul
From C$ 440

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$ 68. Explore other affordable destinations below.

Calgary
Calgary
From C$ 68
Dallas/Fort Worth
Dallas/Fort Worth
From C$ 76
Fort Lauderdale
Fort Lauderdale
From C$ 79
Toronto
Toronto
From C$ 87

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
9,200 reviews
Check prices

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Crew

8.1

Overall

7.4

Food

6.6

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,200 reviews
United Airlines
7.4
Good
9,200 reviews
Check prices

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Crew

8.1

Overall

7.4

Food

6.6

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
Air Canada
7.1
Good
10,656 reviews
United Airlines
7.4
Good
9,200 reviews
Check prices

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Crew

8.1

Overall

7.4

Food

6.6

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

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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 New Delhi
Flights from O'Hare Intl to Dubai
Flights from O'Hare Intl to Mexico City
Flights from O'Hare Intl to Calgary
Flights from O'Hare Intl to Hong Kong

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 26 January 2026.

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

    This month, the top selected destinations from Chicago are Atlanta, Ahmedabad, Mumbai. 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$ 236. While Chicago O'Hare Intl airport is usually cheaper if your destination is Québec City with prices starting at C$ 253. 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 WestJet, Spirit Airlines, and Air Canada to have the cheapest round-trip prices from Chicago. Some of the destinations and prices are as follows: WestJet flights from Chicago to Calgary (C$ 93). Spirit Airlines flights from Chicago to Fort Lauderdale (C$ 102). Air Canada flights from Chicago to Montreal (C$ 104).

  • 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 Montreal from C$ 236 round trip
    Travel from Chicago to Toronto from C$ 237 round trip
    Travel from Chicago to Calgary from C$ 253 round trip
    Travel from Chicago to Vancouver from C$ 359 round trip
    Travel from Chicago to Québec City from C$ 646 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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