Find flights
Airlines

C$ 111+ 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 13/5. 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
11 Apr — 18 Apr1
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 12 March 2026.

Cheapest airline

United Airlines

Good round-trip deal

C$ 121 or less

Good one-way deal

C$ 35 or less
On average, United Airlines currently has the cheapest one-way flight from Chicago (avg. price of C$ 340).
Search Deals
Price to beat on a round-trip flight from Chicago.
Search Deals
Price to beat on a one-way flight from Chicago.
Search Deals

Find flights from Chicago

Enter your travel dates to find the best prices.

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 12 March 2026.

Wed 27/55:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Fri 29/512:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Deal found 8/3C$ 243
Fri 8/55:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Sun 24/512:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Deal found 8/3C$ 244
Wed 27/55:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Thu 28/512:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Deal found 10/3C$ 258
Thu 7/55:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Fri 29/512:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Deal found 8/3C$ 272
Thu 16/412:50 p.m.
ORD
-
YUL
Nonstop2h 15m
Air Canada
Mon 20/46:30 p.m.
YUL
-
ORD
Nonstop2h 35m
Air Canada
Deal found 8/3C$ 272
Thu 7/55:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Sun 24/512:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Deal found 8/3C$ 273
Fri 24/44:05 p.m.
MDW
-
YUL
1 stop5h 40m
Porter Airlines
Tue 28/46:50 a.m.
YUL
-
MDW
1 stop4h 25m
Porter Airlines
Deal found 8/3C$ 274
Thu 16/412:50 p.m.
ORD
-
YUL
Nonstop2h 15m
Air Canada
Sun 19/49:15 a.m.
YUL
-
ORD
1 stop4h 50m
Air Canada
Deal found 10/3C$ 274
Mon 13/411:00 a.m.
MDW
-
YUL
1 stop5h 45m
Porter Airlines
Thu 16/46:50 a.m.
YUL
-
MDW
1 stop4h 25m
Porter Airlines
Deal found 10/3C$ 277
Tue 14/411:00 a.m.
MDW
-
YUL
1 stop4h 30m
Porter Airlines
Sun 19/49:50 a.m.
YUL
-
MDW
1 stop6h 30m
Porter Airlines
Deal found 8/3C$ 280
Sat 28/312:45 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Sun 29/32:30 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 7/3C$ 281
Tue 26/510:25 a.m.
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Mon 1/66:30 a.m.
YUL
-
MDW
1 stop4h 10m
Porter Airlines
Deal found 9/3C$ 282

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

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 1/4

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

Nonstop1h 42m

Toronto Island

Sat 4/4

11:20 a.m.-12:10 p.m.

Nonstop1h 50m

C$ 286

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 1/4

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

Nonstop1h 42m

Toronto Island

Wed 29/4

9:25 a.m.-10:15 a.m.

Nonstop1h 50m

C$ 292

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 22/4

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

Nonstop1h 42m

Toronto Island

Wed 29/4

9:25 a.m.-10:15 a.m.

Nonstop1h 50m

C$ 295

ChicagoMontreal

ORD - YUL

ORDYUL

Chicago O'Hare Intl

Fri 15/5

6:03 p.m.-9:26 p.m.

Nonstop2h 23m

Montreal Pierre Elliott Trudeau Intl

Mon 18/5

6:10 a.m.-8:00 a.m.

Nonstop2h 50m

C$ 320

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 4/4

12:55 p.m.-3:37 p.m.

Nonstop1h 42m

Toronto Island

Mon 6/4

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

Nonstop1h 50m

C$ 320

ChicagoMontreal

ORD - YUL

ORDYUL

Chicago O'Hare Intl

Sat 4/4

6:01 p.m.-12:13 a.m.

1 stop5h 12m

Montreal Pierre Elliott Trudeau Intl

Sat 11/4

5:00 p.m.-6:52 p.m.

Nonstop2h 52m

C$ 334

ChicagoMontreal

ORD - YUL

ORDYUL

Chicago O'Hare Intl

Thu 30/4

6:00 a.m.-1:09 p.m.

1 stop6h 09m

Montreal Pierre Elliott Trudeau Intl

Sat 2/5

5:00 p.m.-6:52 p.m.

Nonstop2h 52m

C$ 334

ChicagoMontreal

ORD - YUL

ORDYUL

Chicago O'Hare Intl

Fri 8/5

5:00 a.m.-1:09 p.m.

1 stop7h 09m

Montreal Pierre Elliott Trudeau Intl

Sun 10/5

6:10 a.m.-8:00 a.m.

Nonstop2h 50m

C$ 334

ChicagoMontreal

ORD - YUL

ORDYUL

Chicago O'Hare Intl

Tue 28/4

6:00 a.m.-1:09 p.m.

1 stop6h 09m

Montreal Pierre Elliott Trudeau Intl

Wed 29/4

6:10 a.m.-8:00 a.m.

Nonstop2h 50m

C$ 334
Quickest round-trip

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 28/5

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

Nonstop1h 40m

Toronto Island

Tue 2/6

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

C$ 337

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/3

Showing 1-10 of 60 resultsSorted by cheapest first
1
2
3
...
6

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 6 March 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$ 159). Flying from Chicago in August will prove the most costly (average of C$ 420). 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.

Etihad Airways
Etihad Airways
From C$ 947
Air India
Air India
From C$ 835
Air Canada
Air Canada
From C$ 147
United Airlines
United Airlines
From C$ 167

What are popular destinations to fly to from Chicago?

From Chicago you can expect to find greater availability for the following destinations: New York (1,465 flights per day), Detroit (958 flights per day) and Toronto (848 flights per day).

Toronto
Toronto
From C$ 123
Calgary
Calgary
From C$ 84
Abu Dhabi Zayed Intl
Abu Dhabi Zayed Intl
From C$ 338
Los Angeles Los Angeles
Los Angeles Los Angeles
From C$ 234

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Houston Hobby, with prices starting at C$ 22. Explore other affordable destinations below.

Houston Hobby
Houston Hobby
From C$ 22
Dallas/Fort Worth
Dallas/Fort Worth
From C$ 56
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From C$ 57
New York
New York
From C$ 57

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
9,418 reviews
Check prices

Entertainment

7.1

Overall

7.4

Comfort

7.3

Crew

8.1

Boarding

7.7

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
9,418 reviews
United Airlines
7.4
Good
9,418 reviews
Check prices

Entertainment

7.1

Overall

7.4

Comfort

7.3

Crew

8.1

Boarding

7.7

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
10,800 reviews
United Airlines
7.4
Good
9,418 reviews
Check prices

Entertainment

7.1

Overall

7.4

Comfort

7.3

Crew

8.1

Boarding

7.7

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

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 Dubai
Flights from O'Hare Intl to Calgary
Flights from O'Hare Intl to New Delhi

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 12 March 2026.

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

    This month, the top selected destinations from Chicago are Atlanta, Boston, Austin. Throughout the year, Boston, Atlanta, 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$ 282. While Chicago O'Hare Intl airport is usually cheaper if your destination is Halifax with prices starting at C$ 288. 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, United Airlines, and Air Canada to have the cheapest round-trip prices from Chicago. Some of the destinations and prices are as follows: Spirit Airlines flights from Chicago to Miami (C$ 98). United Airlines flights from Chicago to Tirana Rinas (C$ 106). Air Canada flights from Chicago to Toronto (C$ 133).

  • 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$ 282 round trip
    Travel from Chicago to Calgary from C$ 288 round trip
    Travel from Chicago to Toronto from C$ 299 round trip
    Travel from Chicago to Vancouver from C$ 390 round trip
    Travel from Chicago to Halifax from C$ 441 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.

See more FAQs

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.