Find flights
Airlines

C$ 100+ 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 28/9. 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
17 Jun — 24 Jun1
1 adult

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 June 2025.

Cheapest airline

Frontier

Good round-trip deal

C$ 134 or less

Good one-way deal

C$ 40 or less
On average, Frontier currently has the cheapest one-way flight from Chicago (avg. price of C$ 221).
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

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 June 2025.

Thu 17/75:30 p.m.ORD - YYC
Nonstop3h 49mWestJet
Tue 22/712:15 p.m.YYC - ORD
Nonstop3h 29mWestJet
Deal found 10/6C$ 215
Thu 18/95:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sat 20/97:30 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 12/6C$ 231
Mon 14/75:30 p.m.ORD - YYC
Nonstop3h 49mMultiple Airlines
Wed 23/711:45 p.m.YYC - ORD
1 stop8h 24mMultiple Airlines
Deal found 10/6C$ 235
Mon 29/92:00 p.m.ORD - YYZ
Nonstop1h 43mAir Canada
Wed 1/104:40 p.m.YYZ - ORD
Nonstop1h 53mAir Canada
Deal found 12/6C$ 237
Thu 18/99:31 p.m.ORD - YYZ
1 stop11h 33mUnited Airlines
Wed 24/95:15 p.m.YYZ - ORD
Nonstop1h 57mUnited Airlines
Deal found 10/6C$ 242
Mon 25/85:30 p.m.ORD - YEG
1 stop7h 57mWestJet
Wed 27/88:00 a.m.YEG - ORD
1 stop7h 44mWestJet
Deal found 10/6C$ 245
Sun 22/68:45 a.m.ORD - YYC
Nonstop3h 53mUnited Airlines
Sat 28/66:15 a.m.YYC - ORD
1 stop12h 48mUnited Airlines
Deal found 12/6C$ 269
Tue 24/69:40 a.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Thu 26/67:55 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Deal found 12/6C$ 269
Mon 22/93:35 p.m.ORD - YYC
1 stop8h 41mAir Canada
Tue 30/91:10 a.m.YYC - ORD
1 stop7h 41mAir Canada
Deal found 11/6C$ 276
Tue 15/76:00 a.m.ORD - YYZ
1 stop5h 05mAmerican Airlines
Tue 15/73:45 p.m.YYZ - ORD
1 stop6h 46mAmerican Airlines
Deal found 12/6C$ 282
Wed 13/89:40 a.m.MDW - YTZ
Nonstop1h 40mAir Transat
Sat 16/87:55 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Deal found 11/6C$ 295
Fri 10/108:40 a.m.ORD - YEG
1 stop8h 26mAir Canada
Sun 12/101:00 a.m.YEG - ORD
1 stop7h 51mAir Canada
Deal found 10/6C$ 308

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 June 2025. 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

Thu 17/7

5:30 p.m.-8:19 p.m.

Nonstop3h 49m

Calgary

Tue 22/7

12:15 p.m.-4:44 p.m.

Nonstop3h 29m

C$ 215

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 18/9

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

Toronto Island

Sat 20/9

7:30 a.m.-8:19 a.m.

Nonstop1h 49m

C$ 231

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Mon 14/7

5:30 p.m.-8:19 p.m.

Nonstop3h 49m

Calgary

Tue 22/7

1:10 a.m.-9:09 a.m.

1 stop6h 59m

C$ 235

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Mon 29/9

2:00 p.m.-4:43 p.m.

Nonstop1h 43m

Toronto Pearson Intl

Wed 1/10

4:40 p.m.-5:33 p.m.

Nonstop1h 53m

C$ 237

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Thu 18/9

9:31 p.m.-10:04 a.m.

1 stop11h 33m

Toronto Pearson Intl

Wed 24/9

5:15 p.m.-6:12 p.m.

Nonstop1h 57m

C$ 242

ChicagoEdmonton

ORD - YEG

ORDYEG

Chicago O'Hare Intl

Mon 25/8

5:30 p.m.-12:27 a.m.

1 stop7h 57m

Edmonton

Wed 27/8

8:00 a.m.-4:44 p.m.

1 stop7h 44m

C$ 245

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sun 22/6

8:45 a.m.-11:38 a.m.

Nonstop3h 53m

Calgary

Sat 28/6

6:15 a.m.-8:03 p.m.

1 stop12h 48m

C$ 269

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 24/6

9:40 a.m.-12:22 p.m.

Nonstop1h 42m

Toronto Island

Thu 26/6

7:55 a.m.-8:45 a.m.

Nonstop1h 50m

C$ 269

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Mon 22/9

3:35 p.m.-11:16 p.m.

1 stop8h 41m

Calgary

Mon 29/9

1:10 a.m.-9:51 a.m.

1 stop7h 41m

C$ 276

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Tue 15/7

6:00 a.m.-12:05 p.m.

1 stop5h 05m

Toronto Pearson Intl

Tue 15/7

3:45 p.m.-9:31 p.m.

1 stop6h 46m

C$ 282

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/6

Showing 1-10 of 60 results
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 9 June 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 40 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, October is the cheapest month in which you can book a flight from Chicago (average of C$ 172). Flying from Chicago in December will prove the most costly (average of C$ 390). 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, United Airlines. These airlines depart to the following popular destinations: Vancouver.

Etihad Airways
Etihad Airways
From C$ 640
Air India
Air India
From C$ 685
Air Canada
Air Canada
From C$ 92
United Airlines
United Airlines
From C$ 154

What are popular destinations to fly to from Chicago?

From Chicago you can expect to find greater availability for the following destinations: Detroit (1,226 flights per day), New York (985 flights per day) and Los Angeles (762 flights per day).

Toronto
Toronto
From C$ 68
New Delhi Indira Gandhi Intl
New Delhi Indira Gandhi Intl
From C$ 370
Calgary
Calgary
From C$ 87
Vancouver Intl
Vancouver Intl
From C$ 142

What is the cheapest place to fly to from Chicago?

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

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From C$ 29
Toronto
Toronto
From C$ 68
Portland
Portland
From C$ 68
Boston Logan Intl
Boston Logan Intl
From C$ 68

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.
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Porter Airlines
8.0
Very good
288 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Delta
8.0
Very good
7,950 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Finnair
7.6
Good
1,290 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
United Airlines
7.4
Good
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.

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 Calgary
Flights from O'Hare Intl to Dubai
Flights from O'Hare Intl to Lisbon
Flights from O'Hare Intl to Halifax
Flights from O'Hare Intl to Edmonton

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 June 2025.

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

    This month, the top selected destinations from Chicago are Athens, Boston, Amman. 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 Edmonton can be found at Chicago O'Hare Intl airport from C$ 215. While Chicago Midway airport is usually cheaper if your destination is Edmonton with prices starting at C$ 231. 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$ 56). Frontier flights from Chicago to Atlanta Hartsfield-Jackson (C$ 75). WestJet flights from Chicago to Calgary (C$ 93).

  • What is the cheapest month to fly from Chicago?

    At the present moment the cheapest month to fly from Chicago is currently October; with December 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$ 215 round trip
    Travel from Chicago to Calgary from C$ 249 round trip
    Travel from Chicago to Montreal from C$ 261 round trip
    Travel from Chicago to Edmonton from C$ 283 round trip
    Travel from Chicago to Vancouver from C$ 346 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.