Find flights
Airlines

C$ 92+ 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 20/1. 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
24 Dec — 31 Dec1
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 19 December 2024.

Cheapest airline

Frontier
On average, Frontier currently has the cheapest one-way flight from Chicago.

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 19 December 2024.

Tue 7/14:00 p.m.ORD - YYC
1 stop8h 18mAir Canada
Mon 27/112:50 a.m.YYC - ORD
1 stop9h 04mAir Canada
Deal found 18/12C$ 255
Tue 18/27:00 a.m.ORD - YYC
1 stop15h 41mMultiple Airlines
Mon 10/36:15 a.m.YYC - ORD
1 stop7h 36mMultiple Airlines
Deal found 18/12C$ 261
Thu 6/35:00 a.m.ORD - YYC
1 stop14h 16mUnited Airlines
Mon 10/37:20 p.m.YYC - ORD
1 stop14h 59mUnited Airlines
Deal found 19/12C$ 268
Sun 12/17:00 a.m.ORD - YYZ
1 stop15h 53mMultiple Airlines
Fri 24/19:25 a.m.YYZ - ORD
1 stop12h 20mMultiple Airlines
Deal found 17/12C$ 293
Sat 11/11:05 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Fri 24/111:20 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 18/12C$ 310
Wed 26/21:39 p.m.ORD - YVR
1 stop10h 51mMultiple Airlines
Sun 2/36:30 a.m.YVR - ORD
1 stop7h 26mMultiple Airlines
Deal found 18/12C$ 340
Sat 1/211:19 a.m.MDW - YYC
1 stop10h 34mKLM
Sat 8/26:35 a.m.YYC - MDW
1 stop10h 08mKLM
Deal found 17/12C$ 349
Sat 11/111:19 a.m.MDW - YYC
1 stop10h 34mDelta
Sat 1/26:35 a.m.YYC - MDW
1 stop10h 12mDelta
Deal found 18/12C$ 357
Sun 2/21:45 p.m.ORD - YYC
1 stop10h 33mDelta
Sun 9/26:35 a.m.YYC - ORD
1 stop9h 54mDelta
Deal found 19/12C$ 357
Fri 17/15:30 a.m.MDW - YTZ
2 stops10h 18mMultiple Airlines
Sun 19/111:20 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Deal found 18/12C$ 359
Wed 22/18:01 p.m.MDW - YVR
1 stop17h 14mMultiple Airlines
Tue 28/19:15 p.m.YVR - MDW
2 stops19h 51mMultiple Airlines
Deal found 18/12C$ 366
Mon 31/34:45 p.m.ORD - YVR
1 stop9h 16mWestJet
Mon 7/46:30 a.m.YVR - ORD
1 stop7h 26mWestJet
Deal found 18/12C$ 374

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 19 December 2024. In the last 7 days, Cheapflights users made a total of 629,999 searches

Fly to

Any airport

Route

Depart

Return

Price

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Tue 7/1

4:00 p.m.-11:18 p.m.

1 stop8h 18m

Calgary

Mon 27/1

12:50 a.m.-10:54 a.m.

1 stop9h 04m

C$ 255

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Tue 18/2

7:00 a.m.-9:41 p.m.

1 stop15h 41m

Calgary

Mon 10/3

6:15 a.m.-2:51 p.m.

1 stop7h 36m

C$ 261

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Thu 6/3

5:00 a.m.-6:16 p.m.

1 stop14h 16m

Calgary

Mon 10/3

7:20 p.m.-11:19 a.m.

1 stop14h 59m

C$ 268

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Mon 13/1

3:25 p.m.-11:53 p.m.

1 stop7h 28m

Toronto Pearson Intl

Thu 16/1

7:00 a.m.-1:50 p.m.

1 stop7h 50m

C$ 288

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 11/1

1:05 p.m.-3:47 p.m.

Nonstop1h 42m

Toronto Island

Fri 24/1

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

Nonstop1h 50m

C$ 310

ChicagoVancouver

ORD - YVR

ORDYVR

Chicago O'Hare Intl

Wed 26/2

1:39 p.m.-10:30 p.m.

1 stop10h 51m

Vancouver Intl

Sun 2/3

6:30 a.m.-3:56 p.m.

1 stop7h 26m

C$ 340

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 1/2

11:19 a.m.-8:53 p.m.

1 stop10h 34m

Calgary

Sat 8/2

6:35 a.m.-5:43 p.m.

1 stop10h 08m

C$ 349

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Mon 13/1

11:51 a.m.-5:46 p.m.

1 stop4h 55m

Toronto Pearson Intl

Mon 13/1

9:00 p.m.-10:13 p.m.

Nonstop2h 13m

C$ 354

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 11/1

11:19 a.m.-8:53 p.m.

1 stop10h 34m

Calgary

Sat 1/2

6:35 a.m.-5:47 p.m.

1 stop10h 12m

C$ 357

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sun 2/2

1:45 p.m.-11:18 p.m.

1 stop10h 33m

Calgary

Sun 9/2

6:35 a.m.-5:29 p.m.

1 stop9h 54m

C$ 357

Flights are sorted by cheapest round-trip flights first.

Deals found on 17/12

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 Pearson Intl. Price data was last updated on 13 December 2024.

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 70 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$ 151). Flying from Chicago in November will prove the most costly (average of C$ 209). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

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.
8.0
Very good
9,551 reviews

Boarding

8.2

Overall

8.0

Food

7.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Reviews

1 / 10

Things were good, crew was good. It was just the flight itself was very rough. Lots of turbulence, probably one of the shakiest flights I've been on. Kids throwing up, kids crying everywhere because of it.

8.0
Very good
9,551 reviews
8.0
Very good
9,551 reviews

Boarding

8.2

Overall

8.0

Food

7.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Reviews

1 / 10

Things were good, crew was good. It was just the flight itself was very rough. Lots of turbulence, probably one of the shakiest flights I've been on. Kids throwing up, kids crying everywhere because of it.

8.0
Very good
8,600 reviews
8.0
Very good
9,551 reviews

Boarding

8.2

Overall

8.0

Food

7.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Reviews

1 / 10

Things were good, crew was good. It was just the flight itself was very rough. Lots of turbulence, probably one of the shakiest flights I've been on. Kids throwing up, kids crying everywhere because of it.

7.8
Good
1,349 reviews
8.0
Very good
9,551 reviews

Boarding

8.2

Overall

8.0

Food

7.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Reviews

1 / 10

Things were good, crew was good. It was just the flight itself was very rough. Lots of turbulence, probably one of the shakiest flights I've been on. Kids throwing up, kids crying everywhere because of it.

7.4
Good
9,048 reviews
8.0
Very good
9,551 reviews

Boarding

8.2

Overall

8.0

Food

7.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Reviews

1 / 10

Things were good, crew was good. It was just the flight itself was very rough. Lots of turbulence, probably one of the shakiest flights I've been on. Kids throwing up, kids crying everywhere because of it.

7.2
Good
10,000 reviews
8.0
Very good
9,551 reviews

Boarding

8.2

Overall

8.0

Food

7.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Reviews

1 / 10

Things were good, crew was good. It was just the flight itself was very rough. Lots of turbulence, probably one of the shakiest flights I've been on. Kids throwing up, kids crying everywhere because of it.

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.

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 19 December 2024.
  • What are the most popular destinations to fly to from Chicago?

    This month, the top selected destinations from Chicago are Mumbai, Ahmedabad, Atlanta. Throughout the year, Atlanta, Boston, Athens 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 O'Hare Intl airport from C$ 222. While Chicago Midway airport is usually cheaper if your destination is Toronto with prices starting at C$ 316. 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 United Airlines 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$ 59). Frontier flights from Chicago to Atlanta Hartsfield-Jackson (C$ 62). United Airlines flights from Chicago to Cancun (C$ 188).

  • What is the cheapest month to fly from Chicago?

    At the present moment the cheapest month to fly from Chicago is currently February; with November 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 Calgary from C$ 222 round trip
    Travel from Chicago to Toronto from C$ 316 round trip
    Travel from Chicago to Vancouver from C$ 367 round trip
    Travel from Chicago to Montreal from C$ 390 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.