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C$ 79+ 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 3/3. 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 — YVR
22 Jan — 29 Jan1
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 17 January 2025.

Cheapest airline

Frontier
On average, Frontier currently has the cheapest one-way flight from Chicago.
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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 17 January 2025.

Thu 20/24:45 p.m.ORD - YYC
Nonstop3h 51mWestJet
Mon 24/211:30 a.m.YYC - ORD
Nonstop3h 26mWestJet
Deal found 15/1C$ 213
Fri 30/55:30 p.m.ORD - YYC
Nonstop3h 49mMultiple Airlines
Tue 3/612:55 a.m.YYC - ORD
1 stop7h 57mMultiple Airlines
Deal found 15/1C$ 259
Thu 20/24:45 p.m.ORD - YVR
1 stop7h 41mWestJet
Thu 27/25:55 a.m.YVR - ORD
1 stop8h 01mWestJet
Deal found 15/1C$ 286
Tue 18/38:45 a.m.ORD - YYC
1 stop13h 56mUnited Airlines
Mon 24/37:20 p.m.YYC - ORD
1 stop13h 13mUnited Airlines
Deal found 14/1C$ 293
Mon 3/32:05 p.m.ORD - YYC
1 stop8h 13mAir Canada
Tue 25/38:30 a.m.YYC - ORD
1 stop9h 11mAir Canada
Deal found 14/1C$ 312
Tue 18/21:05 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 23/211:20 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 15/1C$ 319
Thu 20/24:45 p.m.ORD - YVR
1 stop7h 41mMultiple Airlines
Mon 24/29:15 p.m.YVR - ORD
2 stops17h 16mMultiple Airlines
Deal found 14/1C$ 333
Thu 20/21:05 p.m.MDW - YTZ
Nonstop1h 42mAir Transat
Sun 23/211:20 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Deal found 15/1C$ 349
Thu 30/17:26 a.m.ORD - YYZ
1 stop15h 27mMultiple Airlines
Mon 3/27:00 a.m.YYZ - ORD
1 stop8h 23mMultiple Airlines
Deal found 16/1C$ 362
Tue 18/31:16 p.m.MDW - YYC
1 stop8h 18mDelta
Tue 25/37:44 a.m.YYC - MDW
1 stop9h 34mDelta
Deal found 14/1C$ 374
Wed 9/49:09 p.m.MDW - YVR
1 stop26h 41mMultiple Airlines
Wed 16/49:15 a.m.YVR - MDW
1 stop8h 59mMultiple Airlines
Deal found 16/1C$ 378
Fri 7/25:30 a.m.MDW - YTZ
2 stops10h 18mMultiple Airlines
Sat 8/211:20 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Deal found 15/1C$ 378

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 17 January 2025. 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

Thu 20/2

4:45 p.m.-7:36 p.m.

Nonstop3h 51m

Calgary

Mon 24/2

11:30 a.m.-3:56 p.m.

Nonstop3h 26m

C$ 213

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Fri 30/5

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

Nonstop3h 49m

Calgary

Tue 3/6

12:55 a.m.-9:52 a.m.

1 stop7h 57m

C$ 259

ChicagoVancouver

ORD - YVR

ORDYVR

Chicago O'Hare Intl

Thu 20/2

4:45 p.m.-10:26 p.m.

1 stop7h 41m

Vancouver Intl

Thu 27/2

5:55 a.m.-3:56 p.m.

1 stop8h 01m

C$ 286

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Tue 18/3

8:45 a.m.-9:41 p.m.

1 stop13h 56m

Calgary

Mon 24/3

7:20 p.m.-9:33 a.m.

1 stop13h 13m

C$ 293

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Mon 3/3

2:05 p.m.-9:18 p.m.

1 stop8h 13m

Calgary

Mon 24/3

12:55 a.m.-10:54 a.m.

1 stop8h 59m

C$ 312

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 18/2

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

Nonstop1h 42m

Toronto Island

Sun 23/2

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

Nonstop1h 50m

C$ 319

ChicagoVancouver

ORD - YVR

ORDYVR

Chicago O'Hare Intl

Thu 20/2

4:45 p.m.-10:26 p.m.

1 stop7h 41m

Vancouver Intl

Mon 24/2

9:15 p.m.-4:31 p.m.

2 stops17h 16m

C$ 333

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 20/2

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

Nonstop1h 42m

Toronto Island

Sun 23/2

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

Nonstop1h 50m

C$ 349

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Tue 4/2

5:11 a.m.-11:55 p.m.

1 stop17h 44m

Toronto Pearson Intl

Tue 11/2

7:55 p.m.-6:18 p.m.

1 stop23h 23m

C$ 355

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 18/3

1:16 p.m.-8:34 p.m.

1 stop8h 18m

Calgary

Tue 25/3

7:44 a.m.-6:18 p.m.

1 stop9h 34m

C$ 374

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/1

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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 10 January 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 31 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$ 181). Flying from Chicago in December will prove the most costly (average of C$ 410). 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$ 640

Air Canada

Air Canada

From C$ 133

Emirates

Emirates

From C$ 657

What are popular destinations to fly to from Chicago?

From Chicago you can expect to find greater availability for the following destinations: New York (1,356 flights per day), Detroit (904 flights per day) and Los Angeles (557 flights per day).

Toronto

Toronto

From C$ 130

Abu Dhabi Zayed Intl

Abu Dhabi Zayed Intl

From C$ 383

New Delhi Indira Gandhi Intl

New Delhi Indira Gandhi Intl

From C$ 385

Istanbul

Istanbul

From C$ 376

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Miami, with prices starting at C$ 63. Explore other affordable destinations below.

Miami

Miami

From C$ 44

Pittsburgh

Pittsburgh

From C$ 48

Calgary

Calgary

From C$ 60

Detroit

Detroit

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.
Japan Airlines
8.3
Very good
1,448 reviews
Check prices

Food

7.7

Crew

8.7

Comfort

8.2

Entertainment

7.8

Boarding

8.4

Overall

8.3

Reviews

1 / 10

I like that flight because super nice and friendly. I’m a senior and quick not comfortable to ask what I need help. But would be nicer if they check us if we need any more help because we are not able to leave our seat. However Japan Aniline is my on top priority

Japan Airlines
8.3
Very good
1,448 reviews
Japan Airlines
8.3
Very good
1,448 reviews
Check prices

Food

7.7

Crew

8.7

Comfort

8.2

Entertainment

7.8

Boarding

8.4

Overall

8.3

Reviews

1 / 10

I like that flight because super nice and friendly. I’m a senior and quick not comfortable to ask what I need help. But would be nicer if they check us if we need any more help because we are not able to leave our seat. However Japan Aniline is my on top priority

Alaska Airlines
8.0
Very good
9,681 reviews
Japan Airlines
8.3
Very good
1,448 reviews
Check prices

Food

7.7

Crew

8.7

Comfort

8.2

Entertainment

7.8

Boarding

8.4

Overall

8.3

Reviews

1 / 10

I like that flight because super nice and friendly. I’m a senior and quick not comfortable to ask what I need help. But would be nicer if they check us if we need any more help because we are not able to leave our seat. However Japan Aniline is my on top priority

Delta
8.0
Very good
8,511 reviews
Japan Airlines
8.3
Very good
1,448 reviews
Check prices

Food

7.7

Crew

8.7

Comfort

8.2

Entertainment

7.8

Boarding

8.4

Overall

8.3

Reviews

1 / 10

I like that flight because super nice and friendly. I’m a senior and quick not comfortable to ask what I need help. But would be nicer if they check us if we need any more help because we are not able to leave our seat. However Japan Aniline is my on top priority

Porter Airlines
7.9
Good
276 reviews
Japan Airlines
8.3
Very good
1,448 reviews
Check prices

Food

7.7

Crew

8.7

Comfort

8.2

Entertainment

7.8

Boarding

8.4

Overall

8.3

Reviews

1 / 10

I like that flight because super nice and friendly. I’m a senior and quick not comfortable to ask what I need help. But would be nicer if they check us if we need any more help because we are not able to leave our seat. However Japan Aniline is my on top priority

Aeromexico
7.5
Good
1,849 reviews
Japan Airlines
8.3
Very good
1,448 reviews
Check prices

Food

7.7

Crew

8.7

Comfort

8.2

Entertainment

7.8

Boarding

8.4

Overall

8.3

Reviews

1 / 10

I like that flight because super nice and friendly. I’m a senior and quick not comfortable to ask what I need help. But would be nicer if they check us if we need any more help because we are not able to leave our seat. However Japan Aniline is my on top priority

Browse thousands of different options on Cheapflights for your next trip

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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 Calgary
Flights from O'Hare Intl to Hong Kong
Flights from O'Hare Intl to Ottawa
Flights from O'Hare Intl to Mexico City

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 17 January 2025.

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

    This month, the top selected destinations from Chicago are Ahmedabad, Mumbai, 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 Ottawa can be found at Chicago O'Hare Intl airport from C$ 239. While Chicago Midway airport is usually cheaper if your destination is Toronto with prices starting at C$ 319. 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$ 63). 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 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 Calgary from C$ 239 round trip
    Travel from Chicago to Toronto from C$ 319 round trip
    Travel from Chicago to Abbotsford from C$ 344 round trip
    Travel from Chicago to Vancouver from C$ 372 round trip
    Travel from Chicago to Montreal from C$ 388 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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