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C$ 104+ 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 17/5. 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
26 Feb — 5 Mar1
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 21 February 2025.

Cheapest airline

Frontier

Good round-trip deal

C$ 125 or less

Good one-way deal

C$ 62 or less
On average, Frontier currently has the cheapest one-way flight from Chicago (avg. price of C$ 122).
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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 21 February 2025.

Thu 10/44:45 p.m.ORD - YYC
Nonstop3h 51mWestJet
Mon 14/411:30 a.m.YYC - ORD
Nonstop3h 26mWestJet
Deal found 19/2C$ 230
Fri 4/48:25 p.m.ORD - YYZ
Nonstop1h 41mAir Canada
Wed 9/46:25 a.m.YYZ - ORD
1 stop5h 22mAir Canada
Deal found 20/2C$ 253
Wed 5/38:53 a.m.ORD - YYC
Nonstop3h 46mAir Canada
Wed 12/312:41 p.m.YYC - ORD
Nonstop3h 29mAir Canada
Deal found 19/2C$ 277
Sun 6/44:45 p.m.ORD - YYC
Nonstop3h 51mMultiple Airlines
Sun 13/48:30 a.m.YYC - ORD
1 stop9h 24mMultiple Airlines
Deal found 20/2C$ 283
Wed 9/42:58 p.m.ORD - YVR
1 stop9h 32mMultiple Airlines
Sun 13/43:55 p.m.YVR - ORD
1 stop12h 38mMultiple Airlines
Deal found 20/2C$ 286
Wed 14/55:30 p.m.ORD - YVR
1 stop7h 05mWestJet
Wed 21/57:00 a.m.YVR - ORD
1 stop7h 44mWestJet
Deal found 19/2C$ 295
Tue 1/46:25 p.m.ORD - YYZ
2 stops28h 30mMultiple Airlines
Tue 8/48:00 p.m.YYZ - ORD
1 stop19h 03mMultiple Airlines
Deal found 20/2C$ 298
Sat 5/412:55 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sat 12/411:10 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 21/2C$ 303
Mon 17/35:00 a.m.ORD - YYC
1 stop10h 21mUnited Airlines
Fri 21/36:14 a.m.YYC - ORD
1 stop17h 09mUnited Airlines
Deal found 20/2C$ 312
Thu 10/47:49 p.m.ORD - YUL
1 stop18h 06mMultiple Airlines
Mon 14/43:55 p.m.YUL - ORD
1 stop26h 46mMultiple Airlines
Deal found 20/2C$ 322
Tue 15/45:35 p.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Tue 22/49:30 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Deal found 21/2C$ 334
Mon 7/411:15 a.m.MDW - YUL
1 stop5h 47mPorter Airlines
Mon 14/411:50 a.m.YUL - MDW
1 stop5h 50mPorter Airlines
Deal found 21/2C$ 349

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 21 February 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 10/4

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

Nonstop3h 51m

Calgary

Mon 14/4

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

Nonstop3h 26m

C$ 230

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Fri 4/4

8:25 p.m.-11:06 p.m.

Nonstop1h 41m

Toronto Pearson Intl

Wed 9/4

6:25 a.m.-10:47 a.m.

1 stop5h 22m

C$ 253

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Wed 5/3

8:53 a.m.-11:39 a.m.

Nonstop3h 46m

Calgary

Wed 12/3

12:41 p.m.-5:10 p.m.

Nonstop3h 29m

C$ 277

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sun 6/4

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

Nonstop3h 51m

Calgary

Sun 13/4

8:30 a.m.-6:54 p.m.

1 stop9h 24m

C$ 283

ChicagoVancouver

ORD - YVR

ORDYVR

Chicago O'Hare Intl

Wed 9/4

2:58 p.m.-10:30 p.m.

1 stop9h 32m

Vancouver Intl

Sun 13/4

3:55 p.m.-6:33 a.m.

1 stop12h 38m

C$ 286

ChicagoVancouver

ORD - YVR

ORDYVR

Chicago O'Hare Intl

Wed 14/5

5:30 p.m.-10:35 p.m.

1 stop7h 05m

Vancouver Intl

Wed 21/5

7:00 a.m.-4:44 p.m.

1 stop7h 44m

C$ 295

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Tue 1/4

6:25 p.m.-11:55 p.m.

2 stops28h 30m

Toronto Pearson Intl

Tue 8/4

8:00 p.m.-2:03 p.m.

1 stop19h 03m

C$ 298

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 5/4

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

Nonstop1h 42m

Toronto Island

Sat 12/4

11:10 a.m.-12:00 p.m.

Nonstop1h 50m

C$ 303

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Mon 17/3

5:00 a.m.-2:21 p.m.

1 stop10h 21m

Calgary

Fri 21/3

6:14 a.m.-12:23 a.m.

1 stop17h 09m

C$ 312

ChicagoMontreal

ORD - YUL

ORDYUL

Chicago O'Hare Intl

Thu 10/4

7:49 p.m.-2:55 p.m.

1 stop18h 06m

Montreal Pierre Elliott Trudeau Intl

Mon 14/4

3:55 p.m.-5:41 p.m.

1 stop26h 46m

C$ 322

Flights are sorted by cheapest round-trip flights first.

Deals found on 19/2

Showing 1-10 of 60 results
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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 14 February 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$ 179). Flying from Chicago in December will prove the most costly (average of C$ 405). 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$ 639

Air Canada

Air Canada

From C$ 92

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 (1,526 flights per day), Detroit (978 flights per day) and Orlando (795 flights per day).

Toronto

Toronto

From C$ 100

Abu Dhabi Zayed Intl

Abu Dhabi Zayed Intl

From C$ 385

New Delhi Indira Gandhi Intl

New Delhi Indira Gandhi Intl

From C$ 354

Doha Hamad Intl

Doha Hamad Intl

From C$ 428

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is New York, with prices starting at C$ 50. Explore other affordable destinations below.

New York

New York

From C$ 35

Los Angeles

Los Angeles

From C$ 38

Miami

Miami

From C$ 39

Pittsburgh

Pittsburgh

From C$ 48

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
9,696 reviews
Check prices

Crew

8.5

Food

7.1

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Alaska Airlines
8.0
Very good
9,696 reviews
Alaska Airlines
8.0
Very good
9,696 reviews
Check prices

Crew

8.5

Food

7.1

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Delta
8.0
Very good
8,217 reviews
Alaska Airlines
8.0
Very good
9,696 reviews
Check prices

Crew

8.5

Food

7.1

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Porter Airlines
7.9
Good
276 reviews
Alaska Airlines
8.0
Very good
9,696 reviews
Check prices

Crew

8.5

Food

7.1

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Aeromexico
7.5
Good
1,771 reviews
Alaska Airlines
8.0
Very good
9,696 reviews
Check prices

Crew

8.5

Food

7.1

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

United Airlines
7.4
Good
8,761 reviews
Alaska Airlines
8.0
Very good
9,696 reviews
Check prices

Crew

8.5

Food

7.1

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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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 21 February 2025.

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

    This month, the top selected destinations from Chicago are Atlanta, Mumbai, Ahmedabad. 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 Québec City can be found at Chicago O'Hare Intl airport from C$ 251. While Chicago Midway airport is usually cheaper if your destination is Toronto with prices starting at C$ 297. 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$ 58). Frontier flights from Chicago to Atlanta Hartsfield-Jackson (C$ 62). WestJet flights from Chicago to Calgary (C$ 96).

  • 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$ 251 round trip
    Travel from Chicago to Vancouver from C$ 286 round trip
    Travel from Chicago to Toronto from C$ 297 round trip
    Travel from Chicago to Montreal from C$ 322 round trip
    Travel from Chicago to Québec City from C$ 575 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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