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C$ 108+ 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 25/5. 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
16 Apr — 23 Apr1
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 11 April 2025.

Cheapest airline

Frontier

Good round-trip deal

C$ 105 or less

Good one-way deal

C$ 124 or less
On average, Frontier currently has the cheapest one-way flight from Chicago (avg. price of C$ 123).
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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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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 11 April 2025.

Sat 10/55:30 p.m.ORD - YVR
1 stop8h 40mWestJet
Sun 11/57:00 a.m.YVR - ORD
1 stop7h 44mWestJet
Deal found 10/4C$ 232
Tue 13/58:45 a.m.ORD - YYC
Nonstop3h 56mAir Canada
Sat 24/512:38 p.m.YYC - ORD
Nonstop3h 32mAir Canada
Deal found 10/4C$ 233
Tue 13/58:45 a.m.ORD - YYC
Nonstop3h 56mUnited Airlines
Sat 24/512:38 p.m.YYC - ORD
Nonstop3h 32mUnited Airlines
Deal found 10/4C$ 253
Tue 13/58:45 a.m.ORD - YYC
Nonstop3h 56mMultiple Airlines
Mon 26/512:25 a.m.YYC - ORD
1 stop7h 25mMultiple Airlines
Deal found 9/4C$ 268
Wed 14/56:59 p.m.ORD - YVR
1 stop21h 31mMultiple Airlines
Wed 21/57:00 a.m.YVR - ORD
1 stop7h 44mMultiple Airlines
Deal found 10/4C$ 282
Fri 2/55:30 p.m.ORD - YYC
Nonstop3h 49mWestJet
Sat 10/512:15 p.m.YYC - ORD
Nonstop3h 29mWestJet
Deal found 10/4C$ 284
Mon 5/59:40 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Wed 7/53:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 10/4C$ 307
Sat 5/78:25 p.m.ORD - YYC
Nonstop4h 04mAmerican Airlines
Tue 15/76:29 a.m.YYC - ORD
Nonstop3h 25mAmerican Airlines
Deal found 10/4C$ 316
Mon 26/58:50 a.m.ORD - YYZ
Nonstop1h 59mAir Canada
Mon 2/68:15 a.m.YYZ - ORD
Nonstop1h 54mAir Canada
Deal found 11/4C$ 334
Sun 11/59:40 a.m.MDW - YUL
1 stop5h 20mPorter Airlines
Sun 18/510:45 a.m.YUL - MDW
1 stop7h 09mPorter Airlines
Deal found 10/4C$ 341
Thu 1/59:40 a.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Sun 4/54:05 p.m.YTZ - MDW
Nonstop1h 49mMultiple Airlines
Deal found 8/4C$ 343
Sat 24/59:08 p.m.ORD - YYZ
1 stop14h 22mMultiple Airlines
Tue 27/57:55 a.m.YYZ - ORD
1 stop24h 32mMultiple Airlines
Deal found 10/4C$ 343

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 11 April 2025. In the last 7 days, Cheapflights users made a total of 629,999 searches

Fly to

Vancouver Intl

Route

Depart

Return

Price

ChicagoVancouver

ORD - YVR

ORDYVR

Chicago O'Hare Intl

Sat 10/5

5:30 p.m.-12:10 a.m.

1 stop8h 40m

Vancouver Intl

Sun 11/5

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

1 stop7h 44m

C$ 232

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Tue 13/5

8:45 a.m.-11:41 a.m.

Nonstop3h 56m

Calgary

Sat 24/5

12:38 p.m.-5:10 p.m.

Nonstop3h 32m

C$ 233

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Tue 13/5

8:45 a.m.-11:41 a.m.

Nonstop3h 56m

Calgary

Sat 24/5

12:38 p.m.-5:10 p.m.

Nonstop3h 32m

C$ 253

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Tue 13/5

8:45 a.m.-11:41 a.m.

Nonstop3h 56m

Calgary

Mon 26/5

12:25 a.m.-8:50 a.m.

1 stop7h 25m

C$ 268

ChicagoVancouver

ORD - YVR

ORDYVR

Chicago O'Hare Intl

Wed 14/5

6:59 p.m.-2:30 p.m.

1 stop21h 31m

Vancouver Intl

Wed 21/5

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

1 stop7h 44m

C$ 282

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Fri 2/5

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

Nonstop3h 49m

Calgary

Sat 10/5

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

Nonstop3h 29m

C$ 284

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Mon 5/5

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

Nonstop1h 42m

Toronto Island

Wed 7/5

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

C$ 307

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sat 5/7

8:25 p.m.-11:29 p.m.

Nonstop4h 04m

Calgary

Tue 15/7

6:29 a.m.-10:54 a.m.

Nonstop3h 25m

C$ 316

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Mon 26/5

8:50 a.m.-11:49 a.m.

Nonstop1h 59m

Toronto Pearson Intl

Mon 2/6

8:15 a.m.-9:09 a.m.

Nonstop1h 54m

C$ 334

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Sun 11/5

9:40 a.m.-4:00 p.m.

1 stop5h 20m

Montreal Pierre Elliott Trudeau Intl

Sun 18/5

10:45 a.m.-4:54 p.m.

1 stop7h 09m

C$ 341

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/4

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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 4 April 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$ 177). Flying from Chicago in December will prove the most costly (average of C$ 400). 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$ 512

Air Canada

Air Canada

From C$ 92

United Airlines

United Airlines

From C$ 131

What are popular destinations to fly to from Chicago?

From Chicago you can expect to find greater availability for the following destinations: New York (1,593 flights per day), Detroit (1,208 flights per day) and Los Angeles (661 flights per day).

Toronto

Toronto

From C$ 84

Istanbul

Istanbul

From C$ 376

Abu Dhabi Zayed Intl

Abu Dhabi Zayed Intl

From C$ 391

New Delhi Indira Gandhi Intl

New Delhi Indira Gandhi Intl

From C$ 327

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Orlando, with prices starting at C$ 73. Explore other affordable destinations below.

Orlando

Orlando

From C$ 52

New York

New York

From C$ 75

Calgary

Calgary

From C$ 75

Los Angeles

Los Angeles

From C$ 77

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
9,851 reviews
Check prices

Crew

8.5

Boarding

8.2

Food

7.1

Comfort

7.9

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,851 reviews
Alaska Airlines
8.0
Very good
9,851 reviews
Check prices

Crew

8.5

Boarding

8.2

Food

7.1

Comfort

7.9

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Porter Airlines
8.0
Very good
280 reviews
Alaska Airlines
8.0
Very good
9,851 reviews
Check prices

Crew

8.5

Boarding

8.2

Food

7.1

Comfort

7.9

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,910 reviews
Alaska Airlines
8.0
Very good
9,851 reviews
Check prices

Crew

8.5

Boarding

8.2

Food

7.1

Comfort

7.9

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,636 reviews
Alaska Airlines
8.0
Very good
9,851 reviews
Check prices

Crew

8.5

Boarding

8.2

Food

7.1

Comfort

7.9

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,851 reviews
Check prices

Crew

8.5

Boarding

8.2

Food

7.1

Comfort

7.9

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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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 11 April 2025.

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

    This month, the top selected destinations from Chicago are Atlanta, Boston, Barcelona-El Prat Airport. 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$ 233. While Chicago Midway airport is usually cheaper if your destination is Toronto with prices starting at C$ 303. 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$ 61). WestJet flights from Chicago to Calgary (C$ 95).

  • 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$ 233 round trip
    Travel from Chicago to Vancouver from C$ 249 round trip
    Travel from Chicago to Edmonton from C$ 265 round trip
    Travel from Chicago to Toronto from C$ 303 round trip
    Travel from Chicago to Montreal from C$ 348 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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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.

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