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C$ 109+ 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 22/6. 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
20 May — 27 May1
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 15 May 2025.

Cheapest airline

Frontier

Good round-trip deal

C$ 122 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$ 225).
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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 15 May 2025.

Thu 10/79:40 a.m.MDW - YTZ
Nonstop1h 40mPorter Airlines
Sun 13/77:55 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 14/5C$ 243
Mon 7/79:14 p.m.ORD - YYZ
Nonstop1h 44mUnited Airlines
Mon 6/107:00 a.m.YYZ - ORD
Nonstop1h 58mUnited Airlines
Deal found 14/5C$ 255
Wed 18/67:04 a.m.ORD - YYZ
Nonstop1h 54mAir Canada
Sun 22/68:15 a.m.YYZ - ORD
Nonstop1h 54mAir Canada
Deal found 14/5C$ 261
Thu 5/68:45 a.m.ORD - YYC
Nonstop3h 53mAir Canada
Wed 11/68:30 a.m.YYC - ORD
Nonstop3h 33mAir Canada
Deal found 14/5C$ 262
Fri 25/75:20 p.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Mon 28/77:55 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Deal found 14/5C$ 275
Thu 25/98:25 p.m.ORD - YYC
Nonstop4h 04mAmerican Airlines
Fri 3/106:29 a.m.YYC - ORD
Nonstop3h 25mAmerican Airlines
Deal found 15/5C$ 282
Fri 6/68:01 p.m.ORD - YYC
Nonstop3h 52mLufthansa
Thu 12/67:30 p.m.YYC - ORD
1 stop13h 11mLufthansa
Deal found 14/5C$ 283
Wed 24/97:00 a.m.ORD - YYZ
1 stop4h 32mMultiple Airlines
Wed 1/106:15 a.m.YYZ - ORD
1 stop4h 36mMultiple Airlines
Deal found 14/5C$ 283
Tue 17/67:00 a.m.ORD - YYZ
1 stop6h 44mAmerican Airlines
Tue 17/66:29 p.m.YYZ - ORD
Nonstop2h 00mAmerican Airlines
Deal found 13/5C$ 287
Wed 25/68:01 p.m.ORD - YYC
Nonstop3h 52mUnited Airlines
Wed 2/78:30 a.m.YYC - ORD
Nonstop3h 31mUnited Airlines
Deal found 14/5C$ 298
Sat 31/58:45 a.m.ORD - YYC
1 stop14h 03mMultiple Airlines
Mon 2/612:55 a.m.YYC - ORD
1 stop7h 57mMultiple Airlines
Deal found 14/5C$ 303
Fri 6/68:01 p.m.ORD - YYC
Nonstop3h 52mWestJet
Thu 12/612:15 p.m.YYC - ORD
Nonstop3h 29mWestJet
Deal found 14/5C$ 304

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

Fly to

Vancouver Intl

Route

Depart

Return

Price

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 10/7

9:40 a.m.-12:20 p.m.

Nonstop1h 40m

Toronto Island

Sun 13/7

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

Nonstop1h 50m

C$ 243

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Mon 7/7

9:14 p.m.-11:58 p.m.

Nonstop1h 44m

Toronto Pearson Intl

Mon 6/10

7:00 a.m.-7:58 a.m.

Nonstop1h 58m

C$ 255

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Wed 18/6

7:04 a.m.-9:58 a.m.

Nonstop1h 54m

Toronto Pearson Intl

Sun 22/6

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

Nonstop1h 54m

C$ 261

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Thu 5/6

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

Nonstop3h 53m

Calgary

Wed 11/6

8:30 a.m.-1:03 p.m.

Nonstop3h 33m

C$ 262

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 25/7

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

Nonstop1h 42m

Toronto Island

Mon 28/7

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

Nonstop1h 50m

C$ 275

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Thu 25/9

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

Nonstop4h 04m

Calgary

Fri 3/10

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

Nonstop3h 25m

C$ 282

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Fri 6/6

8:01 p.m.-10:53 p.m.

Nonstop3h 52m

Calgary

Thu 12/6

7:30 p.m.-9:41 a.m.

1 stop13h 11m

C$ 283

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Wed 24/9

7:00 a.m.-12:32 p.m.

1 stop4h 32m

Toronto Pearson Intl

Wed 1/10

6:15 a.m.-9:51 a.m.

1 stop4h 36m

C$ 283

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Tue 17/6

7:00 a.m.-2:44 p.m.

1 stop6h 44m

Toronto Pearson Intl

Tue 17/6

6:29 p.m.-7:29 p.m.

Nonstop2h 00m

C$ 287

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Wed 25/6

8:01 p.m.-10:53 p.m.

Nonstop3h 52m

Calgary

Wed 2/7

8:30 a.m.-1:01 p.m.

Nonstop3h 31m

C$ 298

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/5

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 9 May 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$ 176). Flying from Chicago in December will prove the most costly (average of C$ 397). 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$ 700
Air Canada
Air Canada
From C$ 92
United Airlines
United Airlines
From C$ 146

What are popular destinations to fly to from Chicago?

From Chicago you can expect to find greater availability for the following destinations: New York (1,827 flights per day), Detroit (1,324 flights per day) and Los Angeles (806 flights per day).

Toronto
Toronto
From C$ 77
New Delhi Indira Gandhi Intl
New Delhi Indira Gandhi Intl
From C$ 353
Calgary
Calgary
From C$ 69
New York
New York
From C$ 41

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$ 57. Explore other affordable destinations below.

New York
New York
From C$ 41
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From C$ 41
Washington, D.C.
Washington, D.C.
From C$ 51
Calgary
Calgary
From C$ 69

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

Comfort

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Comfort

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Porter Airlines
8.0
Very good
286 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Comfort

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,946 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Comfort

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,731 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Comfort

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
JetBlue
7.3
Good
2,925 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Comfort

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 Calgary
Flights from O'Hare Intl to Dubai
Flights from O'Hare Intl to Halifax
Flights from O'Hare Intl to Hong Kong
Flights from O'Hare Intl to Amman

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 15 May 2025.

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

    This month, the top selected destinations from Chicago are Atlanta, Boston, Athens. 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$ 191. While Chicago Midway airport is usually cheaper if your destination is Toronto with prices starting at C$ 240. 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$ 57). Frontier flights from Chicago to Atlanta Hartsfield-Jackson (C$ 66). 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 Toronto from C$ 191 round trip
    Travel from Chicago to Calgary from C$ 272 round trip
    Travel from Chicago to Montreal from C$ 317 round trip
    Travel from Chicago to Edmonton from C$ 325 round trip
    Travel from Chicago to Vancouver from C$ 347 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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