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C$ 107+ 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 26/5. 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
4 May — 11 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 29 April 2025.

Cheapest airline

Frontier

Good round-trip deal

C$ 112 or less

Good one-way deal

C$ 68 or less
On average, Frontier currently has the cheapest one-way flight from Chicago (avg. price of C$ 179).
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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 29 April 2025.

Thu 29/52:16 p.m.ORD - YYC
1 stop9h 22mAir Canada
Thu 29/512:55 a.m.YYC - ORD
1 stop9h 29mAir Canada
Deal found 28/4C$ 229
Fri 12/99:15 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 14/97:30 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 28/4C$ 233
Tue 1/78:50 a.m.ORD - YYZ
Nonstop1h 59mAir Canada
Tue 1/72:00 p.m.YYZ - ORD
1 stop5h 53mAir Canada
Deal found 27/4C$ 236
Thu 12/69:40 a.m.MDW - YTZ
Nonstop1h 40mMultiple Airlines
Thu 19/67:55 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Deal found 28/4C$ 237
Sat 24/52:18 p.m.ORD - YTZ
1 stop6h 17mAir Canada
Sun 25/57:25 a.m.YTZ - ORD
1 stop4h 59mAir Canada
Deal found 27/4C$ 249
Tue 27/58:45 a.m.ORD - YYC
1 stop14h 03mUnited Airlines
Tue 3/612:38 p.m.YYC - ORD
Nonstop3h 32mUnited Airlines
Deal found 28/4C$ 263
Sun 25/55:30 p.m.ORD - YYC
Nonstop3h 49mWestJet
Tue 3/612:15 p.m.YYC - ORD
Nonstop3h 29mWestJet
Deal found 28/4C$ 267
Sun 10/89:40 a.m.MDW - YTZ
Nonstop1h 40mAir Transat
Fri 15/83:35 p.m.YTZ - MDW
Nonstop1h 49mAir Transat
Deal found 28/4C$ 270
Tue 3/69:02 p.m.ORD - YVR
1 stop27h 23mMultiple Airlines
Tue 10/67:00 a.m.YVR - ORD
1 stop7h 44mMultiple Airlines
Deal found 28/4C$ 303
Fri 9/58:45 a.m.ORD - YYC
Nonstop3h 56mMultiple Airlines
Mon 12/511:55 p.m.YYC - ORD
1 stop7h 55mMultiple Airlines
Deal found 27/4C$ 305
Tue 24/69:40 a.m.MDW - YTZ
Nonstop1h 42mAPG Airlines
Fri 27/67:55 a.m.YTZ - MDW
Nonstop1h 50mAPG Airlines
Deal found 28/4C$ 326
Thu 26/64:43 p.m.ORD - YYZ
Nonstop1h 54mMultiple Airlines
Sat 12/72:10 p.m.YYZ - ORD
Nonstop1h 54mMultiple Airlines
Deal found 27/4C$ 327

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 29 April 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 29/5

2:16 p.m.-10:38 p.m.

1 stop9h 22m

Calgary

Thu 29/5

12:55 a.m.-11:24 a.m.

1 stop9h 29m

C$ 229

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 6/6

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

Nonstop1h 40m

Toronto Island

Fri 13/6

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

Nonstop1h 50m

C$ 231

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 12/9

9:15 a.m.-11:57 a.m.

Nonstop1h 42m

Toronto Island

Sun 14/9

7:30 a.m.-8:19 a.m.

Nonstop1h 49m

C$ 233

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Tue 1/7

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

Nonstop1h 59m

Toronto Pearson Intl

Tue 1/7

2:00 p.m.-6:53 p.m.

1 stop5h 53m

C$ 236

ChicagoToronto

ORD - YTZ

ORDYTZ

Chicago O'Hare Intl

Sun 8/6

2:07 p.m.-9:35 p.m.

1 stop6h 28m

Toronto Island

Sun 15/6

7:25 a.m.-11:24 a.m.

1 stop4h 59m

C$ 249

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Tue 27/5

8:45 a.m.-9:48 p.m.

1 stop14h 03m

Calgary

Tue 3/6

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

Nonstop3h 32m

C$ 263

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sun 25/5

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

Nonstop3h 49m

Calgary

Tue 3/6

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

Nonstop3h 29m

C$ 267

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sun 10/8

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

Nonstop1h 40m

Toronto Island

Fri 15/8

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

Nonstop1h 49m

C$ 270

ChicagoVancouver

ORD - YVR

ORDYVR

Chicago O'Hare Intl

Tue 3/6

9:02 p.m.-10:25 p.m.

1 stop27h 23m

Vancouver Intl

Tue 10/6

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

1 stop7h 44m

C$ 303

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Fri 9/5

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

Nonstop3h 56m

Calgary

Mon 12/5

11:55 p.m.-8:50 a.m.

1 stop7h 55m

C$ 305

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/4

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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 25 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$ 175). Flying from Chicago in December will prove the most costly (average of C$ 395). 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

United Airlines

United Airlines

From C$ 141

What are popular destinations to fly to from Chicago?

From Chicago you can expect to find greater availability for the following destinations: New York (1,717 flights per day), Detroit (1,278 flights per day) and Los Angeles (719 flights per day).

Toronto

Toronto

From C$ 83

Istanbul

Istanbul

From C$ 376

Abu Dhabi Zayed Intl

Abu Dhabi Zayed Intl

From C$ 391

New York

New York

From C$ 84

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Denver Intl, with prices starting at C$ 40. Explore other affordable destinations below.

Denver Intl

Denver Intl

From C$ 29

Orlando

Orlando

From C$ 50

Calgary

Calgary

From C$ 72

Las Vegas Harry Reid Intl

Las Vegas Harry Reid Intl

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
9,949 reviews
Check prices

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

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
9,949 reviews
Alaska Airlines
8.0
Very good
9,949 reviews
Check prices

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

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
285 reviews
Alaska Airlines
8.0
Very good
9,949 reviews
Check prices

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

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
7,929 reviews
Alaska Airlines
8.0
Very good
9,949 reviews
Check prices

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

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
8,696 reviews
Alaska Airlines
8.0
Very good
9,949 reviews
Check prices

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

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
2,922 reviews
Alaska Airlines
8.0
Very good
9,949 reviews
Check prices

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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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 29 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 Toronto can be found at Chicago Midway airport from C$ 198. While Chicago O'Hare Intl airport is usually cheaper if your destination is Halifax with prices starting at C$ 251. 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$ 94).

  • 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$ 198 round trip
    Travel from Chicago to Calgary from C$ 251 round trip
    Travel from Chicago to Vancouver from C$ 323 round trip
    Travel from Chicago to Montreal from C$ 337 round trip
    Travel from Chicago to Halifax from C$ 455 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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