Find flights
Airlines

C$ 106+ 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 9/5. 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
30 Mar — 6 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 25 March 2025.

Cheapest airline

Frontier

Good round-trip deal

C$ 109 or less

Good one-way deal

C$ 100 or less
On average, Frontier currently has the cheapest one-way flight from Chicago (avg. price of C$ 125).
Search Deals
Price to beat on a round-trip flight from Chicago.
Search Deals
Price to beat on a one-way flight from Chicago.
Search Deals

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 25 March 2025.

Thu 1/55:30 p.m.ORD - YYC
Nonstop3h 49mWestJet
Sat 10/512:15 p.m.YYC - ORD
Nonstop3h 29mWestJet
Deal found 23/3C$ 236
Thu 1/55:30 p.m.ORD - YYC
Nonstop3h 49mMultiple Airlines
Fri 9/512:55 a.m.YYC - ORD
1 stop7h 57mMultiple Airlines
Deal found 24/3C$ 241
Tue 6/58:25 p.m.ORD - YYZ
Nonstop1h 42mAir Canada
Tue 13/56:15 a.m.YYZ - ORD
1 stop4h 37mAir Canada
Deal found 23/3C$ 268
Fri 25/411:15 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 27/43:50 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 23/3C$ 272
Sat 3/53:35 p.m.ORD - YYC
1 stop8h 31mAir Canada
Sat 10/511:55 p.m.YYC - ORD
1 stop7h 55mAir Canada
Deal found 22/3C$ 274
Thu 5/68:25 p.m.ORD - YYC
Nonstop4h 00mAmerican Airlines
Thu 12/66:29 a.m.YYC - ORD
Nonstop3h 25mAmerican Airlines
Deal found 24/3C$ 294
Tue 13/59:02 p.m.ORD - YVR
1 stop27h 23mMultiple Airlines
Tue 20/53:55 p.m.YVR - ORD
1 stop17h 00mMultiple Airlines
Deal found 24/3C$ 295
Tue 6/55:20 p.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Tue 13/57:55 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Deal found 23/3C$ 299
Sat 19/48:52 a.m.ORD - YYC
Nonstop3h 49mUnited Airlines
Mon 28/46:15 a.m.YYC - ORD
1 stop16h 37mUnited Airlines
Deal found 23/3C$ 317
Fri 25/411:15 a.m.MDW - YUL
1 stop4h 32mPorter Airlines
Tue 29/411:50 a.m.YUL - MDW
1 stop5h 50mPorter Airlines
Deal found 22/3C$ 318
Thu 8/510:40 a.m.ORD - YUL
Nonstop2h 16mAir Canada
Thu 15/57:00 a.m.YUL - ORD
1 stop4h 54mAir Canada
Deal found 23/3C$ 324
Thu 8/59:40 a.m.MDW - YTZ
Nonstop1h 42mAir Transat
Thu 15/57:55 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Deal found 24/3C$ 345

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 25 March 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 1/5

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$ 236

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Thu 1/5

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

Nonstop3h 49m

Calgary

Fri 9/5

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

1 stop7h 57m

C$ 241

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Tue 6/5

8:25 p.m.-11:07 p.m.

Nonstop1h 42m

Toronto Pearson Intl

Tue 13/5

6:15 a.m.-9:52 a.m.

1 stop4h 37m

C$ 268

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 25/4

11:15 a.m.-1:57 p.m.

Nonstop1h 42m

Toronto Island

Sun 27/4

3:50 p.m.-4:40 p.m.

Nonstop1h 50m

C$ 272

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sat 3/5

3:35 p.m.-11:06 p.m.

1 stop8h 31m

Calgary

Sat 10/5

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

1 stop7h 55m

C$ 274

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Thu 5/6

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

Nonstop4h 00m

Calgary

Thu 12/6

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

Nonstop3h 25m

C$ 294

ChicagoVancouver

ORD - YVR

ORDYVR

Chicago O'Hare Intl

Tue 13/5

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

1 stop27h 23m

Vancouver Intl

Tue 20/5

3:55 p.m.-10:55 a.m.

1 stop17h 00m

C$ 295

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 6/5

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

Nonstop1h 42m

Toronto Island

Tue 13/5

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

Nonstop1h 49m

C$ 299

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sat 19/4

8:52 a.m.-11:41 a.m.

Nonstop3h 49m

Calgary

Mon 28/4

6:15 a.m.-11:52 p.m.

1 stop16h 37m

C$ 317

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Fri 25/4

11:15 a.m.-4:47 p.m.

1 stop4h 32m

Montreal Pierre Elliott Trudeau Intl

Tue 29/4

11:50 a.m.-4:40 p.m.

1 stop5h 50m

C$ 318

Flights are sorted by cheapest round-trip flights first.

Deals found on 23/3

Showing 1-10 of 60 results
1
2
3
...
6

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 21 March 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$ 181). Flying from Chicago in December will prove the most costly (average of C$ 408). 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$ 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 (1,234 flights per day), Detroit (904 flights per day) and Los Angeles (493 flights per day).

Toronto

Toronto

From C$ 84

New Delhi Indira Gandhi Intl

New Delhi Indira Gandhi Intl

From C$ 359

Istanbul

Istanbul

From C$ 390

Abu Dhabi Zayed Intl

Abu Dhabi Zayed Intl

From C$ 379

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$ 54. Explore other affordable destinations below.

Miami

Miami

From C$ 38

Detroit

Detroit

From C$ 70

Calgary

Calgary

From C$ 75

Edmonton

Edmonton

From C$ 76

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
9,785 reviews
Check prices

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Overall

8.0

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
9,785 reviews
Alaska Airlines
8.0
Very good
9,785 reviews
Check prices

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Overall

8.0

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
7,890 reviews
Alaska Airlines
8.0
Very good
9,785 reviews
Check prices

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Overall

8.0

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
275 reviews
Alaska Airlines
8.0
Very good
9,785 reviews
Check prices

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Overall

8.0

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
8,605 reviews
Alaska Airlines
8.0
Very good
9,785 reviews
Check prices

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Overall

8.0

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
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,785 reviews
Check prices

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Overall

8.0

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 25 March 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, 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 Toronto can be found at Chicago Midway airport from C$ 265. While Chicago O'Hare Intl airport is usually cheaper if your destination is Ottawa with prices starting at C$ 266. 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$ 59). Frontier flights from Chicago to Atlanta Hartsfield-Jackson (C$ 62). WestJet flights from Chicago to Calgary (C$ 97).

  • 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$ 265 round trip
    Travel from Chicago to Calgary from C$ 266 round trip
    Travel from Chicago to Montreal from C$ 314 round trip
    Travel from Chicago to Vancouver from C$ 325 round trip
    Travel from Chicago to Ottawa from C$ 430 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.

See more FAQs

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.

100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.