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Cheap flights from Calgary to Chicago from C$ 176

This is the cheapest one-way flight price, found on 29/11. Prices may vary by date and flight preferences.
YYC — CHI
5 Dec — 12 Dec1
1 adult
Tue 5/12
Tue 12/12

The best prices from Calgary to Chicago are usually found in November or October, booked 83 days in advance, depart on a Tuesday or Thursday and return on a Monday

Flights from Chicago to Calgary

How to find the cheapest flight from Calgary (YYC) to Chicago (CHI)

Discover tips and strategies to find the most affordable flight options for your journey from Calgary (YYC) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 30 November 2023.

Popular in

December

Cheapest in

November

Round-trip from

C$ 500

One-way from

C$ 353
High demand for flights, 22% potential price rise
Search Deals
Best time to find cheap flights, 22% potential price drop
Search Deals
From Calgary to Chicago (CHI)
Search Deals
One-way flight from Calgary to Chicago (CHI)
Search Deals

YYC - CHI

Price

C$ 368 - C$ 619

CHI

Temperature

-5 - 23 °C

CHI

Rainfall

43 - 125 mm

What is the cheapest day to fly round-trip from Calgary to Chicago?

Users have found that leaving on a Monday can be a cost-effective option. It’s possible to save up to 34% on your flight compared to booking on days when demand is much higher.

How far in advance should I book a flight from Calgary to Chicago?

Users have found that booking a flight from Calgary to Chicago at least 21 days early can save you up to 49% on average compared to booking a flight this week. If booking 21 days before your flight isn’t an option for you, users have found flights from Calgary to Chicago for as little as C$ 619 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as C$ 824 for flights departing within the next 3 days.

What is the cheapest month to fly from Calgary to Chicago?

November is one of the best times of the year to fly to Chicago from Calgary. Prices for November average C$ 598 per person but you can even find prices for as low as C$ 286. The most expensive prices can be found in the month of December. Opting for a November flight can save you 27% on your journey compared to booking in December

When is the cheapest time to fly from Calgary to Chicago (YYC - CHI)?

One of the essential ways to save on airfare from Calgary to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 44% on airfare.

Cheap Delta flights from Calgary to Chicago

Explore cheap flight options specifically provided by Delta for the route between Calgary and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 526,253 searches. Data last updated 30 November 2023.
Consider these cheap Delta flights we've found departing from Calgary to Chicago. Deals update often to give you more flight options matching your criteria
Sat 20/17:45 a.m.YYC - ORD
1 stop8h 00mDelta
Tue 23/15:25 p.m.ORD - YYC
1 stop6h 51mDelta
Deal found 29/11C$ 303
Wed 6/1212:30 p.m.YYC - ORD
1 stop8h 33mDelta
Sat 9/123:51 p.m.ORD - YYC
1 stop9h 02mDelta
Deal found 29/11C$ 339
Wed 6/1212:30 p.m.YYC - ORD
2 stops10h 22mDelta
Sat 9/1212:28 p.m.ORD - YYC
2 stops12h 25mDelta
Deal found 29/11C$ 357
Tue 6/212:20 a.m.YYC - ORD
2 stops11h 57mDelta
Wed 14/212:35 p.m.ORD - YYC
1 stop9h 31mDelta
Deal found 29/11C$ 392
Tue 6/212:20 a.m.YYC - ORD
2 stops11h 57mDelta
Wed 14/27:30 a.m.ORD - YYC
1 stop7h 05mDelta
Deal found 30/11C$ 394
Tue 6/212:20 a.m.YYC - ORD
2 stops11h 57mDelta
Wed 14/212:15 p.m.ORD - YYC
2 stops13h 25mDelta
Deal found 29/11C$ 421
Fri 24/512:15 p.m.YYC - ORD
Nonstop3h 28mDelta
Thu 30/512:19 p.m.ORD - YYC
1 stop9h 11mDelta
Deal found 30/11C$ 436
Wed 7/27:45 a.m.YYC - ORD
2 stops12h 53mDelta
Wed 14/212:15 p.m.ORD - YYC
2 stops13h 25mDelta
Deal found 29/11C$ 437
Thu 15/26:20 a.m.YYC - ORD
1 stop10h 38mDelta
Mon 26/212:35 p.m.ORD - YYC
1 stop9h 26mDelta
Deal found 29/11C$ 451

  • One of the most popular airlines travelling from Calgary to Chicago is Delta. Flights on this route from Delta typically cost C$ 442.69 RT, a price that is 68% cheaper than the average Calgary to Chicago flight. The cheapest flight found was C$ 266 RT. The most popular departure airport in Calgary when flying to Chicago is Calgary Airport. The most popular airport to fly into when visiting Chicago is Chicago O'Hare Intl Airport. When flying from Calgary to Chicago, Delta flights are 12% more popular than any other airline flying that same route.

Cheap Air Canada flights from Calgary to Chicago

Explore cheap flight options specifically provided by Air Canada for the route between Calgary and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 526,253 searches. Data last updated 30 November 2023.
Some of the lowest-priced Air Canada flights we've found at this time heading from Calgary to Chicago. Check back soon if you're not seeing flights that suit your needs.
Tue 6/212:50 a.m.YYC - ORD
1 stop8h 22mAir Canada
Wed 14/27:58 p.m.ORD - YYC
Nonstop3h 58mAir Canada
Deal found 29/11C$ 322
Wed 7/26:00 a.m.YYC - ORD
1 stop8h 37mAir Canada
Wed 14/28:46 a.m.ORD - YYC
Nonstop3h 59mAir Canada
Deal found 29/11C$ 328
Wed 7/27:30 a.m.YYC - ORD
1 stop7h 07mAir Canada
Wed 14/27:58 p.m.ORD - YYC
Nonstop3h 58mAir Canada
Deal found 30/11C$ 330
Sat 20/17:45 a.m.YYC - ORD
Nonstop3h 25mAir Canada
Tue 23/17:58 p.m.ORD - YYC
Nonstop3h 58mAir Canada
Deal found 29/11C$ 345
Wed 7/27:45 a.m.YYC - ORD
Nonstop3h 25mAir Canada
Wed 14/27:58 p.m.ORD - YYC
Nonstop3h 58mAir Canada
Deal found 30/11C$ 349
Wed 6/127:30 a.m.YYC - ORD
1 stop7h 07mAir Canada
Sat 9/127:55 p.m.ORD - YYC
Nonstop4h 01mAir Canada
Deal found 29/11C$ 350
Fri 19/11:05 a.m.YYC - ORD
1 stop6h 57mAir Canada
Tue 23/17:58 p.m.ORD - YYC
Nonstop3h 58mAir Canada
Deal found 29/11C$ 353
Wed 10/11:05 a.m.YYC - ORD
1 stop6h 57mAir Canada
Sat 13/12:30 p.m.ORD - YYC
1 stop7h 50mAir Canada
Deal found 29/11C$ 361
Tue 6/212:50 a.m.YYC - ORD
1 stop8h 22mAir Canada
Wed 14/211:00 a.m.ORD - YYC
1 stop12h 43mAir Canada
Deal found 29/11C$ 368

  • If you’re travelling from Calgary to Chicago, one of the more common airlines travelling that route is Air Canada. Flights from Air Canada travelling this route typically cost C$ 451.15 RT. This price is typically 71% cheaper than other airlines that offer Calgary to Chicago flights. When booking this route, the cheapest RT price found was C$ 230. When travelling from Calgary to Chicago on Air Canada, the most popular airport to depart from is Calgary Airport and the most popular airport to arrive at is Chicago O'Hare Intl Airport. When flying from Calgary to Chicago, Air Canada flights are 2% more popular than any other airline flying that same route.

Cheap Calgary to Chicago flights in November & December 2023

Find cheap flight options from Calgary to Chicago specifically for the months of November and December 2023. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 526,253 searches. Prices were last updated on 30 November 2023.
The lowest fares we've come across on flights travelling from Calgary to Chicago in November and December 2023. Check back soon for alternative fares.
Fri 15/126:15 a.m.YYC - ORD
1 stop10h 42mMultiple Airlines
Tue 19/1210:48 p.m.ORD - YYC
1 stop15h 42mMultiple Airlines
Deal found 28/11C$ 278
Fri 15/127:45 a.m.YYC - ORD
2 stops15h 10mDelta
Tue 19/127:05 a.m.ORD - YYC
2 stops15h 10mDelta
Deal found 28/11C$ 303
Wed 13/1210:00 a.m.YYC - ORD
1 stop20h 29mMultiple Airlines
Sun 17/1210:48 p.m.ORD - YYC
1 stop15h 42mMultiple Airlines
Deal found 30/11C$ 319
Wed 6/1212:30 p.m.YYC - ORD
1 stop8h 33mDelta
Sat 9/123:51 p.m.ORD - YYC
1 stop9h 02mDelta
Deal found 29/11C$ 339
Wed 13/1210:00 a.m.YYC - ORD
2 stops13h 07mMultiple Airlines
Sun 17/1210:48 p.m.ORD - YYC
1 stop15h 42mMultiple Airlines
Deal found 30/11C$ 341
Wed 6/127:30 a.m.YYC - ORD
1 stop7h 07mAir Canada
Sat 9/127:55 p.m.ORD - YYC
Nonstop4h 01mAir Canada
Deal found 29/11C$ 350
Sat 2/127:15 a.m.YYC - ORD
1 stop9h 54mMultiple Airlines
Mon 4/1210:48 p.m.ORD - YYC
1 stop26h 17mMultiple Airlines
Deal found 29/11C$ 356
Wed 6/1212:30 p.m.YYC - ORD
2 stops10h 22mDelta
Sat 9/1212:28 p.m.ORD - YYC
2 stops12h 25mDelta
Deal found 29/11C$ 357
Wed 6/127:45 a.m.YYC - ORD
Nonstop3h 27mAir Canada
Sat 9/127:55 p.m.ORD - YYC
Nonstop4h 01mAir Canada
Deal found 29/11C$ 369

Calgary to Chicago 2023 flight deals

Discover exclusive flight deals for travel between Calgary and Chicago in 2023. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 526,253 searches. Data last updated 30 November 2023.
The lowest fares we've come across on flights travelling from Calgary to Chicago in November and December 2023. Check back soon for alternative fares.
Fri 15/126:15 a.m.YYC - ORD
1 stop10h 42mMultiple Airlines
Tue 19/1210:48 p.m.ORD - YYC
1 stop15h 42mMultiple Airlines
Deal found 28/11C$ 278
Fri 15/127:45 a.m.YYC - ORD
2 stops15h 10mDelta
Tue 19/127:05 a.m.ORD - YYC
2 stops15h 10mDelta
Deal found 28/11C$ 303
Wed 13/1210:00 a.m.YYC - ORD
1 stop20h 29mMultiple Airlines
Sun 17/1210:48 p.m.ORD - YYC
1 stop15h 42mMultiple Airlines
Deal found 30/11C$ 319
Wed 6/1212:30 p.m.YYC - ORD
1 stop8h 33mDelta
Sat 9/123:51 p.m.ORD - YYC
1 stop9h 02mDelta
Deal found 29/11C$ 339
Wed 13/1210:00 a.m.YYC - ORD
2 stops13h 07mMultiple Airlines
Sun 17/1210:48 p.m.ORD - YYC
1 stop15h 42mMultiple Airlines
Deal found 30/11C$ 341
Wed 6/127:30 a.m.YYC - ORD
1 stop7h 07mAir Canada
Sat 9/127:55 p.m.ORD - YYC
Nonstop4h 01mAir Canada
Deal found 29/11C$ 350
Sat 2/127:15 a.m.YYC - ORD
1 stop9h 54mMultiple Airlines
Mon 4/1210:48 p.m.ORD - YYC
1 stop26h 17mMultiple Airlines
Deal found 29/11C$ 356
Wed 6/1212:30 p.m.YYC - ORD
2 stops10h 22mDelta
Sat 9/1212:28 p.m.ORD - YYC
2 stops12h 25mDelta
Deal found 29/11C$ 357
Wed 6/127:45 a.m.YYC - ORD
Nonstop3h 27mAir Canada
Sat 9/127:55 p.m.ORD - YYC
Nonstop4h 01mAir Canada
Deal found 29/11C$ 369

Direct flights to Chicago from Calgary

Discover non-stop flight options from Calgary to Chicago. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 526,253 searches. Data last updated 30 November 2023.
To help reduce your travel time, choose from one of these non-stop flights from Calgary to Chicago. If you're looking for other options for flights from Calgary to Chicago, make sure to update the search form at the top of page.
Thu 11/17:45 a.m.YYC - ORD
Nonstop3h 25mUnited Airlines
Sat 13/18:46 a.m.ORD - YYC
Nonstop3h 59mUnited Airlines
Deal found 29/11C$ 345
Wed 7/212:41 p.m.YYC - ORD
Nonstop3h 20mUnited Airlines
Wed 14/27:58 p.m.ORD - YYC
Nonstop3h 58mUnited Airlines
Deal found 29/11C$ 346
Mon 11/127:45 a.m.YYC - ORD
Nonstop3h 27mAir Canada
Thu 14/127:55 p.m.ORD - YYC
Nonstop4h 01mAir Canada
Deal found 29/11C$ 398
Wed 13/1212:41 p.m.YYC - ORD
Nonstop3h 20mUnited Airlines
Wed 20/128:45 a.m.ORD - YYC
Nonstop4h 00mUnited Airlines
Deal found 29/11C$ 509
Fri 15/127:45 a.m.YYC - ORD
Nonstop3h 27mUnited Airlines
Tue 19/128:45 a.m.ORD - YYC
Nonstop4h 00mUnited Airlines
Deal found 28/11C$ 628
Sun 21/17:45 a.m.YYC - ORD
Nonstop3h 25mUnited Airlines
Tue 23/17:58 p.m.ORD - YYC
Nonstop3h 58mUnited Airlines
Deal found 29/11C$ 660
Wed 13/127:45 a.m.YYC - ORD
Nonstop3h 27mUnited Airlines
Sun 17/127:55 p.m.ORD - YYC
Nonstop4h 01mUnited Airlines
Deal found 29/11C$ 673
Wed 14/27:45 a.m.YYC - ORD
Nonstop3h 25mUnited Airlines
Sun 25/28:06 p.m.ORD - YYC
Nonstop3h 50mUnited Airlines
Deal found 29/11C$ 690
Wed 27/1212:41 p.m.YYC - ORD
Nonstop3h 20mUnited Airlines
Wed 3/17:58 p.m.ORD - YYC
Nonstop4h 00mUnited Airlines
Deal found 29/11C$ 692

Calgary to Chicago flights leaving soon

Find last-minute flight options from Calgary to Chicago for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 526,253 searches. Data last updated 30 November 2023.
Users seeking a last-minute flight from Calgary to Chicago should consider booking one of these fares. Tip: verify your flight details before completing your reservation.
Wed 6/1212:30 p.m.YYC - ORD
1 stop8h 33mDelta
Sat 9/123:51 p.m.ORD - YYC
1 stop9h 02mDelta
Deal found 29/11C$ 339
Wed 6/127:30 a.m.YYC - ORD
1 stop7h 07mAir Canada
Sat 9/127:55 p.m.ORD - YYC
Nonstop4h 01mAir Canada
Deal found 29/11C$ 350
Wed 6/1212:30 p.m.YYC - ORD
2 stops10h 22mDelta
Sat 9/1212:28 p.m.ORD - YYC
2 stops12h 25mDelta
Deal found 29/11C$ 357
Wed 6/127:45 a.m.YYC - ORD
Nonstop3h 27mAir Canada
Sat 9/127:55 p.m.ORD - YYC
Nonstop4h 01mAir Canada
Deal found 29/11C$ 369
Tue 5/121:15 a.m.YYC - ORD
1 stop11h 17mAir Canada
Sat 9/127:55 p.m.ORD - YYC
Nonstop4h 01mAir Canada
Deal found 29/11C$ 381
Tue 5/121:15 a.m.YYC - ORD
1 stop11h 17mAir Canada
Sat 9/122:30 p.m.ORD - YYC
1 stop8h 00mAir Canada
Deal found 29/11C$ 396
Sun 10/121:20 a.m.YYC - ORD
1 stop11h 12mAir Canada
Thu 14/127:55 p.m.ORD - YYC
Nonstop4h 01mAir Canada
Deal found 29/11C$ 410
Fri 8/126:15 a.m.YYC - ORD
1 stop10h 42mMultiple Airlines
Mon 11/127:14 p.m.ORD - YYC
2 stops26h 01mMultiple Airlines
Deal found 28/11C$ 464
Fri 8/126:15 a.m.YYC - ORD
1 stop10h 42mMultiple Airlines
Mon 11/129:15 a.m.ORD - YYC
1 stop11h 42mMultiple Airlines
Deal found 28/11C$ 470

One-way flights to Chicago from Calgary

Search for one-way flight options from Calgary to Chicago. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 526,253 searches. Data last updated 30 November 2023.
Take a look at some of the best available options we've come across on one-way flights from Calgary to Chicago. Users needing a return flight from Calgary to Chicago should utilize the search form above.
Fri 12/18:10 a.m.YYC - MDW
1 stop27h 57mMultiple Airlines
Deal found 29/11C$ 176
Sat 13/17:45 a.m.YYC - ORD
1 stop8h 30mDelta
Deal found 29/11C$ 185
Sat 13/17:45 a.m.YYC - ORD
1 stop6h 08mDelta
Deal found 29/11C$ 186
Fri 12/18:10 a.m.YYC - MDW
2 stops15h 34mMultiple Airlines
Deal found 29/11C$ 190
Tue 5/128:10 a.m.YYC - ORD
1 stop24h 05mMultiple Airlines
Deal found 29/11C$ 195
Fri 12/11:05 a.m.YYC - ORD
1 stop6h 57mAir Canada
Deal found 29/11C$ 202
Fri 12/11:05 a.m.YYC - ORD
1 stop6h 57mAir Canada
Deal found 29/11C$ 210
Sat 13/17:45 a.m.YYC - ORD
Nonstop3h 25mAir Canada
Deal found 29/11C$ 221
Sat 13/112:30 a.m.YYC - ORD
2 stops11h 47mDelta
Deal found 29/11C$ 236

Find flights from Calgary to Chicago within your budget

Customize your flight search to find flights from Calgary to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 526,253 searches. Data last updated 30 November 2023.

Fly from

Any airport

Fly to

Any airport

Budget

C$ 278 - C$ 605

Route

Depart

Return

Price

CalgaryChicago O'Hare Intl

YYC - ORD

YYCORD

Calgary

Fri 15/12

1 stop10h 42m

Chicago O'Hare Intl

Tue 19/12

1 stop15h 42m

C$ 278

CalgaryChicago O'Hare Intl

YYC - ORD

YYCORD

Calgary

Sat 20/1

1 stop8h 00m

Chicago O'Hare Intl

Tue 23/1

1 stop6h 51m

C$ 303

CalgaryChicago Midway

YYC - MDW

YYCMDW

Calgary

Wed 7/2

1 stop8h 16m

Chicago Midway

Wed 14/2

2 stops12h 22m

C$ 303

CalgaryChicago O'Hare Intl

YYC - ORD

YYCORD

Calgary

Wed 13/12

1 stop20h 29m

Chicago O'Hare Intl

Sun 17/12

1 stop15h 42m

C$ 319

CalgaryChicago O'Hare Intl

YYC - ORD

YYCORD

Calgary

Tue 6/2

1 stop8h 22m

Chicago O'Hare Intl

Wed 14/2

Nonstop3h 58m

C$ 322

CalgaryChicago O'Hare Intl

YYC - ORD

YYCORD

Calgary

Wed 7/2

1 stop8h 37m

Chicago O'Hare Intl

Wed 14/2

Nonstop3h 59m

C$ 328

CalgaryChicago O'Hare Intl

YYC - ORD

YYCORD

Calgary

Wed 7/2

Nonstop3h 20m

Chicago O'Hare Intl

Wed 14/2

Nonstop3h 58m

C$ 346

CalgaryChicago O'Hare Intl

YYC - ORD

YYCORD

Calgary

Tue 12/12

1 stop17h 41m

Chicago O'Hare Intl

Thu 14/12

1 stop7h 50m

C$ 417

CalgaryChicago O'Hare Intl

YYC - ORD

YYCORD

Calgary

Wed 14/2

1 stop26h 33m

Chicago O'Hare Intl

Mon 26/2

1 stop31h 52m

C$ 605

Flights are sorted by cheapest first

Deals found on 28/11

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 30 November 2023.
See what other customers who have flown with Delta, Air Canada and United Airlines from Calgary to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
3,035 reviews
Check prices

Overall

7.9

Crew

8.5

Comfort

7.9

Boarding

8.0

Entertainment

7.8

Food

7.2

Reviews

1 / 10

On time flights; courteous staff; efficient boarding system! Thank you!

Delta
7.9
Good
3,035 reviews
Delta
7.9
Good
3,035 reviews
Check prices

Overall

7.9

Crew

8.5

Comfort

7.9

Boarding

8.0

Entertainment

7.8

Food

7.2

Reviews

1 / 10

On time flights; courteous staff; efficient boarding system! Thank you!

United Airlines
7.4
Good
1,897 reviews
Delta
7.9
Good
3,035 reviews
Check prices

Overall

7.9

Crew

8.5

Comfort

7.9

Boarding

8.0

Entertainment

7.8

Food

7.2

Reviews

1 / 10

On time flights; courteous staff; efficient boarding system! Thank you!

American Airlines
7.2
Good
2,645 reviews
Delta
7.9
Good
3,035 reviews
Check prices

Overall

7.9

Crew

8.5

Comfort

7.9

Boarding

8.0

Entertainment

7.8

Food

7.2

Reviews

1 / 10

On time flights; courteous staff; efficient boarding system! Thank you!

WestJet
7.2
Good
918 reviews
Delta
7.9
Good
3,035 reviews
Check prices

Overall

7.9

Crew

8.5

Comfort

7.9

Boarding

8.0

Entertainment

7.8

Food

7.2

Reviews

1 / 10

On time flights; courteous staff; efficient boarding system! Thank you!

Air Canada
6.7
Okay
988 reviews
Delta
7.9
Good
3,035 reviews
Check prices

Overall

7.9

Crew

8.5

Comfort

7.9

Boarding

8.0

Entertainment

7.8

Food

7.2

Reviews

1 / 10

On time flights; courteous staff; efficient boarding system! Thank you!

Related info for your journey

Find useful and relevant information for your journey from Calgary to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

What airport do you fly from for flights from Calgary to Chicago?

For a flight from Calgary to Chicago, you will be flying from Calgary. Calgary (YYC) is just 9.3 km from the centre of the city. Calgary is the only Calgary airport and it handles 3 outbound flights to Chicago per day. 8 airlines have flights to Chicago from Calgary on a regular basis.

Can I find flights from Calgary to Chicago for under C$ 300 on Cheapflights?

Yes, there are multiple flights from Calgary to Chicago for under C$ 300. The cheapest flight booked recently is on Multiple Airlines for just C$ 278, but on average you can expect to pay C$ 347.

Are there direct flights from Calgary to Chicago for under C$ 400 on Cheapflights?

Cheapflights has 20 direct flights from Calgary to Chicago under C$ 400. A good price for a direct flight from Calgary to Chicago is less than C$ 707.

Are there last-minute flights available from Calgary to Chicago for under C$ 400?

There are currently 20+ open flights from Calgary to Chicago within the next 7 days for less than C$ 400.

What are the cheapest airlines flying from Calgary to Chicago round-trip?

According to our current data, Delta (C$ 303), Air Canada (C$ 322), and United Airlines (C$ 346) offers the cheapest pricing from Calgary to Chicago. Users have found that Delta is 49% cheaper than the other options available to this destination.

What are the cheapest airlines to fly from Calgary to Chicago one-way?

To fly one-way, consider booking your trip with Delta, which is currently one of the cheapest options available, starting at C$ 185. Air Canada flights start at C$ 202 while deals on WestJet start at C$ 330 one-way.

What are the most popular airlines that fly from Calgary to Chicago?

The most popular airlines flying from Calgary to Chicago are Endeavor Airlines, American Airlines and Air Canada. Something to consider prior to booking your flight.

What are the most reliable airlines from Calgary to Chicago?

Before booking your flight to Chicago from Calgary, check out the most reliable airlines to get you to your destination on time: Emirates (94%), Air Canada (91%), United Airlines( 91%).

What are the cheapest flights from Calgary to Chicago?

The cheapest flight price from Calgary to Chicago is C$ 187. On average you can expect to pay C$ 1,110. The most popular route, (Calgary - Chicago O'Hare Intl), can usually be booked for C$ 274.

What does YYC to ORD mean?

YYC stands for Calgary Airport, while ORD stands for Chicago O'Hare Intl Airport. These codes are often called IATA codes, a set of identifiers established by IATA (International Air Transport Association) that is widely used by airlines and the aviation industry. Ready for more IATA code knowledge? These are related airports for your current travel destination: Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).

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.

Top 8 airlines flying from Calgary to Chicago

Discover the top 8 airlines that operate flights from Calgary to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 526,253 searches. Data last updated 30 November 2023.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 268AverageC$ 535FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 313AverageC$ 612FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
American AirlinesCheapestC$ 344AverageC$ 630FlexibilityNo cancel feeOn-time71%
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DeltaCheapestC$ 357AverageC$ 510FlexibilityNo cancel feeOn-timeN/A
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United AirlinesCheapestC$ 361AverageC$ 601FlexibilityNo cancel feeOn-time69%
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Aer LingusCheapestC$ 506AverageC$ 639FlexibilityNo cancel feeOn-timeN/A
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Endeavor AirlinesCheapestC$ 535AverageC$ 616FlexibilityNo cancel feeOn-timeN/A
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WestJet EncoreCheapestC$ 703AverageC$ 756FlexibilityNo cancel feeOn-timeN/A
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