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Cheap flights from Calgary (YYC) to Chicago (CHI) from $118

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 6/29. 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.
YYC — CHI
May 21 — May 281
From?
To?
Tue 5/21
Tue 5/28
1 adult, Economy
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The best prices from Calgary to Chicago are usually found in January or November, booked 45 days in advance, depart on a Sunday or Wednesday and return on a Tuesday

Cheap flight deals from Calgary to Chicago

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 May 16, 2024.

Popular in

July

Cheapest in

January

Round-trip from

$223

One-way from

$126
High demand for flights, 21% potential price rise
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Best time to find cheap flights, 33% potential price drop
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From Calgary to Chicago (CHI)
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One-way flight from Calgary to Chicago (CHI)
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What is the cheapest day to fly round-trip from Calgary to Chicago?

Users have found that flying from Calgary to Chicago on a Friday typically leans towards higher prices. However, this doesn’t mean you still can’t find a deal. Flexibility with other aspects of your flight can still land a great price for your trip.

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

To save up to 105% on this flight, we recommend booking at least 46 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Calgary to Chicago from $333 1-2 weeks out and tickets from $607 for flights departing within the next 72 hours.

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

January can be a great time to fly to Chicago from Calgary with a flight ticket averaging about $390. Cheapflights users have found deals in the month of January for as cheap as $215. The most expensive prices can be found in the month of July.

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

Unlike at noon, when flights are generally more expensive, you can save up to 42% on flights from Calgary to Chicago by exploring options for tickets in the evening.

Cheap WestJet flights from Calgary to Chicago

Explore cheap flight options specifically provided by WestJet 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 2,637,452 searches. Data last updated May 16, 2024.
Take a peek at the cheapest WestJet flights we've detected traveling from Calgary to Chicago. Come back soon if you're not finding the exact deal you're looking for.
Sun 5/2612:30 pmYYC - ORD
Nonstop3h 35mWestJet
Mon 8/265:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/14$183
Fri 9/612:30 pmYYC - ORD
Nonstop3h 27mWestJet
Fri 9/135:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/15$199
Mon 7/112:30 pmYYC - ORD
Nonstop3h 27mWestJet
Sat 7/65:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/16$200
Tue 8/2012:30 pmYYC - ORD
Nonstop3h 27mWestJet
Tue 8/275:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/16$204
Thu 8/2212:30 pmYYC - ORD
Nonstop3h 27mWestJet
Mon 8/265:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/16$212
Thu 5/2312:30 pmYYC - ORD
Nonstop3h 35mWestJet
Sat 6/15:55 pmORD - YYC
Nonstop3h 27mWestJet
Deal found 5/16$213
Sat 8/2412:30 pmYYC - ORD
Nonstop3h 27mWestJet
Thu 8/295:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/16$226
Fri 8/2312:30 pmYYC - ORD
Nonstop3h 27mWestJet
Thu 8/295:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/16$227
Fri 8/2312:30 pmYYC - ORD
Nonstop3h 27mWestJet
Tue 8/275:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/16$229

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 2,637,452 searches. Data last updated May 16, 2024.
Browse through some of the cheapest Delta flights traveling from Calgary to Chicago. Deals frequently update to provide users with more options.
Wed 8/78:05 amYYC - ORD
2 stops12h 47mDelta
Tue 8/1312:19 pmORD - YYC
1 stop9h 22mDelta
Deal found 5/15$261
Sat 9/76:50 amYYC - ORD
1 stop9h 05mDelta
Tue 9/102:05 pmORD - YYC
1 stop10h 16mDelta
Deal found 5/16$262
Sun 7/284:30 pmYYC - ORD
1 stop6h 26mDelta
Thu 8/15:55 pmORD - YYC
Nonstop3h 45mDelta
Deal found 5/15$267
Wed 8/78:05 amYYC - ORD
2 stops12h 47mDelta
Tue 8/1312:19 pmORD - YYC
2 stops11h 57mDelta
Deal found 5/15$268
Wed 7/178:00 amYYC - ORD
1 stop9h 35mDelta
Wed 7/2412:32 pmORD - YYC
1 stop8h 53mDelta
Deal found 5/16$269
Sat 8/246:50 amYYC - ORD
1 stop9h 05mDelta
Mon 8/265:55 pmORD - YYC
Nonstop3h 45mDelta
Deal found 5/16$278
Thu 9/2612:30 pmYYC - ORD
Nonstop3h 39mDelta
Sun 9/292:05 pmORD - YYC
1 stop10h 16mDelta
Deal found 5/16$280
Thu 8/2212:05 pmYYC - ORD
1 stop10h 49mDelta
Wed 8/287:30 amORD - YYC
1 stop10h 00mDelta
Deal found 5/16$281
Thu 5/236:25 amYYC - ORD
1 stop10h 59mDelta
Sat 6/15:55 pmORD - YYC
Nonstop3h 27mDelta
Deal found 5/16$287

Cheap Calgary to Chicago flights in May & June 2024

Find cheap flight options from Calgary to Chicago specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,637,452 searches. Prices were last updated on May 16, 2024.
These are some of the most attractive deals on flights from Calgary to Chicago in 2024. Check back soon for alternative fares.
Sun 5/2612:30 pmYYC - ORD
Nonstop3h 35mWestJet
Mon 8/265:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/14$183
Thu 5/2312:30 pmYYC - ORD
Nonstop3h 35mWestJet
Sat 6/15:55 pmORD - YYC
Nonstop3h 27mWestJet
Deal found 5/16$213
Thu 5/2312:30 pmYYC - ORD
Nonstop3h 35mWestJet
Sat 6/15:55 pmORD - YYC
Nonstop3h 27mWestJet
Deal found 5/16$229
Tue 6/48:30 amYYC - ORD
Nonstop3h 29mUnited Airlines
Fri 6/77:57 pmORD - YYC
Nonstop3h 46mUnited Airlines
Deal found 5/14$257
Tue 6/47:55 amYYC - ORD
1 stop10h 15mDelta
Fri 6/71:40 pmORD - YYC
1 stop10h 22mDelta
Deal found 5/14$262
Tue 6/43:25 pmYYC - ORD
1 stop6h 30mUnited Airlines
Fri 6/77:57 pmORD - YYC
Nonstop3h 46mUnited Airlines
Deal found 5/14$272
Sun 5/2612:05 pmYYC - ORD
1 stop16h 15mMultiple Airlines
Mon 8/265:55 pmORD - YYC
Nonstop3h 45mMultiple Airlines
Deal found 5/14$275
Fri 6/149:30 pmYYC - ORD
2 stops22h 17mMultiple Airlines
Sun 6/165:55 pmORD - YYC
Nonstop3h 45mMultiple Airlines
Deal found 5/16$284
Fri 6/146:50 pmYYC - ORD
1 stop30h 09mMultiple Airlines
Sun 6/165:55 pmORD - YYC
Nonstop3h 45mMultiple Airlines
Deal found 5/16$285

Calgary to Chicago 2024 flight deals

Discover exclusive flight deals for travel between Calgary and Chicago in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated May 16, 2024.
These are some of the most attractive deals on flights from Calgary to Chicago in 2024. Check back soon for alternative fares.
Sun 5/2612:30 pmYYC - ORD
Nonstop3h 35mWestJet
Mon 8/265:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/14$183
Fri 9/612:30 pmYYC - ORD
Nonstop3h 27mWestJet
Fri 9/135:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/15$199
Wed 7/1712:30 pmYYC - ORD
Nonstop3h 27mWestJet
Wed 7/245:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/16$200
Tue 8/2012:30 pmYYC - ORD
Nonstop3h 27mWestJet
Tue 8/275:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/16$204
Thu 8/2212:30 pmYYC - ORD
Nonstop3h 27mWestJet
Mon 8/265:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/16$212
Thu 5/2312:30 pmYYC - ORD
Nonstop3h 35mWestJet
Sat 6/15:55 pmORD - YYC
Nonstop3h 27mWestJet
Deal found 5/16$213
Sat 8/2412:30 pmYYC - ORD
Nonstop3h 27mWestJet
Thu 8/295:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/16$226
Fri 8/2312:30 pmYYC - ORD
Nonstop3h 27mWestJet
Thu 8/295:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/16$227
Thu 5/2312:30 pmYYC - ORD
Nonstop3h 35mWestJet
Sat 6/15:55 pmORD - YYC
Nonstop3h 27mWestJet
Deal found 5/16$229

Non-stop 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 2,637,452 searches. Data last updated May 16, 2024.
For a shorter flight, select one of these non-stop flights from Calgary to Chicago. Users seeking other options on flights from Calgary to Chicago should update the search form at the top of the page.
Sun 5/2612:30 pmYYC - ORD
Nonstop3h 35mWestJet
Mon 8/265:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/14$183
Fri 9/612:30 pmYYC - ORD
Nonstop3h 27mWestJet
Fri 9/135:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/15$199
Tue 6/48:30 amYYC - ORD
Nonstop3h 29mUnited Airlines
Fri 6/77:57 pmORD - YYC
Nonstop3h 46mUnited Airlines
Deal found 5/14$257
Tue 7/3012:30 pmYYC - ORD
Nonstop3h 27mWestJet
Sun 8/45:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/15$325
Tue 7/2312:30 pmYYC - ORD
Nonstop3h 27mWestJet
Sat 8/35:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/15$336
Fri 10/2512:40 pmYYC - ORD
Nonstop3h 29mAir Canada
Tue 10/299:00 amORD - YYC
Nonstop3h 54mAir Canada
Deal found 5/16$347
Sun 9/2212:30 pmYYC - ORD
Nonstop3h 39mWestJet
Thu 9/265:55 pmORD - YYC
Nonstop3h 50mWestJet
Deal found 5/15$349
Fri 7/512:30 pmYYC - ORD
Nonstop3h 27mWestJet
Sun 7/75:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/15$350
Thu 7/2512:30 pmYYC - ORD
Nonstop3h 27mWestJet
Sat 8/35:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/15$361

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 2,637,452 searches. Data last updated May 16, 2024.
Check out these flights departing soon from Calgary to Chicago. Users should double check the flight they book to ensure it matches the day, time, and destination they're looking for.
Sun 5/2612:30 pmYYC - ORD
Nonstop3h 35mWestJet
Mon 8/265:55 pmORD - YYC
Nonstop3h 45mWestJet
Deal found 5/14$183
Thu 5/2312:30 pmYYC - ORD
Nonstop3h 35mWestJet
Sat 6/15:55 pmORD - YYC
Nonstop3h 27mWestJet
Deal found 5/16$213
Thu 5/2312:30 pmYYC - ORD
Nonstop3h 35mWestJet
Sat 6/15:55 pmORD - YYC
Nonstop3h 27mWestJet
Deal found 5/16$229
Sun 5/2612:05 pmYYC - ORD
1 stop16h 15mMultiple Airlines
Mon 8/265:55 pmORD - YYC
Nonstop3h 45mMultiple Airlines
Deal found 5/14$275
Thu 5/236:25 amYYC - ORD
1 stop10h 59mDelta
Sat 6/15:55 pmORD - YYC
Nonstop3h 27mDelta
Deal found 5/16$287
Sun 5/2612:30 pmYYC - ORD
Nonstop3h 35mMultiple Airlines
Mon 8/2610:57 pmORD - YYC
2 stops19h 01mMultiple Airlines
Deal found 5/14$298
Sat 5/2512:40 pmYYC - ORD
Nonstop3h 29mUnited Airlines
Wed 5/291:12 pmORD - YYC
1 stop9h 31mUnited Airlines
Deal found 5/14$302
Sat 5/258:30 amYYC - ORD
Nonstop3h 29mUnited Airlines
Wed 5/298:45 amORD - YYC
1 stop13h 58mUnited Airlines
Deal found 5/15$307
Sat 5/258:30 amYYC - ORD
Nonstop3h 29mAir Canada
Wed 5/297:57 pmORD - YYC
Nonstop3h 46mAir Canada
Deal found 5/14$324

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 2,637,452 searches. Data last updated May 16, 2024.
If you're seeking multiple options on one-way flights from Calgary to Chicago, be sure to check out these deals, which are updated often. Users needing a return flight from Calgary to Chicago should utilize the search form above.
Sat 6/2912:30 pmYYC - ORD
Nonstop3h 27mWestJet
Deal found 5/15$118
Thu 5/308:30 amYYC - ORD
Nonstop3h 29mAir Canada
Deal found 5/14$120
Mon 7/112:30 pmYYC - ORD
Nonstop3h 27mWestJet
Deal found 5/15$123
Wed 5/2912:40 pmYYC - ORD
Nonstop3h 29mUnited Airlines
Deal found 5/15$124
Thu 6/61:30 pmYYC - ORD
Nonstop3h 25mAmerican Airlines
Deal found 5/16$126
Tue 5/2112:10 amYYC - ORD
1 stop7h 48mAir Canada
Deal found 5/14$131
Tue 8/1311:40 pmYYC - ORD
1 stop8h 21mAir Canada
Deal found 5/14$133
Sat 6/812:30 pmYYC - ORD
Nonstop3h 35mWestJet
Deal found 5/15$135
Mon 6/312:10 amYYC - ORD
1 stop7h 41mAir Canada
Deal found 5/15$136

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 2,637,452 searches. Data last updated May 16, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$183 - $402

Route

Depart

Return

Price

CalgaryChicago O'Hare Intl

YYC - ORD

YYCORD

Calgary

Sun 5/26

Nonstop3h 35m

Chicago O'Hare Intl

Mon 8/26

Nonstop3h 45m

$183

CalgaryChicago O'Hare Intl

YYC - ORD

YYCORD

Calgary

Fri 9/6

Nonstop3h 27m

Chicago O'Hare Intl

Fri 9/13

Nonstop3h 45m

$199

CalgaryChicago O'Hare Intl

YYC - ORD

YYCORD

Calgary

Mon 7/1

Nonstop3h 27m

Chicago O'Hare Intl

Sat 7/6

Nonstop3h 45m

$200

CalgaryChicago O'Hare Intl

YYC - ORD

YYCORD

Calgary

Tue 8/20

Nonstop3h 27m

Chicago O'Hare Intl

Tue 8/27

Nonstop3h 45m

$204

CalgaryChicago O'Hare Intl

YYC - ORD

YYCORD

Calgary

Sat 8/24

1 stop12h 11m

Chicago O'Hare Intl

Tue 8/27

1 stop9h 47m

$260

CalgaryChicago O'Hare Intl

YYC - ORD

YYCORD

Calgary

Wed 8/7

2 stops12h 47m

Chicago O'Hare Intl

Tue 8/13

1 stop9h 22m

$261

CalgaryChicago O'Hare Intl

YYC - ORD

YYCORD

Calgary

Tue 6/4

1 stop6h 30m

Chicago O'Hare Intl

Fri 6/7

Nonstop3h 46m

$272

CalgaryChicago O'Hare Intl

YYC - ORD

YYCORD

Calgary

Mon 6/3

1 stop7h 41m

Chicago O'Hare Intl

Fri 6/7

Nonstop3h 46m

$291

CalgaryChicago O'Hare Intl

YYC - ORD

YYCORD

Calgary

Fri 6/7

Nonstop3h 25m

Chicago O'Hare Intl

Fri 6/14

Nonstop3h 45m

$402

Flights are sorted by cheapest first

Deals found on 5/14

When is the best time to book a flight from Calgary to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Calgary to Chicago. Price data was last updated on May 10, 2024.
To ensure you get the cheapest price possible for a flight from Calgary to Chicago, you should look to book at least 45 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
Search Deals

When is the cheapest time to fly from Calgary to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Calgary to Chicago. Price data was last updated on May 12, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Calgary to Chicago flight should consider departing on Sunday evenings when fares are most often at their lowest. Thursday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
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Average price of flights to Chicago by month

Plan your trip from Calgary to Chicago by taking into account the cheapest months to travel. The average price of a one-way flight from Calgary to Chicago is currently $127 while a round-trip flight costs $252. Price data was last updated on May 12, 2024.

Currently, February is the cheapest month in which you can book a flight from Calgary to Chicago (average of $244). Flying from Calgary to Chicago in June is currently the most expensive (average of $342). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

January

$248

February

$244

March

$280

April

$258

May

$278

June

$342

July

$327

August

$274

September

$258

October

$248

November

$270

December

$248

Temperature and rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average temperature and rainfall totals by month.

CHI

Temperature

23 - 73.4 °F

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 May 16, 2024.
Read reviews from past customers who have flown WestJet, Delta and United Airlines from Calgary to Chicago. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.1
Very good
9,157 reviews
Check prices

Entertainment

7.3

Boarding

8.2

Crew

8.6

Food

7.3

Overall

8.1

Comfort

7.9

Reviews

1 / 10

Paid a lot for our exit row seats and they weren’t that roomy.

Alaska Airlines
8.1
Very good
9,157 reviews
Alaska Airlines
8.1
Very good
9,157 reviews
Check prices

Entertainment

7.3

Boarding

8.2

Crew

8.6

Food

7.3

Overall

8.1

Comfort

7.9

Reviews

1 / 10

Paid a lot for our exit row seats and they weren’t that roomy.

Delta
8.0
Very good
10,673 reviews
Alaska Airlines
8.1
Very good
9,157 reviews
Check prices

Entertainment

7.3

Boarding

8.2

Crew

8.6

Food

7.3

Overall

8.1

Comfort

7.9

Reviews

1 / 10

Paid a lot for our exit row seats and they weren’t that roomy.

WestJet
7.5
Good
2,919 reviews
Alaska Airlines
8.1
Very good
9,157 reviews
Check prices

Entertainment

7.3

Boarding

8.2

Crew

8.6

Food

7.3

Overall

8.1

Comfort

7.9

Reviews

1 / 10

Paid a lot for our exit row seats and they weren’t that roomy.

Porter Airlines
7.4
Good
415 reviews
Alaska Airlines
8.1
Very good
9,157 reviews
Check prices

Entertainment

7.3

Boarding

8.2

Crew

8.6

Food

7.3

Overall

8.1

Comfort

7.9

Reviews

1 / 10

Paid a lot for our exit row seats and they weren’t that roomy.

United Airlines
7.4
Good
10,924 reviews
Alaska Airlines
8.1
Very good
9,157 reviews
Check prices

Entertainment

7.3

Boarding

8.2

Crew

8.6

Food

7.3

Overall

8.1

Comfort

7.9

Reviews

1 / 10

Paid a lot for our exit row seats and they weren’t that roomy.

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?

    Most people fly from Calgary (YYC) if they book a flight from Calgary to Chicago. On average, Calgary has 3 outbound flights to Chicago per day from 4 airlines. Calgary is conveniently located just 5.8 mi from Calgary’s city center.

  • Can I find flights from Calgary to Chicago for under $200 on Cheapflights?

    Yes, there are multiple flights from Calgary to Chicago for under $200. The cheapest flight booked recently is on WestJet for just $183, but on average you can expect to pay $238.

  • Are there nonstop flights from Calgary to Chicago for under $200 on Cheapflights?

    Cheapflights has at least 20 direct flights from Calgary to Chicago under $200. A good price for a nonstop flight from Calgary to Chicago is less than $355.

  • Are there last-minute flights available from Calgary to Chicago for under $200?

    There are currently 20+ open flights from Calgary to Chicago within the next 7 days for less than $200.

  • What days are nonstop flights available from Calgary to Chicago?

    You can find nonstop flights on the following days: Sunday, Monday, Tuesday, Thursday, Friday, Saturday.

  • How many flights depart from Calgary to Chicago on average per day?

    5 flight departures from Calgary to Chicago per day on average.
    Morning (6am - Noon) - 100% of flight departures

  • How long is the flight from Calgary to Chicago?

    There are many flights that can get you from Calgary to Chicago in 3h 35m. Fly via WestJet, Delta, or United Airlines to get the fastest option. The distance between Calgary and Chicago is about 1389 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    Our cheapest airline available from Calgary to Chicago is WestJet. Our recent data shows that you can find tickets from as low as $183 on this airline. Additional options worth looking into are Delta and United Airlines, starting at $261 and $272 round-trip. WestJet is currently priced 53% below the average price you’ll pay for this route.

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

    To fly one-way, consider booking your trip with WestJet, which is currently one of the cheapest options available, starting at $118. Air Canada flights start at $120 while deals on United Airlines start at $124 one-way.

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

    When booking a flight from Calgary to Chicago, you may want to consider flying on American Airlines, Air Canada or United Airlines as they are the most popular for this route.

  • 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: Air Canada (83%), United Airlines (83%), Emirates( 79%).

  • What are the cheapest flights from Calgary to Chicago?

    Looking for the cheapest flight from Calgary to Chicago? While on average our users pay $428, our data indicates the cheapest price to be $137. The most popular route (Calgary - Chicago O'Hare Intl), is priced around $228.

  • What does YYC to ORD mean?

    Calgary Airport is YYC and Chicago O'Hare Intl Airport is ORD. These codes are created by the International Air Transport Association (IATA) and airlines use them to identify the departing and arrival airports in the flight routes they service. Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are some additional IATA codes for airports related to your trip.

  • Can I find deals for flights from Calgary to Chicago that include extra baggage allowance?

    The amount of baggage you can bring on your Calgary to Chicago flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Calgary to Chicago with specific airlines?

    Yes, Cheapflights allows you to browse and filter Calgary to Chicago flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • Can I find deals for flights from Calgary to Chicago that include hotel bookings?

    Yes. In addition to deals on Calgary to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Calgary to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Calgary to Chicago.

  • Can I find deals for business class flights from Calgary to Chicago?

    Yes. Cheapflights offers flight deals from Calgary to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from Calgary to Chicago that allow pets onboard?

    Many airlines flying from Calgary to Chicago offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Calgary to Chicago?

    Yes, you can often find last-minute deals on Calgary to Chicago flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Calgary to Chicago flight deals updated?

    The Calgary to Chicago flight deals you see on this page were last updated on 5/16.

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Alternative routes for Calgary to Chicago
See prices for flight routes from nearby airports that may be better suited for you.

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Top 4 airlines flying from Calgary to Chicago

Discover the top 4 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 2,637,452 searches. Data last updated May 16, 2024.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$167Average$318FlexibilityNo cancel feeOn-time60%
Search WestJet flights
American AirlinesCheapest$193Average$422FlexibilityNo cancel feeOn-time71%
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Air CanadaCheapest$209Average$385FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapest$218Average$357FlexibilityNo cancel feeOn-time69%
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Search flights from Calgary to Chicago by cabin class

Find flights from Calgary to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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Hourly flight availability from Calgary to Chicago

Find hourly flight availability from Calgary to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 16, 2024.
0%of flight departuresEarly morningMidnight to 6 am
100%of flight departuresMorning6 am to noon
0%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
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Weekly flight availability from Calgary to Chicago

Explore weekly flight availability from Calgary to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated May 16, 2024.
Sunday4daily flights
Monday4daily flights
Tuesday4daily flights
Wednesday2daily flights
Thursday4daily flights
Friday4daily flights
Saturday1daily flight

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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 Calgary to Chicago?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Calgary to Chicago. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

Why should you use Cheapflights to find cheap flight tickets from Calgary to Chicago?

Cheapflights helps you find that perfect flight to Chicago from Calgary by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from Calgary to Chicago with no change fees?

Cheapflights does show flights with no change fees to all users. To see these options for flights from Calgary to Chicago, users can toggle the no change fees filter when performing a flight search.

Can Cheapflights notify me if prices for flights from Calgary to Chicago become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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