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Find Chicago to Calgary flights starting at CAD 68.

We've found these cheap flights for you. You can book one-way or return flight tickets.

  • One way
  • Round-trip

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Chicago to Calgary flight time & flight schedules

Flight info.
Departure
Arrival
Weekly Schedule
  1. UA2666

    05:02

    ORD

    2.7h

    06:45

    DEN

    -M---FS
  2. UA2459

    11:44

    DEN

    2.6h

    14:21

    YYC

    SMTWTFS
  3. F92209

    06:15

    MDW

    2.8h

    08:01

    DEN

    SMTWTFS
  4. F92015

    07:00

    DEN

    2.0h

    08:03

    LAS

    SMTWTFS
  5. F81513

    09:40

    LAS

    2.9h

    13:35

    YYC

    SMT-T-S
  6. UA711

    07:00

    ORD

    2.9h

    08:53

    DEN

    SMTWTFS
  7. UA720

    19:05

    DEN

    2.5h

    21:38

    YYC

    SMTWTFS
  8. AC4027

    08:45

    ORD

    3.9h

    Nonstop

    11:38

    YYC

    SMTWTFS
  9. UA764

    09:00

    ORD

    3.9h

    Nonstop

    11:54

    YYC

    SMTWTFS
  10. F91827

    13:54

    ORD

    4.2h

    16:04

    PHX

    SMTWTFS
  11. F81503

    20:40

    PHX

    3.2h

    23:50

    YYC

    -M-W-FS
  12. DL2247

    17:00

    ORD

    3.7h

    19:42

    SLC

    SMTWTFS
  13. DL4113

    20:55

    SLC

    2.3h

    23:15

    YYC

    SMTWTFS
  14. F93173

    17:21

    ORD

    3.0h

    19:24

    DEN

    SMTWTF-
  15. F92015

    07:00

    DEN

    2.0h

    08:03

    LAS

    SMTWTFS
  16. F81513

    09:40

    LAS

    2.9h

    13:35

    YYC

    SMT-T-S
  17. WS1575

    18:26

    ORD

    3.9h

    Nonstop

    21:17

    YYC

    S--W--S

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

We monitor flight fares to help you find the best deals effortlessly

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Find Cheapest Airlines Flying from Chicago to Calgary

Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

FAQ

  • When are flight tickets from Chicago (CHI) to Calgary (YYC) the cheapest?

    Airlines adjust prices for flights from Chicago to Calgary based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.
  • How much are flights from Chicago (CHI) to Calgary (YYC) cost?

    According to Trip.com's data, the lowest price is around CAD 522.
  • How long is the flight from Chicago (CHI) to Calgary (YYC)?

    It takes about 3 hours 53 minutes to fly from Chicago (CHI) to Calgary (YYC).
  • What is the transportation method from the main airport to downtown in Calgary?

    • The distance from Calgary International Airport to downtown is about 9km, by taxi about 20 minutes.
  • What are the most popular airlines that fly from Chicago (CHI) to Calgary (YYC)?

    Airlines with flights from Chicago (CHI) to Calgary (YYC): United Airlines, Delta Air Lines, Qatar Airways, WestJet, British Airways, American Airlines and Air Canada.
  • What's the most popular airline for direct flights from Chicago (CHI) to Calgary (YYC)?

    United Airlines operates 1 direct flights from Chicago (CHI) to Calgary (YYC).
  • How many airports in Calgary (YYC)?

    There are 1 airport(s) in Calgary (YYC): Calgary International Airport.

How to find a cheap flight from Chicago to Calgary

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Chicago to Calgary. Book your flights at the right time and save more.
1
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com

Flight Information for Chicago to Calgary Flights

Cheapest direct flight priceCAD 67
Cheapest return ticket priceCAD 185
Off-season travel monthMarch
Peak season for travelNovember
Flight distance2,248.84km
Average flight time3 hours 53 minutes
Popular airlineUnited Airlines