International route
Cheap flights from Calgary to Chicago
Calgary International Airport (YYC) to O'Hare International Airport (ORD). 1,382 miles, 3h 5m nonstop.
YYC to ORD at a glance
Computed from airline schedules and the fares we track for this route. Refreshed several times a day.
- Distance
- 1,382 milesgreat-circle
- Typical flight time
- 3h 5mnonstop, gate to gate
- Nonstop airlines
- AAUAWNB69 airlinesAmerican, United, Southwest
- Nonstop flights per day
- 16all airlines combined
- Cheapest month
- January 2027over the next six months
- Best day to fly
- Wednesday18% less than Sunday
- Time difference
- 1h aheadChicago vs Calgary
Calgary to Chicago
Round trips from $138
Per traveler, taxes and fees included. Lowest fare we found departs Tue, Jan 19.
Cheapest month: January 2027
See fares on these datesLock any fare free — pay only when you accept your last-minute deal
Or ask an agent on WhatsAppCalgary to Chicago fares by month
Lowest round-trip economy fare per traveler in each of the next six months, taxes and fees included. Select a month to search that date.
Airlines flying Calgary to Chicago
9 airlines fly nonstop with 16 departures a day combined, plus 2 more with one stop.
- ACAir CanadaStar AllianceNonstop · 3 flights a day · first checked bag from $35
- AAAmerican AirlinesoneworldNonstop · 3 flights a day · first checked bag from $40
- UAUnited AirlinesStar AllianceNonstop · 3 flights a day · first checked bag from $40
- WSWestJetNonstop · 2 flights a day · first checked bag from $35
- ASAlaska AirlinesoneworldNonstop · 1 flight a day · first checked bag from $35
- F9Frontier AirlinesLow-costNonstop · 1 flight a day · first checked bag from $55
- B6JetBlueNonstop · 1 flight a day · first checked bag from $40
- WNSouthwest AirlinesLow-costNonstop · 1 flight a day · first checked bag from $35
- NKSpirit AirlinesLow-costNonstop · 1 flight a day · first checked bag from $55
- DLDelta Air LinesSkyTeamConnecting via MSP, DTW, SLC, SEA · first checked bag from $35
- SYSun Country AirlinesLow-costConnecting via MSP · first checked bag from $45
Connecting options
Hubs where one airline can carry you on both legs, most choices first.
- Minneapolis (MSP)DLSY2 airlines
- Detroit (DTW)DL1 airline
- Salt Lake City (SLC)DL1 airline
- Seattle (SEA)DL1 airline
Which airport should I use?
CalgaryChicago has 2 airports. Fares can differ by $50 to $150 round trip between them, so check the alternatives before you book.
Other arrival airports near Chicago
Tips for this route
- American, United, Southwest and JetBlue all fly YYC to ORD nonstop, so compare the total with bags before picking the lowest base fare: the difference between a basic and a standard economy ticket is often less than one checked bag each way.
- January 2027 is the cheapest month to fly over the next six months, with round trips from $138; September 2026 is the most expensive at $183 and up, a difference of $45 per traveler.
- Departing on a Wednesday averages 18% less than a Sunday on this route. If your dates are flexible, shift the outbound by a day or two and check the calendar view before you book.
- Book 6 to 12 weeks ahead; fares climb in the last three weeks and around holidays.
Destination guide
Chicago: Big-shoulders architecture and a lakefront for everyone
Chicago is America's most connected inland hub — O'Hare and Midway between them have nonstops from nearly every US city — so fares are consistently reasonable. The lakefront, the architecture and the food make it a strong long weekend.
Best time to visit: June–September is warm, with festivals almost every weekend (and the highest hotel rates). May and October are cool and cheaper; winter is cold but hotels are a bargain.
Flying the other way? Chicago to CalgaryFares, airlines and tips for ORD to YYC.Ready to compare live fares?
See every airline on YYC–ORD side by side with bags and seat rules spelled out.
Search Calgary to ChicagoCalgary to Chicago: common questions
How long is the flight from Calgary to Chicago?
A nonstop flight from Calgary (YYC) to Chicago (ORD) takes about 3h 5m gate to gate, covering 1,382 miles. Connecting itineraries add the layover, typically 2 to 5 hours more in total.
Which airlines fly nonstop from YYC to ORD?
American Airlines, United Airlines, Southwest Airlines, JetBlue, Alaska Airlines, Spirit Airlines, Frontier Airlines, Air Canada and WestJet operate nonstop flights from Calgary (YYC) to Chicago (ORD), with 16 nonstop departures a day between them. One-stop options connect through MSP, DTW and SLC.
What is the cheapest month to fly from Calgary to Chicago?
Over the next six months, January 2027 has the lowest round-trip fares from Calgary (YYC) to Chicago (ORD), starting at $138 per traveler including taxes and fees. Within any month, Wednesday departures average the lowest prices.
How far in advance should I book Calgary to Chicago flights?
Book 6 to 12 weeks ahead; fares climb in the last three weeks and around holidays. Air1 Tickets includes free cancellation within 24 hours of booking on every fare, so you can lock in a good price and keep looking.
What is the time difference between Calgary and Chicago?
Chicago is 1 hour ahead of Calgary. YYC is on America/Edmonton time and ORD on America/Chicago time. Departure and arrival times in search results are always shown in local time at each airport.
Related routes
Other popular city pairs from the same departure city and to the same destination, with the lowest round-trip fares we found.