
Popular airlines from Calgary International Airport (YYC) to Chicago O'Hare Intl. Airport (ORD)
- WestJet
WestJet
- Porter Airlines
Porter Airlines
- Alaska Airlines
Alaska Airlines
- Delta
Delta
- American Airlines
American Airlines
- Air Canada
Air Canada
- United
United
- Be in the knowGet alerts if flight prices drop or rise*
- Book smarterSave up to 15% on select hotels after you book a flight*
Cheap flights from Calgary to Chicago (YYC-ORD)
Prices were available within the past 7 days and start at €102 for one-way flights and €402 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, 26 Dec - Tue, 30 Dec
YYC
Calgary
ORD
Chicago
€402 Return, found 6 hours ago
€402
Return
found 6 hours ago

Fri, 26 Dec - Tue, 30 Dec
YYC
Calgary
ORD
Chicago
€429 Return, found 6 hours ago
€429
Return
found 6 hours ago

Fri, 26 Dec - Tue, 30 Dec
YYC
Calgary
ORD
Chicago
€446 Return, found 6 hours ago
€446
Return
found 6 hours ago

Fri, 26 Dec - Tue, 30 Dec
YYC
Calgary
ORD
Chicago
€459 Return, found 6 hours ago
€459
Return
found 6 hours ago

Fri, 26 Dec - Tue, 30 Dec
YYC
Calgary
ORD
Chicago
€473 Return, found 6 hours ago
€473
Return
found 6 hours ago

Fri, 26 Dec - Tue, 30 Dec
YYC
Calgary
ORD
Chicago
€477 Return, found 6 hours ago
€477
Return
found 6 hours ago

Fri, 26 Dec - Tue, 30 Dec
YYC
Calgary
ORD
Chicago
€481 Return, found 6 hours ago
€481
Return
found 6 hours ago

Mon, 29 Dec - Mon, 5 Jan
YYC
Calgary
ORD
Chicago
€522 Return, found 6 hours ago
€522
Return
found 6 hours ago

Fri, 26 Dec - Tue, 30 Dec
YYC
Calgary
ORD
Chicago
€541 Return, found 6 hours ago
€541
Return
found 6 hours ago

Mon, 29 Dec - Mon, 5 Jan
YYC
Calgary
ORD
Chicago
€583 Return, found 6 hours ago
€583
Return
found 6 hours ago
Find the cheapest month to fly from Calgary (YYC) to Chicago (ORD)
May is typically the cheapest month to fly
From €128 - €286 per traveller.
Origin airport | Calgary Intl. |
|---|---|
Destination airport | O'Hare Intl. |
Airlines serving | Air Canada, American Airlines, Delta, United, WestJet |
Return price | €401 |
Distance | 2211 km |
Average flight time | 6 hours 4 mins |
Perfect flights from Calgary to Chicago
Embark on an unforgettable journey without breaking the bank with Expedia's incredible deals on cheap flights from Calgary to Chicago. Whether you're aching for a romantic escape with your partner, craving an adventurous solo expedition, or yearning to immerse yourself in the local history and culture, we've got you covered.
Picture yourself strolling through the streets of , surrounded by breathtaking architecture and absorbing the vibrant atmosphere of this captivating city. Indulge in the mouth-watering local specialties, from tantalizing street food to exquisite fine dining. With Expedia, you can experience all of this and more, without sacrificing your budget.
Our flexible Calgary Intl. to O'Hare Intl. ticket options cater to your travel preferences, with incredible one-way fares from €102 and roundtrip prices from €402. Whether you're planning a short city break or a longer adventure, our dynamic pricing ensures that you find the best deals for your journey.
But the magic doesn't stop there. Expedia offers a range of partner services to enhance your trip. Rent a car at O'Hare Intl. and explore and its surrounding areas at your own pace. Discover hidden gems off the beaten path, and create unforgettable memories. We also provide a handpicked selection of accommodations, from charming bed and breakfasts to luxury hotels, ensuring that you have a comfortable and memorable stay.
Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support are designed to make your travel experience seamless and stress-free. So, why wait? Book your to travel arrangements today and embark on the journey of a lifetime in Chicago.
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Top Routes to Chicago
- Newark Liberty Intl. Airport to Chicago (EWR - ORD)
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- Dublin to Chicago (DUB - ORD)
- Budapest to Chicago (BUD - ORD)
- Shannon to Chicago (SNN - ORD)
- Vienna to Chicago (VIE - ORD)
- Vilnius to Chicago (VNO - ORD)
Top Routes from Calgary
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Expedia's Latest Trends
Flights
- Flights from New York (JFK) to Chicago (ORD)
- Flights from Chicago (ORD) to Shannon (SNN)
- Flights from Toronto (YYZ) to Edmonton (YEG)
- Flights from Dublin (DUB) to Edmonton (YEG)
- Flights from Chicago (ORD) to Orlando (MCO)
- Flights from Shannon (SNN) to Chicago (ORD)
- Flights from Chicago (ORD) to Los Angeles (LAX)
- Flights from Dublin (DUB) to Chicago (ORD)
- Flights from Chicago (ORD) to Dallas (DFW)
- Flights from Naples (NAP) to Chicago (ORD)
- Flights from Chicago (ORD) to Las Vegas (LAS)
- Flights from Chicago (ORD) to Dublin (DUB)
- Flights from Edmonton (YEG) to Dublin (DUB)
- Flights from Chicago (ORD) to St. Louis (STL)
- Flights from Philadelphia (PHL) to Chicago (ORD)
- Flights from Chicago (ORD) to Boston (BOS)
- Flights from Chicago (ORD) to Minneapolis - St. Paul (MSP)
- Flights from Los Angeles (LAX) to Chicago (ORD)
- Flights from Chicago (ORD) to Miami (MIA)
- Flights from Orlando (MCO) to Chicago (ORD)
- Flights from Vancouver (YVR) to Banff (YBA)
- Flights from Chicago (ORD) to Nashville (BNA)
- Flights from Chicago (ORD) to Seattle (SEA)
- Flights from Cork (ORK) to Chicago (ORD)
- Flights from Chicago (ORD) to Indianapolis (IND)
- Flights from New York (LGA) to Chicago (ORD)
- Flights from Chicago (ORD) to New York (LGA)
- Flights from Toronto (YYZ) to Chicago (ORD)
- Flights from Chicago (ORD) to Detroit (DTW)
- Flights from Chicago (ORD) to San Francisco (SFO)
*Available to Expedia members.