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Cheap flights from Calgary to Chicago from C$ 140
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 23/1. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — CHI
26 Nov — 3 Dec1
Cheapflights Tip: The best prices from Calgary to Chicago are usually found in April or February, booked 66 days in advance, depart on a Friday or Saturday and return on a Wednesday
Find flight deals from Calgary to Chicago
Cheapest flights from Calgary to ChicagoExplore the most affordable flight options available from Calgary to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 27 October 2025.
Explore the most affordable flight options available from Calgary to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 27 October 2025.
Tue 28/1012:37 p.m.YYC - ORD
Nonstop3h 33mUnited Airlines
Sat 1/118:45 a.m.ORD - YYC
Nonstop3h 50mUnited Airlines
Deal found 27/10C$ 269
Mon 24/1112:37 p.m.YYC - ORD
Nonstop3h 33mLufthansa
Tue 2/128:45 a.m.ORD - YYC
Nonstop3h 50mLufthansa
Deal found 25/10C$ 273
Mon 24/119:00 a.m.YYC - ORD
Nonstop3h 35mWestJet
Fri 5/122:20 p.m.ORD - YYC
Nonstop3h 55mWestJet
Deal found 26/10C$ 274
Mon 24/119:00 a.m.YYC - ORD
Nonstop3h 35mMultiple Airlines
Tue 2/124:22 p.m.ORD - YYC
1 stop20h 22mMultiple Airlines
Deal found 25/10C$ 288
Thu 13/116:30 a.m.YYC - ORD
1 stop16h 01mAmerican Airlines
Mon 17/1110:05 p.m.ORD - YYC
1 stop14h 39mAmerican Airlines
Deal found 26/10C$ 290
Mon 24/119:00 a.m.YYC - ORD
Nonstop3h 35mMultiple Airlines
Wed 3/128:00 a.m.ORD - YYC
1 stop12h 09mMultiple Airlines
Deal found 26/10C$ 291
Sat 1/1112:37 p.m.YYC - ORD
Nonstop3h 33mUnited Airlines
Sat 8/118:45 a.m.ORD - YYC
Nonstop3h 50mUnited Airlines
Deal found 26/10C$ 295
Mon 24/1111:40 p.m.YYC - ORD
2 stops10h 38mAir Canada
Tue 2/122:00 p.m.ORD - YYC
1 stop7h 39mAir Canada
Deal found 25/10C$ 297
Sat 22/112:13 p.m.YYC - ORD
1 stop8h 46mUnited Airlines
Sat 29/118:45 a.m.ORD - YYC
Nonstop3h 50mUnited Airlines
Deal found 24/10C$ 302
Sun 23/115:35 a.m.YYC - ORD
1 stop8h 20mAir Canada
Tue 2/122:00 p.m.ORD - YYC
1 stop7h 39mAir Canada
Deal found 26/10C$ 304
Wed 29/105:45 a.m.YYC - ORD
1 stop8h 25mAir Canada
Sat 1/113:35 p.m.ORD - YYC
1 stop9h 09mAir Canada
Deal found 27/10C$ 306
Wed 24/126:30 a.m.YYC - MDW
1 stop9h 49mDelta
Wed 31/1211:48 a.m.MDW - YYC
1 stop10h 18mDelta
Deal found 27/10C$ 311
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 27 October 2025.
Cheapflights Fare Finder
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 629,999 searches. Data last updated 27 October 2025.
Use the filters below to find and compare flights from Calgary to Chicago that are best for you.
Fly from
Calgary
Fly to
Chicago
Route
Depart
Return
Price
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Mon 24/11
12:37 p.m.-5:10 p.m.
Nonstop3h 33m
Chicago O'Hare Intl
Tue 2/12
8:45 a.m.-11:35 a.m.
Nonstop3h 50m
C$ 273
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Thu 27/11
12:37 p.m.-5:12 p.m.
Nonstop3h 35m
Chicago O'Hare Intl
Tue 2/12
8:45 a.m.-11:35 a.m.
Nonstop3h 50m
C$ 295
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Thu 27/11
12:37 p.m.-5:12 p.m.
Nonstop3h 35m
Chicago O'Hare Intl
Sat 29/11
8:45 a.m.-11:35 a.m.
Nonstop3h 50m
C$ 295
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Tue 25/11
12:37 p.m.-5:10 p.m.
Nonstop3h 33m
Chicago O'Hare Intl
Sat 29/11
8:45 a.m.-11:35 a.m.
Nonstop3h 50m
C$ 295
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Mon 24/11
2:13 p.m.-11:59 p.m.
1 stop8h 46m
Chicago O'Hare Intl
Tue 2/12
8:45 a.m.-11:35 a.m.
Nonstop3h 50m
C$ 302
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Sat 22/11
2:13 p.m.-11:59 p.m.
1 stop8h 46m
Chicago O'Hare Intl
Sat 29/11
8:45 a.m.-11:35 a.m.
Nonstop3h 50m
C$ 302
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Thu 11/12
12:41 p.m.-9:21 p.m.
1 stop7h 40m
Chicago O'Hare Intl
Mon 15/12
1:35 p.m.-11:13 p.m.
1 stop10h 38m
C$ 311
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Thu 4/12
7:35 a.m.-9:56 p.m.
2 stops13h 21m
Chicago O'Hare Intl
Sat 6/12
8:50 a.m.-1:40 p.m.
1 stop5h 50m
C$ 311
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Sat 22/11
6:35 a.m.-3:04 p.m.
1 stop7h 29m
Chicago O'Hare Intl
Wed 3/12
8:55 a.m.-8:57 p.m.
2 stops13h 02m
C$ 311
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Mon 24/11
6:35 a.m.-4:52 p.m.
1 stop9h 17m
Chicago O'Hare Intl
Fri 5/12
8:50 a.m.-1:40 p.m.
1 stop5h 50m
C$ 311
Showing 1-10 of 35 results
Best time to book a flight from Calgary to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Calgary with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Calgary to Chicago
How far ahead should I 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 24 October 2025.
To ensure you get the cheapest price possible for a flight from Calgary to Chicago, you should look to book at least 66 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.
What is the cheapest month to book a flight from Calgary to Chicago?
Currently, April is the cheapest month in which you can book a flight from Calgary to Chicago (average of C$ 151). Flying from Calgary to Chicago in July is currently the most expensive (average of C$ 218). 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.
What is the cheapest time of day to fly from YYC to CHI?
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 27 October 2025.
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 67% on airfare.
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 27 October 2025.
The most flights from YYC to CHI are scheduled on a Monday (9 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (7 on average).
How much does it cost to fly round-trip from Calgary to Chicago?
What’s the top layover airport for flights from Calgary to Chicago?
Share of one-stop round-trip flights from Calgary to Chicago chosen by Cheapflights users in the past 12 months, using the same layover each way.
Toronto (YYZ) – chosen by Cheapflights users on 62% of one-stop itineraries from Calgary to Chicago on Cheapflights.
What’s the cheapest layover airport for flights from Calgary to Chicago?
Average round-trip fare for 1-stop flights from Calgary to Chicago, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Ottawa (YOW) is the most affordable 1-stop option, with an average round-trip price of C$ 260.
What’s the fastest layover option from Calgary to Chicago?
Shortest average travel time for 1-stop one-way flights from Calgary to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via Minneapolis (MSP) have the shortest average one-way travel time for 1-stop routes: 5h 31m.
Which airport typically offers the quickest layover for flights from Calgary to Chicago?
Average layover duration for 1-stop one-way flights from Calgary to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Minneapolis (MSP) offer the fastest connection on this route, with an average layover time of 0h 49m.
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 27 October 2025.
Read through reviews of airlines operating flights from Calgary to Chicago, such as Delta,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.9
Overall
7.9
Entertainment
7.9
Boarding
8.2
Crew
8.5
Food
7.3
Reviews
1 / 20
10.0
ExcellentMary,Oct 2025
AMS - PDX
Comfort
7.9
Overall
7.9
Entertainment
7.9
Boarding
8.2
Crew
8.5
Food
7.3
Reviews
1 / 20
10.0
ExcellentMary,Oct 2025
AMS - PDX
Comfort
7.9
Overall
7.9
Entertainment
7.9
Boarding
8.2
Crew
8.5
Food
7.3
Reviews
1 / 20
10.0
ExcellentMary,Oct 2025
AMS - PDX
Comfort
7.9
Overall
7.9
Entertainment
7.9
Boarding
8.2
Crew
8.5
Food
7.3
Reviews
1 / 20
10.0
ExcellentMary,Oct 2025
AMS - PDX
Comfort
7.9
Overall
7.9
Entertainment
7.9
Boarding
8.2
Crew
8.5
Food
7.3
Reviews
1 / 20
10.0
ExcellentMary,Oct 2025
AMS - PDX
Comfort
7.9
Overall
7.9
Entertainment
7.9
Boarding
8.2
Crew
8.5
Food
7.3
Reviews
1 / 20
10.0
ExcellentMary,Oct 2025
AMS - PDX
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.
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.
Alternative routes for Calgary to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Top 5 airlines flying from Calgary to Chicago
Discover the top 5 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 629,999 searches. Data last updated 27 October 2025.
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 helps you search for flights from Calgary to Chicago via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.
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?
Of course! You can now track prices for flights from Calgary to Chicago and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.