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Cheap Flights from Calgary to Chicago

Hi, I've summed up all the key info for Calgary to Chicago flights

Cheapest one-way

S$ 167
Westjet Tue, Oct 6

57% below next 30d avg. (S$ 385)

Cheapest return

S$ 285
Air Canada Wed, Oct 21

53% below next 30d avg. (S$ 609)

Best time to book

October Cheapest month
January Peak month

Fastest flight

3h 33m 3m faster than avg. (3h 36m)

Recommended airlines

With a lowest one-way fare of S$ 167 , travelers can expect an average price of S$ 385 for upcoming trips, while round-trip tickets start at S$ 285 . Flights typically take around 3h 36m , but the fastest nonstop option completes the journey in just 3h 33m minutes. Flights to Chicago can arrive at: O'Hare International Airport (ORD) , Chicago Midway International Airport (MDW) and Chicago Rockford International Airport (RFD). The most common route connects Calgary International Airport and O'Hare International Airport (YYC–ORD). To secure the best rates, booking 40 days in advance is recommended, and the cheapest travel days are Tuesday, Wednesday, and Saturday .

Updated 5d ago · This content is an AI-powered summary based on Trip.com data. Prices and availability are subject to change. Please refer to actual prices, availability, and travel conditions.

Explore the cheapest one-way and round-trip flights from Calgary to Chicago over the next 90 days, with one-way fares from S$ 167 and round-trip from S$ 285. Based on Trip.com's latest 7-day flight data.

      • Cheapest nonstop
        YYC 12:37
        3h 33m
        Direct
        ORD 17:10
        Calgary - Chicago | Fri, Oct 30 | United Airlines
        ORD 08:40
        3h 55m
        Direct
        YYC 12:35
        Chicago - Calgary | Tue, Nov 3 | United Airlines
        S$ 291 S$ 391
        26% off
        26% off
        S$ 391 S$ 291
      • YYC 12:00
        3h 40m
        Direct
        ORD 16:40
        Calgary - Chicago | Fri, Sep 25 | Westjet
        ORD 17:30
        3h 55m
        Direct
        YYC 20:25
        Chicago - Calgary | Tue, Sep 29 | Westjet
        S$ 294 S$ 391
        25% off
        25% off
        S$ 391 S$ 294
      • YYC 12:00
        3h 40m
        Direct
        ORD 16:40
        Calgary - Chicago | Mon, Sep 21 | Westjet
        ORD 17:30
        3h 55m
        Direct
        YYC 20:25
        Chicago - Calgary | Sun, Sep 27 | Westjet
        S$ 294 S$ 391
        25% off
        25% off
        S$ 391 S$ 294
      • YYC 00:55
        8h 17m
        1 stop
        ORD 10:12
        Calgary - Chicago | Wed, Oct 21 | Air Canada
        ORD 08:40
        3h 48m
        Direct
        YYC 11:28
        Chicago - Calgary | Sat, Oct 24 | United Airlines
        S$ 285
        27% off
        S$ 391 S$ 285
      • YYC 23:55
        8h 5m
        1 stop
        ORD 09:00
        Calgary - Chicago | Fri, Oct 16 | Air Canada
        ORD 08:40
        3h 48m
        Direct
        YYC 11:28
        Chicago - Calgary | Fri, Oct 23 | United Airlines
        S$ 285
        27% off
        S$ 391 S$ 285
      • YYC 00:55
        8h 17m
        1 stop
        ORD 10:12
        Calgary - Chicago | Tue, Oct 20 | Air Canada
        ORD 08:45
        8h 12m
        1 stop
        YYC 15:57
        Chicago - Calgary | Fri, Oct 23 | Air Canada
        S$ 287
        27% off
        S$ 391 S$ 287
      • YYC 06:00
        8h 38m
        1 stop
        ORD 15:38
        Calgary - Chicago | Fri, Oct 30 | Air Canada
        ORD 08:40
        3h 55m
        Direct
        YYC 12:35
        Chicago - Calgary | Tue, Nov 3 | United Airlines
        S$ 291
        26% off
        S$ 391 S$ 291
      • YYC 06:00
        8h 38m
        1 stop
        ORD 15:38
        Calgary - Chicago | Thu, Oct 29 | Air Canada
        ORD 08:40
        3h 55m
        Direct
        YYC 12:35
        Chicago - Calgary | Tue, Nov 3 | United Airlines
        S$ 291
        26% off
        S$ 391 S$ 291
      • YYC 00:50
        7h 10m
        1 stop
        ORD 09:00
        Calgary - Chicago | Sat, Oct 17 | Air Canada
        ORD 08:40
        3h 48m
        Direct
        YYC 11:28
        Chicago - Calgary | Wed, Oct 21 | United Airlines
        S$ 291
        26% off
        S$ 391 S$ 291
      • YYC 06:30
        7h 25m
        1 stop
        ORD 14:55
        Calgary - Chicago | Tue, Sep 29 | Air Canada
        ORD 06:00
        16h 48m
        1 stop
        YYC 21:48
        Chicago - Calgary | Fri, Oct 2 | United Airlines
        S$ 297
        24% off
        S$ 391 S$ 297
      • YYC 13:00
        17h 25m
        1 stop
        CHI 14:00
        Calgary - Chicago | Wed, Sep 16 | Normal Airline
        CHI 15:00
        6h
        Direct
        YYC 16:00
        Chicago - Calgary | Fri, Sep 18 | Normal Airline
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      • Cheapest nonstop
        YYC 12:00
        3h 40m
        Direct
        ORD 16:40
        Calgary - Chicago | Tue, Oct 6 | Westjet
        S$ 167 S$ 237
        30% off
        30% off
        S$ 237 S$ 167
      • YYC 13:51
        3h 45m
        Direct
        ORD 18:36
        Calgary - Chicago | Thu, Oct 22 | American Airlines
        S$ 178 S$ 237
        25% off
        25% off
        S$ 237 S$ 178
      • YYC 13:37
        3h 33m
        Direct
        ORD 17:10
        Calgary - Chicago | Thu, Nov 12 | United Airlines
        S$ 180 S$ 237
        24% off
        24% off
        S$ 237 S$ 180
      • YYC 06:00
        7h 52m
        1 stop
        ORD 14:52
        Calgary - Chicago | Wed, Sep 16 | Air Canada
        S$ 170
        28% off
        S$ 237 S$ 170
      • YYC 01:00
        8h 12m
        1 stop
        ORD 10:12
        Calgary - Chicago | Thu, Oct 22 | Air Canada
        S$ 174
        27% off
        S$ 237 S$ 174
      • YYC 01:00
        8h 12m
        1 stop
        ORD 10:12
        Calgary - Chicago | Sun, Oct 25 | Air Canada
        S$ 174
        27% off
        S$ 237 S$ 174
      • YYC 01:00
        8h 12m
        1 stop
        ORD 10:12
        Calgary - Chicago | Wed, Oct 21 | Air Canada
        S$ 175
        26% off
        S$ 237 S$ 175
      • YYC 01:45
        9h 22m
        1 stop
        ORD 11:07
        Calgary - Chicago | Wed, Nov 4 | Air Canada
        S$ 175
        26% off
        S$ 237 S$ 175
      • YYC 00:55
        8h 17m
        1 stop
        ORD 10:12
        Calgary - Chicago | Fri, Oct 16 | Air Canada
        S$ 175
        26% off
        S$ 237 S$ 175
      • YYC 23:55
        8h 5m
        1 stop
        ORD 09:00
        Calgary - Chicago | Sat, Sep 19 | Air Canada
        S$ 179
        24% off
        S$ 237 S$ 179
      • YYC 13:00
        17h 25m
        1 stop
        CHI 14:00
        Calgary - Chicago | Wed, Sep 16 | Normal Airline
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Flight.News
Over the past 7 days, flights from Calgary to Chicago have operated an average of 15 times per day, with 33.0% on-time departure rate and 93.2% on-time arrival rate.

Which airlines are the most popular for Calgary to Chicago flights?

You can choose from 1 airlines flying from Calgary to Chicago, including Westjet, and . Westjet currently offers the cheapest direct ticket on this route.
Westjet logo Westjet
Airlines are determined based on actual purchased flight tickets from Calgary to Chicago according to previous 12 months data from Trip.com.

Flying from Calgary to Chicago

The distance between Calgary and Chicago is approximately 2,248.84km. It takes around 3 hours 36 minutes on average to fly from Calgary to Chicago. Based on Trip.com's data, travel demand peaks in January. The off-season for travel is October.

Cheapest one-way flight price S$ 167
Cheapest return ticket price S$ 285
Off-season for travel October
Peak season for travel January
Flight distance 2,248.84km
Average flight time 3 hours 36 minutes
Popular airline Westjet
Frequency ～19/week
Flight statistics for the Calgary–Chicago route are based on aggregated booking data from Trip.com over the past 12 months.

Trip.com Price Insights on Flights from Calgary to Chicago.

What is the cheapest month for one-way flights from Calgary to Chicago?

The average price of one-way flights from Calgary to Chicago purchased by Trip.com users by month over the past 12 months.

Based on Trip.com’s data, the cheapest month for flights from Calgary to Chicago is November, with an average price of S$ 168, and the most expensive month is July, with an average price of up to S$ 385.

S$ 385
S$ 277
S$ 168
S$ 60
    Cheapest
  • S$ 273
    Sep
  • S$ 218
    Oct
  • S$ 168
    Nov
  • S$ 320
    Dec
  • S$ 233
    Jan
  • S$ 223
    Feb
  • S$ 270
    Mar
  • S$ 230
    Apr
  • S$ 190
    May
  • S$ 256
    Jun
  • S$ 385
    Jul
  • S$ 327
    Aug

What is the cheapest month for round-trip flights from Calgary to Chicago?

The average price of round-trip flights from Calgary to Chicago purchased by Trip.com users by month over the past 12 months.

Based on Trip.com’s data, the cheapest month for round-trip flights from Calgary to Chicago is November, with an average price of S$ 223, and the most expensive month is July, with an average price of up to S$ 626.

S$ 626
S$ 425
S$ 223
S$ 22
    Cheapest
  • S$ 229
    Sep
  • S$ 277
    Oct
  • S$ 223
    Nov
  • S$ 273
    Dec
  • S$ 340
    Jan
  • S$ 342
    Feb
  • S$ 474
    Mar
  • S$ 300
    Apr
  • S$ 363
    May
  • S$ 357
    Jun
  • S$ 626
    Jul
  • S$ 587
    Aug

Frequently Asked Questions

  • Which airlines offer the cheapest flights from Calgary to Chicago?

    Based on Trip.com data, Westjet offers Cheapest nonstop one-way flights from S$ 167 (for example, YYC–ORD on Tue, Oct 6). For a Cheapest nonstop return flight, Air Canada offers fares from S$ 285, departing on Wed, Oct 21 and returning on Sat, Oct 24.
  • At the moment, you can catch a direct flight from Calgary to Chicago with the following airlines, including: Westjet Selected airlines are based on historical data collected from flight bookings users made on Trip.com within the last 90 days.
  • It takes about 3 hours 36 minutes to fly from Calgary (YYC) to Chicago (CHI).
  • By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Calgary to Chicago is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.
  • On average, 31 direct flights operate each week between Calgary and Chicago. See below the schedules of the main airlines serving this route:
    Westjet: S/M/T/W/T/F/S – WS1610 (departure at 14:02)
  • Here are some tips for finding the best flight deals from Calgary to Chicago on Trip.com:
    · Be flexible with your travel dates. The cheapest flight is currently on Tue, Oct 6, with one-way fares from just S$ 167.
    · Compare airlines. Westjet currently offers the lowest fares on this route.
    · Set up a price alert to track fare changes without searching every day.
    · Check Trip.com regularly for flight deals and available promo codes.
    · Avoid peak season or book early. January is generally the busiest month for travel to Chicago.
    · Get exclusive promo codes on the Trip.com app.
  • The cheapest month to book a flight from Calgary to Chicago is usually October, when demand is lower.
  • After crunching the numbers on our September flight calendar, it's currently cheapest to fly from Calgary to Chicago on September 15, 2026 with Westjet, with prices starting at S$ 173.
  • Flights to Chicago can arrive at: O'Hare International Airport (ORD), Chicago Midway International Airport (MDW) and Chicago Rockford International Airport (RFD). The most common route connects Calgary International Airport and O'Hare International Airport (YYC–ORD).
  • The time difference between Chicago and Calgary is 0m.
  • Tickets can only be changed or cancelled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.
  • Based on Trip.com data for flights departing in the next 30 days, the average one-way fare from Calgary to Chicago is S$ 385. Fares vary by travel date, airline and availability.
  • Based on Trip.com data for travel in the next 30 days, the average round-trip fare from Calgary to Chicago is S$ 609. The final price depends on the outbound and return dates, airline and fare conditions.
  • Enter Calgary and Chicago, choose your travel dates and passengers, then compare flights by price, duration and baggage. Select a fare, review the change and cancellation rules, enter traveller details and complete payment to receive your confirmation.
  • Westjet and Porter Airlinesare the most popular budget airlines flying from Calgary to Chicago. Check baggage, seat and payment fees before comparing the final price.

Find Cheap Flights & Deals on Trip.com

Note: Prices shown on this page are the lowest estimated prices found in the last 24 hours and include all taxes and fees.

Book with no extra fees

Prices displayed on this page are all-inclusive (incl. taxes, fuel surcharges, Civil Aviation Development Fund, etc.), and all fees are shown before payment. Charges for checked baggage, meals, Wi-Fi, and other optional services may also appear in the flight cards.

Real-time pricing updates

Prices, availability, and travel information on this page have been updated within the last 24 hours, and with many routes refreshed in real time. The more popular the route, the more accurate the data.

Change & Cancellation Policy

Trip.com shows the change and cancellation rules for each ticket during the booking process, including all related fees and conditions. Please refer to the following scenarios:
Voluntary cancellation/change:
To request a change or cancellation, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and flight segment, and submit your request. Please note that additional charges may apply based on the airline’s fare rules.
Cancellation/change due to a flight schedule change:
If your flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For full details of change and cancellation policies, please refer to the customer support pages.