Cheap flights from Calgary to Chicago

Calgary
YYC
Chicago FSS
CHI

Flight deals from Calgary to Chicago

Below you can see the best deals on flights Calgary — Chicago for upcoming dates. Direct and connecting flights from various airlines — compare prices and choose the right ticket.

The lowest price for the next 2 months is on 19 September, from $139.

Top 10 cheap flights from Calgary to Chicago

WS
$ 174

Calgary — Chicago

12:00—16:40
10 Sep 2026
3 h 40 m
Direct flight
WS
$ 174

Calgary — Chicago

12:00—16:40
11 Sep 2026
3 h 40 m
Direct flight
WS
$ 174

Calgary — Chicago

12:00—16:40
28 Aug 2026
3 h 40 m
Direct flight
WS
$ 174

Calgary — Chicago

12:00—16:40
6 Sep 2026
3 h 40 m
Direct flight
WS
$ 174

Calgary — Chicago

12:00—16:40
29 Aug 2026
3 h 40 m
Direct flight
WS
$ 174

Calgary — Chicago

12:00—16:40
5 Sep 2026
3 h 40 m
Direct flight
AC
AC
$ 175

Calgary — Chicago

01:00—10:15
12 Sep 2026
8 h 15 m
1 stop
AC
AC
$ 176

Calgary — Chicago

01:00—10:15
9 Sep 2026
8 h 15 m
1 stop
AC
AC
$ 176

Calgary — Chicago

01:00—10:15
8 Sep 2026
8 h 15 m
1 stop
AC
AC
$ 176

Calgary — Chicago

01:00—10:15
15 Sep 2026
8 h 15 m
1 stop

Prices were found in the last 72 hours and may change — check the exact price when you continue.

About the Calgary — Chicago flight

Looking for cheap flights from Calgary to Chicago? Compare fares from different airlines, check the flight schedule and travel time — and book your Calgary — Chicago ticket online at the best price.

The route has direct flights — around 64 flights per week, flights are operated by American Airlines, United Airlines, WestJet, British Airways, a nonstop flight takes about 3 h 35 min, the distance between the cities is around 2,255 km.

Planning your trip? You may find our Chicago travel guide, how to get from the airport into town and Chicago weather forecast useful. To catch a low fare, use the low-price calendar and the monthly price chart on this page.

Facts about this route

from $139Min. price
SeptemberCheapest
AugustPeak season
YesDirect flights
2,255 kmDistance
3 h 35 minTravel time
4Airlines
64 / wkFlights

Flight schedule from Calgary to Chicago

The table shows direct flights from Calgary to Chicago on the selected date. The flight takes approximately 3 h 35 min. Regular flights are operated by American Airlines, United Airlines, WestJet and British Airways. Departures from Calgary International Airport airports, arrivals at O'Hare International Airport, Chicago Midway International Airport and Midway International Airport.

For each flight, the following details are shown: departure time (local), arrival city and airport, flight number and airline, terminal or gate, and status. Click on a flight to open its details and go to ticket search. To view flights on a different day, change the date above the table.

Today
Any time
Last update: 16 Aug 2026

Flight ticket prices by day: Calgary — Chicago

Below is a calendar of the lowest flight ticket prices for Calgary — Chicago by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from $139 in September, and the most expensive are around $174 in August. If your travel dates are flexible, the calendar will help you find the best price for your preferred period. To view round-trip fares, switch to the "Round trip" tab above the calendar, select your departure date — and the right-hand calendar will highlight the lowest prices for return flights on each day.

 
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Prices by month

Average one-way fares from Calgary to Chicago by month. Tickets are usually cheapest in November (around $128) and priciest in July (about $179) — use the table and chart below to pick the best time to fly.

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
Jan$138lowMay$147mediumSep$138low
Feb$133lowJun$161highOct$133low
Mar$142mediumJul$179highNov$128low
Apr$147mediumAug$174highDec$170high

Some values are estimated based on seasonality.

When to fly

Weather in Chicago: it is warmest in July (up to 27 °C on average) and coolest in January (around 0 °C). The driest month is November.

Tickets are usually cheapest in September and most expensive in August. Compare prices and weather by month in the charts below to pick the best time to fly.

Temperature · Chicago

Dry and wet days · Chicago

Wind speed and direction · Chicago

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How to get the best deal on a Calgary — Chicago ticket

  • Book ahead: fares for Calgary — Chicago are usually lower 3–8 weeks before departure than at the last minute.
  • Play with your dates — Tuesday, Wednesday and Saturday departures are often cheaper than Friday and Sunday.
  • The cheapest month to fly to Chicago is usually September — plan your trip around it if your dates are flexible.
  • Compare direct and connecting flights: nonstop is faster, while a connection is sometimes noticeably cheaper.
  • Watch the low-price calendar and the monthly price trend on this page — they make it easier to catch a good date.
  • Travelling light? Pick a cabin-baggage-only fare — tickets without checked luggage are noticeably cheaper.
  • Get to the airport in good time — about 2–3 hours before an international departure and roughly an hour before a domestic one.

Airlines

Flights on the Calgary — Chicago route are operated by 4 airlines; American Airlines runs the most flights (around 38% of all flights). Compare carriers, flight shares and schedules below.

  • American AirlinesAA
    8x/week
    WebsiteFleet: 965211M pax/year
    • Direct flight YYC → ORD8x/week
      Duration
      3h 39m
      Days
      MTWTFSS
    37.5%Open →
  • United AirlinesUA
    8x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight YYC → ORD8x/week
      Duration
      3h 34m
      Days
      MTWTFSS
    37.5%Open →
  • WestJetWS
    5x/week
    WebsiteFleet: 15325M pax/year
    • Direct flight YYC → ORD5x/week
      Duration
      3h 40m
      Days
      MTWTFSS
    21.9%Open →
  • British AirwaysBA
    1x/week
    WebsiteFleet: 29243M pax/year
    • Direct flight YYC → ORD1x/week
    3.1%Open →

Cities and airports on the Calgary — Chicago route

Flights Calgary — Chicago depart from Calgary International Airport and arrive at O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.

Departure

Calgary

YYC
Canada
About the cityHow to get thereWeatherAll about the country Canada
Arrival

Chicago

CHI
United States
About the cityHow to get thereWeatherAll about the country United States
Departure airports
Arrival airports

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Frequently asked questions about the Calgary — Chicago flight

How long is the flight from Calgary to Chicago?

A nonstop Calgary — Chicago flight takes about 3 h 35 min — the distance between the cities is around 2,255 km.

How far is it from Calgary to Chicago?

The distance from Calgary to Chicago is about 2,255 km, which a nonstop flight covers in around 3 h 35 min.

Are there direct flights from Calgary to Chicago?

Yes, there are nonstop flights Calgary — Chicago — around 64 flights per week.

Which airlines fly from Calgary to Chicago?

Airlines operating Calgary — Chicago include American Airlines, United Airlines, WestJet, British Airways. See the full list with schedules in the "Airlines" section on this page.

Which airports do Calgary — Chicago flights use?

Flights from Calgary depart from Calgary International Airport, and arrive at O'Hare International Airport, Chicago Midway International Airport, Midway International Airport. If a city has more than one airport, check which one your ticket uses before you travel.

How much is a ticket from Calgary to Chicago?

The price of a Calgary — Chicago ticket depends on your travel date, season and demand: it is usually cheapest to fly in September, and most expensive in August. Tickets typically cost between $139 and $174. Check the current lowest fare and low-price calendar on this page.

When is the best time to book flights Calgary — Chicago?

Flights Calgary — Chicago are usually cheaper when booked in advance — a few weeks before departure and away from peak dates; the most budget-friendly month to fly is September. Compare prices by month in the price trend chart on this page.

How can I find the cheapest flights from Calgary to Chicago?

To catch a low fare Calgary — Chicago, book a few weeks in advance, keep your dates flexible, and compare airlines and connecting options. The low-price calendar and monthly price chart on this page show the cheapest days and months at a glance: the most budget-friendly month to fly is usually September.

How early should I arrive at the airport?

For international flights, plan to be at the airport about 2–3 hours before departure, and around an hour before a domestic flight. Allow extra time during busy travel seasons and at large hubs, where check-in and security lines can be longer.

Where else you can fly from Calgary

See all
VancouverTorontoEdmontonKelownaSaskatoonWinnipegMontrealSeattleOttawaReginaNanaimoVictoriaGrande PrairieKamloopsFort McMurrayLos AngelesPrince GeorgeHoustonHalifaxPhoenixMinneapolisSan FranciscoLas VegasDenverNew York CityPentictonFort St. JohnComoxPuerto VallartaFrankfurt am MainCranbrookAtlantaLondonCancunPortlandNashvilleLondonDallasBostonYellowknife

Where else you can fly from Chicago

See all
New York CityTorontoDetroitWashington, D.C.AtlantaMinneapolisLos AngelesSeattleBostonDallasHoustonOrlandoDenverNashvilleLondonIndianapolisSan DiegoMontrealSt. LouisMilwaukeeCharlottePhiladelphiaColumbusKansas CityMiamiPhoenixLas VegasCincinnatiGrand RapidsDes MoinesRaleighSan FranciscoMadisonDaytonGreen BayTampaPittsburghLouisvilleKnoxvilleRochester

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