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Cheap Flights from Calgary (YYC) to Chicago (CHIA)

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      1. Home
      2. Canada
      3. Calgary
      4. Chicago

      Compare Calgary to Chicago flight deals

      Find the cheapest month or even day of the year to fly to Chicago

      Book the best Chicago fare with no extra fees

      TrustScore 4.4 out of 5 4.4 out of 5 based on 19,786 reviews Trustpilot
      Flight dealsCheapest monthFind the best routeRoute infoFAQsTips and advice

      Flight deals from Calgary to Chicago

      Looking for a cheap last-minute deal or the best return flight from Calgary to Chicago? Find the lowest prices on one-way and return tickets right here.
      Chicago.£144 per passenger.Departing Sat, 31 May, returning Sat, 7 Jun.Return flight with United.Outbound indirect flight with United, departs from Calgary on Sat, 31 May, arriving in Chicago O'Hare International.Inbound indirect flight with United, departs from Chicago O'Hare International on Sat, 7 Jun, arriving in Calgary.Price includes taxes and charges.From £144, select.
      Sat, 31 MayYYC - ORD with United
      1 stop
      Sat, 7 JunORD - YYC with United
      1 stop
      from £144
      Chicago.£146 per passenger.Departing Tue, 25 Nov, returning Tue, 2 Dec.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Calgary on Tue, 25 Nov, arriving in Chicago O'Hare International.Inbound indirect flight with Air Canada, departs from Chicago O'Hare International on Tue, 2 Dec, arriving in Calgary.Price includes taxes and charges.From £146, select.
      Tue, 25 NovYYC - ORD with Air Canada
      1 stop
      Tue, 2 DecORD - YYC with Air Canada
      1 stop
      from £146
      Chicago.£158 per passenger.Departing Sat, 31 May, returning Fri, 6 Jun.Return flight with Air Canada.Outbound direct flight with Air Canada departs from Calgary on Sat, 31 May, arriving in Chicago O'Hare International.Inbound direct flight with Air Canada departs from Chicago O'Hare International on Fri, 6 Jun, arriving in Calgary.Price includes taxes and charges.From £158, select.
      Air Canada
      Sat, 31 MayYYC - ORD with Air Canada
      Direct
      Air Canada
      Fri, 6 JunORD - YYC with Air Canada
      Direct
      from £158
      Chicago.£159 per passenger.Departing Tue, 25 Nov, returning Wed, 21 Jan.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Calgary on Tue, 25 Nov, arriving in Chicago O'Hare International.Inbound indirect flight with Air Canada, departs from Chicago O'Hare International on Wed, 21 Jan, arriving in Calgary.Price includes taxes and charges.From £159, select.
      Tue, 25 NovYYC - ORD with Air Canada
      1 stop
      Wed, 21 JanORD - YYC with Air Canada
      1 stop
      from £159
      Chicago.£166 per passenger.Departing Wed, 20 Aug, returning Tue, 26 Aug.Return flight with Delta.Outbound indirect flight with Delta, departs from Calgary on Wed, 20 Aug, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Tue, 26 Aug, arriving in Calgary.Price includes taxes and charges.From £166, select.
      Wed, 20 AugYYC - MDW with Delta
      1 stop
      Tue, 26 AugMDW - YYC with Delta
      1 stop
      from £166
      Chicago.£166 per passenger.Departing Wed, 1 Oct, returning Wed, 15 Oct.Return flight with Delta.Outbound indirect flight with Delta, departs from Calgary on Wed, 1 Oct, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Wed, 15 Oct, arriving in Calgary.Price includes taxes and charges.From £166, select.
      Wed, 1 OctYYC - ORD with Delta
      1 stop
      Wed, 15 OctORD - YYC with Delta
      1 stop
      from £166
      Chicago.£166 per passenger.Departing Thu, 4 Sep, returning Tue, 9 Sep.Return flight with Delta.Outbound indirect flight with Delta, departs from Calgary on Thu, 4 Sep, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Tue, 9 Sep, arriving in Calgary.Price includes taxes and charges.From £166, select.
      Thu, 4 SepYYC - ORD with Delta
      1 stop
      Tue, 9 SepORD - YYC with Delta
      1 stop
      from £166
      Chicago.£166 per passenger.Departing Tue, 3 Jun, returning Thu, 5 Jun.Return flight with Delta.Outbound indirect flight with Delta, departs from Calgary on Tue, 3 Jun, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Thu, 5 Jun, arriving in Calgary.Price includes taxes and charges.From £166, select.
      Tue, 3 JunYYC - MDW with Delta
      1 stop
      Thu, 5 JunORD - YYC with Delta
      1 stop
      from £166
      How did we find these deals? The deals you see here are the lowest prices for flight tickets from Calgary to Chicago found in the last 4 days, and are subject to change and availability.

      Find the cheapest month to fly from Calgary to Chicago

      We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Calgary to Chicago flights are currently cheapest in June.
      May
      from £178
      Jun
      from £166
      Jul
      from £166
      Aug
      from £166
      Sep
      from £166
      Oct
      from £166
      Nov
      from £209
      Dec
      from £197
      Jan
      from £176
      Feb
      Find prices
      Mar
      from £196
      Apr
      Find prices

      Direct flights from Calgary to Chicago

      Alternative Calgary to Chicago routes

      Looking for the cheapest, fastest or easiest route from Calgary to Chicago? You could fly into the following airports instead.

      Calgary to Chicago: Flight information

      The things to know before you go.
      Cheapest flight found£144
      Cheapest month to flyMay
      Average flight time3 hrs, 28 mins
      Most popular airlineQatar Airways
      Average flights per week74

      Finding cheap flights from Calgary to Chicago: Frequently asked questions

      There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
      The best price we found for a return flight from Calgary to Chicago is £144. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
      3 hours and 28 minutes is the average flight time from Calgary to Chicago.
      Qatar Airways, American Airlines and British Airways fly direct from Calgary to Chicago.
      As of May 2025, there are 74 flights per week flying from Calgary to Chicago.
      The cheapest month to fly from Calgary to Chicago is usually May 2025.
      After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Calgary Airport to Chicago on Saturday, 31 May 2025.
      Yes – the average flight time is 3 hours and 28 minutes.
      We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
      We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
      In May, the average temperature is usually around 13°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
      Currently, United and Air Canada offer the cheapest flight tickets to Chicago.

      Travelling from Calgary International Airport (YYC) to Chicago: what you need to know

      • Expect to be in the air for 3 hours 50 minutes. That's the average duration of a direct flight from Calgary International Airport to Chicago.

      • Chicago is one hour ahead of Calgary, where Calgary International Airport is located. Chicago follows the UTC-5 timezone.

      • Calgary International Airport (YYC) to O'Hare International Airport (ORD) is the most traveled route, with 22 departures a week to choose from. If you prefer a later start to the day, the last flight from YYC to ORD is with American Airlines at 13:27. Go for the first departure operated by American Airlines at 06:29 if you want to fly out earlier.

      • For a smooth journey, arrive at the airport two hours ahead of international flights and an hour before domestic departures. This ensures you have enough time to board your YYC to Chicago flight.

      • If you're jetting off during a bank holiday or another peak period, give yourself extra time. A good rule is two hours ahead of domestic flights and up to four hours before international departures. Queues at check-in and security will be longer.

      • You can book a direct Calgary International Airport to Chicago ticket. Start your journey at YYC and end it at O'Hare International Airport (ORD).

      • There's a good selection of airlines that offer direct flights from Calgary International Airport to Chicago, such as:

        • United Airlines

        • American Airlines

        • WestJet

      • Located around 6 miles from central Calgary, YYC can be reached in about 20 minutes by car. The journey on public transport will take roughly 1 hour.

      • Catching an early flight from Calgary International Airport to Chicago? Avoid the hassle of rushing to the airport (and enjoy a little extra shut-eye) by choosing one of these hotels near YYC:

        • Acclaim Hotel by Clique

        • Divya Sutra Plaza and Conference Centre Calgary Airport

        • Hampton Inn by Hilton Calgary Airport North

      • When it comes to Calgary International Airport's on-time performance, data shows 65.39% of flights meet their scheduled arrival time.

      • YYC is located at 2000 Airport Road Northeast.

      How to find the cheapest flights from Calgary International Airport (YYC) to Chicago

      • The lowest price we've found for a one-way Calgary International Airport to Chicago flight is £78. The cheapest price for a return flight is £144. Remember fares may change due to demand at the time of booking.

      • To pick up cheap flights from YYC to Chicago, book your journey one month ahead of your departure date.

      • Organise your trip for May. That's the best month for scoring the biggest deals on Calgary International Airport to Chicago tickets. If you have flexibility with your dates, use the 'Whole month' tool to access the cheapest price across each month.

      • You don't need to keep looking every day to find out if fares have dropped when you set up a Price Alert. We'll update you the moment there's an extra saving on cheap flights from YYC to Chicago.

      • Tailor your trip with filters. Choose your ideal departure and arrival times, total journey duration and airlines. You can also sort the results by 'Cheapest,' 'Best' or 'Fastest' flights from Calgary International Airport to Chicago.

      Airports in Chicago

      O'Hare International Airport (ORD)

      • The distance from O'Hare International Airport (ORD) to central Chicago is roughly 25 miles. It takes about 35 minutes to get to the centre driving.

      • If you're using public transport, expect a journey time of around 55 minutes.

      • If you're arriving on a late flight from Calgary International Airport to Chicago, nothing beats the convenience of staying close to the terminal. Grab your bags from the carousel and then be showered and relaxing not long after at one of these accommodation options near ORD:

        • Super 8 by Wyndham Chicago OHare Airport

        • Hilton Chicago OHare Airport

        • DoubleTree by Hilton Chicago OHare Airport-Rosemont

      • Get your adventure underway by picking up an O'Hare International Airport rental car. Grab a set of wheels from Routes Car Rentals, Dollar or Budget and explore beyond Chicago's usual tourist stops.

      • Booking your ride from O'Hare International Airport about four weeks ahead of your flight from YYC to Chicago can help you secure the lowest rate.

      • The address for ORD is 10000 West O'Hare.

      Chicago Midway International Airport (MDW)

      • The centre of Chicago is about 12 miles from Chicago Midway International Airport (MDW). Once your flight from Calgary International Airport to Chicago has hit the runway and you've made your way to arrivals, expect a drive of around 20 minutes.

      • If you choose to travel on public transport, you'll reach the centre in 45 minutes or so.

      • Hang up the 'Do not disturb' sign and relax at a hotel near MDW. Here are a few options where you can put your feet up after your YYC to Chicago flight:

        • Holiday Inn Chicago Midway Airport S by IHG

        • Carlton Inn Midway

        • Skylark Motel

      • Forget about inconvenient public transport schedules or waiting in a long cab line. Grab a Chicago Midway International Airport rental car and blaze your own trail. Compare offers from Dollar, Hertz and Budget.

      • Score the best price by booking your ride from MDW four weeks in advance. You'll also have access to a bigger selection of vehicles.

      • The address for Chicago Midway International Airport is 5700 South Cicero.

      Chicago Rockford International Airport (RFD)

      • Chicago Rockford International Airport (RFD) is around 85 miles from the centre of Chicago. It takes about 1 hour 25 minutes to get to the city centre in a cab or ride-share once you've stepped off your flight from Calgary International Airport to Chicago.

      • Public transport can get you there in around 4 hours 15 minutes.

      • Choose a hotel near RFD and go from landing to lounging in your room in a flash. Whether you're coming in on a late YYC to Chicago flight or just want to simplify your travel plans, these accommodation options are all about convenience:

        • OYO Hotel at Chicago Rockford International Airport, IL

        • Hotel Weston Rfd

        • Super 8 by Wyndham Rockford South

      • Whether you'd like a budget-friendly compact for a solo trip or a roomy SUV to transport your group, you'll find the ideal Chicago Rockford International Airport rental car for your needs. Browse the range of wheels available here from names such as Budget, Alamo and National.

      • Rental agencies sometimes offer discounts on early bookings, so secure your ride from RFD ahead of your flight from Calgary International Airport to Chicago. A little planning can save you money.

      • Chicago Rockford International Airport is located at 2 Airport Cir.

      Best time to go to Chicago

      • Before booking your flights from Calgary International Airport to Chicago, consider which time of year works best for you. High season in Chicago offers a lively atmosphere and plenty of activities, while the low season brings better hotel deals and fewer crowds.

      • Before booking a Calgary International Airport to Chicago plane ticket, think about the weather you're most comfortable in. July is the warmest month in Chicago, with temperatures ranging from 15ºC (59ºF) to 29ºC (84ºF).

      • If you like cooler conditions, search for a cheap ticket from YYC to Chicago in January when temperatures average between -12ºC (10ºF) and 3ºC (37ºF).

      More about Chicago

      • When it comes to looking for somewhere to rest your head, you'll find the best stays in Chicago right here. Explore these hotels once you've booked your flight from Calgary International Airport to Chicago:

        • Hotel Saint Clair - Magnificent Mile

        • Warwick Allerton Chicago

        • The Whitehall Hotel - BW Premier Collection

      • There are so many things to do and see in this city it can be hard to know where to begin. Art Institute of Chicago, Millennium Park and LandShark Beer Garden at Navy Pier are highlights which should be on every Chicago itinerary.

      Explore more of United States

      • You've seen Chicago, now it's time to discover other parts of United States. Journey around 280 miles south-east to Columbus to tick off its must-visit sights. From Franklin Park Conservatory and Botanical Gardens to Ohio Statehouse and German Village, you've got a jam-packed schedule ahead.

      • If you're ready to explore another well-known destination in United States, consider Indianapolis, roughly 160 miles south-east of Chicago. The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo are among its highlights.

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      Plan the rest of your trip from Calgary to Chicago

      • Car hire in Chicago
      • Hotels in Chicago

      Prices shown on this page are estimated lowest prices only. Found in the last 45 days.

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