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Cheap Flights from Chicago Midway to Calgary

Compare Chicago Midway to Calgary flight deals

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

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Flight deals from Chicago Midway Airport to Calgary Airport

Looking for a cheap last-minute deal or the best return flight from Chicago Midway Airport to Calgary Airport? If you want to travel next month, return fares start from R 5,150. Find the lowest prices on one-way and return tickets right here.
Calgary.R 2,073 per passenger.Departing Tue, 28 Apr.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Tue, 28 Apr, arriving in Calgary.Price includes taxes and charges.From R 2,073, select.
Calgary.R 2,219 per passenger.Departing Sat, 26 Sep.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Sat, 26 Sep, arriving in Calgary.Price includes taxes and charges.From R 2,219, select.
Calgary.R 2,296 per passenger.Departing Sun, 3 May.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sun, 3 May, arriving in Calgary.Price includes taxes and charges.From R 2,296, select.
Calgary.R 2,406 per passenger.Departing Tue, 17 Mar.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Tue, 17 Mar, arriving in Calgary.Price includes taxes and charges.From R 2,406, select.
Calgary.R 3,497 per passenger.Departing Tue, 30 Jun.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Tue, 30 Jun, arriving in Calgary.Price includes taxes and charges.From R 3,497, select.
Calgary.R 4,214 per passenger.Departing Wed, 5 Aug.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Wed, 5 Aug, arriving in Calgary.Price includes taxes and charges.From R 4,214, select.
Calgary.R 4,365 per passenger.Departing Wed, 22 Jul.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Wed, 22 Jul, arriving in Calgary.Price includes taxes and charges.From R 4,365, select.
Calgary.R 4,890 per passenger.Departing Thu, 8 Oct.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Thu, 8 Oct, arriving in Calgary.Price includes taxes and charges.From R 4,890, select.

Find the cheapest month to fly from Chicago Midway to Calgary

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to Calgary flights are currently cheapest in April.
Mar
from R 2,406
Apr
from R 2,073
May
from R 2,296
Jun
from R 3,497
Jul
from R 4,365
Aug
from R 4,214
Sep
from R 2,219
Oct
from R 4,890
Nov
Find prices
Dec
Find prices
Jan
Find prices
Feb
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Chicago Midway to Calgary: Alternative routes

Compare routes from Chicago Midway to Calgary below. You may find an airport to fly into that's cheaper, faster, or easier than Calgary.

Calgary

8km from central Calgary
ClosestCheapest
from R 2,073
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Chicago to Calgary: Flight information

The things to know before you go.
Cheapest flight foundR 2,073
Cheapest month to flyApril

Finding cheap flights from Chicago Midway to Calgary: Frequently asked questions

The best price we found for a return flight from Chicago Midway to Calgary is R 4,563. 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.
Currently, there are no airlines that fly direct from Chicago Midway to Calgary. But we found flights with one or more stops from R 4,563.
As of March 2026, there are no flights flying from Chicago Midway to Calgary.
The cheapest month to fly from Chicago Midway to Calgary is usually April.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to Calgary Airport on Saturday, 25 April 2026.
No airlines currently offer direct flights between Chicago Midway Airport and Calgary Airport. Most routes have one or more stops.
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 Calgary 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 Calgary is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, Frontier Airlines offers the cheapest flight tickets to Calgary.

Flying from Chicago Midway International Airport (MDW) to Calgary International Airport (YYC): what you need to know

  • The timezone in Calgary is UTC-6, which is one hour behind Chicago.

  • To ensure you get on your MDW to YYC flight, allow plenty of time for things like baggage drop and finding your gate. Turning up two hours ahead of international departures and an hour before domestic flights is the standard rule.

  • Flying during a peak time such as July? Major public holidays and other popular seasons can lead to longer lines at check-in and security. Be extra cautious and get there up to four hours ahead of international flights and two hours before a domestic departure.

  • If you'd like to add a stop to your trip, simply deselect 'Direct flights only' when searching for your ticket from Chicago Midway International Airport to Calgary International Airport. These are the most popular stopovers between MDW and YYC:

    • Minneapolis-St. Paul International Airport

    • Denver International Airport

    • Nashville International Airport

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

  • Right now, R 2,073 is the cheapest price we've found for a one-way Chicago Midway International Airport to Calgary International Airport flight. The best price for a return ticket is R 4,563. Keep in mind that fares may change due to availability when booking.

  • To get your hands on cheap tickets from MDW to YYC, book early. Airlines tend to offer their best fares when flights are first released.

  • If you're willing to be flexible with your travel dates, use the 'Whole month' tool. It'll show you the lowest price across every month when searching for your flight from Chicago Midway International Airport to Calgary International Airport.

  • You won't have to check back in every day to find out if fares have gone down when you set up a Price Alert. We'll notify you as soon as there's a better deal on cheap flights from MDW to YYC.

  • Pick your preferred departure and arrival times, number of stops and airlines with the filters. Or sort your results by 'Cheapest' to get the best deals on flights from Chicago Midway International Airport to Calgary International Airport.

Handy information about Chicago Midway International Airport (MDW)

  • You'll find MDW at 5700 South Cicero.

  • Of all flights departing from Chicago Midway International Airport, 77.88% arrive as scheduled at their destination.

  • Central Chicago to Chicago Midway International Airport is approximately 19 kilometres. Depending on traffic, it'll take you about 20 minutes to get there if you're ride-sharing, catching a cab or driving.

  • The trip on public transport takes roughly 45 minutes.

  • Searching for a handy hotel near MDW? If you're boarding an early flight from Chicago Midway International Airport to Calgary International Airport, these stays will put you moments from check-in:

Arriving at Calgary International Airport (YYC)

Getting from Calgary International Airport (YYC) to central Calgary

  • YYC is located at 2000 Airport Road Northeast.

  • Calgary International Airport is roughly 16 kilometres from central Calgary. The drive time takes about 20 minutes.

  • If you're travelling on public transport, expect a journey of around 1 hour.

When to fly to Calgary International Airport (YYC)

  • The quietest month for a flight from Chicago Midway International Airport to Calgary International Airport is February, while July is the busiest. Choose the best time to go to Calgary based on whether you prefer a faster pace or a more relaxed vibe.

  • Lock in your flight from Chicago Midway International Airport to Calgary International Airport for August if you want to go to Calgary during its warmest month. You can expect temperatures of between 8ºC (46ºF) and 26ºC (79ºF).

  • For cooler conditions, look for a cheap ticket from MDW to YYC in December. Temperatures average between -18ºC (0ºF) and 0ºC (32ºF) then.

Explore more of Canada

  • Calgary is easy to fall in love with, but there are so many other parts of Canada waiting to be discovered. About 274 kilometres north of Calgary, a trip to Edmonton will keep you on the move. Start with attractions like Royal Alberta Museum, Fort Edmonton Park and Alberta Legislature Building.

  • If you're eager to discover another major destination in Canada, head for Kelowna, about 402 kilometres west of Calgary. Kasugai Japanese Garden, Waterfront Park and BC Wine Museum & VQA Wine Shop are key reasons to visit.

Plan the rest of your trip from Chicago to Calgary

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