Find flights
When to book
Airlines
FAQs

Cheap flights from Alberta to Chicago Midway Airport from C$ 190

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 2/7. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — MDW
17 Jun — 24 Jun1
1 adult

Cheap flight deals from Alberta to Midway

Keep the following information in mind while searching for Alberta to Midway flight deals. Data was last updated 12 June 2025.

Round-trip from

C$ 328

One-way from

C$ 190

Popular in

December

Cheapest in

April

Average price

C$ 334
Delta
  • Delta
  • 9/9-17/9
  • 3 total stops
  • 18h 51m total
  • Alberta to Chicago
Search Deals
Delta
  • Delta
  • 2/7
  • 1 total stop
  • 9h 55m total
  • Alberta to Chicago
Search Deals
Highest demand for flights based on searches. 22% potential increase in price (C$ 153 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease (C$ 32 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2025
Search Deals

Find flight deals from Alberta to Midway

Cheapest flights from Alberta to Midway
Explore the most affordable flight options available from Alberta to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 12 June 2025.

Tue 17/66:45 a.m.YYC - MDW
1 stop9h 55mDelta
Tue 24/61:47 p.m.MDW - YYC
1 stop8h 10mDelta
Deal found 11/6C$ 328
Tue 8/79:25 a.m.YEG - MDW
1 stop7h 14mDelta
Tue 15/79:25 a.m.MDW - YEG
2 stops12h 53mDelta
Deal found 10/6C$ 413
Fri 25/712:30 a.m.YYC - MDW
1 stop21h 05mMultiple Airlines
Sat 2/86:20 a.m.MDW - YYC
2 stops19h 24mMultiple Airlines
Deal found 11/6C$ 476
Tue 8/76:45 p.m.YEG - MDW
1 stop13h 00mMultiple Airlines
Tue 15/79:40 a.m.MDW - YEG
1 stop12h 38mMultiple Airlines
Deal found 10/6C$ 507
Wed 16/78:05 a.m.YEG - MDW
2 stops23h 40mPorter Airlines
Tue 22/79:40 a.m.MDW - YEG
2 stops13h 55mPorter Airlines
Deal found 12/6C$ 546
Mon 21/77:00 a.m.YYC - MDW
2 stops32h 24mPorter Airlines
Tue 5/85:20 p.m.MDW - YYC
2 stops29h 00mPorter Airlines
Deal found 11/6C$ 629
Wed 29/107:00 a.m.YEG - MDW
2 stops13h 44mWestJet
Sat 1/1110:35 a.m.MDW - YEG
2 stops13h 14mWestJet
Deal found 10/6C$ 738
Fri 25/712:30 a.m.YYC - MDW
1 stop20h 12mWestJet
Sat 2/812:43 p.m.MDW - YYC
1 stop10h 32mWestJet
Deal found 11/6C$ 882

Cheapflights Fare Finder

Customize your flight search to find flights from Alberta to Midway 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 12 June 2025.
Use the filters below to find and compare flights from Alberta to Chicago Midway Airport that are best for you.

Fly from

Alberta

Fly to

Midway

Route

Depart

Return

Price

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 9/9

6:40 a.m.-5:37 p.m.

1 stop9h 57m

Chicago Midway

Wed 17/9

1:00 p.m.-8:54 p.m.

2 stops8h 54m

C$ 328

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Tue 8/7

9:25 a.m.-5:39 p.m.

1 stop7h 14m

Chicago Midway

Tue 15/7

9:25 a.m.-9:18 p.m.

2 stops12h 53m

C$ 413

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 25/7

12:30 a.m.-10:35 p.m.

1 stop21h 05m

Chicago Midway

Sat 2/8

6:20 a.m.-12:44 a.m.

2 stops19h 24m

C$ 476

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Tue 8/7

6:45 p.m.-8:45 a.m.

1 stop13h 00m

Chicago Midway

Tue 15/7

9:40 a.m.-9:18 p.m.

1 stop12h 38m

C$ 507

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Wed 16/7

8:05 a.m.-8:45 a.m.

2 stops23h 40m

Chicago Midway

Tue 22/7

9:40 a.m.-10:35 p.m.

2 stops13h 55m

C$ 546

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 21/7

7:00 a.m.-4:24 p.m.

2 stops32h 24m

Chicago Midway

Tue 5/8

5:20 p.m.-9:20 p.m.

2 stops29h 00m

C$ 629

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Tue 8/7

9:25 a.m.-5:39 p.m.

1 stop7h 14m

Chicago Midway

Sat 12/7

12:43 p.m.-1:57 p.m.

2 stops26h 14m

C$ 738

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 25/7

12:30 a.m.-9:42 p.m.

1 stop20h 12m

Chicago Midway

Sat 2/8

12:43 p.m.-10:15 p.m.

1 stop10h 32m

C$ 882

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 2/7

6:45 a.m.-5:40 p.m.

1 stop9h 55m

C$ 190

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 4/10

7:00 a.m.-11:09 p.m.

2 stops15h 09m

C$ 227

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/6

Showing 1-10 of 16 results
1
2

Best time to book a flight from Alberta to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Alberta 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 Alberta to Chicago Midway Airport

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 43.0 mm.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated 12 June 2025.
To help decide which airline to fly from Alberta to Chicago, see what other customers have to say about Porter Airlines, Delta and WestJet. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
288 reviews
Check prices

Overall

8.0

Entertainment

7.0

Comfort

8.1

Food

7.6

Boarding

8.2

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Porter Airlines
8.0
Very good
288 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Overall

8.0

Entertainment

7.0

Comfort

8.1

Food

7.6

Boarding

8.2

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Delta
8.0
Very good
7,946 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Overall

8.0

Entertainment

7.0

Comfort

8.1

Food

7.6

Boarding

8.2

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
WestJet
7.2
Good
2,868 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Overall

8.0

Entertainment

7.0

Comfort

8.1

Food

7.6

Boarding

8.2

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

Related info for your journey

Find useful and relevant information for your journey from Alberta to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Alberta to Chicago Midway Airport one-way?

    C$ 190 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on Porter Airlines and WestJet, with prices starting from C$ 261 and C$ 414, respectively.

  • What are the most popular routes from Alberta to Chicago Midway Airport?

    Most travellers choose Calgary - Chicago Midway, Edmonton - Chicago Midway or Grande Prairie - Chicago Midway when deciding on the best route from Alberta to Chicago Midway Airport.

  • Can I find deals for flights from Alberta to Midway that include hotel bookings?

    Yes. In addition to deals on Alberta to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Alberta to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Alberta to Midway.

  • Can I find deals for business class flights from Alberta to Midway?

    Yes. Cheapflights offers flight deals from Alberta to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Alberta to Chicago Midway Airport?

    Currently, January is the cheapest month in which you can book a flight from Alberta to Chicago Midway Airport (average of C$ 243). Flying from Alberta to Chicago Midway Airport in November is currently the most expensive (average of C$ 312). 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.

See more FAQs

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 Alberta to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Pearson Intl to O'Hare Intl flights
Toronto Island to Midway flights
Vancouver Intl to O'Hare Intl flights
Pearson Intl to Midway flights
Pierre Elliott Trudeau Intl to O'Hare Intl flights
Pierre Elliott Trudeau Intl to Midway flights
Toronto Island to O'Hare Intl flights
Québec City to O'Hare Intl flights
Calgary to O'Hare Intl flights
Winnipeg to O'Hare Intl flights
Ottawa to O'Hare Intl flights
Vancouver Intl to Midway flights
Region of Waterloo Intl to O'Hare Intl flights
Hamilton to O'Hare Intl flights
Edmonton to O'Hare Intl flights
Québec City to Midway flights
Calgary to Midway flights
Edmonton to Midway flights
Halifax to O'Hare Intl flights
Ottawa to Midway flights
St John to O'Hare Intl flights
Halifax to Midway flights
Saskatoon to O'Hare Intl flights
Moncton to O'Hare Intl flights
St. John's to O'Hare Intl flights
Victoria to O'Hare Intl flights
Regina to O'Hare Intl flights
Kelowna to O'Hare Intl flights
Kelowna to Midway flights
Nanaimo to O'Hare Intl flights
Comox to O'Hare Intl flights
Saskatoon to Midway flights
Grande Prairie to O'Hare Intl flights
Grande Prairie to Midway flights
Fort McMurray to O'Hare Intl flights
London to O'Hare Intl flights
Victoria to Midway flights
Sudbury to O'Hare Intl flights
Kingston to O'Hare Intl flights
Deer Lake to O'Hare Intl flights

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 Alberta to Midway?

Cheapflights makes it easy to find Alberta to Midway flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Alberta to Midway?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Midway from Alberta.

Can Cheapflights find flights from Alberta to Midway with no change fees?

Certainly. Search results for flights to Midway from Alberta shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Alberta to Midway become cheaper?

Yes! Start tracking prices for Alberta to Midway flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.