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Cheap flights from Calgary to Chicago from C$ 268

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Calgary to Chicago departing on 28/8. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Calgary to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
7:45 a.m. - 5:37 p.m.
YYC
-
MDW
9h 52m
2 stops
Delta Logo
9:55 a.m. - 12:13 a.m.
MDW
-
YYC
14h 18m
2 stops
C$ 358Delta
Wed, 18 Nov - Mon, 23 Nov
Delta Logo
7:45 a.m. - 9:10 p.m.
YYC
-
MDW
13h 25m
2 stops
Delta Logo
6:00 a.m. - 12:13 a.m.
MDW
-
YYC
18h 13m
2 stops
C$ 368Delta
Wed, 18 Nov - Sat, 21 Nov
Delta Logo
7:45 a.m. - 3:50 p.m.
YYC
-
MDW
8h 05m
1 stop
Delta Logo
12:30 p.m. - 12:13 a.m.
MDW
-
YYC
11h 43m
2 stops
C$ 408Delta
Tue, 17 Nov - Mon, 23 Nov
Delta Logo
7:45 a.m. - 3:50 p.m.
YYC
-
MDW
8h 05m
1 stop
Delta Logo
12:30 p.m. - 12:13 a.m.
MDW
-
YYC
11h 43m
2 stops
C$ 435Delta
Wed, 18 Nov - Fri, 20 Nov
Delta Logo
7:45 a.m. - 3:50 p.m.
YYC
-
MDW
8h 05m
1 stop
Delta Logo
12:30 p.m. - 12:13 a.m.
MDW
-
YYC
11h 43m
2 stops
C$ 444Delta
Thu, 19 Nov - Sat, 21 Nov
Delta Logo
7:00 a.m. - 4:39 p.m.
YYC
-
MDW
8h 39m
2 stops
Delta Logo
12:28 p.m. - 8:30 p.m.
MDW
-
YYC
9h 02m
1 stop
C$ 457Delta
Mon, 26 Oct - Fri, 30 Oct
Delta Logo
12:30 a.m. - 9:52 a.m.
YYC
-
MDW
8h 22m
1 stop
Delta Logo
12:28 p.m. - 12:12 a.m.
MDW
-
YYC
11h 44m
2 stops
C$ 467Delta
Thu, 29 Oct - Mon, 2 Nov
Delta Logo
7:45 a.m. - 3:50 p.m.
YYC
-
MDW
8h 05m
1 stop
Delta Logo
12:30 p.m. - 9:54 p.m.
MDW
-
YYC
9h 24m
1 stop
C$ 470Delta
Wed, 18 Nov - Sun, 22 Nov
Delta Logo
7:00 a.m. - 4:39 p.m.
YYC
-
MDW
8h 39m
2 stops
Delta Logo
10:58 a.m. - 7:14 p.m.
MDW
-
YYC
9h 16m
1 stop
C$ 473Delta
Mon, 26 Oct - Fri, 30 Oct
Delta Logo
7:45 a.m. - 10:25 p.m.
YYC
-
MDW
13h 40m
2 stops
Delta Logo
12:28 p.m. - 12:12 a.m.
MDW
-
YYC
11h 44m
2 stops
C$ 480Delta
Fri, 30 Oct - Mon, 2 Nov

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WestJet flights from Calgary to Chicago Midway Airport

Our best WestJet deals on Calgary to Chicago Midway Airport flight tickets
WestJet
17 Jul
YYC7:00 a.m.Calgary
14h 15m
1 stop
MDW10:15 p.m.Chicago Midway
19 Jul
MDW1:18 p.m.Chicago Midway
7h 57m
1 stop
YYC8:15 p.m.Calgary
C$ 1,144
WestJet
17 Jul
YYC7:00 a.m.Calgary
14h 15m
1 stop
MDW10:15 p.m.Chicago Midway
19 Jul
MDW1:18 p.m.Chicago Midway
7h 57m
1 stop
YYC8:15 p.m.Calgary
C$ 1,145
WestJet
17 Jul
YYC7:00 a.m.Calgary
10h 25m
2 stops
MDW6:25 p.m.Chicago Midway
19 Jul
MDW9:19 a.m.Chicago Midway
11h 56m
1 stop
YYC8:15 p.m.Calgary
C$ 1,161

Porter Airlines flights from Calgary to Chicago Midway Airport

Our best Porter Airlines deals on Calgary to Chicago Midway Airport flight tickets
Porter Airlines
22 Jul
YYC12:00 p.m.Calgary
20h 40m
2 stops
MDW9:40 a.m.Chicago Midway
27 Jul
MDW10:25 a.m.Chicago Midway
13h 08m
2 stops
YYC10:33 p.m.Calgary
C$ 1,045
Porter Airlines
22 Jul
YYC12:00 p.m.Calgary
20h 40m
2 stops
MDW9:40 a.m.Chicago Midway
27 Jul
MDW10:25 a.m.Chicago Midway
13h 08m
2 stops
YYC10:33 p.m.Calgary
C$ 1,093
Porter Airlines
22 Jul
YYC12:00 p.m.Calgary
20h 40m
2 stops
MDW9:40 a.m.Chicago Midway
27 Jul
MDW10:25 a.m.Chicago Midway
13h 08m
2 stops
YYC10:33 p.m.Calgary
C$ 1,113

momondo Fare Finder

 
Customize your flight search to find flights from Calgary to Chicago Midway Airport 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, momondo users made 96,600 searches. Data last updated 13 July 2026.
Use the filters below to find and compare flights from Calgary to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 18/11

7:45 a.m.-5:37 p.m.

2 stops9h 52m

Chicago Midway

Mon 23/11

9:55 a.m.-12:13 a.m.

2 stops14h 18m

C$ 358

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 18/11

7:45 a.m.-9:10 p.m.

2 stops13h 25m

Chicago Midway

Sat 21/11

6:00 a.m.-12:13 a.m.

2 stops18h 13m

C$ 368

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 17/11

7:45 a.m.-3:50 p.m.

1 stop8h 05m

Chicago Midway

Mon 23/11

12:30 p.m.-12:13 a.m.

2 stops11h 43m

C$ 408

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 18/11

7:45 a.m.-3:50 p.m.

1 stop8h 05m

Chicago Midway

Fri 20/11

12:30 p.m.-12:13 a.m.

2 stops11h 43m

C$ 435

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 19/11

7:45 a.m.-3:50 p.m.

1 stop8h 05m

Chicago Midway

Sat 21/11

12:30 p.m.-12:13 a.m.

2 stops11h 43m

C$ 444

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 26/10

7:00 a.m.-4:39 p.m.

2 stops8h 39m

Chicago Midway

Fri 30/10

12:28 p.m.-8:30 p.m.

1 stop9h 02m

C$ 457

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 29/10

12:30 a.m.-9:52 a.m.

1 stop8h 22m

Chicago Midway

Mon 2/11

12:28 p.m.-12:12 a.m.

2 stops11h 44m

C$ 467
Quickest round-trip

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 18/11

7:45 a.m.-3:50 p.m.

1 stop8h 05m

Chicago Midway

Sun 22/11

12:30 p.m.-9:54 p.m.

1 stop9h 24m

C$ 470

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 26/10

7:00 a.m.-4:39 p.m.

2 stops8h 39m

Chicago Midway

Fri 30/10

10:58 a.m.-7:14 p.m.

1 stop9h 16m

C$ 473

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 30/10

7:45 a.m.-10:25 p.m.

2 stops13h 40m

Chicago Midway

Mon 2/11

12:28 p.m.-12:12 a.m.

2 stops11h 44m

C$ 480

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Calgary to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Can stopping save me money on Calgary to Chicago Midway Airport flights?

You could potentially save up to 34% on your flight if you consider stops on a Calgary to Chicago Midway Airport flight.

When to book flights from Calgary to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Calgary to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Calgary to Chicago Midway Airport (YYC to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Calgary to Chicago Midway Airport

Fastest flight time

6h 30m

Direct flights

None
The fastest flight from Calgary to Chicago Midway Airport takes 6h 30m
There are no direct flights from Calgary to Chicago Midway Airport. There are no popular flight routes from Calgary to Chicago Midway Airport.
Search flight deals

Frequently asked questions about flying from Calgary to Chicago Midway Airport

  • How far is Calgary to Chicago Midway by plane?

    The straight-line distance from Calgary to Chicago Midway is 2247.1 km. In terms of flight time, this usually takes a little over 6h 30m.

  • When did momondo last update prices for flights from Calgary Airport to Chicago Midway Airport?

    Prices for flights from Calgary Airport to Chicago Midway Airport are refreshed on a daily basis.

  • How old do you have to be to fly from Calgary Airport to Chicago Midway Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Calgary Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Hammond
Munster
Valparaiso
Portage

Why use momondo?

Why should I use momondo to find a flight deal from Calgary to Chicago?

It is quick and easy to find Calgary to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Calgary to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Calgary with this policy.

How can momondo help me find flights from Calgary to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from Calgary. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Calgary to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Calgary are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Chicago Midway Airport trip

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