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Cheap flights from Calgary to Chicago from C$ 269

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 25/12. 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. - 9:10 p.m.
YYC
-
MDW
13h 25m
2 stops
Delta Logo
9:30 a.m. - 9:54 p.m.
MDW
-
YYC
12h 24m
2 stops
C$ 374Delta
Mon, 23 Nov - Thu, 26 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$ 418Delta
Wed, 11 Nov - Wed, 25 Nov
Delta Logo
7:45 a.m. - 3:50 p.m.
YYC
-
MDW
8h 05m
1 stop
Delta Logo
9:55 a.m. - 12:13 a.m.
MDW
-
YYC
14h 18m
2 stops
C$ 436Delta
Wed, 11 Nov - Tue, 24 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$ 461Delta
Wed, 11 Nov - Tue, 24 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$ 464Delta
Mon, 26 Oct - Wed, 28 Oct
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$ 465Delta
Mon, 26 Oct - Fri, 30 Oct
Delta Logo
12:30 a.m. - 9:52 a.m.
YYC
-
MDW
8h 22m
1 stop
Delta Logo
9:59 a.m. - 8:15 p.m.
MDW
-
YYC
10h 16m
2 stops
C$ 471Delta
Thu, 29 Oct - Mon, 2 Nov
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$ 482Delta
Thu, 29 Oct - Mon, 2 Nov
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$ 488Delta
Fri, 30 Oct - Mon, 2 Nov
Delta Logo
12:20 a.m. - 9:50 a.m.
YYC
-
MDW
8h 30m
1 stop
Delta Logo
1:28 p.m. - 8:15 p.m.
MDW
-
YYC
7h 47m
1 stop
C$ 492Delta
Thu, 1 Oct - Tue, 6 Oct

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Delta flights from Calgary to Chicago Midway Airport

Our best Delta deals on Calgary to Chicago Midway Airport flight tickets
Delta
23 Nov
YYC7:45 a.m.Calgary
13h 25m
2 stops
MDW9:10 p.m.Chicago Midway
26 Nov
MDW9:30 a.m.Chicago Midway
12h 24m
2 stops
YYC9:54 p.m.Calgary
C$ 374
Delta
11 Nov
YYC7:45 a.m.Calgary
8h 05m
1 stop
MDW3:50 p.m.Chicago Midway
23 Nov
MDW9:55 a.m.Chicago Midway
14h 18m
2 stops
YYC12:13 a.m.Calgary
C$ 418
Delta
11 Nov
YYC7:45 a.m.Calgary
8h 05m
1 stop
MDW3:50 p.m.Chicago Midway
24 Nov
MDW9:55 a.m.Chicago Midway
14h 18m
2 stops
YYC12:13 a.m.Calgary
C$ 436

WestJet flights from Calgary to Chicago Midway Airport

Our best WestJet deals on Calgary to Chicago Midway Airport flight tickets
WestJet
31 Jul
YYC7:00 a.m.Calgary
14h 15m
1 stop
MDW10:15 p.m.Chicago Midway
3 Aug
MDW1:25 p.m.Chicago Midway
7h 50m
1 stop
YYC8:15 p.m.Calgary
C$ 1,140
WestJet
30 Jul
YYC12:20 a.m.Calgary
20h 55m
1 stop
MDW10:15 p.m.Chicago Midway
3 Aug
MDW6:42 p.m.Chicago Midway
23h 18m
2 stops
YYC5:00 p.m.Calgary
C$ 1,171
WestJet
31 Jul
YYC7:00 a.m.Calgary
14h 15m
1 stop
MDW10:15 p.m.Chicago Midway
2 Aug
MDW9:19 a.m.Chicago Midway
11h 56m
1 stop
YYC8:15 p.m.Calgary
C$ 1,175

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 19 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

Mon 23/11

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

2 stops13h 25m

Chicago Midway

Thu 26/11

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

2 stops12h 24m

C$ 374

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 11/11

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

1 stop8h 05m

Chicago Midway

Wed 25/11

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

2 stops11h 43m

C$ 418

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 11/11

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

1 stop8h 05m

Chicago Midway

Tue 24/11

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

2 stops14h 18m

C$ 436

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 11/11

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

1 stop8h 05m

Chicago Midway

Tue 24/11

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

1 stop9h 24m

C$ 461

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 26/10

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

2 stops8h 39m

Chicago Midway

Wed 28/10

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

1 stop9h 02m

C$ 464

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$ 465

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 29/10

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

1 stop8h 22m

Chicago Midway

Mon 2/11

9:59 a.m.-8:15 p.m.

2 stops10h 16m

C$ 471

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$ 482

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$ 488
Quickest round-trip

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 1/10

12:20 a.m.-9:50 a.m.

1 stop8h 30m

Chicago Midway

Tue 6/10

1:28 p.m.-8:15 p.m.

1 stop7h 47m

C$ 492

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

5h 24m

Direct flights

None
The fastest flight from Calgary to Chicago Midway Airport takes 5h 24m
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 5h 24m.

  • 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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