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Cheap flights from Calgary to Chicago from C$ 245

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 11/9. 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. - 4:50 p.m.
YYC
-
MDW
8h 05m
1 stop
Delta Logo
12:30 p.m. - 11:13 p.m.
MDW
-
YYC
11h 43m
2 stops
C$ 411Delta
Wed, 21 Oct - Sat, 24 Oct
Delta Logo
7:15 a.m. - 10:10 p.m.
YYC
-
MDW
13h 55m
2 stops
Delta Logo
12:30 p.m. - 8:54 p.m.
MDW
-
YYC
9h 24m
1 stop
C$ 414Delta
Thu, 29 Oct - Mon, 2 Nov
Delta Logo
7:45 a.m. - 4:50 p.m.
YYC
-
MDW
8h 05m
1 stop
Delta Logo
6:00 a.m. - 11:13 p.m.
MDW
-
YYC
18h 13m
2 stops
C$ 415Delta
Thu, 29 Oct - Mon, 2 Nov
Delta Logo
7:45 a.m. - 4:50 p.m.
YYC
-
MDW
8h 05m
1 stop
Delta Logo
12:30 p.m. - 8:54 p.m.
MDW
-
YYC
9h 24m
1 stop
C$ 457Delta
Fri, 30 Oct - Mon, 2 Nov
Delta Logo
7:45 a.m. - 4:50 p.m.
YYC
-
MDW
8h 05m
1 stop
Delta Logo
12:30 p.m. - 8:54 p.m.
MDW
-
YYC
9h 24m
1 stop
C$ 488Delta
Fri, 30 Oct - Mon, 2 Nov
WestJet Logo
6:50 a.m. - 1:15 p.m.
YYC
-
MDW
5h 25m
1 stop
WestJet Logo
2:05 p.m. - 8:49 p.m.
MDW
-
YYC
7h 44m
1 stop
C$ 508WestJet
Wed, 2 Sep - Thu, 10 Sep
Delta Logo
6:35 a.m. - 1:20 p.m.
YYC
-
MDW
5h 45m
1 stop
Delta Logo
10:48 a.m. - 5:10 p.m.
MDW
-
YYC
7h 22m
1 stop
C$ 519Delta
Fri, 11 Sep - Sun, 20 Sep
Delta Logo
12:20 a.m. - 11:56 a.m.
YYC
-
MDW
10h 36m
1 stop
Delta Logo
1:00 p.m. - 8:05 p.m.
MDW
-
YYC
8h 05m
1 stop
C$ 537Delta
Tue, 13 Oct - Sun, 18 Oct
Delta Logo
8:55 a.m. - 4:25 p.m.
YYC
-
MDW
6h 30m
1 stop
Delta Logo
12:30 p.m. - 8:54 p.m.
MDW
-
YYC
9h 24m
1 stop
C$ 550Delta
Thu, 12 Nov - Wed, 18 Nov
Multiple Airlines Logo
7:00 a.m. - 10:11 p.m.
YYC
-
MDW
14h 11m
1 stop
Multiple Airlines Logo
12:27 p.m. - 9:50 p.m.
MDW
-
YYC
10h 23m
1 stop
C$ 558Multiple Airlines
Sat, 29 Aug - Tue, 1 Sep

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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
21 Oct
YYC7:45 a.m.Calgary
8h 05m
1 stop
MDW4:50 p.m.Chicago Midway
24 Oct
MDW12:30 p.m.Chicago Midway
11h 43m
2 stops
YYC11:13 p.m.Calgary
C$ 411
Delta
29 Oct
YYC7:15 a.m.Calgary
13h 55m
2 stops
MDW10:10 p.m.Chicago Midway
2 Nov
MDW12:30 p.m.Chicago Midway
9h 24m
1 stop
YYC8:54 p.m.Calgary
C$ 414
Delta
14 Nov
YYC7:45 a.m.Calgary
8h 05m
1 stop
MDW4:50 p.m.Chicago Midway
17 Nov
MDW12:30 p.m.Chicago Midway
9h 24m
1 stop
YYC8:54 p.m.Calgary
C$ 415

WestJet flights from Calgary to Chicago Midway Airport

Our best WestJet deals on Calgary to Chicago Midway Airport flight tickets
WestJet
2 Sep
YYC6:50 a.m.Calgary
5h 25m
1 stop
MDW1:15 p.m.Chicago Midway
10 Sep
MDW2:05 p.m.Chicago Midway
7h 44m
1 stop
YYC8:49 p.m.Calgary
C$ 508
WestJet
25 Jun
YYC11:00 a.m.Calgary
6h 31m
1 stop
MDW6:31 p.m.Chicago Midway
28 Jun
MDW1:26 p.m.Chicago Midway
7h 39m
1 stop
YYC8:05 p.m.Calgary
C$ 1,148
WestJet
28 Jun
YYC11:00 a.m.Calgary
21h 14m
1 stop
MDW9:14 a.m.Chicago Midway
30 Jun
MDW1:26 p.m.Chicago Midway
7h 39m
1 stop
YYC8:05 p.m.Calgary
C$ 1,186

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 14 June 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 21/10

7:45 a.m.-4:50 p.m.

1 stop8h 05m

Chicago Midway

Sat 24/10

12:30 p.m.-11:13 p.m.

2 stops11h 43m

C$ 411

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 29/10

7:15 a.m.-10:10 p.m.

2 stops13h 55m

Chicago Midway

Mon 2/11

12:30 p.m.-8:54 p.m.

1 stop9h 24m

C$ 414

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 29/10

7:45 a.m.-4:50 p.m.

1 stop8h 05m

Chicago Midway

Mon 2/11

6:00 a.m.-11:13 p.m.

2 stops18h 13m

C$ 415

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 30/10

7:45 a.m.-4:50 p.m.

1 stop8h 05m

Chicago Midway

Mon 2/11

12:30 p.m.-8:54 p.m.

1 stop9h 24m

C$ 457

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 30/10

7:45 a.m.-4:50 p.m.

1 stop8h 05m

Chicago Midway

Mon 2/11

12:30 p.m.-8:54 p.m.

1 stop9h 24m

C$ 488

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 2/9

6:50 a.m.-1:15 p.m.

1 stop5h 25m

Chicago Midway

Thu 10/9

2:05 p.m.-8:49 p.m.

1 stop7h 44m

C$ 508
Quickest round-trip

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 11/9

6:35 a.m.-1:20 p.m.

1 stop5h 45m

Chicago Midway

Sun 20/9

10:48 a.m.-5:10 p.m.

1 stop7h 22m

C$ 519

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 13/10

12:20 a.m.-11:56 a.m.

1 stop10h 36m

Chicago Midway

Sun 18/10

1:00 p.m.-8:05 p.m.

1 stop8h 05m

C$ 537

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 12/11

8:55 a.m.-4:25 p.m.

1 stop6h 30m

Chicago Midway

Wed 18/11

12:30 p.m.-8:54 p.m.

1 stop9h 24m

C$ 550

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 29/8

7:00 a.m.-10:11 p.m.

1 stop14h 11m

Chicago Midway

Tue 1/9

12:27 p.m.-9:50 p.m.

1 stop10h 23m

C$ 558

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 25m

Direct flights

None
The fastest flight from Calgary to Chicago Midway Airport takes 5h 25m
There are no direct flights from Calgary to Chicago Midway Airport. There are no popular flight routes from Calgary to Chicago Midway Airport.
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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 25m.

  • 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

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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