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Cheap flights from Calgary to Chicago from C$ 189

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 27/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Calgary to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:30 a.m. - 4:16 p.m.
YYC
-
MDW
8h 46m1 stop
Delta Logo
9:53 a.m. - 11:02 p.m.
MDW
-
YYC
14h 09m2 stops
C$ 309Delta
Sat, 7 Feb - Tue, 10 Feb
Delta Logo
6:45 a.m. - 1:25 p.m.
YYC
-
MDW
5h 40m1 stop
Delta Logo
2:05 p.m. - 8:45 p.m.
MDW
-
YYC
7h 40m1 stop
C$ 316Delta
Fri, 13 Mar - Mon, 16 Mar
Delta Logo
12:30 a.m. - 12:46 p.m.
YYC
-
MDW
11h 16m2 stops
Delta Logo
9:50 a.m. - 7:12 p.m.
MDW
-
YYC
10h 22m2 stops
C$ 347Delta
Mon, 9 Feb - Tue, 17 Feb
Delta Logo
6:30 a.m. - 1:09 p.m.
YYC
-
MDW
5h 39m1 stop
Delta Logo
9:33 a.m. - 8:54 p.m.
MDW
-
YYC
12h 21m2 stops
C$ 354Delta
Thu, 29 Jan - Thu, 5 Feb
Multiple Airlines Logo
6:30 p.m. - 3:20 p.m.
YYC
-
MDW
19h 50m1 stop
Multiple Airlines Logo
11:05 a.m. - 12:05 a.m.
MDW
-
YYC
14h 00m1 stop
C$ 423Multiple Airlines
Sat, 7 Feb - Tue, 10 Feb
Delta Logo
6:40 a.m. - 1:32 p.m.
YYC
-
MDW
5h 52m1 stop
Delta Logo
1:00 p.m. - 6:25 p.m.
MDW
-
YYC
6h 25m1 stop
C$ 464Delta
Wed, 6 May - Wed, 13 May
Multiple Airlines Logo
6:30 p.m. - 10:10 a.m.
YYC
-
MDW
14h 40m1 stop
Multiple Airlines Logo
11:19 a.m. - 9:19 p.m.
MDW
-
YYC
11h 00m1 stop
C$ 475Multiple Airlines
Wed, 11 Feb - Wed, 11 Mar
Multiple Airlines Logo
6:30 p.m. - 10:10 a.m.
YYC
-
MDW
14h 40m1 stop
Multiple Airlines Logo
6:00 a.m. - 5:26 p.m.
MDW
-
YYC
12h 26m2 stops
C$ 478Multiple Airlines
Wed, 11 Feb - Wed, 11 Mar
Multiple Airlines Logo
6:30 p.m. - 10:05 a.m.
YYC
-
MDW
14h 35m1 stop
Multiple Airlines Logo
11:05 a.m. - 8:58 p.m.
MDW
-
YYC
10h 53m1 stop
C$ 479Multiple Airlines
Thu, 29 Jan - Thu, 5 Feb
Multiple Airlines Logo
12:30 a.m. - 7:07 p.m.
YYC
-
MDW
17h 37m1 stop
Multiple Airlines Logo
6:00 a.m. - 7:09 p.m.
MDW
-
YYC
14h 09m1 stop
C$ 484Multiple Airlines
Mon, 9 Feb - Tue, 17 Feb

Delta flights from Calgary to Chicago Midway Airport

Our best Delta deals on Calgary to Chicago Midway Airport flight tickets
Delta
7 Feb
YYC6:30 a.m.Calgary
8h 46m
1 stop
MDW4:16 p.m.Chicago Midway
10 Feb
MDW9:53 a.m.Chicago Midway
14h 09m
2 stops
YYC11:02 p.m.Calgary
C$ 309
Find similar
Delta
9 Feb
YYC12:30 a.m.Calgary
11h 16m
2 stops
MDW12:46 p.m.Chicago Midway
17 Feb
MDW9:50 a.m.Chicago Midway
10h 22m
2 stops
YYC7:12 p.m.Calgary
C$ 347
Find similar
Delta
29 Jan
YYC6:30 a.m.Calgary
5h 39m
1 stop
MDW1:09 p.m.Chicago Midway
5 Feb
MDW9:33 a.m.Chicago Midway
12h 21m
2 stops
YYC8:54 p.m.Calgary
C$ 354
Find similar

WestJet flights from Calgary to Chicago Midway Airport

Our best WestJet deals on Calgary to Chicago Midway Airport flight tickets
WestJet
6 Feb
YYC12:15 a.m.Calgary
11h 31m
2 stops
MDW12:46 p.m.Chicago Midway
10 Feb
MDW9:33 a.m.Chicago Midway
16h 10m
2 stops
YYC12:43 a.m.Calgary
C$ 649
Find similar
WestJet
18 Apr
YYC6:30 a.m.Calgary
10h 24m
2 stops
MDW5:54 p.m.Chicago Midway
26 Apr
MDW9:27 a.m.Chicago Midway
10h 53m
2 stops
YYC7:20 p.m.Calgary
C$ 689
Find similar
WestJet
10 Feb
YYC3:15 p.m.Calgary
20h 31m
2 stops
MDW12:46 p.m.Chicago Midway
17 Feb
MDW9:34 a.m.Chicago Midway
16h 09m
2 stops
YYC12:43 a.m.Calgary
C$ 719
Find similar

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 2 January 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

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 7/2

6:30 a.m.-4:16 p.m.

1 stop8h 46m

Chicago Midway

Tue 10/2

9:53 a.m.-11:02 p.m.

2 stops14h 09m

C$ 309

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 13/3

6:45 a.m.-1:25 p.m.

1 stop5h 40m

Chicago Midway

Mon 16/3

2:05 p.m.-8:45 p.m.

1 stop7h 40m

C$ 316

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 9/2

12:30 a.m.-12:46 p.m.

2 stops11h 16m

Chicago Midway

Tue 17/2

9:50 a.m.-7:12 p.m.

2 stops10h 22m

C$ 347

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 29/1

6:30 a.m.-1:09 p.m.

1 stop5h 39m

Chicago Midway

Thu 5/2

9:33 a.m.-8:54 p.m.

2 stops12h 21m

C$ 354

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 7/2

6:30 p.m.-3:20 p.m.

1 stop19h 50m

Chicago Midway

Tue 10/2

11:05 a.m.-12:05 a.m.

1 stop14h 00m

C$ 423

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 6/5

6:40 a.m.-1:32 p.m.

1 stop5h 52m

Chicago Midway

Wed 13/5

1:00 p.m.-6:25 p.m.

1 stop6h 25m

C$ 464

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 11/2

6:30 p.m.-10:10 a.m.

1 stop14h 40m

Chicago Midway

Wed 11/3

11:19 a.m.-9:19 p.m.

1 stop11h 00m

C$ 475

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 11/2

6:30 p.m.-10:10 a.m.

1 stop14h 40m

Chicago Midway

Wed 11/3

6:00 a.m.-5:26 p.m.

2 stops12h 26m

C$ 478

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 29/1

6:30 p.m.-10:05 a.m.

1 stop14h 35m

Chicago Midway

Thu 5/2

11:05 a.m.-8:58 p.m.

1 stop10h 53m

C$ 479

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 9/2

12:30 a.m.-7:07 p.m.

1 stop17h 37m

Chicago Midway

Tue 17/2

6:00 a.m.-7:09 p.m.

1 stop14h 09m

C$ 484

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 21% 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 39m

Direct flights

None
The fastest flight from Calgary to Chicago Midway Airport takes 5h 39m
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

  • 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 39m.

  • 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
Munster
Hammond
Merrillville

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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