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Cheap flights from Calgary to Chicago from C$ 176

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 24/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult

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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
1:51 p.m. - 8:54 p.m.
MDW
-
YYC
8h 03m1 stop
C$ 315Delta
Sat, 31 Jan - Mon, 2 Feb
Multiple Airlines Logo
9:45 p.m. - 11:45 a.m.
YYC
-
MDW
13h 00m2 stops
Multiple Airlines Logo
5:01 p.m. - 7:09 p.m.
MDW
-
YYC
27h 08m1 stop
C$ 322Multiple Airlines
Wed, 21 Jan - Fri, 23 Jan
Multiple Airlines Logo
12:30 a.m. - 11:45 a.m.
YYC
-
MDW
10h 15m1 stop
Multiple Airlines Logo
7:30 a.m. - 8:17 p.m.
MDW
-
YYC
13h 47m2 stops
C$ 323Multiple Airlines
Thu, 29 Jan - Fri, 6 Feb
Multiple Airlines Logo
12:30 a.m. - 11:45 a.m.
YYC
-
MDW
10h 15m1 stop
Multiple Airlines Logo
9:38 a.m. - 7:09 p.m.
MDW
-
YYC
10h 31m1 stop
C$ 328Multiple Airlines
Thu, 29 Jan - Sat, 31 Jan
Multiple Airlines Logo
12:30 a.m. - 12:05 p.m.
YYC
-
MDW
10h 35m1 stop
Multiple Airlines Logo
5:01 p.m. - 7:09 p.m.
MDW
-
YYC
27h 08m1 stop
C$ 329Multiple Airlines
Tue, 20 Jan - Fri, 23 Jan
Multiple Airlines Logo
6:30 a.m. - 11:44 p.m.
YYC
-
MDW
16h 14m2 stops
Multiple Airlines Logo
7:30 a.m. - 7:09 p.m.
MDW
-
YYC
12h 39m1 stop
C$ 337Multiple Airlines
Mon, 23 Feb - Tue, 3 Mar
Multiple Airlines Logo
7:55 a.m. - 11:44 p.m.
YYC
-
MDW
14h 49m1 stop
Multiple Airlines Logo
7:30 a.m. - 7:09 p.m.
MDW
-
YYC
12h 39m1 stop
C$ 341Multiple Airlines
Mon, 23 Feb - Tue, 3 Mar
Multiple Airlines Logo
12:20 p.m. - 1:08 p.m.
YYC
-
MDW
23h 48m1 stop
Multiple Airlines Logo
9:04 p.m. - 6:17 p.m.
MDW
-
YYC
22h 13m2 stops
C$ 365Multiple Airlines
Sun, 22 Feb - Sun, 1 Mar
Multiple Airlines Logo
12:30 a.m. - 12:05 p.m.
YYC
-
MDW
10h 35m1 stop
Multiple Airlines Logo
11:05 a.m. - 12:05 a.m.
MDW
-
YYC
14h 00m1 stop
C$ 375Multiple Airlines
Mon, 2 Feb - Tue, 10 Feb
Delta Logo
6:30 a.m. - 10:22 p.m.
YYC
-
MDW
14h 52m2 stops
Delta Logo
1:26 p.m. - 8:54 p.m.
MDW
-
YYC
8h 28m2 stops
C$ 384Delta
Sat, 31 Jan - Mon, 2 Feb

Delta flights from Calgary to Chicago Midway Airport

Our best Delta deals on Calgary to Chicago Midway Airport flight tickets
Delta
31 Jan
YYC6:30 a.m.Calgary
8h 46m
1 stop
MDW4:16 p.m.Chicago Midway
2 Feb
MDW1:51 p.m.Chicago Midway
8h 03m
1 stop
YYC8:54 p.m.Calgary
C$ 315
Delta
31 Jan
YYC6:30 a.m.Calgary
14h 52m
2 stops
MDW10:22 p.m.Chicago Midway
2 Feb
MDW1:26 p.m.Chicago Midway
8h 28m
2 stops
YYC8:54 p.m.Calgary
C$ 384
Delta
22 Jan
YYC6:30 a.m.Calgary
5h 39m
1 stop
MDW1:09 p.m.Chicago Midway
25 Jan
MDW1:26 p.m.Chicago Midway
12h 18m
2 stops
YYC12:44 a.m.Calgary
C$ 405

WestJet flights from Calgary to Chicago Midway Airport

Our best WestJet deals on Calgary to Chicago Midway Airport flight tickets
WestJet
22 Jan
YYC8:55 a.m.Calgary
23h 58m
1 stop
MDW9:53 a.m.Chicago Midway
25 Jan
MDW9:50 a.m.Chicago Midway
12h 04m
1 stop
YYC8:54 p.m.Calgary
C$ 977
WestJet
21 Jan
YYC9:45 p.m.Calgary
11h 08m
2 stops
MDW9:53 a.m.Chicago Midway
23 Jan
MDW9:50 a.m.Chicago Midway
10h 25m
2 stops
YYC7:15 p.m.Calgary
C$ 1,027

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 8 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 31/1

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

1 stop8h 46m

Chicago Midway

Mon 2/2

1:51 p.m.-8:54 p.m.

1 stop8h 03m

C$ 315

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 21/1

9:45 p.m.-11:45 a.m.

2 stops13h 00m

Chicago Midway

Fri 23/1

5:01 p.m.-7:09 p.m.

1 stop27h 08m

C$ 322

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 29/1

12:30 a.m.-11:45 a.m.

1 stop10h 15m

Chicago Midway

Fri 6/2

7:30 a.m.-8:17 p.m.

2 stops13h 47m

C$ 323

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 29/1

12:30 a.m.-11:45 a.m.

1 stop10h 15m

Chicago Midway

Sat 31/1

9:38 a.m.-7:09 p.m.

1 stop10h 31m

C$ 328

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 20/1

12:30 a.m.-12:05 p.m.

1 stop10h 35m

Chicago Midway

Fri 23/1

5:01 p.m.-7:09 p.m.

1 stop27h 08m

C$ 329

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 23/2

6:30 a.m.-11:44 p.m.

2 stops16h 14m

Chicago Midway

Tue 3/3

7:30 a.m.-7:09 p.m.

1 stop12h 39m

C$ 337

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 23/2

7:55 a.m.-11:44 p.m.

1 stop14h 49m

Chicago Midway

Tue 3/3

7:30 a.m.-7:09 p.m.

1 stop12h 39m

C$ 341

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sun 22/2

12:20 p.m.-1:08 p.m.

1 stop23h 48m

Chicago Midway

Sun 1/3

9:04 p.m.-6:17 p.m.

2 stops22h 13m

C$ 365

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 2/2

12:30 a.m.-12:05 p.m.

1 stop10h 35m

Chicago Midway

Tue 10/2

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

1 stop14h 00m

C$ 375

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 31/1

6:30 a.m.-10:22 p.m.

2 stops14h 52m

Chicago Midway

Mon 2/2

1:26 p.m.-8:54 p.m.

2 stops8h 28m

C$ 384

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 32m

Direct flights

None
The fastest flight from Calgary to Chicago Midway Airport takes 5h 32m
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 32m.

  • 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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