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Cheap flights from Calgary to Chicago from C$ 171

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 25/2. 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.
Multiple Airlines Logo
8:15 p.m. - 4:16 p.m.
YYC
-
MDW
19h 01m
2 stops
Multiple Airlines Logo
7:15 a.m. - 7:09 p.m.
MDW
-
YYC
12h 54m
1 stop
C$ 326Multiple Airlines
Wed, 25 Feb - Wed, 4 Mar
Multiple Airlines Logo
7:35 p.m. - 11:41 p.m.
YYC
-
MDW
27h 06m
1 stop
Multiple Airlines Logo
7:15 a.m. - 7:09 p.m.
MDW
-
YYC
12h 54m
1 stop
C$ 328Multiple Airlines
Wed, 25 Feb - Wed, 4 Mar
Delta Logo
6:30 a.m. - 1:05 p.m.
YYC
-
MDW
5h 35m
1 stop
Delta Logo
2:05 p.m. - 8:45 p.m.
MDW
-
YYC
7h 40m
1 stop
C$ 337Delta
Wed, 4 Mar - Wed, 11 Mar
Delta Logo
6:30 a.m. - 1:05 p.m.
YYC
-
MDW
5h 35m
1 stop
Delta Logo
1:28 p.m. - 8:54 p.m.
MDW
-
YYC
8h 26m
2 stops
C$ 343Delta
Thu, 26 Feb - Fri, 27 Feb
Delta Logo
6:30 a.m. - 1:05 p.m.
YYC
-
MDW
5h 35m
1 stop
Delta Logo
1:49 p.m. - 8:54 p.m.
MDW
-
YYC
8h 05m
1 stop
C$ 373Delta
Thu, 26 Feb - Fri, 27 Feb
Delta Logo
6:30 a.m. - 5:37 p.m.
YYC
-
MDW
10h 07m
2 stops
Delta Logo
9:34 a.m. - 8:54 p.m.
MDW
-
YYC
12h 20m
2 stops
C$ 394Delta
Thu, 26 Feb - Thu, 5 Mar
Delta Logo
6:30 a.m. - 5:37 p.m.
YYC
-
MDW
10h 07m
2 stops
Delta Logo
9:50 a.m. - 7:12 p.m.
MDW
-
YYC
10h 22m
2 stops
C$ 400Delta
Wed, 25 Feb - Wed, 4 Mar
Delta Logo
6:30 a.m. - 1:06 p.m.
YYC
-
MDW
5h 36m
1 stop
Delta Logo
9:50 a.m. - 7:12 p.m.
MDW
-
YYC
10h 22m
2 stops
C$ 421Delta
Wed, 11 Feb - Mon, 16 Feb
Delta Logo
9:15 a.m. - 5:54 p.m.
YYC
-
MDW
7h 39m
1 stop
Delta Logo
9:27 a.m. - 6:25 p.m.
MDW
-
YYC
9h 58m
1 stop
C$ 429Delta
Thu, 30 Apr - Sun, 3 May
Delta Logo
6:40 a.m. - 1:32 p.m.
YYC
-
MDW
5h 52m
1 stop
Delta Logo
9:30 a.m. - 6:25 p.m.
MDW
-
YYC
9h 55m
1 stop
C$ 473Delta
Sat, 25 Apr - Fri, 8 May

Delta flights from Calgary to Chicago Midway Airport

Our best Delta deals on Calgary to Chicago Midway Airport flight tickets
Delta
4 Mar
YYC6:30 a.m.Calgary
10h 07m
2 stops
MDW5:37 p.m.Chicago Midway
11 Mar
MDW9:35 a.m.Chicago Midway
12h 10m
2 stops
YYC8:45 p.m.Calgary
C$ 337
Delta
26 Feb
YYC6:30 a.m.Calgary
5h 35m
1 stop
MDW1:05 p.m.Chicago Midway
27 Feb
MDW1:28 p.m.Chicago Midway
8h 26m
2 stops
YYC8:54 p.m.Calgary
C$ 343
Delta
26 Feb
YYC6:30 a.m.Calgary
5h 35m
1 stop
MDW1:05 p.m.Chicago Midway
27 Feb
MDW1:49 p.m.Chicago Midway
8h 05m
1 stop
YYC8:54 p.m.Calgary
C$ 373

WestJet flights from Calgary to Chicago Midway Airport

Our best WestJet deals on Calgary to Chicago Midway Airport flight tickets
WestJet
26 Feb
YYC6:30 p.m.Calgary
13h 24m
2 stops
MDW8:54 a.m.Chicago Midway
2 Mar
MDW10:49 a.m.Chicago Midway
11h 09m
2 stops
YYC8:58 p.m.Calgary
C$ 718
WestJet
25 Mar
YYC12:15 a.m.Calgary
11h 14m
2 stops
MDW12:29 p.m.Chicago Midway
30 Mar
MDW9:30 a.m.Chicago Midway
11h 41m
2 stops
YYC8:11 p.m.Calgary
C$ 781
WestJet
26 Feb
YYC7:00 a.m.Calgary
10h 40m
2 stops
MDW6:40 p.m.Chicago Midway
27 Feb
MDW9:34 a.m.Chicago Midway
12h 24m
2 stops
YYC8:58 p.m.Calgary
C$ 799

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 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

Wed 25/2

8:15 p.m.-4:16 p.m.

2 stops19h 01m

Chicago Midway

Wed 4/3

7:15 a.m.-7:09 p.m.

1 stop12h 54m

C$ 326

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 25/2

7:35 p.m.-11:41 p.m.

1 stop27h 06m

Chicago Midway

Wed 4/3

7:15 a.m.-7:09 p.m.

1 stop12h 54m

C$ 328

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 4/3

6:30 a.m.-1:05 p.m.

1 stop5h 35m

Chicago Midway

Wed 11/3

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

1 stop7h 40m

C$ 337

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 26/2

6:30 a.m.-1:05 p.m.

1 stop5h 35m

Chicago Midway

Fri 27/2

1:28 p.m.-8:54 p.m.

2 stops8h 26m

C$ 343

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 26/2

6:30 a.m.-1:05 p.m.

1 stop5h 35m

Chicago Midway

Fri 27/2

1:49 p.m.-8:54 p.m.

1 stop8h 05m

C$ 373

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 26/2

6:30 a.m.-5:37 p.m.

2 stops10h 07m

Chicago Midway

Thu 5/3

9:34 a.m.-8:54 p.m.

2 stops12h 20m

C$ 394

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 25/2

6:30 a.m.-5:37 p.m.

2 stops10h 07m

Chicago Midway

Wed 4/3

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

2 stops10h 22m

C$ 400

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 11/2

6:30 a.m.-1:06 p.m.

1 stop5h 36m

Chicago Midway

Mon 16/2

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

2 stops10h 22m

C$ 421

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 30/4

9:15 a.m.-5:54 p.m.

1 stop7h 39m

Chicago Midway

Sun 3/5

9:27 a.m.-6:25 p.m.

1 stop9h 58m

C$ 429

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 25/4

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

1 stop5h 52m

Chicago Midway

Fri 8/5

9:30 a.m.-6:25 p.m.

1 stop9h 55m

C$ 473

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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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