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Cheap flights from Calgary to Chicago from C$ 191

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 26/3. 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
6:45 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$ 317Delta
Thu, 26 Mar - Mon, 30 Mar
Delta Logo
6:30 a.m. - 1:06 p.m.
YYC
-
MDW
5h 36m1 stop
Delta Logo
1:51 p.m. - 8:54 p.m.
MDW
-
YYC
8h 03m1 stop
C$ 355Delta
Mon, 2 Feb - Mon, 9 Feb
Delta Logo
6:30 a.m. - 1:09 p.m.
YYC
-
MDW
5h 39m1 stop
Delta Logo
9:50 a.m. - 11:05 p.m.
MDW
-
YYC
14h 15m2 stops
C$ 373Delta
Fri, 30 Jan - Thu, 26 Feb
Multiple Airlines Logo
12:30 a.m. - 12:05 p.m.
YYC
-
MDW
10h 35m1 stop
Multiple Airlines Logo
11:05 a.m. - 9:03 p.m.
MDW
-
YYC
10h 58m2 stops
C$ 384Multiple Airlines
Mon, 2 Feb - Tue, 10 Feb
Delta Logo
6:30 a.m. - 5:37 p.m.
YYC
-
MDW
10h 07m2 stops
Delta Logo
9:50 a.m. - 7:12 p.m.
MDW
-
YYC
10h 22m2 stops
C$ 401Delta
Thu, 19 Feb - Thu, 26 Feb
Delta Logo
6:30 a.m. - 1:05 p.m.
YYC
-
MDW
5h 35m1 stop
Delta Logo
1:29 p.m. - 12:43 a.m.
MDW
-
YYC
12h 14m2 stops
C$ 412Delta
Fri, 13 Feb - Sun, 15 Feb
Multiple Airlines Logo
7:35 p.m. - 11:54 p.m.
YYC
-
MDW
27h 19m1 stop
Multiple Airlines Logo
7:15 a.m. - 7:09 p.m.
MDW
-
YYC
12h 54m1 stop
C$ 417Multiple Airlines
Sun, 1 Mar - Wed, 4 Mar
Delta Logo
7:00 a.m. - 6:40 p.m.
YYC
-
MDW
10h 40m2 stops
Delta Logo
9:34 a.m. - 8:54 p.m.
MDW
-
YYC
12h 20m2 stops
C$ 425Delta
Wed, 18 Feb - Wed, 25 Feb
Delta Logo
7:00 a.m. - 6:36 p.m.
YYC
-
MDW
10h 36m2 stops
Delta Logo
9:50 a.m. - 7:12 p.m.
MDW
-
YYC
10h 22m2 stops
C$ 428Delta
Mon, 2 Feb - Thu, 26 Feb
Delta Logo
6:30 a.m. - 1:09 p.m.
YYC
-
MDW
5h 39m1 stop
Delta Logo
9:50 a.m. - 7:12 p.m.
MDW
-
YYC
10h 22m2 stops
C$ 449Delta
Tue, 27 Jan - Thu, 26 Feb

Delta flights from Calgary to Chicago Midway Airport

Our best Delta deals on Calgary to Chicago Midway Airport flight tickets
Delta
26 Mar
YYC6:45 a.m.Calgary
5h 40m
1 stop
MDW1:25 p.m.Chicago Midway
30 Mar
MDW2:05 p.m.Chicago Midway
7h 40m
1 stop
YYC8:45 p.m.Calgary
C$ 317
Find similar
Delta
2 Feb
YYC6:30 a.m.Calgary
5h 36m
1 stop
MDW1:06 p.m.Chicago Midway
9 Feb
MDW1:51 p.m.Chicago Midway
8h 03m
1 stop
YYC8:54 p.m.Calgary
C$ 355
Find similar
Delta
30 Jan
YYC6:30 a.m.Calgary
5h 39m
1 stop
MDW1:09 p.m.Chicago Midway
26 Feb
MDW9:50 a.m.Chicago Midway
14h 15m
2 stops
YYC11:05 p.m.Calgary
C$ 373
Find similar

WestJet flights from Calgary to Chicago Midway Airport

Our best WestJet deals on Calgary to Chicago Midway Airport flight tickets
WestJet
3 Feb
YYC9:00 a.m.Calgary
22h 52m
2 stops
MDW8:52 a.m.Chicago Midway
10 Feb
MDW9:33 a.m.Chicago Midway
16h 10m
2 stops
YYC12:43 a.m.Calgary
C$ 647
Find similar
WestJet
18 Apr
YYC12:15 a.m.Calgary
16h 39m
2 stops
MDW5:54 p.m.Chicago Midway
23 Apr
MDW9:27 a.m.Chicago Midway
11h 01m
2 stops
YYC7:28 p.m.Calgary
C$ 672
Find similar
WestJet
17 Apr
YYC6:30 a.m.Calgary
10h 24m
2 stops
MDW5:54 p.m.Chicago Midway
20 Apr
MDW9:27 a.m.Chicago Midway
11h 01m
2 stops
YYC7:28 p.m.Calgary
C$ 675
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 6 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

Thu 26/3

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

1 stop5h 40m

Chicago Midway

Mon 30/3

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

1 stop7h 40m

C$ 317

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 2/2

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

1 stop5h 36m

Chicago Midway

Mon 9/2

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

1 stop8h 03m

C$ 355

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 30/1

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

1 stop5h 39m

Chicago Midway

Thu 26/2

9:50 a.m.-11:05 p.m.

2 stops14h 15m

C$ 373

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.-9:03 p.m.

2 stops10h 58m

C$ 384

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 19/2

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

2 stops10h 07m

Chicago Midway

Thu 26/2

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

2 stops10h 22m

C$ 401

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 13/2

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

1 stop5h 35m

Chicago Midway

Sun 15/2

1:29 p.m.-12:43 a.m.

2 stops12h 14m

C$ 412

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sun 1/3

7:35 p.m.-11:54 p.m.

1 stop27h 19m

Chicago Midway

Wed 4/3

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

1 stop12h 54m

C$ 417

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 18/2

7:00 a.m.-6:40 p.m.

2 stops10h 40m

Chicago Midway

Wed 25/2

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

2 stops12h 20m

C$ 425

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 2/2

7:00 a.m.-6:36 p.m.

2 stops10h 36m

Chicago Midway

Thu 26/2

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

2 stops10h 22m

C$ 428

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 27/1

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

1 stop5h 39m

Chicago Midway

Thu 26/2

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

2 stops10h 22m

C$ 449

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 35m

Direct flights

None
The fastest flight from Calgary to Chicago Midway Airport takes 5h 35m
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 35m.

  • 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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