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Cheap flights from Calgary to Chicago from C$ 180

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.
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
11:45 a.m. - 11:02 p.m.
MDW
-
YYC
12h 17m2 stops
C$ 310Delta
Sat, 17 Jan - Sat, 24 Jan
Delta Logo
6:45 a.m. - 1:23 p.m.
YYC
-
MDW
5h 38m1 stop
Delta Logo
2:03 p.m. - 8:45 p.m.
MDW
-
YYC
7h 42m1 stop
C$ 311Delta
Thu, 26 Mar - Mon, 30 Mar
Multiple Airlines Logo
7:35 p.m. - 7:24 p.m.
YYC
-
MDW
22h 49m1 stop
Multiple Airlines Logo
9:38 a.m. - 7:09 p.m.
MDW
-
YYC
10h 31m1 stop
C$ 318Multiple Airlines
Sat, 17 Jan - Sat, 24 Jan
Multiple Airlines Logo
12:30 a.m. - 10:31 a.m.
YYC
-
MDW
9h 01m1 stop
Multiple Airlines Logo
8:28 a.m. - 3:12 p.m.
MDW
-
YYC
31h 44m2 stops
C$ 338Multiple Airlines
Tue, 13 Jan - Fri, 16 Jan
Multiple Airlines Logo
9:45 p.m. - 11:31 a.m.
YYC
-
MDW
12h 46m2 stops
Multiple Airlines Logo
12:50 p.m. - 12:20 p.m.
MDW
-
YYC
24h 30m1 stop
C$ 364Multiple Airlines
Wed, 7 Jan - Sun, 11 Jan
Delta Logo
7:15 a.m. - 9:45 p.m.
YYC
-
MDW
13h 30m2 stops
Delta Logo
6:00 a.m. - 11:06 p.m.
MDW
-
YYC
18h 06m2 stops
C$ 370Delta
Tue, 14 Apr - Thu, 16 Apr
Delta Logo
8:55 a.m. - 9:45 p.m.
YYC
-
MDW
11h 50m1 stop
Delta Logo
10:35 a.m. - 7:09 p.m.
MDW
-
YYC
9h 34m1 stop
C$ 381Delta
Tue, 14 Apr - Thu, 16 Apr
Delta Logo
12:30 a.m. - 9:51 a.m.
YYC
-
MDW
8h 21m1 stop
Delta Logo
6:00 a.m. - 11:06 p.m.
MDW
-
YYC
18h 06m2 stops
C$ 382Delta
Mon, 13 Apr - Thu, 16 Apr
Multiple Airlines Logo
7:35 p.m. - 11:45 a.m.
YYC
-
MDW
15h 10m1 stop
Multiple Airlines Logo
12:50 p.m. - 12:20 p.m.
MDW
-
YYC
24h 30m1 stop
C$ 394Multiple Airlines
Wed, 7 Jan - Sun, 11 Jan
Delta Logo
6:30 a.m. - 1:09 p.m.
YYC
-
MDW
5h 39m1 stop
Delta Logo
1:49 p.m. - 8:54 p.m.
MDW
-
YYC
8h 05m1 stop
C$ 399Delta
Mon, 12 Jan - Wed, 14 Jan

Delta flights from Calgary to Chicago Midway Airport

Our best Delta deals on Calgary to Chicago Midway Airport flight tickets
Delta
17 Jan
YYC6:30 a.m.Calgary
8h 46m
1 stop
MDW4:16 p.m.Chicago Midway
24 Jan
MDW11:45 a.m.Chicago Midway
12h 17m
2 stops
YYC11:02 p.m.Calgary
C$ 310
Find similar
Delta
26 Mar
YYC6:45 a.m.Calgary
5h 38m
1 stop
MDW1:23 p.m.Chicago Midway
30 Mar
MDW2:03 p.m.Chicago Midway
7h 42m
1 stop
YYC8:45 p.m.Calgary
C$ 311
Find similar
Delta
14 Apr
YYC7:15 a.m.Calgary
13h 30m
2 stops
MDW9:45 p.m.Chicago Midway
16 Apr
MDW6:00 a.m.Chicago Midway
18h 06m
2 stops
YYC11:06 p.m.Calgary
C$ 370
Find similar

WestJet flights from Calgary to Chicago Midway Airport

Our best WestJet deals on Calgary to Chicago Midway Airport flight tickets
WestJet
14 Feb
YYC12:30 a.m.Calgary
8h 36m
1 stop
MDW10:06 a.m.Chicago Midway
20 Feb
MDW10:53 a.m.Chicago Midway
11h 05m
2 stops
YYC8:58 p.m.Calgary
C$ 851
Find similar
WestJet
14 Feb
YYC12:30 a.m.Calgary
8h 36m
1 stop
MDW10:06 a.m.Chicago Midway
20 Feb
MDW10:53 a.m.Chicago Midway
11h 05m
2 stops
YYC8:58 p.m.Calgary
C$ 853
Find similar
WestJet
14 Feb
YYC12:30 a.m.Calgary
8h 36m
1 stop
MDW10:06 a.m.Chicago Midway
20 Feb
MDW10:53 a.m.Chicago Midway
11h 05m
2 stops
YYC8:58 p.m.Calgary
C$ 854
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 4 December 2025.
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 17/1

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

1 stop8h 46m

Chicago Midway

Sat 24/1

11:45 a.m.-11:02 p.m.

2 stops12h 17m

C$ 310

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 26/3

6:45 a.m.-1:23 p.m.

1 stop5h 38m

Chicago Midway

Mon 30/3

2:03 p.m.-8:45 p.m.

1 stop7h 42m

C$ 311

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 17/1

7:35 p.m.-7:24 p.m.

1 stop22h 49m

Chicago Midway

Sat 24/1

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

1 stop10h 31m

C$ 318

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 13/1

12:30 a.m.-10:31 a.m.

1 stop9h 01m

Chicago Midway

Fri 16/1

8:28 a.m.-3:12 p.m.

2 stops31h 44m

C$ 338

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 7/1

9:45 p.m.-11:31 a.m.

2 stops12h 46m

Chicago Midway

Sun 11/1

12:50 p.m.-12:20 p.m.

1 stop24h 30m

C$ 364

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 14/4

7:15 a.m.-9:45 p.m.

2 stops13h 30m

Chicago Midway

Thu 16/4

6:00 a.m.-11:06 p.m.

2 stops18h 06m

C$ 370

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 14/4

8:55 a.m.-9:45 p.m.

1 stop11h 50m

Chicago Midway

Thu 16/4

10:35 a.m.-7:09 p.m.

1 stop9h 34m

C$ 381

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 13/4

12:30 a.m.-9:51 a.m.

1 stop8h 21m

Chicago Midway

Thu 16/4

6:00 a.m.-11:06 p.m.

2 stops18h 06m

C$ 382

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 7/1

7:35 p.m.-11:45 a.m.

1 stop15h 10m

Chicago Midway

Sun 11/1

12:50 p.m.-12:20 p.m.

1 stop24h 30m

C$ 394

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 12/1

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

1 stop5h 39m

Chicago Midway

Wed 14/1

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

1 stop8h 05m

C$ 399

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 38m.

  • 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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