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Cheap flights from Calgary to Chicago from C$ 190

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 10/1. 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. - 1:09 p.m.
YYC
-
MDW
5h 39m1 stop
Delta Logo
9:50 a.m. - 11:02 p.m.
MDW
-
YYC
14h 12m2 stops
C$ 308Delta
Wed, 14 Jan - Sun, 18 Jan
Delta Logo
6:30 a.m. - 10:22 p.m.
YYC
-
MDW
14h 52m2 stops
Delta Logo
9:33 a.m. - 8:54 p.m.
MDW
-
YYC
12h 21m2 stops
C$ 335Delta
Sat, 24 Jan - Sat, 31 Jan
Delta Logo
6:30 a.m. - 1:09 p.m.
YYC
-
MDW
5h 39m1 stop
Delta Logo
1:51 p.m. - 8:54 p.m.
MDW
-
YYC
8h 03m1 stop
C$ 356Delta
Sun, 25 Jan - Sun, 1 Feb
Delta Logo
9:15 a.m. - 6:31 p.m.
YYC
-
MDW
8h 16m1 stop
Delta Logo
9:20 a.m. - 6:40 p.m.
MDW
-
YYC
10h 20m2 stops
C$ 371Delta
Tue, 26 May - Sat, 30 May
Multiple Airlines Logo
12:30 a.m. - 12:05 p.m.
YYC
-
MDW
10h 35m1 stop
Multiple Airlines Logo
5:01 p.m. - 4:15 p.m.
MDW
-
YYC
24h 14m2 stops
C$ 405Multiple Airlines
Mon, 26 Jan - Fri, 30 Jan
Multiple Airlines Logo
12:30 a.m. - 11:45 a.m.
YYC
-
MDW
10h 15m1 stop
Multiple Airlines Logo
5:01 p.m. - 4:15 p.m.
MDW
-
YYC
24h 14m2 stops
C$ 408Multiple Airlines
Thu, 22 Jan - Fri, 30 Jan
Multiple Airlines Logo
12:30 a.m. - 11:45 a.m.
YYC
-
MDW
10h 15m1 stop
Multiple Airlines Logo
5:01 p.m. - 4:15 p.m.
MDW
-
YYC
24h 14m2 stops
C$ 412Multiple Airlines
Sat, 24 Jan - Sun, 1 Feb
Delta Logo
6:30 p.m. - 8:42 a.m.
YYC
-
MDW
13h 12m2 stops
Delta Logo
1:00 p.m. - 6:25 p.m.
MDW
-
YYC
6h 25m1 stop
C$ 430Delta
Tue, 26 May - Sat, 30 May
Delta Logo
8:55 a.m. - 10:07 p.m.
YYC
-
MDW
12h 12m1 stop
Delta Logo
9:32 a.m. - 8:54 p.m.
MDW
-
YYC
12h 22m2 stops
C$ 452Delta
Thu, 15 Jan - Wed, 21 Jan
Delta Logo
9:15 a.m. - 6:31 p.m.
YYC
-
MDW
8h 16m1 stop
Delta Logo
1:00 p.m. - 6:25 p.m.
MDW
-
YYC
6h 25m1 stop
C$ 461Delta
Tue, 26 May - Sat, 30 May

Delta flights from Calgary to Chicago Midway Airport

Our best Delta deals on Calgary to Chicago Midway Airport flight tickets
Delta
14 Jan
YYC6:30 a.m.Calgary
5h 39m
1 stop
MDW1:09 p.m.Chicago Midway
18 Jan
MDW9:50 a.m.Chicago Midway
14h 12m
2 stops
YYC11:02 p.m.Calgary
C$ 308
Find similar
Delta
24 Jan
YYC6:30 a.m.Calgary
14h 52m
2 stops
MDW10:22 p.m.Chicago Midway
31 Jan
MDW9:33 a.m.Chicago Midway
12h 21m
2 stops
YYC8:54 p.m.Calgary
C$ 335
Find similar
Delta
23 Jan
YYC6:30 a.m.Calgary
5h 39m
1 stop
MDW1:09 p.m.Chicago Midway
28 Jan
MDW9:33 a.m.Chicago Midway
12h 21m
2 stops
YYC8:54 p.m.Calgary
C$ 336
Find similar

WestJet flights from Calgary to Chicago Midway Airport

Our best WestJet deals on Calgary to Chicago Midway Airport flight tickets
WestJet
26 Jan
YYC12:15 a.m.Calgary
11h 34m
2 stops
MDW12:49 p.m.Chicago Midway
30 Jan
MDW10:48 a.m.Chicago Midway
11h 14m
2 stops
YYC9:02 p.m.Calgary
C$ 702
Find similar
WestJet
13 Jan
YYC12:15 a.m.Calgary
16h 19m
2 stops
MDW5:34 p.m.Chicago Midway
18 Jan
MDW6:14 p.m.Chicago Midway
22h 46m
2 stops
YYC4:00 p.m.Calgary
C$ 730
Find similar
WestJet
15 Feb
YYC6:30 p.m.Calgary
13h 23m
2 stops
MDW8:53 a.m.Chicago Midway
18 Feb
MDW9:34 a.m.Chicago Midway
16h 09m
2 stops
YYC12:43 a.m.Calgary
C$ 793
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 11 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

Wed 14/1

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

1 stop5h 39m

Chicago Midway

Sun 18/1

9:50 a.m.-11:02 p.m.

2 stops14h 12m

C$ 308

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 24/1

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

2 stops14h 52m

Chicago Midway

Sat 31/1

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

2 stops12h 21m

C$ 335

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sun 25/1

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

1 stop5h 39m

Chicago Midway

Sun 1/2

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

1 stop8h 03m

C$ 356

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 26/5

9:15 a.m.-6:31 p.m.

1 stop8h 16m

Chicago Midway

Sat 30/5

9:20 a.m.-6:40 p.m.

2 stops10h 20m

C$ 371

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 26/1

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

1 stop10h 35m

Chicago Midway

Fri 30/1

5:01 p.m.-4:15 p.m.

2 stops24h 14m

C$ 405

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 22/1

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

1 stop10h 15m

Chicago Midway

Fri 30/1

5:01 p.m.-4:15 p.m.

2 stops24h 14m

C$ 408

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 24/1

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

1 stop10h 15m

Chicago Midway

Sun 1/2

5:01 p.m.-4:15 p.m.

2 stops24h 14m

C$ 412

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 26/5

6:30 p.m.-8:42 a.m.

2 stops13h 12m

Chicago Midway

Sat 30/5

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

1 stop6h 25m

C$ 430

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 15/1

8:55 a.m.-10:07 p.m.

1 stop12h 12m

Chicago Midway

Wed 21/1

9:32 a.m.-8:54 p.m.

2 stops12h 22m

C$ 452

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 26/5

9:15 a.m.-6:31 p.m.

1 stop8h 16m

Chicago Midway

Sat 30/5

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

1 stop6h 25m

C$ 461

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

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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