Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Calgary to Chicago from C$ 175

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 14/1. 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

Save money when you book flights with momondo

Big names, great deals

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Calgary to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
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$ 353Delta
Tue, 26 May - Sat, 30 May
Multiple Airlines Logo
9:45 p.m. - 12:05 p.m.
YYC
-
MDW
13h 20m2 stops
Multiple Airlines Logo
5:01 p.m. - 11:43 a.m.
MDW
-
YYC
19h 42m1 stop
C$ 357Multiple Airlines
Mon, 2 Feb - Mon, 9 Feb
Multiple Airlines Logo
9:45 p.m. - 12:05 p.m.
YYC
-
MDW
13h 20m2 stops
Multiple Airlines Logo
5:01 p.m. - 11:43 a.m.
MDW
-
YYC
19h 42m1 stop
C$ 360Multiple Airlines
Mon, 2 Feb - Mon, 9 Feb
Multiple Airlines Logo
8:55 a.m. - 10:19 p.m.
YYC
-
MDW
12h 24m1 stop
Multiple Airlines Logo
6:20 a.m. - 7:09 p.m.
MDW
-
YYC
13h 49m1 stop
C$ 372Multiple Airlines
Thu, 15 Jan - Thu, 22 Jan
Multiple Airlines Logo
9:45 p.m. - 10:34 a.m.
YYC
-
MDW
11h 49m2 stops
Multiple Airlines Logo
11:05 a.m. - 12:05 a.m.
MDW
-
YYC
14h 00m1 stop
C$ 404Multiple Airlines
Mon, 12 Jan - Tue, 20 Jan
Multiple Airlines Logo
6:30 a.m. - 11:51 p.m.
YYC
-
MDW
16h 21m2 stops
Multiple Airlines Logo
11:05 a.m. - 8:58 p.m.
MDW
-
YYC
10h 53m1 stop
C$ 407Multiple Airlines
Thu, 19 Feb - Fri, 20 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$ 411Multiple Airlines
Mon, 2 Feb - Tue, 10 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$ 412Delta
Tue, 26 May - Sat, 30 May
Delta Logo
12:15 a.m. - 12:51 p.m.
YYC
-
MDW
11h 36m2 stops
Delta Logo
10:48 a.m. - 7:09 p.m.
MDW
-
YYC
9h 21m1 stop
C$ 434Delta
Mon, 19 Jan - Thu, 22 Jan
Multiple Airlines Logo
9:35 p.m. - 10:19 p.m.
YYC
-
MDW
23h 44m2 stops
Multiple Airlines Logo
6:20 a.m. - 7:09 p.m.
MDW
-
YYC
13h 49m1 stop
C$ 448Multiple Airlines
Thu, 15 Jan - Thu, 22 Jan

Delta flights from Calgary to Chicago Midway Airport

Our best Delta deals on Calgary to Chicago Midway Airport flight tickets
Delta
22 Jan
YYC7:40 a.m.Calgary
9h 56m
2 stops
MDW6:36 p.m.Chicago Midway
28 Jan
MDW9:33 a.m.Chicago Midway
12h 21m
2 stops
YYC8:54 p.m.Calgary
C$ 309
Find similar
Delta
22 Jan
YYC6:30 a.m.Calgary
5h 39m
1 stop
MDW1:09 p.m.Chicago Midway
28 Jan
MDW1:49 p.m.Chicago Midway
8h 05m
1 stop
YYC8:54 p.m.Calgary
C$ 336
Find similar
Delta
26 May
YYC9:15 a.m.Calgary
8h 16m
1 stop
MDW6:31 p.m.Chicago Midway
30 May
MDW9:20 a.m.Chicago Midway
10h 20m
2 stops
YYC6:40 p.m.Calgary
C$ 353
Find similar

WestJet flights from Calgary to Chicago Midway Airport

Our best WestJet deals on Calgary to Chicago Midway Airport flight tickets
WestJet
8 Jan
YYC7:00 a.m.Calgary
10h 32m
2 stops
MDW6:32 p.m.Chicago Midway
17 Jan
MDW1:28 p.m.Chicago Midway
12h 16m
2 stops
YYC12:44 a.m.Calgary
C$ 764
Find similar
WestJet
8 Jan
YYC6:30 a.m.Calgary
5h 39m
1 stop
MDW1:09 p.m.Chicago Midway
17 Jan
MDW1:28 p.m.Chicago Midway
12h 16m
2 stops
YYC12:44 a.m.Calgary
C$ 786
Find similar
WestJet
8 Jan
YYC6:30 a.m.Calgary
11h 02m
1 stop
MDW6:32 p.m.Chicago Midway
17 Jan
MDW11:21 a.m.Chicago Midway
8h 48m
1 stop
YYC7:09 p.m.Calgary
C$ 932
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 20 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

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$ 353

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 2/2

9:45 p.m.-12:05 p.m.

2 stops13h 20m

Chicago Midway

Mon 9/2

5:01 p.m.-11:43 a.m.

1 stop19h 42m

C$ 357

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 2/2

9:45 p.m.-12:05 p.m.

2 stops13h 20m

Chicago Midway

Mon 9/2

5:01 p.m.-11:43 a.m.

1 stop19h 42m

C$ 360

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 15/1

8:55 a.m.-10:19 p.m.

1 stop12h 24m

Chicago Midway

Thu 22/1

6:20 a.m.-7:09 p.m.

1 stop13h 49m

C$ 372

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 12/1

9:45 p.m.-10:34 a.m.

2 stops11h 49m

Chicago Midway

Tue 20/1

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

1 stop14h 00m

C$ 404

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 19/2

6:30 a.m.-11:51 p.m.

2 stops16h 21m

Chicago Midway

Fri 20/2

11:05 a.m.-8:58 p.m.

1 stop10h 53m

C$ 407

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$ 411

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$ 412

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 19/1

12:15 a.m.-12:51 p.m.

2 stops11h 36m

Chicago Midway

Thu 22/1

10:48 a.m.-7:09 p.m.

1 stop9h 21m

C$ 434

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 15/1

9:35 p.m.-10:19 p.m.

2 stops23h 44m

Chicago Midway

Thu 22/1

6:20 a.m.-7:09 p.m.

1 stop13h 49m

C$ 448

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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

8h 16m

Direct flights

None
The fastest flight from Calgary to Chicago Midway Airport takes 8h 16m
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 8h 16m.

  • 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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Mon 19/1
Mon 26/1
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago