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Cheap flights from Calgary to Chicago from C$ 196

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 16/5. 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

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. - 5:56 p.m.
YYC
-
MDW
10h 11m
1 stop
Delta Logo
6:23 a.m. - 8:30 p.m.
MDW
-
YYC
15h 07m
2 stops
C$ 383Delta
Wed, 27 May - Wed, 3 Jun
Delta Logo
6:45 a.m. - 5:56 p.m.
YYC
-
MDW
10h 11m
1 stop
Delta Logo
1:22 p.m. - 8:05 p.m.
MDW
-
YYC
7h 43m
1 stop
C$ 398Delta
Wed, 27 May - Sat, 30 May
Delta Logo
6:40 a.m. - 5:58 p.m.
YYC
-
MDW
10h 18m
2 stops
Delta Logo
9:27 a.m. - 8:40 p.m.
MDW
-
YYC
12h 13m
2 stops
C$ 405Delta
Wed, 22 Apr - Wed, 29 Apr
Delta Logo
7:40 a.m. - 6:36 p.m.
YYC
-
MDW
9h 56m
2 stops
Delta Logo
9:27 a.m. - 8:40 p.m.
MDW
-
YYC
12h 13m
2 stops
C$ 419Delta
Sat, 2 May - Wed, 6 May
Delta Logo
6:45 a.m. - 5:52 p.m.
YYC
-
MDW
10h 07m
1 stop
Delta Logo
9:49 a.m. - 10:59 p.m.
MDW
-
YYC
14h 10m
2 stops
C$ 432Delta
Sat, 11 Jul - Mon, 13 Jul
Delta Logo
6:45 a.m. - 1:19 p.m.
YYC
-
MDW
5h 34m
1 stop
Delta Logo
1:22 p.m. - 8:05 p.m.
MDW
-
YYC
7h 43m
1 stop
C$ 445Delta
Sat, 16 May - Sat, 23 May
Delta Logo
6:45 a.m. - 5:56 p.m.
YYC
-
MDW
10h 11m
1 stop
Delta Logo
1:22 p.m. - 8:05 p.m.
MDW
-
YYC
7h 43m
1 stop
C$ 446Delta
Fri, 8 May - Tue, 12 May
Delta Logo
6:45 a.m. - 5:56 p.m.
YYC
-
MDW
10h 11m
1 stop
Delta Logo
9:23 a.m. - 10:57 p.m.
MDW
-
YYC
14h 34m
2 stops
C$ 449Delta
Wed, 20 May - Sun, 24 May
Delta Logo
6:45 a.m. - 5:56 p.m.
YYC
-
MDW
10h 11m
1 stop
Delta Logo
9:54 a.m. - 7:40 p.m.
MDW
-
YYC
10h 46m
2 stops
C$ 454Delta
Mon, 25 May - Tue, 9 Jun
Delta Logo
6:45 a.m. - 5:52 p.m.
YYC
-
MDW
10h 07m
1 stop
Delta Logo
9:49 a.m. - 10:59 p.m.
MDW
-
YYC
14h 10m
2 stops
C$ 456Delta
Sat, 11 Jul - Wed, 15 Jul

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Delta flights from Calgary to Chicago Midway Airport

Our best Delta deals on Calgary to Chicago Midway Airport flight tickets
Delta
27 May
YYC6:45 a.m.Calgary
10h 11m
1 stop
MDW5:56 p.m.Chicago Midway
3 Jun
MDW6:23 a.m.Chicago Midway
15h 07m
2 stops
YYC8:30 p.m.Calgary
C$ 383
Delta
27 May
YYC6:45 a.m.Calgary
10h 11m
1 stop
MDW5:56 p.m.Chicago Midway
30 May
MDW1:22 p.m.Chicago Midway
7h 43m
1 stop
YYC8:05 p.m.Calgary
C$ 398
Delta
22 Apr
YYC6:40 a.m.Calgary
10h 18m
2 stops
MDW5:58 p.m.Chicago Midway
29 Apr
MDW9:27 a.m.Chicago Midway
12h 13m
2 stops
YYC8:40 p.m.Calgary
C$ 405

WestJet flights from Calgary to Chicago Midway Airport

Our best WestJet deals on Calgary to Chicago Midway Airport flight tickets
WestJet
22 Apr
YYC6:30 a.m.Calgary
10h 28m
2 stops
MDW5:58 p.m.Chicago Midway
23 Apr
MDW9:29 a.m.Chicago Midway
10h 43m
2 stops
YYC7:12 p.m.Calgary
C$ 1,025
WestJet
30 Apr
YYC6:50 p.m.Calgary
14h 06m
2 stops
MDW9:56 a.m.Chicago Midway
7 May
MDW9:23 a.m.Chicago Midway
11h 17m
2 stops
YYC7:40 p.m.Calgary
C$ 1,030
WestJet
29 Apr
YYC8:00 p.m.Calgary
12h 56m
2 stops
MDW9:56 a.m.Chicago Midway
3 May
MDW9:27 a.m.Chicago Midway
11h 38m
1 stop
YYC8:05 p.m.Calgary
C$ 1,038

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 18 April 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

Cheapest round-trip

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 27/5

6:45 a.m.-5:56 p.m.

1 stop10h 11m

Chicago Midway

Wed 3/6

6:23 a.m.-8:30 p.m.

2 stops15h 07m

C$ 383

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 27/5

6:45 a.m.-5:56 p.m.

1 stop10h 11m

Chicago Midway

Sat 30/5

1:22 p.m.-8:05 p.m.

1 stop7h 43m

C$ 398

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 22/4

6:40 a.m.-5:58 p.m.

2 stops10h 18m

Chicago Midway

Wed 29/4

9:27 a.m.-8:40 p.m.

2 stops12h 13m

C$ 405

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 2/5

7:40 a.m.-6:36 p.m.

2 stops9h 56m

Chicago Midway

Wed 6/5

9:27 a.m.-8:40 p.m.

2 stops12h 13m

C$ 419

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 11/7

6:45 a.m.-5:52 p.m.

1 stop10h 07m

Chicago Midway

Mon 13/7

9:49 a.m.-10:59 p.m.

2 stops14h 10m

C$ 432
Quickest round-trip

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 16/5

6:45 a.m.-1:19 p.m.

1 stop5h 34m

Chicago Midway

Sat 23/5

1:22 p.m.-8:05 p.m.

1 stop7h 43m

C$ 445

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 8/5

6:45 a.m.-5:56 p.m.

1 stop10h 11m

Chicago Midway

Tue 12/5

1:22 p.m.-8:05 p.m.

1 stop7h 43m

C$ 446

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 20/5

6:45 a.m.-5:56 p.m.

1 stop10h 11m

Chicago Midway

Sun 24/5

9:23 a.m.-10:57 p.m.

2 stops14h 34m

C$ 449

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 25/5

6:45 a.m.-5:56 p.m.

1 stop10h 11m

Chicago Midway

Tue 9/6

9:54 a.m.-7:40 p.m.

2 stops10h 46m

C$ 454

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 11/7

6:45 a.m.-5:52 p.m.

1 stop10h 07m

Chicago Midway

Wed 15/7

9:49 a.m.-10:59 p.m.

2 stops14h 10m

C$ 456

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 34% 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

7h 03m

Direct flights

None
The fastest flight from Calgary to Chicago Midway Airport takes 7h 03m
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

Frequently asked questions about flying from Calgary to Chicago Midway Airport

  • 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 7h 03m.

  • 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
Merrillville
Hammond
Munster

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

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