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Cheap flights from Calgary to Chicago from C$ 197

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 14/4. 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
6:40 a.m. - 5:58 p.m.
YYC
-
MDW
10h 18m
2 stops
Delta Logo
6:23 a.m. - 10:57 p.m.
MDW
-
YYC
17h 34m
2 stops
C$ 315Delta
Mon, 4 May - Thu, 7 May
Delta Logo
7:00 a.m. - 6:36 p.m.
YYC
-
MDW
10h 36m
2 stops
Delta Logo
9:23 a.m. - 7:40 p.m.
MDW
-
YYC
11h 17m
2 stops
C$ 362Delta
Mon, 4 May - Thu, 7 May
Delta Logo
11:00 a.m. - 5:58 p.m.
YYC
-
MDW
5h 58m
1 stop
Delta Logo
9:22 a.m. - 10:20 p.m.
MDW
-
YYC
13h 58m
2 stops
C$ 375Delta
Mon, 4 May - Thu, 7 May
Delta Logo
6:30 a.m. - 1:24 p.m.
YYC
-
MDW
5h 54m
1 stop
Delta Logo
9:27 a.m. - 8:40 p.m.
MDW
-
YYC
12h 13m
2 stops
C$ 383Delta
Sat, 11 Apr - Sat, 18 Apr
Delta Logo
12:15 a.m. - 12:29 p.m.
YYC
-
MDW
11h 14m
2 stops
Delta Logo
9:27 a.m. - 7:28 p.m.
MDW
-
YYC
11h 01m
2 stops
C$ 386Delta
Sat, 11 Apr - Sun, 19 Apr
Delta Logo
6:30 a.m. - 1:24 p.m.
YYC
-
MDW
5h 54m
1 stop
Delta Logo
9:27 a.m. - 8:40 p.m.
MDW
-
YYC
12h 13m
2 stops
C$ 395Delta
Sat, 11 Apr - Tue, 14 Apr
Delta Logo
9:55 p.m. - 1:32 p.m.
YYC
-
MDW
14h 37m
2 stops
Delta Logo
9:22 a.m. - 10:20 p.m.
MDW
-
YYC
13h 58m
2 stops
C$ 431Delta
Mon, 4 May - Thu, 7 May
Delta Logo
6:40 a.m. - 1:32 p.m.
YYC
-
MDW
5h 52m
1 stop
Delta Logo
1:24 p.m. - 8:05 p.m.
MDW
-
YYC
7h 41m
1 stop
C$ 443Delta
Tue, 28 Apr - Sun, 3 May
Delta Logo
6:30 a.m. - 1:24 p.m.
YYC
-
MDW
5h 54m
1 stop
Delta Logo
2:05 p.m. - 8:45 p.m.
MDW
-
YYC
7h 40m
1 stop
C$ 446Delta
Tue, 7 Apr - Wed, 8 Apr
Delta Logo
6:30 a.m. - 1:24 p.m.
YYC
-
MDW
5h 54m
1 stop
Delta Logo
9:27 a.m. - 7:28 p.m.
MDW
-
YYC
11h 01m
2 stops
C$ 455Delta
Sun, 12 Apr - Sun, 19 Apr

Delta flights from Calgary to Chicago Midway Airport

Our best Delta deals on Calgary to Chicago Midway Airport flight tickets
Delta
4 May
YYC11:00 a.m.Calgary
5h 58m
1 stop
MDW5:58 p.m.Chicago Midway
7 May
MDW9:23 a.m.Chicago Midway
11h 17m
2 stops
YYC7:40 p.m.Calgary
C$ 362
Delta
4 May
YYC11:00 a.m.Calgary
5h 58m
1 stop
MDW5:58 p.m.Chicago Midway
7 May
MDW9:22 a.m.Chicago Midway
13h 58m
2 stops
YYC10:20 p.m.Calgary
C$ 375
Delta
11 Apr
YYC6:30 a.m.Calgary
5h 54m
1 stop
MDW1:24 p.m.Chicago Midway
18 Apr
MDW9:27 a.m.Chicago Midway
12h 13m
2 stops
YYC8:40 p.m.Calgary
C$ 383

WestJet flights from Calgary to Chicago Midway Airport

Our best WestJet deals on Calgary to Chicago Midway Airport flight tickets
WestJet
6 Mar
YYC8:15 p.m.Calgary
13h 06m
2 stops
MDW10:21 a.m.Chicago Midway
16 Mar
MDW9:35 a.m.Chicago Midway
10h 53m
2 stops
YYC7:28 p.m.Calgary
C$ 919
WestJet
2 Mar
YYC7:00 a.m.Calgary
10h 40m
2 stops
MDW6:40 p.m.Chicago Midway
6 Mar
MDW9:50 a.m.Chicago Midway
10h 22m
2 stops
YYC7:12 p.m.Calgary
C$ 948
WestJet
2 Mar
YYC6:30 a.m.Calgary
5h 35m
1 stop
MDW1:05 p.m.Chicago Midway
6 Mar
MDW9:50 a.m.Chicago Midway
10h 22m
2 stops
YYC7:12 p.m.Calgary
C$ 956

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 27 February 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

Mon 4/5

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

2 stops10h 18m

Chicago Midway

Thu 7/5

6:23 a.m.-10:57 p.m.

2 stops17h 34m

C$ 315

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 4/5

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

2 stops10h 36m

Chicago Midway

Thu 7/5

9:23 a.m.-7:40 p.m.

2 stops11h 17m

C$ 362

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 4/5

11:00 a.m.-5:58 p.m.

1 stop5h 58m

Chicago Midway

Thu 7/5

9:22 a.m.-10:20 p.m.

2 stops13h 58m

C$ 375

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 11/4

6:30 a.m.-1:24 p.m.

1 stop5h 54m

Chicago Midway

Sat 18/4

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

2 stops12h 13m

C$ 383

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 11/4

12:15 a.m.-12:29 p.m.

2 stops11h 14m

Chicago Midway

Sun 19/4

9:27 a.m.-7:28 p.m.

2 stops11h 01m

C$ 386

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 11/4

6:30 a.m.-1:24 p.m.

1 stop5h 54m

Chicago Midway

Tue 14/4

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

2 stops12h 13m

C$ 395

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 4/5

9:55 p.m.-1:32 p.m.

2 stops14h 37m

Chicago Midway

Thu 7/5

9:22 a.m.-10:20 p.m.

2 stops13h 58m

C$ 431

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 28/4

6:40 a.m.-1:32 p.m.

1 stop5h 52m

Chicago Midway

Sun 3/5

1:24 p.m.-8:05 p.m.

1 stop7h 41m

C$ 443

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 7/4

6:30 a.m.-1:24 p.m.

1 stop5h 54m

Chicago Midway

Wed 8/4

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

1 stop7h 40m

C$ 446

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sun 12/4

6:30 a.m.-1:24 p.m.

1 stop5h 54m

Chicago Midway

Sun 19/4

9:27 a.m.-7:28 p.m.

2 stops11h 01m

C$ 455

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

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

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