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Cheap flights from Calgary to Chicago from C$ 219

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 3/3. 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. - 1:25 p.m.
YYC
-
MDW
5h 55m
1 stop
Delta Logo
2:05 p.m. - 8:45 p.m.
MDW
-
YYC
7h 40m
1 stop
C$ 314Delta
Mon, 30 Mar - Tue, 7 Apr
Delta Logo
6:30 a.m. - 10:31 p.m.
YYC
-
MDW
15h 01m
2 stops
Delta Logo
9:30 a.m. - 11:02 p.m.
MDW
-
YYC
14h 32m
2 stops
C$ 316Delta
Tue, 24 Mar - Wed, 1 Apr
Delta Logo
6:40 a.m. - 1:32 p.m.
YYC
-
MDW
5h 52m
1 stop
Delta Logo
9:27 a.m. - 8:40 p.m.
MDW
-
YYC
12h 13m
2 stops
C$ 346Delta
Sat, 18 Apr - Tue, 21 Apr
Delta Logo
6:40 a.m. - 10:28 p.m.
YYC
-
MDW
14h 48m
2 stops
Delta Logo
6:00 a.m. - 11:00 p.m.
MDW
-
YYC
18h 00m
2 stops
C$ 347Delta
Tue, 28 Apr - Sat, 2 May
Delta Logo
6:30 a.m. - 4:14 p.m.
YYC
-
MDW
8h 44m
1 stop
Delta Logo
1:10 p.m. - 11:02 p.m.
MDW
-
YYC
10h 52m
2 stops
C$ 368Delta
Sat, 7 Mar - Tue, 10 Mar
Delta Logo
6:40 a.m. - 1:32 p.m.
YYC
-
MDW
5h 52m
1 stop
Delta Logo
9:23 a.m. - 10:57 p.m.
MDW
-
YYC
14h 34m
2 stops
C$ 383Delta
Sat, 2 May - Mon, 11 May
Multiple Airlines Logo
6:25 p.m. - 10:05 a.m.
YYC
-
MDW
14h 40m
1 stop
Multiple Airlines Logo
6:00 a.m. - 5:10 p.m.
MDW
-
YYC
12h 10m
1 stop
C$ 409Multiple Airlines
Sat, 25 Apr - Wed, 29 Apr
Delta Logo
7:40 a.m. - 10:28 p.m.
YYC
-
MDW
13h 48m
2 stops
Delta Logo
9:27 a.m. - 8:40 p.m.
MDW
-
YYC
12h 13m
2 stops
C$ 414Delta
Sat, 18 Apr - Tue, 21 Apr
Delta Logo
6:40 a.m. - 10:28 p.m.
YYC
-
MDW
14h 48m
2 stops
Delta Logo
9:22 a.m. - 8:30 p.m.
MDW
-
YYC
12h 08m
2 stops
C$ 416Delta
Sat, 2 May - Thu, 7 May
Delta Logo
6:40 a.m. - 1:32 p.m.
YYC
-
MDW
5h 52m
1 stop
Delta Logo
6:00 a.m. - 5:10 p.m.
MDW
-
YYC
12h 10m
1 stop
C$ 417Delta
Sat, 2 May - Wed, 6 May

Delta flights from Calgary to Chicago Midway Airport

Our best Delta deals on Calgary to Chicago Midway Airport flight tickets
Delta
18 Apr
YYC6:40 a.m.Calgary
5h 52m
1 stop
MDW1:32 p.m.Chicago Midway
20 Apr
MDW2:12 p.m.Chicago Midway
7h 28m
1 stop
YYC8:40 p.m.Calgary
C$ 314
Delta
24 Mar
YYC6:30 a.m.Calgary
5h 55m
1 stop
MDW1:25 p.m.Chicago Midway
1 Apr
MDW9:30 a.m.Chicago Midway
14h 32m
2 stops
YYC11:02 p.m.Calgary
C$ 316
Delta
18 Apr
YYC6:40 a.m.Calgary
5h 52m
1 stop
MDW1:32 p.m.Chicago Midway
21 Apr
MDW9:27 a.m.Chicago Midway
12h 13m
2 stops
YYC8:40 p.m.Calgary
C$ 346

WestJet flights from Calgary to Chicago Midway Airport

Our best WestJet deals on Calgary to Chicago Midway Airport flight tickets
WestJet
13 Feb
YYC5:15 p.m.Calgary
16h 48m
2 stops
MDW11:03 a.m.Chicago Midway
15 Feb
MDW11:01 a.m.Chicago Midway
9h 08m
1 stop
YYC7:09 p.m.Calgary
C$ 1,048
WestJet
13 Feb
YYC7:15 a.m.Calgary
10h 25m
2 stops
MDW6:40 p.m.Chicago Midway
15 Feb
MDW9:34 a.m.Chicago Midway
16h 09m
2 stops
YYC12:43 a.m.Calgary
C$ 1,696
WestJet
16 Feb
YYC6:30 a.m.Calgary
5h 35m
1 stop
MDW1:05 p.m.Chicago Midway
20 Feb
MDW10:49 a.m.Chicago Midway
9h 20m
1 stop
YYC7:09 p.m.Calgary
C$ 2,046

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 8 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 30/3

6:30 a.m.-1:25 p.m.

1 stop5h 55m

Chicago Midway

Tue 7/4

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

1 stop7h 40m

C$ 314

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 24/3

6:30 a.m.-10:31 p.m.

2 stops15h 01m

Chicago Midway

Wed 1/4

9:30 a.m.-11:02 p.m.

2 stops14h 32m

C$ 316

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 18/4

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

1 stop5h 52m

Chicago Midway

Tue 21/4

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

2 stops12h 13m

C$ 346

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 28/4

6:40 a.m.-10:28 p.m.

2 stops14h 48m

Chicago Midway

Sat 2/5

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

2 stops18h 00m

C$ 347

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 7/3

6:30 a.m.-4:14 p.m.

1 stop8h 44m

Chicago Midway

Tue 10/3

1:10 p.m.-11:02 p.m.

2 stops10h 52m

C$ 368

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 2/5

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

1 stop5h 52m

Chicago Midway

Mon 11/5

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

2 stops14h 34m

C$ 383

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 25/4

6:25 p.m.-10:05 a.m.

1 stop14h 40m

Chicago Midway

Wed 29/4

6:00 a.m.-5:10 p.m.

1 stop12h 10m

C$ 409

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 18/4

7:40 a.m.-10:28 p.m.

2 stops13h 48m

Chicago Midway

Tue 21/4

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

2 stops12h 13m

C$ 414

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 2/5

6:40 a.m.-10:28 p.m.

2 stops14h 48m

Chicago Midway

Thu 7/5

9:22 a.m.-8:30 p.m.

2 stops12h 08m

C$ 416

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 2/5

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

1 stop5h 52m

Chicago Midway

Wed 6/5

6:00 a.m.-5:10 p.m.

1 stop12h 10m

C$ 417

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 32m

Direct flights

None
The fastest flight from Calgary to Chicago Midway Airport takes 5h 32m
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 32m.

  • 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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