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Cheap flights from Calgary to Chicago from C$ 207

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 2/5. 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
1 adult, Economy, 0 bags

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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. - 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$ 379Delta
Sat, 2 May - Tue, 5 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$ 386Delta
Wed, 20 May - Sun, 24 May
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$ 396Delta
Sat, 2 May - Tue, 5 May
Multiple Airlines Logo
7:00 a.m. - 6:37 p.m.
YYC
-
MDW
10h 37m
1 stop
Multiple Airlines Logo
6:00 a.m. - 5:10 p.m.
MDW
-
YYC
12h 10m
1 stop
C$ 441Multiple Airlines
Sat, 2 May - Tue, 5 May
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$ 448Delta
Sat, 2 May - Tue, 5 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$ 454Delta
Wed, 20 May - Sun, 24 May
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$ 472Delta
Sat, 30 May - Sun, 31 May
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$ 473Delta
Sat, 30 May - Sun, 31 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$ 474Delta
Wed, 29 Apr - Sun, 3 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$ 502Delta
Wed, 29 Apr - Sun, 3 May

Delta flights from Calgary to Chicago Midway Airport

Our best Delta deals on Calgary to Chicago Midway Airport flight tickets
Delta
2 May
YYC6:40 a.m.Calgary
5h 52m
1 stop
MDW1:32 p.m.Chicago Midway
5 May
MDW9:27 a.m.Chicago Midway
12h 13m
2 stops
YYC8:40 p.m.Calgary
C$ 379
Delta
20 May
YYC6:45 a.m.Calgary
10h 11m
1 stop
MDW5:56 p.m.Chicago Midway
24 May
MDW9:23 a.m.Chicago Midway
14h 34m
2 stops
YYC10:57 p.m.Calgary
C$ 386
Delta
2 May
YYC7:40 a.m.Calgary
13h 48m
2 stops
MDW10:28 p.m.Chicago Midway
5 May
MDW9:27 a.m.Chicago Midway
12h 13m
2 stops
YYC8:40 p.m.Calgary
C$ 396

WestJet flights from Calgary to Chicago Midway Airport

Our best WestJet deals on Calgary to Chicago Midway Airport flight tickets
WestJet
20 Apr
YYC12:30 a.m.Calgary
8h 26m
1 stop
MDW9:56 a.m.Chicago Midway
23 Apr
MDW9:29 a.m.Chicago Midway
10h 43m
2 stops
YYC7:12 p.m.Calgary
C$ 1,023
WestJet
20 Apr
YYC12:15 a.m.Calgary
11h 28m
2 stops
MDW12:43 p.m.Chicago Midway
23 Apr
MDW9:29 a.m.Chicago Midway
10h 43m
2 stops
YYC7:12 p.m.Calgary
C$ 1,030
WestJet
22 Apr
YYC8:15 p.m.Calgary
12h 41m
2 stops
MDW9:56 a.m.Chicago Midway
29 Apr
MDW10:41 a.m.Chicago Midway
7h 29m
1 stop
YYC5:10 p.m.Calgary
C$ 1,039

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 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

Sat 2/5

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

1 stop5h 52m

Chicago Midway

Tue 5/5

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

2 stops12h 13m

C$ 379

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$ 386

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 2/5

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

2 stops13h 48m

Chicago Midway

Tue 5/5

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

2 stops12h 13m

C$ 396

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 2/5

7:00 a.m.-6:37 p.m.

1 stop10h 37m

Chicago Midway

Tue 5/5

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

1 stop12h 10m

C$ 441

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 2/5

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

2 stops13h 48m

Chicago Midway

Tue 5/5

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

2 stops12h 13m

C$ 448

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$ 454
Quickest round-trip

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 30/5

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

1 stop5h 34m

Chicago Midway

Sun 31/5

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

1 stop7h 43m

C$ 472

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 30/5

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

1 stop5h 34m

Chicago Midway

Sun 31/5

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

1 stop7h 43m

C$ 473

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 29/4

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$ 474

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 29/4

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$ 502

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 36m

Direct flights

None
The fastest flight from Calgary to Chicago Midway Airport takes 5h 36m
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 5h 36m.

  • 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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