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Cheap flights from Calgary to Chicago from C$ 211

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 25/4. 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
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. - 10:28 p.m.
YYC
-
MDW
14h 48m
2 stops
Delta Logo
9:29 a.m. - 11:00 p.m.
MDW
-
YYC
14h 31m
2 stops
C$ 366Delta
Sat, 25 Apr - Tue, 28 Apr
Delta Logo
7:40 a.m. - 10:28 p.m.
YYC
-
MDW
13h 48m
2 stops
Delta Logo
9:29 a.m. - 11:00 p.m.
MDW
-
YYC
14h 31m
2 stops
C$ 369Delta
Tue, 21 Apr - Tue, 28 Apr
Delta Logo
6:45 a.m. - 1:19 p.m.
YYC
-
MDW
5h 34m
1 stop
Delta Logo
9:30 a.m. - 8:44 p.m.
MDW
-
YYC
12h 14m
2 stops
C$ 373Delta
Sat, 30 May - Sat, 19 Sep
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$ 384Delta
Sat, 25 Apr - Mon, 27 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$ 386Delta
Tue, 21 Apr - Mon, 27 Apr
Delta Logo
6:45 a.m. - 10:17 p.m.
YYC
-
MDW
14h 32m
2 stops
Delta Logo
9:17 a.m. - 8:38 p.m.
MDW
-
YYC
12h 21m
2 stops
C$ 412Delta
Wed, 1 Jul - Sat, 4 Jul
Delta Logo
6:45 a.m. - 5:56 p.m.
YYC
-
MDW
10h 11m
1 stop
Delta Logo
9:22 a.m. - 8:30 p.m.
MDW
-
YYC
12h 08m
2 stops
C$ 423Delta
Thu, 28 May - Mon, 1 Jun
Delta Logo
6:45 a.m. - 5:56 p.m.
YYC
-
MDW
10h 11m
1 stop
Delta Logo
9:22 a.m. - 8:30 p.m.
MDW
-
YYC
12h 08m
2 stops
C$ 438Delta
Thu, 28 May - Mon, 1 Jun
Delta Logo
6:45 a.m. - 5:56 p.m.
YYC
-
MDW
10h 11m
1 stop
Delta Logo
9:22 a.m. - 8:30 p.m.
MDW
-
YYC
12h 08m
2 stops
C$ 442Delta
Thu, 28 May - Mon, 1 Jun
Delta Logo
6:40 a.m. - 1:32 p.m.
YYC
-
MDW
5h 52m
1 stop
Delta Logo
9:22 a.m. - 8:30 p.m.
MDW
-
YYC
12h 08m
2 stops
C$ 443Delta
Tue, 5 May - Tue, 12 May

Delta flights from Calgary to Chicago Midway Airport

Our best Delta deals on Calgary to Chicago Midway Airport flight tickets
Delta
25 Apr
YYC6:40 a.m.Calgary
14h 48m
2 stops
MDW10:28 p.m.Chicago Midway
28 Apr
MDW9:29 a.m.Chicago Midway
14h 31m
2 stops
YYC11:00 p.m.Calgary
C$ 366
Delta
21 Apr
YYC7:40 a.m.Calgary
13h 48m
2 stops
MDW10:28 p.m.Chicago Midway
28 Apr
MDW9:29 a.m.Chicago Midway
14h 31m
2 stops
YYC11:00 p.m.Calgary
C$ 369
Delta
30 May
YYC6:45 a.m.Calgary
5h 34m
1 stop
MDW1:19 p.m.Chicago Midway
19 Sep
MDW9:30 a.m.Chicago Midway
12h 14m
2 stops
YYC8:44 p.m.Calgary
C$ 373

WestJet flights from Calgary to Chicago Midway Airport

Our best WestJet deals on Calgary to Chicago Midway Airport flight tickets
WestJet
31 Mar
YYC6:30 a.m.Calgary
5h 55m
1 stop
MDW1:25 p.m.Chicago Midway
9 Apr
MDW10:45 a.m.Chicago Midway
9h 24m
1 stop
YYC7:09 p.m.Calgary
C$ 1,032
WestJet
3 Apr
YYC10:00 a.m.Calgary
21h 53m
2 stops
MDW8:53 a.m.Chicago Midway
18 Apr
MDW6:38 p.m.Chicago Midway
20h 50m
2 stops
YYC2:28 p.m.Calgary
C$ 1,058
WestJet
3 Apr
YYC6:30 a.m.Calgary
11h 10m
1 stop
MDW6:40 p.m.Chicago Midway
18 Apr
MDW9:46 a.m.Chicago Midway
11h 54m
1 stop
YYC8:40 p.m.Calgary
C$ 1,095

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 24 March 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 25/4

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

2 stops14h 48m

Chicago Midway

Tue 28/4

9:29 a.m.-11:00 p.m.

2 stops14h 31m

C$ 366

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 21/4

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

2 stops13h 48m

Chicago Midway

Tue 28/4

9:29 a.m.-11:00 p.m.

2 stops14h 31m

C$ 369
Quickest round-trip

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 30/5

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

1 stop5h 34m

Chicago Midway

Sat 19/9

9:30 a.m.-8:44 p.m.

2 stops12h 14m

C$ 373

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 25/4

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

1 stop5h 52m

Chicago Midway

Mon 27/4

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

2 stops12h 13m

C$ 384

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 21/4

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

2 stops13h 48m

Chicago Midway

Mon 27/4

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

2 stops12h 13m

C$ 386

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 1/7

6:45 a.m.-10:17 p.m.

2 stops14h 32m

Chicago Midway

Sat 4/7

9:17 a.m.-8:38 p.m.

2 stops12h 21m

C$ 412

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 28/5

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

1 stop10h 11m

Chicago Midway

Mon 1/6

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

2 stops12h 08m

C$ 423

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 28/5

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

1 stop10h 11m

Chicago Midway

Mon 1/6

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

2 stops12h 08m

C$ 438

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 28/5

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

1 stop10h 11m

Chicago Midway

Mon 1/6

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

2 stops12h 08m

C$ 442

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 5/5

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

1 stop5h 52m

Chicago Midway

Tue 12/5

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

2 stops12h 08m

C$ 443

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 34m

Direct flights

None
The fastest flight from Calgary to Chicago Midway Airport takes 5h 34m
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 34m.

  • 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
Munster
Hammond

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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