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Cheap flights from Calgary to Chicago from C$ 231

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 6/6. 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
7:45 a.m. - 9:45 p.m.
YYC
-
MDW
13h 00m
2 stops
Delta Logo
12:30 p.m. - 8:54 p.m.
MDW
-
YYC
9h 24m
1 stop
C$ 348Delta
Tue, 27 Oct - Sat, 31 Oct
Delta Logo
6:45 a.m. - 1:07 p.m.
YYC
-
MDW
5h 22m
1 stop
Delta Logo
1:47 p.m. - 8:32 p.m.
MDW
-
YYC
7h 45m
1 stop
C$ 374Delta
Tue, 15 Sep - Wed, 23 Sep
Delta Logo
7:45 a.m. - 9:45 p.m.
YYC
-
MDW
13h 00m
2 stops
Delta Logo
12:30 p.m. - 8:54 p.m.
MDW
-
YYC
9h 24m
1 stop
C$ 381Delta
Tue, 27 Oct - Sat, 31 Oct
Delta Logo
6:45 a.m. - 6:33 p.m.
YYC
-
MDW
10h 48m
2 stops
Delta Logo
9:59 a.m. - 11:09 p.m.
MDW
-
YYC
14h 10m
2 stops
C$ 383Delta
Thu, 20 Aug - Sat, 22 Aug
Delta Logo
7:45 a.m. - 4:50 p.m.
YYC
-
MDW
8h 05m
1 stop
Delta Logo
12:30 p.m. - 11:13 p.m.
MDW
-
YYC
11h 43m
2 stops
C$ 445Delta
Sat, 10 Oct - Tue, 13 Oct
Delta Logo
6:45 a.m. - 6:33 p.m.
YYC
-
MDW
10h 48m
2 stops
Delta Logo
1:52 p.m. - 8:35 p.m.
MDW
-
YYC
7h 43m
1 stop
C$ 450Delta
Thu, 20 Aug - Wed, 26 Aug
Multiple Airlines Logo
9:00 p.m. - 11:12 a.m.
YYC
-
MDW
13h 12m
2 stops
Multiple Airlines Logo
6:00 a.m. - 5:10 p.m.
MDW
-
YYC
12h 10m
1 stop
C$ 455Multiple Airlines
Mon, 17 Aug - Wed, 26 Aug
Delta Logo
6:35 a.m. - 1:11 p.m.
YYC
-
MDW
5h 36m
1 stop
Delta Logo
1:47 p.m. - 8:32 p.m.
MDW
-
YYC
7h 45m
1 stop
C$ 479Delta
Fri, 11 Sep - Mon, 14 Sep
Delta Logo
6:45 a.m. - 6:33 p.m.
YYC
-
MDW
10h 48m
2 stops
Delta Logo
9:24 a.m. - 8:35 p.m.
MDW
-
YYC
12h 11m
2 stops
C$ 481Delta
Thu, 20 Aug - Tue, 25 Aug
Multiple Airlines Logo
12:30 a.m. - 11:09 a.m.
YYC
-
MDW
9h 39m
1 stop
Multiple Airlines Logo
6:00 a.m. - 5:10 p.m.
MDW
-
YYC
12h 10m
1 stop
C$ 507Multiple Airlines
Tue, 18 Aug - Wed, 26 Aug

WestJet flights from Calgary to Chicago Midway Airport

Our best WestJet deals on Calgary to Chicago Midway Airport flight tickets
WestJet
13 Aug
YYC6:50 a.m.Calgary
5h 23m
1 stop
MDW1:13 p.m.Chicago Midway
18 Aug
MDW1:57 p.m.Chicago Midway
7h 43m
1 stop
YYC8:40 p.m.Calgary
C$ 710
WestJet
6 Jun
YYC10:15 a.m.Calgary
6h 41m
1 stop
MDW5:56 p.m.Chicago Midway
8 Jun
MDW1:26 p.m.Chicago Midway
7h 39m
1 stop
YYC8:05 p.m.Calgary
C$ 1,089
WestJet
8 Jun
YYC8:10 a.m.Calgary
9h 08m
2 stops
MDW6:18 p.m.Chicago Midway
13 Jun
MDW6:35 p.m.Chicago Midway
26h 30m
1 stop
YYC8:05 p.m.Calgary
C$ 1,105

Delta flights from Calgary to Chicago Midway Airport

Our best Delta deals on Calgary to Chicago Midway Airport flight tickets
Delta
27 Oct
YYC7:45 a.m.Calgary
13h 00m
2 stops
MDW9:45 p.m.Chicago Midway
31 Oct
MDW12:30 p.m.Chicago Midway
9h 24m
1 stop
YYC8:54 p.m.Calgary
C$ 348
Delta
15 Sep
YYC6:45 a.m.Calgary
5h 22m
1 stop
MDW1:07 p.m.Chicago Midway
23 Sep
MDW1:47 p.m.Chicago Midway
7h 45m
1 stop
YYC8:32 p.m.Calgary
C$ 374
Delta
27 Oct
YYC7:45 a.m.Calgary
13h 00m
2 stops
MDW9:45 p.m.Chicago Midway
31 Oct
MDW12:30 p.m.Chicago Midway
9h 24m
1 stop
YYC8:54 p.m.Calgary
C$ 381

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 25 May 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

Tue 27/10

7:45 a.m.-9:45 p.m.

2 stops13h 00m

Chicago Midway

Sat 31/10

12:30 p.m.-8:54 p.m.

1 stop9h 24m

C$ 348
Quickest round-trip

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 15/9

6:45 a.m.-1:07 p.m.

1 stop5h 22m

Chicago Midway

Wed 23/9

1:47 p.m.-8:32 p.m.

1 stop7h 45m

C$ 374

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 27/10

7:45 a.m.-9:45 p.m.

2 stops13h 00m

Chicago Midway

Sat 31/10

12:30 p.m.-8:54 p.m.

1 stop9h 24m

C$ 381

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 20/8

6:45 a.m.-6:33 p.m.

2 stops10h 48m

Chicago Midway

Sat 22/8

9:59 a.m.-11:09 p.m.

2 stops14h 10m

C$ 383

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 10/10

7:45 a.m.-4:50 p.m.

1 stop8h 05m

Chicago Midway

Tue 13/10

12:30 p.m.-11:13 p.m.

2 stops11h 43m

C$ 445

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 20/8

6:45 a.m.-6:33 p.m.

2 stops10h 48m

Chicago Midway

Wed 26/8

1:52 p.m.-8:35 p.m.

1 stop7h 43m

C$ 450

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 17/8

9:00 p.m.-11:12 a.m.

2 stops13h 12m

Chicago Midway

Wed 26/8

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

1 stop12h 10m

C$ 455

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 11/9

6:35 a.m.-1:11 p.m.

1 stop5h 36m

Chicago Midway

Mon 14/9

1:47 p.m.-8:32 p.m.

1 stop7h 45m

C$ 479

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 20/8

6:45 a.m.-6:33 p.m.

2 stops10h 48m

Chicago Midway

Tue 25/8

9:24 a.m.-8:35 p.m.

2 stops12h 11m

C$ 481

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 18/8

12:30 a.m.-11:09 a.m.

1 stop9h 39m

Chicago Midway

Wed 26/8

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

1 stop12h 10m

C$ 507

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 22m

Direct flights

None
The fastest flight from Calgary to Chicago Midway Airport takes 5h 22m
There are no direct flights from Calgary to Chicago Midway Airport. There are no popular flight routes from Calgary to Chicago Midway Airport.
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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 22m.

  • 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

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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