Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Calgary to Chicago from C$ 217

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 5/9. 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

Save money when you book flights with momondo

Big names, great deals

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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
1:00 p.m. - 8:54 p.m.
MDW
-
YYC
8h 54m
2 stops
C$ 363Delta
Tue, 27 Oct - Sat, 31 Oct
Delta Logo
7:45 a.m. - 9:45 p.m.
YYC
-
MDW
13h 00m
2 stops
Delta Logo
6:00 a.m. - 11:13 p.m.
MDW
-
YYC
18h 13m
2 stops
C$ 364Delta
Thu, 29 Oct - Mon, 2 Nov
Delta Logo
7:45 a.m. - 9:45 p.m.
YYC
-
MDW
13h 00m
2 stops
Delta Logo
9:30 a.m. - 8:54 p.m.
MDW
-
YYC
12h 24m
2 stops
C$ 381Delta
Tue, 27 Oct - Sat, 31 Oct
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$ 441Delta
Thu, 29 Oct - Mon, 2 Nov
Delta Logo
7:00 a.m. - 4:15 p.m.
YYC
-
MDW
8h 15m
1 stop
Delta Logo
1:51 p.m. - 8:35 p.m.
MDW
-
YYC
7h 44m
1 stop
C$ 481Delta
Wed, 12 Aug - Mon, 17 Aug
Delta Logo
6:45 a.m. - 1:10 p.m.
YYC
-
MDW
5h 25m
1 stop
Delta Logo
1:51 p.m. - 8:35 p.m.
MDW
-
YYC
7h 44m
1 stop
C$ 491Delta
Fri, 14 Aug - Mon, 17 Aug
Delta Logo
7:00 a.m. - 4:15 p.m.
YYC
-
MDW
8h 15m
1 stop
Delta Logo
1:51 p.m. - 8:35 p.m.
MDW
-
YYC
7h 44m
1 stop
C$ 492Delta
Wed, 12 Aug - Mon, 17 Aug
Delta Logo
12:30 a.m. - 9:59 a.m.
YYC
-
MDW
8h 29m
1 stop
Delta Logo
6:05 a.m. - 5:10 p.m.
MDW
-
YYC
12h 05m
1 stop
C$ 514Delta
Tue, 11 Aug - Sat, 15 Aug
Delta Logo
11:00 a.m. - 6:37 p.m.
YYC
-
MDW
6h 37m
1 stop
Delta Logo
12:30 p.m. - 8:54 p.m.
MDW
-
YYC
9h 24m
1 stop
C$ 516Delta
Fri, 23 Oct - Sat, 5 Dec
Delta Logo
12:30 a.m. - 9:59 a.m.
YYC
-
MDW
8h 29m
1 stop
Delta Logo
12:46 p.m. - 9:50 p.m.
MDW
-
YYC
10h 04m
1 stop
C$ 537Delta
Tue, 11 Aug - Wed, 19 Aug

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
MDW1:00 p.m.Chicago Midway
8h 54m
2 stops
YYC8:54 p.m.Calgary
C$ 363
Delta
29 Oct
YYC7:45 a.m.Calgary
13h 00m
2 stops
MDW9:45 p.m.Chicago Midway
2 Nov
MDW6:00 a.m.Chicago Midway
18h 13m
2 stops
YYC11:13 p.m.Calgary
C$ 364
Delta
27 Oct
YYC7:45 a.m.Calgary
13h 00m
2 stops
MDW9:45 p.m.Chicago Midway
31 Oct
MDW9:30 a.m.Chicago Midway
12h 24m
2 stops
YYC8:54 p.m.Calgary
C$ 381

WestJet flights from Calgary to Chicago Midway Airport

Our best WestJet deals on Calgary to Chicago Midway Airport flight tickets
WestJet
12 Jun
YYC11:00 a.m.Calgary
6h 31m
1 stop
MDW6:31 p.m.Chicago Midway
14 Jun
MDW9:17 a.m.Chicago Midway
11h 48m
1 stop
YYC8:05 p.m.Calgary
C$ 1,081
WestJet
8 Jun
YYC10:15 a.m.Calgary
7h 03m
1 stop
MDW6:18 p.m.Chicago Midway
11 Jun
MDW9:54 a.m.Chicago Midway
8h 06m
1 stop
YYC5:00 p.m.Calgary
C$ 1,124
WestJet
8 Jun
YYC8:10 a.m.Calgary
9h 08m
2 stops
MDW6:18 p.m.Chicago Midway
13 Jun
MDW9:54 a.m.Chicago Midway
8h 06m
1 stop
YYC5:00 p.m.Calgary
C$ 1,125

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 31 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

1:00 p.m.-8:54 p.m.

2 stops8h 54m

C$ 363

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 29/10

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

2 stops13h 00m

Chicago Midway

Mon 2/11

6:00 a.m.-11:13 p.m.

2 stops18h 13m

C$ 364

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 27/10

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

2 stops13h 00m

Chicago Midway

Sat 31/10

9:30 a.m.-8:54 p.m.

2 stops12h 24m

C$ 381

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 29/10

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

2 stops13h 00m

Chicago Midway

Mon 2/11

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

1 stop9h 24m

C$ 441

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 12/8

7:00 a.m.-4:15 p.m.

1 stop8h 15m

Chicago Midway

Mon 17/8

1:51 p.m.-8:35 p.m.

1 stop7h 44m

C$ 481
Quickest round-trip

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 14/8

6:45 a.m.-1:10 p.m.

1 stop5h 25m

Chicago Midway

Mon 17/8

1:51 p.m.-8:35 p.m.

1 stop7h 44m

C$ 491

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 12/8

7:00 a.m.-4:15 p.m.

1 stop8h 15m

Chicago Midway

Mon 17/8

1:51 p.m.-8:35 p.m.

1 stop7h 44m

C$ 492

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 11/8

12:30 a.m.-9:59 a.m.

1 stop8h 29m

Chicago Midway

Sat 15/8

6:05 a.m.-5:10 p.m.

1 stop12h 05m

C$ 514

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 23/10

11:00 a.m.-6:37 p.m.

1 stop6h 37m

Chicago Midway

Sat 5/12

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

1 stop9h 24m

C$ 516

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 11/8

12:30 a.m.-9:59 a.m.

1 stop8h 29m

Chicago Midway

Wed 19/8

12:46 p.m.-9:50 p.m.

1 stop10h 04m

C$ 537

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 24m

Direct flights

None
The fastest flight from Calgary to Chicago Midway Airport takes 5h 24m
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 24m.

  • 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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Tue 30/6
Tue 7/7
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago