Find Cheap Flights from Calgary to Chicago Midway (YYC - MDW)

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Looking for a cheap flight? 25% of our users found flights on this route for C$ 469 or less.

FAQs for Booking Calgary to Chicago Midway Flights

How long does a flight from Calgary to Chicago Midway take?
An average nonstop flight takes 5h 18m, covering a distance of 2247 km.
Which airlines provide the cheapest flights from Calgary to Chicago Midway?
In the past 3 days, the cheapest round-trip tickets were found on Delta (C$ 403)
Do I need a passport to fly between Calgary and Chicago Midway?
Yes.

Book cheap flights from Calgary to Chicago Midway (round-trip)

Airports
Origin
Calgary
C$ 403
only
C$ 403
Destination
Chicago
C$ 403
only
C$ 403
Wed, 11 Apr
YYC
MDW
9h 04m
Tue, 17 Apr
MDW
YYC
7h 15m
C$ 403
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
FLL
BOS
Good 6.3

Food and nice crew

No tvs and bad WiFi

AMS
JFK
Excellent 8.3

The seat in Comfort+ was comfortable. The crew was very professional and also friendly and pleasant. The flight departed on time and arrived early.

Food was mediocre.

JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

SLC
CUN
Mediocre 2.0

Your company has the worst customer service ever! You ruined our family vacation and just have horrible policies I can’t believe it! Will never purchase anything off your website again! You suck!

ATL
MDW
Okay 4.6

Flight delayed 2 hrs

Wed, 25 Apr
YYC
MDW
6h 29m
Sat, 28 Apr
MDW
YYC
9h 53m
C$ 412
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

SLC
YYZ
Excellent 9.6

Z

AMS
JFK
Excellent 8.3

The seat in Comfort+ was comfortable. The crew was very professional and also friendly and pleasant. The flight departed on time and arrived early.

Food was mediocre.

FLL
BOS
Good 6.3

Food and nice crew

No tvs and bad WiFi

LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

Wed, 11 Apr
YYC
MDW
5h 40m
Sat, 14 Apr
MDW
YYC
9h 53m
C$ 496
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

SLC
YYZ
Excellent 9.6

Z

SLC
CUN
Mediocre 2.0

Your company has the worst customer service ever! You ruined our family vacation and just have horrible policies I can’t believe it! Will never purchase anything off your website again! You suck!

Wed, 7 Mar
YYC
MDW
6h 22m
Sat, 10 Mar
MDW
YYC
5h 48m
C$ 516
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
SLC
YYZ
Excellent 9.6

Z

FLL
BOS
Good 6.3

Food and nice crew

No tvs and bad WiFi

LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

ATL
MDW
Okay 4.6

Flight delayed 2 hrs

AMS
JFK
Excellent 8.3

The seat in Comfort+ was comfortable. The crew was very professional and also friendly and pleasant. The flight departed on time and arrived early.

Food was mediocre.

Sun, 4 Mar
YYC
MDW
5h 36m
Mon, 5 Mar
MDW
YYC
7h 57m
C$ 518
Trip: 2 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
MSP
CLT
Mediocre 2.0

Delayed

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

SLC
CUN
Mediocre 2.0

Your company has the worst customer service ever! You ruined our family vacation and just have horrible policies I can’t believe it! Will never purchase anything off your website again! You suck!

JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

Wed, 23 May
YYC
MDW
6h 48m
Wed, 30 May
MDW
YYC
7h 38m
C$ 535
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
FLL
BOS
Good 6.3

Food and nice crew

No tvs and bad WiFi

AMS
JFK
Excellent 8.3

The seat in Comfort+ was comfortable. The crew was very professional and also friendly and pleasant. The flight departed on time and arrived early.

Food was mediocre.

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

ATL
MDW
Okay 4.6

Flight delayed 2 hrs

Wed, 7 Mar
YYC
MDW
13h 22m
Mon, 12 Mar
MDW
YYC
10h 43m
C$ 554
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

SLC
CUN
Mediocre 2.0

Your company has the worst customer service ever! You ruined our family vacation and just have horrible policies I can’t believe it! Will never purchase anything off your website again! You suck!

JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

Sat, 19 May
YYC
MDW
7h 40m
Wed, 23 May
MDW
YYC
10h 52m
C$ 561
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

MSP
CLT
Mediocre 2.0

Delayed

FLL
BOS
Good 6.3

Food and nice crew

No tvs and bad WiFi

FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

Thu, 1 Mar
YYC
MDW
9h 26m
Mon, 5 Mar
MDW
YYC
10h 43m
C$ 568
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
AMS
JFK
Excellent 8.3

The seat in Comfort+ was comfortable. The crew was very professional and also friendly and pleasant. The flight departed on time and arrived early.

Food was mediocre.

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

MSP
CLT
Mediocre 2.0

Delayed

Thu, 5 Apr
YYC
MDW
5h 40m
Tue, 17 Apr
MDW
YYC
7h 15m
C$ 568
Trip: 13 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
SLC
CUN
Mediocre 2.0

Your company has the worst customer service ever! You ruined our family vacation and just have horrible policies I can’t believe it! Will never purchase anything off your website again! You suck!

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

SLC
YYZ
Excellent 9.6

Z

ATL
MDW
Okay 4.6

Flight delayed 2 hrs

MSP
CLT
Mediocre 2.0

Delayed

Wed, 11 Apr
YYC
MDW
5h 40m
Thu, 19 Apr
MDW
YYC
8h 14m
C$ 568
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

SLC
CUN
Mediocre 2.0

Your company has the worst customer service ever! You ruined our family vacation and just have horrible policies I can’t believe it! Will never purchase anything off your website again! You suck!

FLL
BOS
Good 6.3

Food and nice crew

No tvs and bad WiFi

ATL
MDW
Okay 4.6

Flight delayed 2 hrs

Thu, 12 Apr
YYC
MDW
9h 04m
Tue, 17 Apr
MDW
YYC
7h 15m
C$ 568
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

SLC
CUN
Mediocre 2.0

Your company has the worst customer service ever! You ruined our family vacation and just have horrible policies I can’t believe it! Will never purchase anything off your website again! You suck!

LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

FLL
BOS
Good 6.3

Food and nice crew

No tvs and bad WiFi

FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

Mon, 16 Apr
YYC
MDW
5h 40m
Tue, 17 Apr
MDW
YYC
7h 15m
C$ 568
Trip: 2 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
MSP
CLT
Mediocre 2.0

Delayed

AMS
JFK
Excellent 8.3

The seat in Comfort+ was comfortable. The crew was very professional and also friendly and pleasant. The flight departed on time and arrived early.

Food was mediocre.

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

ATL
MDW
Okay 4.6

Flight delayed 2 hrs

SLC
CUN
Mediocre 2.0

Your company has the worst customer service ever! You ruined our family vacation and just have horrible policies I can’t believe it! Will never purchase anything off your website again! You suck!

Tue, 17 Apr
YYC
MDW
6h 29m
Thu, 19 Apr
MDW
YYC
8h 14m
C$ 568
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

FLL
BOS
Good 6.3

Food and nice crew

No tvs and bad WiFi

SLC
CUN
Mediocre 2.0

Your company has the worst customer service ever! You ruined our family vacation and just have horrible policies I can’t believe it! Will never purchase anything off your website again! You suck!

LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

SLC
YYZ
Excellent 9.6

Z

Wed, 13 Jun
YYC
MDW
7h 03m
Sat, 16 Jun
MDW
YYC
5h 26m
C$ 568
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

SLC
YYZ
Excellent 9.6

Z

LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

MSP
CLT
Mediocre 2.0

Delayed

Sat, 16 Jun
YYC
MDW
5h 18m
Tue, 3 Jul
MDW
YYC
11h 05m
C$ 575
Trip: 18 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
AMS
JFK
Excellent 8.3

The seat in Comfort+ was comfortable. The crew was very professional and also friendly and pleasant. The flight departed on time and arrived early.

Food was mediocre.

MSP
CLT
Mediocre 2.0

Delayed

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

Sat, 16 Jun
YYC
MDW
5h 18m
Wed, 11 Jul
MDW
YYC
11h 05m
C$ 587
Trip: 26 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

FLL
BOS
Good 6.3

Food and nice crew

No tvs and bad WiFi

SLC
YYZ
Excellent 9.6

Z

ATL
MDW
Okay 4.6

Flight delayed 2 hrs

Tue, 22 May
YYC
MDW
6h 48m
Sun, 27 May
MDW
YYC
5h 18m
C$ 589
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

FLL
BOS
Good 6.3

Food and nice crew

No tvs and bad WiFi

FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

MSP
CLT
Mediocre 2.0

Delayed

SLC
CUN
Mediocre 2.0

Your company has the worst customer service ever! You ruined our family vacation and just have horrible policies I can’t believe it! Will never purchase anything off your website again! You suck!

Wed, 23 May
YYC
MDW
6h 48m
Sun, 27 May
MDW
YYC
5h 18m
C$ 589
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

FLL
BOS
Good 6.3

Food and nice crew

No tvs and bad WiFi

LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

AMS
JFK
Excellent 8.3

The seat in Comfort+ was comfortable. The crew was very professional and also friendly and pleasant. The flight departed on time and arrived early.

Food was mediocre.

Thu, 26 Apr
YYC
MDW
5h 40m
Tue, 1 May
MDW
YYC
7h 53m
C$ 594
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
SLC
CUN
Mediocre 2.0

Your company has the worst customer service ever! You ruined our family vacation and just have horrible policies I can’t believe it! Will never purchase anything off your website again! You suck!

JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

SLC
YYZ
Excellent 9.6

Z

Calgary to Chicago Midway Flight Information

Flights Arrive in Chicago Midway
Flights Depart from Calgary
Flight Price C$ 403
Distance 2247 km
Airlines Delta
*
Prices are per person, are for e–tickets and include all taxes & fees in CAD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

We compile tonnes of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

If you have more questions or if you have a bad price to report to us,
please send us an and someone from our team will get back to you promptly.

^
The fares displayed include all taxes and fees for economy class travel and were found by the provider in the last 72 hours. Seats are limited and may not be available on all flights and days. Fares are subject to change and may not be available on all flights or dates of travel. Some carriers charge additional fees for extra checked bags. Please check the carriers' sites.