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

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When looking for a cheap flight, consider that 25% of our users selected a flight on this route for C$ 508 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 26m, 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$ 354) and Multiple Airlines (C$ 2822)
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$ 354
only
C$ 354
Destination
Chicago
C$ 354
only
C$ 354
Tue, 16 Jan
YYC
MDW
5h 26m
Wed, 17 Jan
MDW
YYC
7h 38m
C$ 354
Trip: 2 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13622 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ALB
DTW
Okay 4.0

Good seat

Delayed by 1 hr

CMH
BOS
Excellent 10.0

Courteous crew and smooth flight

Nothing

TPA
LGA
Good 7.3

Barking dogs. 4 around us! Middle seat.

SFO
SEA
Excellent 10.0

The t.v. 's at each seat

Nothing

CVG
BOS
Good 7.0

Friendly crew with modern plane

Why am I paying for first class for just snacks I can buy in an airport shop?

Tue, 16 Jan
YYC
MDW
5h 26m
Tue, 6 Feb
MDW
YYC
7h 58m
C$ 400
Trip: 22 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13622 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ATL
EWR
Okay 5.0

Crew was nice. Flight very smooth

We had to get seats at boarding because of the flight delay. She offered us two seats in the back. I knew they don't pushback so I said no. She had given the woman ahead of me two seats in comfort plus. Did not offer that and was rude. There were at least a few empty seats in that area. As a courtesy to us having 1)been delayed in Costa Rica. And then 2) a long wait for the connecting flight in Atlanta it would have been reasonable to offer those seats. Which remained empty

CMH
BOS
Excellent 10.0

Courteous crew and smooth flight

Nothing

TPA
LGA
Good 7.3

Barking dogs. 4 around us! Middle seat.

ALB
DTW
Okay 4.0

Good seat

Delayed by 1 hr

NAS
JFK
Excellent 8.0

Good service smooth flight

The food on bosrd

Fri, 8 Dec
YYC
MDW
6h 44m
Sun, 10 Dec
MDW
YYC
5h 46m
C$ 437
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13622 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SFO
SEA
Excellent 10.0

The t.v. 's at each seat

Nothing

DTW
CVG
Excellent 10.0

Everything was excellent

Excellent job and keep it up

PDX
LAX
Mediocre 2.0

none of it

It was Terrible I will never do it again

ALB
DTW
Okay 4.0

Good seat

Delayed by 1 hr

AMS
DTW
Excellent 10.0

Everything was Excellent

Excellent job and keep it up

Tue, 13 Feb
YYC
MDW
5h 26m
Fri, 23 Feb
MDW
YYC
7h 53m
C$ 448
Trip: 11 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13622 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LAX
GEG
Excellent 10.0

Flight was faster than expected, comfy seats, check in was fast and easy.

ATL
EWR
Okay 5.0

Crew was nice. Flight very smooth

We had to get seats at boarding because of the flight delay. She offered us two seats in the back. I knew they don't pushback so I said no. She had given the woman ahead of me two seats in comfort plus. Did not offer that and was rude. There were at least a few empty seats in that area. As a courtesy to us having 1)been delayed in Costa Rica. And then 2) a long wait for the connecting flight in Atlanta it would have been reasonable to offer those seats. Which remained empty

CVG
BOS
Good 7.0

Friendly crew with modern plane

Why am I paying for first class for just snacks I can buy in an airport shop?

DTW
CVG
Excellent 10.0

Everything was excellent

Excellent job and keep it up

MSP
ATL
Good 6.6

On the MSP to ATL leg the gate crew made a huge deal about checking rolling bags. They even stopped us at check-in and nearly begged us to check our bags pointing to the backed up jetway. But we had a lot of unpacking to do before checking our bags so we politely declined three times. On getting to our seats there were at least 8 open slots for bags near us. I heard a crew member call forward to say "tell them no more rollaboards" so they forced everyone left to check. On departure they slammed shut several very large empty overheads. WTF

Sat, 25 Nov
YYC
MDW
7h 41m
Tue, 28 Nov
MDW
YYC
5h 47m
C$ 556
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13622 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ATL
EWR
Okay 5.0

Crew was nice. Flight very smooth

We had to get seats at boarding because of the flight delay. She offered us two seats in the back. I knew they don't pushback so I said no. She had given the woman ahead of me two seats in comfort plus. Did not offer that and was rude. There were at least a few empty seats in that area. As a courtesy to us having 1)been delayed in Costa Rica. And then 2) a long wait for the connecting flight in Atlanta it would have been reasonable to offer those seats. Which remained empty

CMH
BOS
Excellent 10.0

Courteous crew and smooth flight

Nothing

LAX
GEG
Excellent 10.0

Flight was faster than expected, comfy seats, check in was fast and easy.

PDX
LAX
Mediocre 2.0

none of it

It was Terrible I will never do it again

DTW
CVG
Excellent 10.0

Everything was excellent

Excellent job and keep it up

Sun, 25 Mar
YYC
MDW
5h 31m
Wed, 28 Mar
MDW
YYC
7h 38m
C$ 610
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13622 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
DTW
CVG
Excellent 10.0

Everything was excellent

Excellent job and keep it up

ALB
DTW
Okay 4.0

Good seat

Delayed by 1 hr

LAX
GEG
Excellent 10.0

Flight was faster than expected, comfy seats, check in was fast and easy.

CVG
BOS
Good 7.0

Friendly crew with modern plane

Why am I paying for first class for just snacks I can buy in an airport shop?

CMH
BOS
Excellent 10.0

Courteous crew and smooth flight

Nothing

Thu, 8 Feb
YYC
MDW
5h 26m
Sun, 11 Feb
MDW
YYC
7h 38m
C$ 616
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13622 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ALB
DTW
Okay 4.0

Good seat

Delayed by 1 hr

AMS
DTW
Excellent 10.0

Everything was Excellent

Excellent job and keep it up

LAX
GEG
Excellent 10.0

Flight was faster than expected, comfy seats, check in was fast and easy.

TPA
LGA
Good 7.3

Barking dogs. 4 around us! Middle seat.

PDX
LAX
Mediocre 2.0

none of it

It was Terrible I will never do it again

Wed, 11 Apr
YYC
MDW
16h 27m
Wed, 18 Apr
MDW
YYC
15h 58m
C$ 2822
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
*
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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.