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

Search hundreds of travel sites at once for deals on flights to Chicago Midway

Depart
Return
Any month
Compare vs. KAYAK |

Calgary to Chicago Midway Flight Information

Flights Arrive in Chicago Midway
Flights Depart from Calgary
Flight Price C$ 552
Distance 2,248 km
Airlines Delta

FAQs for Booking Calgary to Chicago Midway Flights

How long does a flight from Calgary to Chicago Midway take?
There are no direct flights for this route listed on KAYAK, the shortest multi-flight duration is 5h 23m.
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$ 552) and Multiple Airlines (C$ 1006)
What’s the cheapest day of the week to fly from Calgary to Chicago Midway?
For Calgary to Chicago Midway, Saturday is the cheapest day to fly on average and Wednesday is the most expensive. Flying from Chicago Midway back to Calgary, the best deals are generally found on Wednesday, with Friday being the most expensive.

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

Airports
Origin
Calgary
C$ 552
only
C$ 552
Destination
Chicago
C$ 552
only
C$ 552
Sat, 12 Jan
YYC
Calgary
MDW
Chicago Midway
5h 36m
Sun, 20 Jan
MDW
Chicago Midway
YYC
Calgary
11h 48m
C$ 552
Trip: 9 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 21,950 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
ATL
CLE
Excellent 10.0

Pros: I’m always pleased with our delta flights to and from Atlanta. Our flight was on time, the comfort plus seats are comfy enough, and the flights are quick and easy.

Cons: Everything was great on our flight.

LAX
HNL
Good 6.0

Pros: One of the flight attendants was nice.

Cons: 5+ hours and just some bagged snacks. Had to wait forever for soda. Screen was difficult to work - touch wasn’t working. Much smaller program selection than flights 6 days ago from RSW to LAX via ATL.

ANC
SEA
Excellent 9.0

Pros: Everything was fine. Delta did a great job.

Cons: The kid screaming in my ear for 3 hours

DTW
LAX
Excellent 10.0

Pros: Everything went smoothly. Baggage was at carousel before we were, a first.

Cons: Everything was fine.

ATL
PHX
Excellent 9.3

Cons: Got a stiff neck cause the seat would not go back. Makes it difficult to see the entertainment with my progressive lenses

Sun, 23 Dec
YYC
Calgary
MDW
Chicago Midway
27h 55m
Thu, 27 Dec
MDW
Chicago Midway
YYC
Calgary
11h 05m
C$ 1006
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Thu, 31 Jan
YYC
Calgary
MDW
Chicago Midway
6h 41m
Sun, 3 Feb
MDW
Chicago Midway
YYC
Calgary
7h 44m
C$ 553
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 21,950 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
ATL
PHX
Excellent 9.3

Cons: Got a stiff neck cause the seat would not go back. Makes it difficult to see the entertainment with my progressive lenses

MKE
LGA
Good 7.3

Pros: Boarding was easy, plane clean, snacks good.

Cons: Small plane but that’s not really fixable

SEA
GEG
Mediocre 2.0

Cons: The pplane was two hours late to depart due to technical issues.

RDU
JFK
Mediocre 2.0

Pros: Nothing

Cons: I missed my flight due to Tsa

BDL
ATL
Excellent 9.3

Pros: New plane with great entertainment arrived 30 mins early

Sat, 27 Apr
YYC
Calgary
MDW
Chicago Midway
5h 23m
Sat, 4 May
MDW
Chicago Midway
YYC
Calgary
5h 29m
C$ 556
Trip: 8 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 21,950 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
ANC
SEA
Excellent 9.0

Pros: Everything was fine. Delta did a great job.

Cons: The kid screaming in my ear for 3 hours

SEA
GEG
Mediocre 2.0

Cons: The pplane was two hours late to depart due to technical issues.

MKE
LGA
Good 7.3

Pros: Boarding was easy, plane clean, snacks good.

Cons: Small plane but that’s not really fixable

FCO
ATL
Good 7.0

Pros: THe crew was super

Cons: Confort no good very tight seats Movies hard to understand Announcements hard to hear

ATL
PHX
Excellent 9.3

Cons: Got a stiff neck cause the seat would not go back. Makes it difficult to see the entertainment with my progressive lenses

Mon, 29 Apr
YYC
Calgary
MDW
Chicago Midway
8h 35m
Mon, 6 May
MDW
Chicago Midway
YYC
Calgary
9h 54m
C$ 582
Trip: 8 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 21,950 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
MKE
LGA
Good 7.3

Pros: Boarding was easy, plane clean, snacks good.

Cons: Small plane but that’s not really fixable

ATL
MCI
Excellent 10.0

Pros: Nice people

Cons: Waiting at gate in KC

ANC
SEA
Excellent 9.0

Pros: Everything was fine. Delta did a great job.

Cons: The kid screaming in my ear for 3 hours

SEA
GEG
Mediocre 2.0

Cons: The pplane was two hours late to depart due to technical issues.

FCO
ATL
Good 7.0

Pros: THe crew was super

Cons: Confort no good very tight seats Movies hard to understand Announcements hard to hear

Mon, 11 Feb
YYC
Calgary
MDW
Chicago Midway
9h 47m
Thu, 21 Feb
MDW
Chicago Midway
YYC
Calgary
11h 48m
C$ 654
Trip: 11 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 21,950 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
MKE
LGA
Good 7.3

Pros: Boarding was easy, plane clean, snacks good.

Cons: Small plane but that’s not really fixable

BOS
PHL
Excellent 8.6

Pros: We left early

RDU
JFK
Mediocre 2.0

Pros: Nothing

Cons: I missed my flight due to Tsa

FCO
ATL
Good 7.0

Pros: THe crew was super

Cons: Confort no good very tight seats Movies hard to understand Announcements hard to hear

ATL
PHX
Excellent 9.3

Cons: Got a stiff neck cause the seat would not go back. Makes it difficult to see the entertainment with my progressive lenses

Wed, 1 May
YYC
Calgary
MDW
Chicago Midway
9h 42m
Wed, 8 May
MDW
Chicago Midway
YYC
Calgary
10h 22m
C$ 680
Trip: 8 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 21,950 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
ANC
SEA
Excellent 9.0

Pros: Everything was fine. Delta did a great job.

Cons: The kid screaming in my ear for 3 hours

ATL
PHX
Excellent 9.3

Cons: Got a stiff neck cause the seat would not go back. Makes it difficult to see the entertainment with my progressive lenses

FCO
ATL
Good 7.0

Pros: THe crew was super

Cons: Confort no good very tight seats Movies hard to understand Announcements hard to hear

DTW
LAX
Excellent 10.0

Pros: Everything went smoothly. Baggage was at carousel before we were, a first.

Cons: Everything was fine.

ATL
MCI
Excellent 10.0

Pros: Nice people

Cons: Waiting at gate in KC

Thu, 7 Feb
YYC
Calgary
MDW
Chicago Midway
6h 41m
Sat, 16 Feb
MDW
Chicago Midway
YYC
Calgary
11h 23m
C$ 712
Trip: 10 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 21,950 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
RDU
JFK
Mediocre 2.0

Pros: Nothing

Cons: I missed my flight due to Tsa

DTW
LAX
Excellent 10.0

Pros: Everything went smoothly. Baggage was at carousel before we were, a first.

Cons: Everything was fine.

FCO
ATL
Good 7.0

Pros: THe crew was super

Cons: Confort no good very tight seats Movies hard to understand Announcements hard to hear

SEA
GEG
Mediocre 2.0

Cons: The pplane was two hours late to depart due to technical issues.

BOS
PHL
Excellent 8.6

Pros: We left early

Sun, 28 Apr
YYC
Calgary
MDW
Chicago Midway
7h 03m
Sun, 5 May
MDW
Chicago Midway
YYC
Calgary
9h 54m
C$ 744
Trip: 8 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 21,950 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
ATL
PHX
Excellent 9.3

Cons: Got a stiff neck cause the seat would not go back. Makes it difficult to see the entertainment with my progressive lenses

FCO
ATL
Good 7.0

Pros: THe crew was super

Cons: Confort no good very tight seats Movies hard to understand Announcements hard to hear

ATL
CLE
Excellent 10.0

Pros: I’m always pleased with our delta flights to and from Atlanta. Our flight was on time, the comfort plus seats are comfy enough, and the flights are quick and easy.

Cons: Everything was great on our flight.

LAX
HNL
Good 6.0

Pros: One of the flight attendants was nice.

Cons: 5+ hours and just some bagged snacks. Had to wait forever for soda. Screen was difficult to work - touch wasn’t working. Much smaller program selection than flights 6 days ago from RSW to LAX via ATL.

RDU
JFK
Mediocre 2.0

Pros: Nothing

Cons: I missed my flight due to Tsa

Fri, 8 Feb
YYC
Calgary
MDW
Chicago Midway
9h 47m
Sun, 10 Feb
MDW
Chicago Midway
YYC
Calgary
7h 44m
C$ 748
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 21,950 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
BOS
PHL
Excellent 8.6

Pros: We left early

ATL
CLE
Excellent 10.0

Pros: I’m always pleased with our delta flights to and from Atlanta. Our flight was on time, the comfort plus seats are comfy enough, and the flights are quick and easy.

Cons: Everything was great on our flight.

MKE
LGA
Good 7.3

Pros: Boarding was easy, plane clean, snacks good.

Cons: Small plane but that’s not really fixable

SEA
GEG
Mediocre 2.0

Cons: The pplane was two hours late to depart due to technical issues.

BDL
ATL
Excellent 9.3

Pros: New plane with great entertainment arrived 30 mins early

Sat, 29 Dec
YYC
Calgary
MDW
Chicago Midway
5h 43m
Tue, 8 Jan
MDW
Chicago Midway
YYC
Calgary
7h 44m
C$ 755
Trip: 11 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 21,950 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
BDL
ATL
Excellent 9.3

Pros: New plane with great entertainment arrived 30 mins early

MKE
LGA
Good 7.3

Pros: Boarding was easy, plane clean, snacks good.

Cons: Small plane but that’s not really fixable

SEA
GEG
Mediocre 2.0

Cons: The pplane was two hours late to depart due to technical issues.

ATL
PHX
Excellent 9.3

Cons: Got a stiff neck cause the seat would not go back. Makes it difficult to see the entertainment with my progressive lenses

ATL
CLE
Excellent 10.0

Pros: I’m always pleased with our delta flights to and from Atlanta. Our flight was on time, the comfort plus seats are comfy enough, and the flights are quick and easy.

Cons: Everything was great on our flight.

Thu, 14 Feb
YYC
Calgary
MDW
Chicago Midway
10h 48m
Mon, 18 Feb
MDW
Chicago Midway
YYC
Calgary
7h 44m
C$ 755
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 21,950 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
SEA
GEG
Mediocre 2.0

Cons: The pplane was two hours late to depart due to technical issues.

DTW
LAX
Excellent 10.0

Pros: Everything went smoothly. Baggage was at carousel before we were, a first.

Cons: Everything was fine.

BDL
ATL
Excellent 9.3

Pros: New plane with great entertainment arrived 30 mins early

ANC
SEA
Excellent 9.0

Pros: Everything was fine. Delta did a great job.

Cons: The kid screaming in my ear for 3 hours

LAX
HNL
Good 6.0

Pros: One of the flight attendants was nice.

Cons: 5+ hours and just some bagged snacks. Had to wait forever for soda. Screen was difficult to work - touch wasn’t working. Much smaller program selection than flights 6 days ago from RSW to LAX via ATL.

Fri, 15 Feb
YYC
Calgary
MDW
Chicago Midway
6h 41m
Mon, 18 Feb
MDW
Chicago Midway
YYC
Calgary
7h 44m
C$ 819
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 21,950 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
ATL
PHX
Excellent 9.3

Cons: Got a stiff neck cause the seat would not go back. Makes it difficult to see the entertainment with my progressive lenses

ATL
CLE
Excellent 10.0

Pros: I’m always pleased with our delta flights to and from Atlanta. Our flight was on time, the comfort plus seats are comfy enough, and the flights are quick and easy.

Cons: Everything was great on our flight.

SEA
GEG
Mediocre 2.0

Cons: The pplane was two hours late to depart due to technical issues.

FCO
ATL
Good 7.0

Pros: THe crew was super

Cons: Confort no good very tight seats Movies hard to understand Announcements hard to hear

BDL
ATL
Excellent 9.3

Pros: New plane with great entertainment arrived 30 mins early

Fri, 4 Jan
YYC
Calgary
MDW
Chicago Midway
8h 03m
Mon, 7 Jan
MDW
Chicago Midway
YYC
Calgary
11h 04m
C$ 861
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 21,950 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
LAX
HNL
Good 6.0

Pros: One of the flight attendants was nice.

Cons: 5+ hours and just some bagged snacks. Had to wait forever for soda. Screen was difficult to work - touch wasn’t working. Much smaller program selection than flights 6 days ago from RSW to LAX via ATL.

RDU
JFK
Mediocre 2.0

Pros: Nothing

Cons: I missed my flight due to Tsa

FCO
ATL
Good 7.0

Pros: THe crew was super

Cons: Confort no good very tight seats Movies hard to understand Announcements hard to hear

ANC
SEA
Excellent 9.0

Pros: Everything was fine. Delta did a great job.

Cons: The kid screaming in my ear for 3 hours

ATL
PHX
Excellent 9.3

Cons: Got a stiff neck cause the seat would not go back. Makes it difficult to see the entertainment with my progressive lenses

Fri, 28 Dec
YYC
Calgary
MDW
Chicago Midway
8h 03m
Tue, 1 Jan
MDW
Chicago Midway
YYC
Calgary
8h 47m
C$ 978
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 21,950 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
DTW
LAX
Excellent 10.0

Pros: Everything went smoothly. Baggage was at carousel before we were, a first.

Cons: Everything was fine.

BDL
ATL
Excellent 9.3

Pros: New plane with great entertainment arrived 30 mins early

LAX
HNL
Good 6.0

Pros: One of the flight attendants was nice.

Cons: 5+ hours and just some bagged snacks. Had to wait forever for soda. Screen was difficult to work - touch wasn’t working. Much smaller program selection than flights 6 days ago from RSW to LAX via ATL.

ATL
CLE
Excellent 10.0

Pros: I’m always pleased with our delta flights to and from Atlanta. Our flight was on time, the comfort plus seats are comfy enough, and the flights are quick and easy.

Cons: Everything was great on our flight.

MKE
LGA
Good 7.3

Pros: Boarding was easy, plane clean, snacks good.

Cons: Small plane but that’s not really fixable

Sun, 23 Dec
YYC
Calgary
MDW
Chicago Midway
6h 31m
Sun, 30 Dec
MDW
Chicago Midway
YYC
Calgary
7h 13m
C$ 1015
Trip: 8 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 21,950 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
ATL
PHX
Excellent 9.3

Cons: Got a stiff neck cause the seat would not go back. Makes it difficult to see the entertainment with my progressive lenses

ATL
MCI
Excellent 10.0

Pros: Nice people

Cons: Waiting at gate in KC

DTW
LAX
Excellent 10.0

Pros: Everything went smoothly. Baggage was at carousel before we were, a first.

Cons: Everything was fine.

MKE
LGA
Good 7.3

Pros: Boarding was easy, plane clean, snacks good.

Cons: Small plane but that’s not really fixable

SEA
GEG
Mediocre 2.0

Cons: The pplane was two hours late to depart due to technical issues.

Tue, 30 Apr
YYC
Calgary
MDW
Chicago Midway
5h 56m
Tue, 7 May
MDW
Chicago Midway
YYC
Calgary
7h 36m
C$ 1035
Trip: 8 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 21,950 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
ATL
MCI
Excellent 10.0

Pros: Nice people

Cons: Waiting at gate in KC

ATL
CLE
Excellent 10.0

Pros: I’m always pleased with our delta flights to and from Atlanta. Our flight was on time, the comfort plus seats are comfy enough, and the flights are quick and easy.

Cons: Everything was great on our flight.

ANC
SEA
Excellent 9.0

Pros: Everything was fine. Delta did a great job.

Cons: The kid screaming in my ear for 3 hours

FCO
ATL
Good 7.0

Pros: THe crew was super

Cons: Confort no good very tight seats Movies hard to understand Announcements hard to hear

BOS
PHL
Excellent 8.6

Pros: We left early

Fri, 15 Feb
YYC
Calgary
MDW
Chicago Midway
6h 41m
Sun, 17 Feb
MDW
Chicago Midway
YYC
Calgary
7h 44m
C$ 1039
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 21,950 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
MKE
LGA
Good 7.3

Pros: Boarding was easy, plane clean, snacks good.

Cons: Small plane but that’s not really fixable

RDU
JFK
Mediocre 2.0

Pros: Nothing

Cons: I missed my flight due to Tsa

ATL
PHX
Excellent 9.3

Cons: Got a stiff neck cause the seat would not go back. Makes it difficult to see the entertainment with my progressive lenses

ATL
CLE
Excellent 10.0

Pros: I’m always pleased with our delta flights to and from Atlanta. Our flight was on time, the comfort plus seats are comfy enough, and the flights are quick and easy.

Cons: Everything was great on our flight.

FCO
ATL
Good 7.0

Pros: THe crew was super

Cons: Confort no good very tight seats Movies hard to understand Announcements hard to hear

Mon, 24 Dec
YYC
Calgary
MDW
Chicago Midway
7h 24m
Thu, 27 Dec
MDW
Chicago Midway
YYC
Calgary
7h 54m
C$ 1211
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 21,950 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
FCO
ATL
Good 7.0

Pros: THe crew was super

Cons: Confort no good very tight seats Movies hard to understand Announcements hard to hear

BOS
PHL
Excellent 8.6

Pros: We left early

MKE
LGA
Good 7.3

Pros: Boarding was easy, plane clean, snacks good.

Cons: Small plane but that’s not really fixable

ANC
SEA
Excellent 9.0

Pros: Everything was fine. Delta did a great job.

Cons: The kid screaming in my ear for 3 hours

LAX
HNL
Good 6.0

Pros: One of the flight attendants was nice.

Cons: 5+ hours and just some bagged snacks. Had to wait forever for soda. Screen was difficult to work - touch wasn’t working. Much smaller program selection than flights 6 days ago from RSW to LAX via ATL.

Wed, 2 Jan
YYC
Calgary
MDW
Chicago Midway
6h 31m
Sat, 5 Jan
MDW
Chicago Midway
YYC
Calgary
11h 23m
C$ 1345
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 21,950 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
LAX
HNL
Good 6.0

Pros: One of the flight attendants was nice.

Cons: 5+ hours and just some bagged snacks. Had to wait forever for soda. Screen was difficult to work - touch wasn’t working. Much smaller program selection than flights 6 days ago from RSW to LAX via ATL.

RDU
JFK
Mediocre 2.0

Pros: Nothing

Cons: I missed my flight due to Tsa

FCO
ATL
Good 7.0

Pros: THe crew was super

Cons: Confort no good very tight seats Movies hard to understand Announcements hard to hear

ATL
PHX
Excellent 9.3

Cons: Got a stiff neck cause the seat would not go back. Makes it difficult to see the entertainment with my progressive lenses

DTW
LAX
Excellent 10.0

Pros: Everything went smoothly. Baggage was at carousel before we were, a first.

Cons: Everything was fine.

*
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.