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 $465 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 36m, covering a distance of 1396 miles.
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 ($304) and Multiple Airlines ($692)
Do I need a passport to fly between Calgary and Chicago Midway?
Yes.
What’s the cheapest day of the week to fly Calgary to Chicago Midway?
For Calgary to Chicago Midway, Tuesday is the cheapest day to fly on average and Saturday is the most expensive. Flying from Chicago Midway back to Calgary, the best deals are generally found on Saturday, with Thursday being the most expensive.

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

Airports
Origin
Calgary
$304
only
$304
Destination
Chicago
$304
only
$304
Tue, Apr 17
YYC
MDW
6h 29m
Sat, Apr 21
MDW
YYC
9h 53m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16124 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
DCA
Good 6.6

The movie availability was very much appreciated.

Although my TSA Pre check number was on my flight coming into Atlanta, it wss not on my fight leaving Atlanta. That caused me to arrive at my gate 5 mins before boarding time and prevented me from having time to eat breakfast before my flight.

DTW
RSW
Excellent 9.6

Free movies. Clean and modern look to airplane.

Could not get wifi to work.

LAX
SFO
Good 7.6

Crew was wonderful, fine flight, very prompt

Was unable to board an earlier flight without paying $75. If there are seats it shouldn't be so difficult to be moved.

DCA
ATL
Excellent 10.0

The in-flight movie was very much appreciated.

SLC
RAP
Excellent 8.6

Crowded boarding area, but no standing around for long. Quick boarding. Entertainment not available so can't rate that. Good crew

Wed, Apr 18
YYC
MDW
9h 04m
Sat, Apr 21
MDW
YYC
9h 53m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16124 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
LAX
SFO
Good 7.6

Crew was wonderful, fine flight, very prompt

Was unable to board an earlier flight without paying $75. If there are seats it shouldn't be so difficult to be moved.

SLC
RAP
Excellent 8.6

Crowded boarding area, but no standing around for long. Quick boarding. Entertainment not available so can't rate that. Good crew

DTW
SLC
Okay 5.3

Its a 3.5 hr flight. No charging outlets available. Food options very limited by the time they got to me, row 26. No in -seat entertainment screen. Hard seats.

ATL
DCA
Good 6.6

The movie availability was very much appreciated.

Although my TSA Pre check number was on my flight coming into Atlanta, it wss not on my fight leaving Atlanta. That caused me to arrive at my gate 5 mins before boarding time and prevented me from having time to eat breakfast before my flight.

CUN
ATL
Good 7.0

Staff was friendly. Flight was smooth.

Media kept freezing. They had to reboot the system several times.

Fri, Mar 23
YYC
MDW
10h 07m
Sun, Mar 25
MDW
YYC
12h 39m
Trip: 3 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Mar 21
YYC
MDW
10h 07m
Tue, Mar 27
MDW
YYC
7h 57m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16124 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
DCA
Good 6.6

The movie availability was very much appreciated.

Although my TSA Pre check number was on my flight coming into Atlanta, it wss not on my fight leaving Atlanta. That caused me to arrive at my gate 5 mins before boarding time and prevented me from having time to eat breakfast before my flight.

BDL
CVG
Okay 4.0

Great pilot..

Jam packed too small and the lady flight attendant was to bossy and not that welcoming, she was more interested in being more of a drill sergeant than the comfort of the passengers

VPS
ATL
Good 7.3

Quick boarding. Nice crew. No food or entertainment so I couldn't rate those. N/A should be a choice

CUN
ATL
Good 7.0

Staff was friendly. Flight was smooth.

Media kept freezing. They had to reboot the system several times.

DTW
SLC
Okay 5.3

Its a 3.5 hr flight. No charging outlets available. Food options very limited by the time they got to me, row 26. No in -seat entertainment screen. Hard seats.

Sat, Mar 10
YYC
MDW
7h 41m
Sat, Mar 17
MDW
YYC
7h 41m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16124 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
TGU
Mediocre 2.0

The service was horribly they dilate my flight 24 hours and I lose my flight yesterday because from Washington to Atlanta the flight was late and from Atlanta to Tegucigalpa leave early

LAX
IND
Excellent 10.0

The comfort, space, quiet, snacks

ATL
DCA
Good 6.6

The movie availability was very much appreciated.

Although my TSA Pre check number was on my flight coming into Atlanta, it wss not on my fight leaving Atlanta. That caused me to arrive at my gate 5 mins before boarding time and prevented me from having time to eat breakfast before my flight.

VPS
ATL
Good 7.3

Quick boarding. Nice crew. No food or entertainment so I couldn't rate those. N/A should be a choice

DCA
ATL
Excellent 10.0

The in-flight movie was very much appreciated.

Wed, Apr 11
YYC
MDW
7h 34m
Tue, Apr 17
MDW
YYC
7h 15m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16124 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
DCA
Good 6.6

The movie availability was very much appreciated.

Although my TSA Pre check number was on my flight coming into Atlanta, it wss not on my fight leaving Atlanta. That caused me to arrive at my gate 5 mins before boarding time and prevented me from having time to eat breakfast before my flight.

ATL
TGU
Mediocre 2.0

The service was horribly they dilate my flight 24 hours and I lose my flight yesterday because from Washington to Atlanta the flight was late and from Atlanta to Tegucigalpa leave early

LAX
IND
Excellent 10.0

The comfort, space, quiet, snacks

DCA
ATL
Excellent 10.0

The in-flight movie was very much appreciated.

VPS
ATL
Good 7.3

Quick boarding. Nice crew. No food or entertainment so I couldn't rate those. N/A should be a choice

Tue, Mar 20
YYC
MDW
10h 07m
Tue, Mar 27
MDW
YYC
7h 57m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16124 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
BDL
CVG
Okay 4.0

Great pilot..

Jam packed too small and the lady flight attendant was to bossy and not that welcoming, she was more interested in being more of a drill sergeant than the comfort of the passengers

SLC
RAP
Excellent 8.6

Crowded boarding area, but no standing around for long. Quick boarding. Entertainment not available so can't rate that. Good crew

VPS
ATL
Good 7.3

Quick boarding. Nice crew. No food or entertainment so I couldn't rate those. N/A should be a choice

ATL
SLC
Excellent 10.0

Quick boarding for a big plane. Lots of room for overhead luggage. Two beverage services. Nice crew!

LAX
SFO
Good 7.6

Crew was wonderful, fine flight, very prompt

Was unable to board an earlier flight without paying $75. If there are seats it shouldn't be so difficult to be moved.

Thu, Mar 1
YYC
MDW
6h 39m
Mon, Mar 5
MDW
YYC
7h 57m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16124 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
LAX
SFO
Good 7.6

Crew was wonderful, fine flight, very prompt

Was unable to board an earlier flight without paying $75. If there are seats it shouldn't be so difficult to be moved.

BDL
CVG
Okay 4.0

Great pilot..

Jam packed too small and the lady flight attendant was to bossy and not that welcoming, she was more interested in being more of a drill sergeant than the comfort of the passengers

VPS
ATL
Good 7.3

Quick boarding. Nice crew. No food or entertainment so I couldn't rate those. N/A should be a choice

ATL
SLC
Excellent 10.0

Quick boarding for a big plane. Lots of room for overhead luggage. Two beverage services. Nice crew!

DTW
SLC
Okay 5.3

Its a 3.5 hr flight. No charging outlets available. Food options very limited by the time they got to me, row 26. No in -seat entertainment screen. Hard seats.

Tue, Mar 13
YYC
MDW
7h 43m
Tue, Mar 20
MDW
YYC
7h 57m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16124 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
DCA
ATL
Excellent 10.0

The in-flight movie was very much appreciated.

BDL
CVG
Okay 4.0

Great pilot..

Jam packed too small and the lady flight attendant was to bossy and not that welcoming, she was more interested in being more of a drill sergeant than the comfort of the passengers

VPS
ATL
Good 7.3

Quick boarding. Nice crew. No food or entertainment so I couldn't rate those. N/A should be a choice

ATL
TGU
Mediocre 2.0

The service was horribly they dilate my flight 24 hours and I lose my flight yesterday because from Washington to Atlanta the flight was late and from Atlanta to Tegucigalpa leave early

SLC
RAP
Excellent 8.6

Crowded boarding area, but no standing around for long. Quick boarding. Entertainment not available so can't rate that. Good crew

Sat, Apr 14
YYC
MDW
14h 15m
Mon, Apr 16
MDW
YYC
7h 15m
Trip: 3 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Mar 22
YYC
MDW
5h 36m
Tue, Mar 27
MDW
YYC
7h 57m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16124 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
SLC
Excellent 10.0

Quick boarding for a big plane. Lots of room for overhead luggage. Two beverage services. Nice crew!

LAX
IND
Excellent 10.0

The comfort, space, quiet, snacks

CUN
ATL
Good 7.0

Staff was friendly. Flight was smooth.

Media kept freezing. They had to reboot the system several times.

BDL
CVG
Okay 4.0

Great pilot..

Jam packed too small and the lady flight attendant was to bossy and not that welcoming, she was more interested in being more of a drill sergeant than the comfort of the passengers

LAX
SFO
Good 7.6

Crew was wonderful, fine flight, very prompt

Was unable to board an earlier flight without paying $75. If there are seats it shouldn't be so difficult to be moved.

Tue, Apr 17
YYC
MDW
9h 04m
Thu, Apr 19
MDW
YYC
8h 14m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16124 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
SLC
Excellent 10.0

Quick boarding for a big plane. Lots of room for overhead luggage. Two beverage services. Nice crew!

LAX
IND
Excellent 10.0

The comfort, space, quiet, snacks

DTW
RSW
Excellent 9.6

Free movies. Clean and modern look to airplane.

Could not get wifi to work.

DTW
SLC
Okay 5.3

Its a 3.5 hr flight. No charging outlets available. Food options very limited by the time they got to me, row 26. No in -seat entertainment screen. Hard seats.

LAX
SFO
Good 7.6

Crew was wonderful, fine flight, very prompt

Was unable to board an earlier flight without paying $75. If there are seats it shouldn't be so difficult to be moved.

Wed, Apr 11
YYC
MDW
5h 40m
Thu, Apr 19
MDW
YYC
8h 14m
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16124 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
SLC
RAP
Excellent 8.6

Crowded boarding area, but no standing around for long. Quick boarding. Entertainment not available so can't rate that. Good crew

LAX
SFO
Good 7.6

Crew was wonderful, fine flight, very prompt

Was unable to board an earlier flight without paying $75. If there are seats it shouldn't be so difficult to be moved.

CUN
ATL
Good 7.0

Staff was friendly. Flight was smooth.

Media kept freezing. They had to reboot the system several times.

ATL
DCA
Good 6.6

The movie availability was very much appreciated.

Although my TSA Pre check number was on my flight coming into Atlanta, it wss not on my fight leaving Atlanta. That caused me to arrive at my gate 5 mins before boarding time and prevented me from having time to eat breakfast before my flight.

DTW
RSW
Excellent 9.6

Free movies. Clean and modern look to airplane.

Could not get wifi to work.

Tue, Apr 17
YYC
MDW
5h 40m
Wed, Apr 18
MDW
YYC
7h 15m
Trip: 2 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16124 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
DTW
RSW
Excellent 9.6

Free movies. Clean and modern look to airplane.

Could not get wifi to work.

VPS
ATL
Good 7.3

Quick boarding. Nice crew. No food or entertainment so I couldn't rate those. N/A should be a choice

LAX
SFO
Good 7.6

Crew was wonderful, fine flight, very prompt

Was unable to board an earlier flight without paying $75. If there are seats it shouldn't be so difficult to be moved.

DCA
ATL
Excellent 10.0

The in-flight movie was very much appreciated.

SLC
RAP
Excellent 8.6

Crowded boarding area, but no standing around for long. Quick boarding. Entertainment not available so can't rate that. Good crew

Fri, Mar 23
YYC
MDW
10h 07m
Tue, Mar 27
MDW
YYC
7h 57m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16124 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
LAX
SFO
Good 7.6

Crew was wonderful, fine flight, very prompt

Was unable to board an earlier flight without paying $75. If there are seats it shouldn't be so difficult to be moved.

ATL
DCA
Good 6.6

The movie availability was very much appreciated.

Although my TSA Pre check number was on my flight coming into Atlanta, it wss not on my fight leaving Atlanta. That caused me to arrive at my gate 5 mins before boarding time and prevented me from having time to eat breakfast before my flight.

ATL
TGU
Mediocre 2.0

The service was horribly they dilate my flight 24 hours and I lose my flight yesterday because from Washington to Atlanta the flight was late and from Atlanta to Tegucigalpa leave early

DCA
ATL
Excellent 10.0

The in-flight movie was very much appreciated.

ATL
SLC
Excellent 10.0

Quick boarding for a big plane. Lots of room for overhead luggage. Two beverage services. Nice crew!

Wed, Mar 21
YYC
MDW
10h 07m
Thu, Mar 29
MDW
YYC
10h 55m
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16124 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
DCA
ATL
Excellent 10.0

The in-flight movie was very much appreciated.

BDL
CVG
Okay 4.0

Great pilot..

Jam packed too small and the lady flight attendant was to bossy and not that welcoming, she was more interested in being more of a drill sergeant than the comfort of the passengers

SLC
RAP
Excellent 8.6

Crowded boarding area, but no standing around for long. Quick boarding. Entertainment not available so can't rate that. Good crew

LAX
IND
Excellent 10.0

The comfort, space, quiet, snacks

ATL
DCA
Good 6.6

The movie availability was very much appreciated.

Although my TSA Pre check number was on my flight coming into Atlanta, it wss not on my fight leaving Atlanta. That caused me to arrive at my gate 5 mins before boarding time and prevented me from having time to eat breakfast before my flight.

Sat, Mar 10
YYC
MDW
10h 23m
Tue, Mar 13
MDW
YYC
10h 43m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16124 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
SLC
Excellent 10.0

Quick boarding for a big plane. Lots of room for overhead luggage. Two beverage services. Nice crew!

CUN
ATL
Good 7.0

Staff was friendly. Flight was smooth.

Media kept freezing. They had to reboot the system several times.

SLC
RAP
Excellent 8.6

Crowded boarding area, but no standing around for long. Quick boarding. Entertainment not available so can't rate that. Good crew

ATL
DCA
Good 6.6

The movie availability was very much appreciated.

Although my TSA Pre check number was on my flight coming into Atlanta, it wss not on my fight leaving Atlanta. That caused me to arrive at my gate 5 mins before boarding time and prevented me from having time to eat breakfast before my flight.

DCA
ATL
Excellent 10.0

The in-flight movie was very much appreciated.

Wed, Mar 21
YYC
MDW
7h 43m
Mon, Mar 26
MDW
YYC
5h 50m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16124 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
TGU
Mediocre 2.0

The service was horribly they dilate my flight 24 hours and I lose my flight yesterday because from Washington to Atlanta the flight was late and from Atlanta to Tegucigalpa leave early

DCA
ATL
Excellent 10.0

The in-flight movie was very much appreciated.

BDL
CVG
Okay 4.0

Great pilot..

Jam packed too small and the lady flight attendant was to bossy and not that welcoming, she was more interested in being more of a drill sergeant than the comfort of the passengers

VPS
ATL
Good 7.3

Quick boarding. Nice crew. No food or entertainment so I couldn't rate those. N/A should be a choice

ATL
DCA
Good 6.6

The movie availability was very much appreciated.

Although my TSA Pre check number was on my flight coming into Atlanta, it wss not on my fight leaving Atlanta. That caused me to arrive at my gate 5 mins before boarding time and prevented me from having time to eat breakfast before my flight.

Tue, Mar 20
YYC
MDW
10h 07m
Mon, Mar 26
MDW
YYC
5h 50m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16124 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
LAX
SFO
Good 7.6

Crew was wonderful, fine flight, very prompt

Was unable to board an earlier flight without paying $75. If there are seats it shouldn't be so difficult to be moved.

SLC
RAP
Excellent 8.6

Crowded boarding area, but no standing around for long. Quick boarding. Entertainment not available so can't rate that. Good crew

CUN
ATL
Good 7.0

Staff was friendly. Flight was smooth.

Media kept freezing. They had to reboot the system several times.

LAX
IND
Excellent 10.0

The comfort, space, quiet, snacks

DTW
RSW
Excellent 9.6

Free movies. Clean and modern look to airplane.

Could not get wifi to work.

Tue, Mar 20
YYC
MDW
10h 07m
Thu, Mar 29
MDW
YYC
10h 55m
Trip: 10 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16124 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
DCA
ATL
Excellent 10.0

The in-flight movie was very much appreciated.

DTW
SLC
Okay 5.3

Its a 3.5 hr flight. No charging outlets available. Food options very limited by the time they got to me, row 26. No in -seat entertainment screen. Hard seats.

SLC
RAP
Excellent 8.6

Crowded boarding area, but no standing around for long. Quick boarding. Entertainment not available so can't rate that. Good crew

ATL
SLC
Excellent 10.0

Quick boarding for a big plane. Lots of room for overhead luggage. Two beverage services. Nice crew!

ATL
DCA
Good 6.6

The movie availability was very much appreciated.

Although my TSA Pre check number was on my flight coming into Atlanta, it wss not on my fight leaving Atlanta. That caused me to arrive at my gate 5 mins before boarding time and prevented me from having time to eat breakfast before my flight.

Calgary to Chicago Midway Flight Information

Flights Arrive in Chicago Midway
Flights Depart from Calgary
Flight Price $304
Distance 1396 miles
Airlines Delta
*
Prices are per person and are for e–tickets and include all taxes & fees in USD.

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.

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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.