Find Cheap Flights from Winnipeg to Chicago Midway (YWG - MDW)

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Looking for a cheap flight? 25% of our users found flights on this route for $366 or less.

FAQs for Booking Winnipeg to Chicago Midway Flights

How long does a flight from Winnipeg to Chicago Midway take?
An average nonstop flight takes 4h 48m, covering a distance of 722 miles.
Which airlines provide the cheapest flights from Winnipeg to Chicago Midway?
In the past 3 days, the cheapest round-trip tickets were found on Delta ($420)
Do I need a passport to fly between Winnipeg and Chicago Midway?
Yes.
What’s the cheapest day of the week to fly Winnipeg to Chicago Midway?
For Winnipeg to Chicago Midway, Friday is the cheapest day to fly on average and Saturday is the most expensive. Flying from Chicago Midway back to Winnipeg, the best deals are generally found on Thursday, with Wednesday being the most expensive.

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

Airports
Origin
Winnipeg
$420
only
$420
Destination
Chicago
$420
only
$420
Fri, Jan 19
YWG
MDW
4h 48m
Sun, Jan 21
MDW
YWG
3h 55m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ORF
BOS
Excellent 10.0

Flight attendant Gillian Awesome. Crew was fun and made my kids first flight great.

DTW
PHL
Excellent 8.0

Made it out of Detroit that same day! Friendly flight attendants!

Flight was delayed. And then cancelled. We were booked into a later flight 8 hours later that was also delayed again due to weather but we did make it out of Detroit that night. Other people were not as lucky.

SFO
LAX
Good 7.6

Everyone was really nice and responsive.

Seats are a little older. Not as comfortable as other flights. But not bad.

PHL
MSP
Mediocre 2.0

The flight itself was fine.

The flight was delayed and it set off a slew of connection problems.

ATL
OMA
Good 6.0

Check-in agent was very pleasant even through having to deal with a number of cancelled flights.

Flight was delayed shortly before it was scheduled for boarding, which resulted in further delays/cancellations along the journey. Earlier notification may have allowed me to remain in Atlanta a night or two longer with my family as opposed to having had to spend many additional hours sitting uncomfortably in an airport.

Mon, Feb 12
YWG
MDW
4h 48m
Mon, Feb 26
MDW
YWG
3h 49m
Trip: 15 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SFO
LAX
Good 7.6

Everyone was really nice and responsive.

Seats are a little older. Not as comfortable as other flights. But not bad.

MSP
LAS
Good 6.6

comfortable seats

delay delay delay

ATL
OMA
Good 6.0

Check-in agent was very pleasant even through having to deal with a number of cancelled flights.

Flight was delayed shortly before it was scheduled for boarding, which resulted in further delays/cancellations along the journey. Earlier notification may have allowed me to remain in Atlanta a night or two longer with my family as opposed to having had to spend many additional hours sitting uncomfortably in an airport.

DTW
PHL
Excellent 8.0

Made it out of Detroit that same day! Friendly flight attendants!

Flight was delayed. And then cancelled. We were booked into a later flight 8 hours later that was also delayed again due to weather but we did make it out of Detroit that night. Other people were not as lucky.

ORF
BOS
Excellent 10.0

Flight attendant Gillian Awesome. Crew was fun and made my kids first flight great.

Fri, Apr 6
YWG
MDW
5h 15m
Tue, Apr 10
MDW
YWG
5h 44m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ORF
BOS
Excellent 10.0

Flight attendant Gillian Awesome. Crew was fun and made my kids first flight great.

OMA
MSP
Okay 4.4

Gate agent was fantastic! Her positive demeanor made for the delays and cancellations to not seem as much of an issue. She was extremely pleasant when explaining what was happening to flights, connections, etc. She was helpful when checking boarding passes to ensure that travellers were ok for their flight.

Again, last minute notification of delayed or cancelled flights made things somewhat worrisome. The late notification led to me missing my nest connection in Minneapolis, and having to sleep in the airport until the following morning in order to transfer my ticket to another flight leaving in the morning/afternoon/evening...very nerve-wracking to say the least.

MSP
LAS
Good 6.6

comfortable seats

delay delay delay

ORD
MSP
Okay 4.0

I needed to run real fast to the connection flight and gladly got there on time.

MSP
YEG
Good 7.6

Upon arriving in Minneapolis-St. Paul, it was a struggle to determine whether or not my bags had made it, whether or not I needed to collect them from baggage claim due to the cancellations/delays, and if I was even going to be able to transfer my ticket. Flight arrived late in the evening when most flights were basically complete for the day. Luckily, I happened upon a red-eye arrival, and spoke to an agent at that gate (Taj). Taj was without a doubt, THE BEST GATE AGENT I HAVE ENCOUNTERED IN MY 40+ YEARS OF TRAVELLING!! I explained my situation to him, and he immediately asked to see my travel info. He proceeded to get me on a flight much earlier than originally anticipated, upgraded me to Premium fare status, and did his best to re-route my luggage (which he informed me was still sitting in ATLANTA 18 hours after having left there...) - how does someone get on a flight, and their check-in get noted, but their luggage does not get put on said flight?? Things that make you go hmmmmm.... All that aside...I will be planning a trip to Minneapolis-St. Paul specifically to take a gift of appreciation to Taj! Well done on this end Delta - Taj is an excellent example of intelligent customer service.

Last minute notifications of delays/cancellations. Luggage was not placed on my original departing flight from Atlanta 18 HOURS EARLIER...not cool Delta. As a result, I did not receive my luggage for another 2 1/2 days .

Thu, Mar 29
YWG
MDW
5h 15m
Mon, Apr 2
MDW
YWG
3h 55m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
PHL
MSP
Mediocre 2.0

The flight itself was fine.

The flight was delayed and it set off a slew of connection problems.

ATL
OMA
Good 6.0

Check-in agent was very pleasant even through having to deal with a number of cancelled flights.

Flight was delayed shortly before it was scheduled for boarding, which resulted in further delays/cancellations along the journey. Earlier notification may have allowed me to remain in Atlanta a night or two longer with my family as opposed to having had to spend many additional hours sitting uncomfortably in an airport.

MSP
SFO
Good 7.0

Delayed take off and waited for the bridgr

MSP
LAS
Good 6.6

comfortable seats

delay delay delay

ORF
BOS
Excellent 10.0

Flight attendant Gillian Awesome. Crew was fun and made my kids first flight great.

Sat, Jan 20
YWG
MDW
9h 37m
Sun, Jan 21
MDW
YWG
6h 22m
Trip: 2 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
PHL
MSP
Mediocre 2.0

The flight itself was fine.

The flight was delayed and it set off a slew of connection problems.

MSP
LAS
Good 6.6

comfortable seats

delay delay delay

CUN
MSP
Okay 4.3

The Cancun airport provides a terrible experience for transferring between flights, especially if you need to change from the international terminal to a domestic terminal or vice-versa. There is no way to get between terminals inside security and the free shuttle is slow and overcrowded. Meanwhile, one is forced to run a gauntlet of taxi and shuttle drivers trying to get you to pay them exorbitant fees to drive you to your terminal. Once you finally arrive you discover that there is no dedicated baggage recheck for an international arrival. Just don't buy a ticket that transfers in CUN.

ATL
OMA
Good 6.0

Check-in agent was very pleasant even through having to deal with a number of cancelled flights.

Flight was delayed shortly before it was scheduled for boarding, which resulted in further delays/cancellations along the journey. Earlier notification may have allowed me to remain in Atlanta a night or two longer with my family as opposed to having had to spend many additional hours sitting uncomfortably in an airport.

MSP
YVR
Mediocre 2.0

I was rerouted.

No one would reissue me a ticket for the next flight. Delta and West Jet kept saying the other company should do this, and in the end no one did and I had to purchase another ticket.

Fri, May 18
YWG
MDW
5h 15m
Mon, May 21
MDW
YWG
3h 55m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
OMA
MSP
Okay 4.4

Gate agent was fantastic! Her positive demeanor made for the delays and cancellations to not seem as much of an issue. She was extremely pleasant when explaining what was happening to flights, connections, etc. She was helpful when checking boarding passes to ensure that travellers were ok for their flight.

Again, last minute notification of delayed or cancelled flights made things somewhat worrisome. The late notification led to me missing my nest connection in Minneapolis, and having to sleep in the airport until the following morning in order to transfer my ticket to another flight leaving in the morning/afternoon/evening...very nerve-wracking to say the least.

SFO
LAX
Good 7.6

Everyone was really nice and responsive.

Seats are a little older. Not as comfortable as other flights. But not bad.

MSP
LAS
Good 6.6

comfortable seats

delay delay delay

MSP
YVR
Mediocre 2.0

I was rerouted.

No one would reissue me a ticket for the next flight. Delta and West Jet kept saying the other company should do this, and in the end no one did and I had to purchase another ticket.

CUN
MSP
Okay 4.3

The Cancun airport provides a terrible experience for transferring between flights, especially if you need to change from the international terminal to a domestic terminal or vice-versa. There is no way to get between terminals inside security and the free shuttle is slow and overcrowded. Meanwhile, one is forced to run a gauntlet of taxi and shuttle drivers trying to get you to pay them exorbitant fees to drive you to your terminal. Once you finally arrive you discover that there is no dedicated baggage recheck for an international arrival. Just don't buy a ticket that transfers in CUN.

*
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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.

Winnipeg to Chicago Midway Flight Information

Flights Arrive in Chicago Midway
Flights Depart from Winnipeg
Flight Price $420
Distance 722 miles
Airlines Delta