Find Cheap Flights from Chicago Midway to Cancun (MDW - CUN)

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Good to Know

Average Price:
$479
(avg. price over the last 2 weeks)
Good Deal:
$406
or less (round trip)

When to Book Flights from Chicago Midway to Cancun

Flight prices as travel date approaches
-1 day
-2 days

Top tips for Finding a Cheap Flight

Looking for a cheap flight? 25% of our users found flights on this route for $405 or less.
The cheapest flight from Chicago Midway to Cancun was found 14 days before departure, on average.
Book at least 1 week before departure in order to get a below-average price.
Morning departure is around 1% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for Booking Chicago Midway to Cancun Flights

How long does a flight from Chicago Midway to Cancun take?
An average nonstop flight takes 5h 29m, covering a distance of 1434 miles.
How many flights are there between Chicago Midway and Cancun?
There are 44 (nonstop) flights between Chicago Midway and Cancun per week, averaging 6 per day.
Which airlines provide the cheapest flights from Chicago Midway to Cancun?
In the past 3 days, the cheapest round-trip tickets were found on Aeromexico ($302), Multiple Airlines ($329) and Volaris ($347).
Do I need a passport to fly between Chicago Midway and Cancun?
Yes.
Which airlines fly most frequently between Chicago Midway and Cancun?
Southwest (6 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Chicago Midway to Cancun?
For Chicago Midway to Cancun, Friday is the cheapest day to fly on average and Thursday is the most expensive. Flying from Cancun back to Chicago Midway, the best deals are generally found on Wednesday, with Sunday being the most expensive.

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

Airports
Origin
Chicago
$302
only
$302
Destination
Cancun
$302
only
$302
Fri, Apr 20
MDW
CUN
14h 38m
Mon, Apr 23
CUN
MDW
31h 32m
Trip: 4 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 5565 reviews
Overall
7.4
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
MEX
CUN
Mediocre 2.0

Nothing!!!!

A horrible flight!!! We arrived at 5:04pm then we sat on the tamarac for 40 minutes before they could find a gate for us!!!! What a horrible lack of management!’ Who runs this airport/airline!? At the end they moved us to completly different terminal!!! Had to find a new transportation to the hotel!!! Again, what a horrible display of management skills!!

MEX
GRU
Excellent 8.3

over booked flight

MEX
BOS
Excellent 10.0

we flew clase premier and really enjoyed it. there was cheese and wine to start, then a chicken breast with potatoes along with a courgette salad and then asparagus on the side. the movie selection was good, the seats were comfortable... we were very happy with it.

nothing

SMF
GDL
Excellent 10.0

Everything was as expected.

ORD
MEX
Mediocre 2.0

I never took the flight since Kayak’s blames me for not in putting the correct name of the passenger. Your policy on name change is ridiculous. I never input my name as the passenger. The ticket was for my aunt. Kayak has been the worst experience I have received.

Sun, Feb 25
MDW
CUN
15h 09m
Wed, Feb 28
CUN
MDW
7h 40m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Fri, Jun 15
MDW
CUN
9h 05m
Mon, Jun 18
CUN
MDW
14h 13m
Trip: 4 days
6.6GoodShow reviews
Overall 6.6 Good
Based on 496 reviews
Overall
7.1
Boarding
7.3
Comfort
6.7
Crew
7.6
Entertainment
5.2
Food
5.6
HMO
MEX
Good 7.0

The bad is the rules on the baggage

MID
MEX
Okay 5.0

Buying the extra space is worth it.

Volaris didn’t tell us what happened and didn’t tell us we were going to board late.

MEX
MID
Excellent 8.0

Quick and relatively cheap.

It was too cold.

MEX
JFK
Mediocre 2.0

Nothing.

Kiosks in Mexico City on the way back were closed in the middle of the day. There was no one to talk to or get my boarding pass. Horrible old planes with tiniest seating. Never again.

MEX
SAT
Excellent 8.0

Everything was ok.

Sat, Apr 14
MDW
CUN
8h 42m
Sun, Apr 15
CUN
MDW
15h 54m
Trip: 2 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 5565 reviews
Overall
7.4
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
GDL
LAX
Excellent 10.0

The staff was friendly and helpful. They gave us food which I was not expecting. They had an in-flight movie as well which was unexpected.

MEX
BOS
Excellent 10.0

we flew clase premier and really enjoyed it. there was cheese and wine to start, then a chicken breast with potatoes along with a courgette salad and then asparagus on the side. the movie selection was good, the seats were comfortable... we were very happy with it.

nothing

YVR
MEX
Excellent 8.6

The person in Aeromexico balcony didn't have training to attend clientes in the best way. She didn't know how to add miles to my number of fidelity and she told me that she can't change my seat to the aisle, because the sistem was not working and her english was very poor too... Very poor service.

TIJ
MEX
Good 7.3

Entertainiment system, nice footrest

No complaints

MEX
GRU
Excellent 8.3

over booked flight

Mon, Mar 5
MDW
CUN
6h 22m
Tue, Mar 6
CUN
MDW
6h 11m
Trip: 2 days
Overall 0.0 Poor
Based on 0 reviews
Mon, Apr 23
MDW
CUN
9h 24m
Tue, Apr 24
CUN
MDW
26h 10m
Trip: 2 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 5565 reviews
Overall
7.4
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
LAX
GDL
Excellent 9.6

How they offered food and snacks and drinks crew was friendly

Boarding took a bit long but other than that everything was perfect

CUN
MEX
Excellent 8.0

The crew

The front desk staff

GDL
LAX
Excellent 10.0

The staff was friendly and helpful. They gave us food which I was not expecting. They had an in-flight movie as well which was unexpected.

JFK
MEX
Mediocre 2.0

Terrible

Terrible

LAX
GDL
Excellent 10.0

Friendly staff.

Mon, Apr 2
MDW
CUN
6h 37m
Thu, Apr 12
CUN
MDW
8h 35m
Trip: 11 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Mar 27
MDW
CUN
7h 04m
Mon, Apr 2
CUN
MDW
18h 18m
Trip: 7 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 5565 reviews
Overall
7.4
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
TIJ
MEX
Good 7.3

Entertainiment system, nice footrest

No complaints

ORD
MEX
Mediocre 2.0

I never took the flight since Kayak’s blames me for not in putting the correct name of the passenger. Your policy on name change is ridiculous. I never input my name as the passenger. The ticket was for my aunt. Kayak has been the worst experience I have received.

MEX
CUN
Mediocre 2.0

Nothing!!!!

A horrible flight!!! We arrived at 5:04pm then we sat on the tamarac for 40 minutes before they could find a gate for us!!!! What a horrible lack of management!’ Who runs this airport/airline!? At the end they moved us to completly different terminal!!! Had to find a new transportation to the hotel!!! Again, what a horrible display of management skills!!

CUN
MEX
Excellent 8.0

The crew

The front desk staff

GDL
LAX
Excellent 10.0

The staff was friendly and helpful. They gave us food which I was not expecting. They had an in-flight movie as well which was unexpected.

Tue, Apr 3
MDW
CUN
6h 58m
Thu, Apr 12
CUN
MDW
8h 35m
Trip: 10 days
Overall 0.0 Poor
Based on 0 reviews
Sun, Jul 29
MDW
CUN
11h 47m
Fri, Aug 3
CUN
MDW
15h 51m
Trip: 6 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 5565 reviews
Overall
7.4
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
LAX
GDL
Excellent 10.0

Friendly staff.

SMF
GDL
Excellent 10.0

Everything was as expected.

GDL
LAX
Excellent 10.0

The staff was friendly and helpful. They gave us food which I was not expecting. They had an in-flight movie as well which was unexpected.

LAX
GDL
Excellent 9.6

How they offered food and snacks and drinks crew was friendly

Boarding took a bit long but other than that everything was perfect

MEX
GRU
Excellent 8.3

over booked flight

Thu, Apr 19
MDW
CUN
13h 35m
Wed, Apr 25
CUN
MDW
15h 54m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Tue, May 22
MDW
CUN
9h 30m
Tue, May 29
CUN
MDW
7h 53m
Trip: 8 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 5565 reviews
Overall
7.4
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
MEX
GRU
Excellent 8.3

over booked flight

YVR
MEX
Excellent 8.6

The person in Aeromexico balcony didn't have training to attend clientes in the best way. She didn't know how to add miles to my number of fidelity and she told me that she can't change my seat to the aisle, because the sistem was not working and her english was very poor too... Very poor service.

CUN
MEX
Excellent 8.0

The crew

The front desk staff

ORD
MEX
Mediocre 2.0

I never took the flight since Kayak’s blames me for not in putting the correct name of the passenger. Your policy on name change is ridiculous. I never input my name as the passenger. The ticket was for my aunt. Kayak has been the worst experience I have received.

JFK
MEX
Mediocre 2.0

Terrible

Terrible

Mon, Mar 12
MDW
CUN
6h 22m
Tue, Mar 13
CUN
MDW
6h 09m
Trip: 2 days
Overall 0.0 Poor
Based on 0 reviews
Wed, May 23
MDW
CUN
8h 02m
Tue, May 29
CUN
MDW
7h 53m
Trip: 7 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 5565 reviews
Overall
7.4
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
YVR
MEX
Excellent 8.6

The person in Aeromexico balcony didn't have training to attend clientes in the best way. She didn't know how to add miles to my number of fidelity and she told me that she can't change my seat to the aisle, because the sistem was not working and her english was very poor too... Very poor service.

CUN
MEX
Excellent 8.0

The crew

The front desk staff

JFK
MEX
Mediocre 2.0

Terrible

Terrible

GDL
LAX
Excellent 10.0

The staff was friendly and helpful. They gave us food which I was not expecting. They had an in-flight movie as well which was unexpected.

LAX
GDL
Excellent 10.0

Friendly staff.

Sun, Feb 25
MDW
CUN
15h 09m
Fri, Mar 2
CUN
MDW
9h 39m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Thu, May 24
MDW
CUN
14h 41m
Sun, May 27
CUN
MDW
17h 35m
Trip: 4 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 5565 reviews
Overall
7.4
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
MEX
CUN
Mediocre 2.0

Nothing!!!!

A horrible flight!!! We arrived at 5:04pm then we sat on the tamarac for 40 minutes before they could find a gate for us!!!! What a horrible lack of management!’ Who runs this airport/airline!? At the end they moved us to completly different terminal!!! Had to find a new transportation to the hotel!!! Again, what a horrible display of management skills!!

CUN
MEX
Excellent 8.0

The crew

The front desk staff

GDL
LAX
Excellent 10.0

The staff was friendly and helpful. They gave us food which I was not expecting. They had an in-flight movie as well which was unexpected.

LAX
GDL
Excellent 10.0

Friendly staff.

ORD
MEX
Mediocre 2.0

I never took the flight since Kayak’s blames me for not in putting the correct name of the passenger. Your policy on name change is ridiculous. I never input my name as the passenger. The ticket was for my aunt. Kayak has been the worst experience I have received.

Sat, Apr 28
MDW
CUN
5h 29m
Thu, May 3
CUN
MDW
14h 13m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Sun, Jul 1
MDW
CUN
13h 40m
Mon, Jul 9
CUN
MDW
15h 55m
Trip: 9 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 5565 reviews
Overall
7.4
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
MEX
GRU
Excellent 8.3

over booked flight

JFK
MEX
Mediocre 2.0

Terrible

Terrible

GDL
LAX
Excellent 10.0

The staff was friendly and helpful. They gave us food which I was not expecting. They had an in-flight movie as well which was unexpected.

YVR
MEX
Excellent 8.6

The person in Aeromexico balcony didn't have training to attend clientes in the best way. She didn't know how to add miles to my number of fidelity and she told me that she can't change my seat to the aisle, because the sistem was not working and her english was very poor too... Very poor service.

MEX
BOS
Excellent 10.0

we flew clase premier and really enjoyed it. there was cheese and wine to start, then a chicken breast with potatoes along with a courgette salad and then asparagus on the side. the movie selection was good, the seats were comfortable... we were very happy with it.

nothing

Fri, Jul 20
MDW
CUN
9h 37m
Tue, Jul 24
CUN
MDW
8h 25m
Trip: 5 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 5565 reviews
Overall
7.4
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
MEX
GRU
Excellent 8.3

over booked flight

ORD
MEX
Mediocre 2.0

I never took the flight since Kayak’s blames me for not in putting the correct name of the passenger. Your policy on name change is ridiculous. I never input my name as the passenger. The ticket was for my aunt. Kayak has been the worst experience I have received.

LAX
GDL
Excellent 10.0

Friendly staff.

TIJ
MEX
Good 7.3

Entertainiment system, nice footrest

No complaints

JFK
MEX
Mediocre 2.0

Terrible

Terrible

Thu, Apr 26
MDW
CUN
6h 20m
Thu, May 3
CUN
MDW
14h 13m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Show more results

Chicago Midway to Cancun Flight Information

Flights Arrive in Cancun
Flights Depart from Chicago Midway
Flight Price $302
Distance 1434 miles
Airlines Aeromexico, Volaris
*
Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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.