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

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FAQs for Booking Cancun to Chicago Midway Flights

How long does a flight from Cancun to Chicago Midway take?
An average nonstop flight takes 7h 12m, covering a distance of 1434 miles.
How many flights are there between Cancun and Chicago Midway?
There are 47 (nonstop) flights between Cancun and Chicago Midway per week, averaging 6 per day.
Which airlines provide the cheapest flights from Cancun to Chicago Midway?
In the past 3 days, the cheapest round-trip tickets were found on Delta ($245) and Aeromexico ($254)
Do I need a passport to fly between Cancun and Chicago Midway?
Yes.
Which airlines fly most frequently between Cancun and Chicago Midway?
Southwest (6 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Cancun to Chicago Midway?
For Cancun to Chicago Midway, Wednesday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Chicago Midway back to Cancun, the best deals are generally found on Friday, with Thursday being the most expensive.

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

Airports
Origin
Cancun
$245
only
$245
Destination
Chicago
$245
only
$245
Wed, Apr 18
CUN
MDW
8h 31m
Mon, Apr 30
MDW
CUN
6h 45m
Trip: 13 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
PVR
MSP
Good 7.3

They have few movies selection that was good

I like being in a big space faster. And clean good service I

FLL
DTW
Excellent 10.0

I like service

GDL
ATL
Excellent 9.6

Expensive food

DEN
JFK
Good 6.3

Comfortable seats. Good entertainment

Going to Denver was delayed and now return trip delayed We were give 3 separate reasons. Poor communication. Just telling me a flight will be delayed is not communication. Lack of a free snack was disappointing. May have to rethink flying Delta next time.

EWR
DTW
Mediocre 3.3

I've always wanted to go to all five Manhattan boroughs in one day. Thanks to Delta, that happened.

The plane broke down as we were about to take off. Delta rebooked everyone on to new flights because it was pretty obvious that plane was not going to be fixed in time. The crew did their best given the situation. The situation was absolute bs though - we had to take a cab to JFK for our new flight and do the whole security thing again and all that annoying stuff. Thanks for wasting 8 hours of my life, Delta.

Tue, Apr 24
CUN
MDW
10h 34m
Mon, Apr 30
MDW
CUN
9h 34m
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
MEX
GRU
Excellent 8.3

over booked flight

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

LAX
GDL
Excellent 10.0

Friendly staff.

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!!

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.

Thu, Apr 26
CUN
MDW
8h 31m
Mon, Apr 30
MDW
CUN
6h 58m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
EWR
Excellent 8.6

No LCD screen for entertainment.

BJX
LAX
Excellent 8.0

I liked the check-in kiosk, but only because I had no bags to check. I liked being able to choose my own seat. I liked that the flight was uneventful. I liked the staff at all stages, they were friendly and helpful.

They made me shove my purse into my knapsack to fit within their two bag policy. That's a first for me. My Delta flight did not do that.

PIT
ATL
Excellent 10.0

I have always known of airlines to offer preboarding to those military members in uniform or on official orders. Delta took it one step further and allows prior service members to board also.

EWR
DTW
Mediocre 3.3

I've always wanted to go to all five Manhattan boroughs in one day. Thanks to Delta, that happened.

The plane broke down as we were about to take off. Delta rebooked everyone on to new flights because it was pretty obvious that plane was not going to be fixed in time. The crew did their best given the situation. The situation was absolute bs though - we had to take a cab to JFK for our new flight and do the whole security thing again and all that annoying stuff. Thanks for wasting 8 hours of my life, Delta.

JFK
CDG
Excellent 10.0

The food and the service

Wed, Apr 25
CUN
MDW
8h 31m
Mon, Apr 30
MDW
CUN
6h 58m
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
CUN
MEX
Excellent 8.0

The crew

The front desk staff

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!!

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

Wed, Apr 11
CUN
MDW
8h 31m
Wed, Apr 25
MDW
CUN
8h 42m
Trip: 15 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
PIT
ATL
Excellent 10.0

I have always known of airlines to offer preboarding to those military members in uniform or on official orders. Delta took it one step further and allows prior service members to board also.

EWR
DTW
Mediocre 3.3

I've always wanted to go to all five Manhattan boroughs in one day. Thanks to Delta, that happened.

The plane broke down as we were about to take off. Delta rebooked everyone on to new flights because it was pretty obvious that plane was not going to be fixed in time. The crew did their best given the situation. The situation was absolute bs though - we had to take a cab to JFK for our new flight and do the whole security thing again and all that annoying stuff. Thanks for wasting 8 hours of my life, Delta.

BJX
LAX
Excellent 8.0

I liked the check-in kiosk, but only because I had no bags to check. I liked being able to choose my own seat. I liked that the flight was uneventful. I liked the staff at all stages, they were friendly and helpful.

They made me shove my purse into my knapsack to fit within their two bag policy. That's a first for me. My Delta flight did not do that.

SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

PVR
MSP
Good 7.3

They have few movies selection that was good

I like being in a big space faster. And clean good service I

Thu, Apr 26
CUN
MDW
8h 35m
Sun, Apr 29
MDW
CUN
9h 41m
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
GRU
Excellent 8.3

over booked flight

SMF
GDL
Excellent 10.0

Everything was as expected.

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

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.

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
CUN
MDW
7h 12m
Mon, Apr 30
MDW
CUN
13h 35m
Trip: 3 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

TIJ
MEX
Good 7.3

Entertainiment system, nice footrest

No complaints

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.

LAX
GDL
Excellent 10.0

Friendly staff.

CUN
MEX
Excellent 8.0

The crew

The front desk staff

Sat, Mar 10
CUN
MDW
12h 48m
Thu, Mar 15
MDW
CUN
13h 40m
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
LAX
GDL
Excellent 10.0

Friendly staff.

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

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

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!!

Sun, Apr 15
CUN
MDW
10h 34m
Sun, Apr 29
MDW
CUN
5h 32m
Trip: 15 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
GDL
ATL
Excellent 9.6

Expensive food

BOS
LGA
Mediocre 2.0

We were in the plane for 3 hours before we could depart. No one offered us a drink or snack.

PVR
MSP
Good 7.3

They have few movies selection that was good

I like being in a big space faster. And clean good service I

FLL
DTW
Excellent 10.0

I like service

DEN
JFK
Good 6.3

Comfortable seats. Good entertainment

Going to Denver was delayed and now return trip delayed We were give 3 separate reasons. Poor communication. Just telling me a flight will be delayed is not communication. Lack of a free snack was disappointing. May have to rethink flying Delta next time.

Tue, Mar 27
CUN
MDW
13h 57m
Sun, Apr 1
MDW
CUN
9h 25m
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
JFK
MEX
Mediocre 2.0

Terrible

Terrible

LAX
GDL
Excellent 10.0

Friendly staff.

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!!

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

Mon, Apr 16
CUN
MDW
10h 24m
Mon, Apr 30
MDW
CUN
8h 00m
Trip: 15 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
JFK
CDG
Excellent 10.0

The food and the service

BOS
LGA
Mediocre 2.0

We were in the plane for 3 hours before we could depart. No one offered us a drink or snack.

PIT
ATL
Excellent 10.0

I have always known of airlines to offer preboarding to those military members in uniform or on official orders. Delta took it one step further and allows prior service members to board also.

PVR
MSP
Good 7.3

They have few movies selection that was good

I like being in a big space faster. And clean good service I

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

Wed, Mar 28
CUN
MDW
8h 39m
Wed, Apr 4
MDW
CUN
8h 42m
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
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

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 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

SMF
GDL
Excellent 10.0

Everything was as expected.

Tue, Apr 17
CUN
MDW
8h 09m
Mon, Apr 30
MDW
CUN
5h 35m
Trip: 14 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
BOS
LGA
Mediocre 2.0

We were in the plane for 3 hours before we could depart. No one offered us a drink or snack.

PIT
ATL
Excellent 10.0

I have always known of airlines to offer preboarding to those military members in uniform or on official orders. Delta took it one step further and allows prior service members to board also.

FLL
DTW
Excellent 10.0

I like service

PVR
MSP
Good 7.3

They have few movies selection that was good

I like being in a big space faster. And clean good service I

JFK
CDG
Excellent 10.0

The food and the service

Wed, Apr 11
CUN
MDW
8h 31m
Sun, Apr 15
MDW
CUN
6h 45m
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

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.

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.

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

Wed, Apr 18
CUN
MDW
7h 25m
Sun, Apr 29
MDW
CUN
6h 58m
Trip: 12 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
GDL
ATL
Excellent 9.6

Expensive food

DEN
JFK
Good 6.3

Comfortable seats. Good entertainment

Going to Denver was delayed and now return trip delayed We were give 3 separate reasons. Poor communication. Just telling me a flight will be delayed is not communication. Lack of a free snack was disappointing. May have to rethink flying Delta next time.

ATL
EWR
Excellent 8.6

No LCD screen for entertainment.

FLL
DTW
Excellent 10.0

I like service

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

Thu, Apr 19
CUN
MDW
8h 31m
Mon, Apr 30
MDW
CUN
6h 58m
Trip: 12 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
BOS
LGA
Mediocre 2.0

We were in the plane for 3 hours before we could depart. No one offered us a drink or snack.

PVR
MSP
Good 7.3

They have few movies selection that was good

I like being in a big space faster. And clean good service I

DEN
JFK
Good 6.3

Comfortable seats. Good entertainment

Going to Denver was delayed and now return trip delayed We were give 3 separate reasons. Poor communication. Just telling me a flight will be delayed is not communication. Lack of a free snack was disappointing. May have to rethink flying Delta next time.

SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

GDL
ATL
Excellent 9.6

Expensive food

Thu, Apr 26
CUN
MDW
8h 31m
Mon, May 7
MDW
CUN
6h 32m
Trip: 12 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!!

JFK
MEX
Mediocre 2.0

Terrible

Terrible

TIJ
MEX
Good 7.3

Entertainiment system, nice footrest

No complaints

SMF
GDL
Excellent 10.0

Everything was as expected.

MEX
GRU
Excellent 8.3

over booked flight

Fri, Apr 20
CUN
MDW
10h 34m
Mon, Apr 30
MDW
CUN
5h 35m
Trip: 11 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
EWR
DTW
Mediocre 3.3

I've always wanted to go to all five Manhattan boroughs in one day. Thanks to Delta, that happened.

The plane broke down as we were about to take off. Delta rebooked everyone on to new flights because it was pretty obvious that plane was not going to be fixed in time. The crew did their best given the situation. The situation was absolute bs though - we had to take a cab to JFK for our new flight and do the whole security thing again and all that annoying stuff. Thanks for wasting 8 hours of my life, Delta.

PVR
MSP
Good 7.3

They have few movies selection that was good

I like being in a big space faster. And clean good service I

SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

GDL
ATL
Excellent 9.6

Expensive food

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

Tue, Apr 24
CUN
MDW
8h 31m
Tue, May 1
MDW
CUN
9h 37m
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
TIJ
MEX
Good 7.3

Entertainiment system, nice footrest

No complaints

CUN
MEX
Excellent 8.0

The crew

The front desk staff

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.

JFK
MEX
Mediocre 2.0

Terrible

Terrible

Sat, Apr 21
CUN
MDW
10h 32m
Mon, Apr 30
MDW
CUN
13h 35m
Trip: 10 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
GDL
ATL
Excellent 9.6

Expensive food

ATL
EWR
Excellent 8.6

No LCD screen for entertainment.

PVR
MSP
Good 7.3

They have few movies selection that was good

I like being in a big space faster. And clean good service I

EWR
DTW
Mediocre 3.3

I've always wanted to go to all five Manhattan boroughs in one day. Thanks to Delta, that happened.

The plane broke down as we were about to take off. Delta rebooked everyone on to new flights because it was pretty obvious that plane was not going to be fixed in time. The crew did their best given the situation. The situation was absolute bs though - we had to take a cab to JFK for our new flight and do the whole security thing again and all that annoying stuff. Thanks for wasting 8 hours of my life, Delta.

PIT
ATL
Excellent 10.0

I have always known of airlines to offer preboarding to those military members in uniform or on official orders. Delta took it one step further and allows prior service members to board also.

Cancun to Chicago Midway Flight Information

Flights Arrive in Chicago Midway
Flights Depart from Cancun
Flight Price $245
Distance 1434 miles
Airlines Delta, Aeromexico
*
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Here's why:

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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.