Find Cheap Flights from Chicago to Cancun (CHI - CUN)

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Good to Know

Low Season:
January
Best time to beat the crowds
2%
expected price decrease
High Season:
December
Most popular time to fly
2%
expected price increase
Average Price:
$433
(avg. price over the last 2 weeks)
Good Deal:
$313
or less (round trip)

When to Book Flights from Chicago to Cancun

Average price per month
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 $312 or less.
The cheapest flight from Chicago to Cancun was found 1 day before departure, on average.
Book at least 1 week before departure in order to get a below-average price.
Morning departure is around 36% more expensive 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 to Cancun Flights

How long does a flight from Chicago to Cancun take?
An average nonstop flight takes 3h 30m, covering a distance of 1441 miles.
How many flights are there between Chicago and Cancun?
There are 142 (nonstop) flights between Chicago and Cancun per week, averaging 18 per day.
Which airlines provide the cheapest flights from Chicago to Cancun?
In the past 3 days, the cheapest round-trip tickets were found on Aeromexico ($177), Frontier ($209) and Multiple Airlines ($213).
Do I need a passport to fly between Chicago and Cancun?
Yes.
Which airlines fly most frequently between Chicago and Cancun?
United (7 times daily), Southwest (6 times daily), American Airlines (2 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Chicago to Cancun?
For Chicago to Cancun, Friday is the cheapest day to fly on average and Monday is the most expensive. Flying from Cancun back to Chicago, the best deals are generally found on Wednesday, with Monday being the most expensive.

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

Airports
Origin
Chicago
$177
only
$177
$382
only
$382
Destination
Cancun
$177
only
$177
Fri, May 18
ORD
CUN
12h 52m
Tue, May 22
CUN
ORD
13h 24m
Trip: 5 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 5467 reviews
Overall
7.4
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
UIO
MEX
Okay 4.3

El vuelo es helado. Es tarde en la noche y sin mantas!

LAX
MEX
Okay 4.0

Free food and drinks. A lot of movies to choose from

My golf bag for then doesn’t count as a normal bag, so they charge $150 per trip. Absolutely robbery. As well, internet on the plane is well over $100. Again, robbery.

GDL
MEX
Okay 5.3

2 problems - there wasn't enough time scheduled between my connection in mexico city when i was coming from florida to get through customs so I missed my connection and there wasn't any aeromexico staff around to assist. - the personal screens in each seat on the last flight from Mx city to Guadalajara couldn't be shut off and I was forced to have commercials being flashed very close in front of my face when I wanted to relax.

2 problems - there wasn't enough time scheduled between my connection in mexico city when i was coming from florida to get through customs so I missed my connection and there wasn't any aeromexico staff around to assist. - the personal screens in each seat on the last flight from Mx city to Guadalajara couldn't be shut off and I was forced to have commercials being flashed very close in front of my face when I wanted to relax.

MEX
MIA
Okay 5.3

2 problems - there wasn't enough time scheduled between my connection in mexico city when i was coming from florida to get through customs so I missed my connection and there wasn't any aeromexico staff around to assist. - the personal screens in each seat on the last flight from Mx city to Guadalajara couldn't be shut off and I was forced to have commercials being flashed very close in front of my face when I wanted to relax.

2 problems - there wasn't enough time scheduled between my connection in mexico city when i was coming from florida to get through customs so I missed my connection and there wasn't any aeromexico staff around to assist. - the personal screens in each seat on the last flight from Mx city to Guadalajara couldn't be shut off and I was forced to have commercials being flashed very close in front of my face when I wanted to relax.

MTY
ICN
Good 6.0

Not much

Korean translation sucked. Also food was bad.

Tue, Mar 20
ORD
CUN
3h 53m
Wed, Mar 21
CUN
ORD
4h 04m
Trip: 2 days
8.0ExcellentShow reviews
Overall 8.0 Excellent
Based on 1 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
SLC
DEN
Mediocre 3.0

We left on time and arrived early

All of the extra fees. Absolutely ridiculous. It would have been less expensive to take another airline.

MSP
TPA
Okay 4.6

Smooth flight. On time.

Very tight seating. Seat trays were the size of an iPhone. Seats didn’t recline. 30 rows with 6 per row. Had to pay for pop, water, and coffee.

BUF
MCO
Good 7.3

Flight was great. Checkin etc was great

DEN
SFO
Mediocre 2.0

The crew was rude to the passengers. They charge form 9$ to 40$ for seat selection. Charge for a Carry on bag (anything that doesn't fit under your seat). The flights had maintenance issue, hence delayed. I will absolutely avoid traveling with frontier in the future.

BUF
MCO
Mediocre 3.3

The service was Ok, but our flight was 4 hours delayed and it wasn't mechanical or weather related delay, the airline made a scheduling error, we almost missed our car rental and we didn't get to our destination til really late at night when it should been there in the daytime. Overall, won't fly with them again

Sat, Mar 17
ORD
CUN
3h 50m
Wed, Mar 21
CUN
ORD
4h 04m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Feb 24
ORD
CUN
3h 40m
Thu, Mar 1
CUN
ORD
4h 05m
Trip: 6 days
9.3ExcellentShow reviews
Overall 9.3 Excellent
Based on 2 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.7
ORD
CLT
Mediocre 3.0

Three hours delay. I paid for a upgrade to first class. But because of the flight change i didn't get to keep my upgrade and I had to beg for a refund. I have had two trips in the past 5 days and all flights have been anywhere from 1 to 3 hours late. Worst experience with AA I have had in a long time.

ORD
CUN
Excellent 8.6

No entertainment. There wasn't even a drop down screen for a movie.

LAS
DFW
Excellent 8.0

Flight was punctual and service was good.

Gate change

DFW
FLL
Excellent 8.0

No issues at all

N/A

LHR
ORD
Mediocre 2.0

Nothing really. I will never book from Kayak ever

Everything

Sat, Apr 7
ORD
CUN
3h 40m
Thu, Apr 19
CUN
ORD
3h 50m
Trip: 13 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 23 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.4
ORD
CUN
Good 6.3

Been on lots of planes super rough takeoff turbulence was awful landing was not good

ORD
CUN
Mediocre 2.0

Flight was delayed for 4 hours due to airplane maintenance

GRR
IAH
Good 6.0

Pay for food, cold on plane entire time, everyone bundled up in blankets, jackets but staff friendly

IAH
CUN
Mediocre 2.0

poor service, rude flight attendants, no leg room, dirty plane...

poor service, rude flight attendants, no leg room, dirty plane...

ORD
CUN
Excellent 8.0

Early arrival

No free snacks

Tue, Feb 27
ORD
CUN
3h 30m
Thu, Mar 8
CUN
ORD
3h 48m
Trip: 10 days
4.3OkayShow reviews
Overall 4.3 Okay
Based on 1 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
MCO
ORD
Mediocre 3.6

Family of 5 of infant and toddler did not sit together.

ORD
CUN
Okay 4.3

Not that many passengers so many of us got our own row! All the extra fees though? Just fly on a nicer airline, cost ends up being the same with better service.

Crew was loud and ubnoxious while we waited to board. On the unprofessional side. Flight attendants were going on about their social lives and my kids didn’t need to hear all that adult stuff. Fees?! Oh smack. Get ready! Take lots of extra $$

BOS
MCO
Excellent 10.0

Everything

MYR
BOS
Good 6.5

Ticket price

Baggage fees are nearly double the cost of the ticket

IAH
SAN
Okay 5.5

Seats were awful. My shoulders were in so much pain after but I guess that's what you have to expect with Spirit

Thu, Jun 21
ORD
CUN
8h 21m
Mon, Jun 25
CUN
ORD
12h 48m
Trip: 5 days
6.6GoodShow reviews
Overall 6.6 Good
Based on 486 reviews
Overall
7.2
Boarding
7.3
Comfort
6.8
Crew
7.6
Entertainment
5.2
Food
5.6
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.

HMO
MEX
Good 7.0

The bad is the rules on the baggage

GDL
SJC
Okay 4.0

Charge way too much. Charged to pick a seat when doing check in from the app. Only reason doing check in from app was so I wouldn’t get charged for getting boarding pass at desk.

GDL
PDX
Okay 4.0

The direct flight and on time

Got no service from the staff called them over and over they would never come back to me after they said they would be right back

MEX
MID
Excellent 8.0

Quick and relatively cheap.

It was too cold.

Fri, May 11
ORD
CUN
8h 49m
Mon, May 14
CUN
ORD
13h 24m
Trip: 4 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 5467 reviews
Overall
7.4
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
MEX
BOG
Excellent 9.6

On board service, entertainment and food was a nice surprise. Wine and beer offered free of charge with the meal, great movie selection without charge as well and very helpful crew during the boarding process. Seats in economy had plenty of leg room and space on the sides.

Food was good and better than my experience with other airlines but still not as good as it use to be a few years ago.

SFO
MEX
Excellent 10.0

LAX
MEX
Okay 4.0

Free food and drinks. A lot of movies to choose from

My golf bag for then doesn’t count as a normal bag, so they charge $150 per trip. Absolutely robbery. As well, internet on the plane is well over $100. Again, robbery.

MEX
PDX
Excellent 9.3

Entertainment, crew, personal USB charger

no wine (not even for purchase)

MEX
EZE
Excellent 8.6

Great experience overall on this flight, only problem was that my lie-flat seat was broken and would only recline. Good food, great crew. Staff at Aeromexico Premier Salon Lounge were OUTSTANDING! Food could have more assortment, but was better than most lounges in the USA.

lie-flat seat was broken and would only recline, so didn't really get what I paid for. I wasn't the only person with the problem, as 2 other seats were the same. MEX airport desperate need renovation. It looks like something from the 60's that hasn't been maintained well. Not up to standard for a country's Capital City.

Mon, Apr 2
MDW
CUN
6h 37m
Wed, Apr 11
CUN
MDW
6h 23m
Trip: 10 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16027 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
BOS
ATL
Okay 4.0

Comfort Plus allowed us to board early, useful USB ports.

DTW
YOW
Excellent 9.3

Please see above. Sherry was amazing

Plane was small and older but it was a short flight

ATL
MEX
Excellent 10.0

Flight was on time, crew was friendly, plane was clean, and boarding was painless and efficient. Food was served which was a huge plus. I appreciate having a choice of almonds for a snack.

ECP
ATL
Excellent 9.6

We have been on 6 flights over the last 8 days, all with Delta and we have already started telling people how wonderful the service was. Sherry on this last flight was amazing, working so hard all by herself as our flight attendant. We were very impressed. And the pilots all came out to say goodbye and thank you. All very nice...esp for me who needed some wheelchair assistance. We will certainly fly with you again in the future.

Smaller plane but ok for short flight

GDL
ATL
Excellent 9.0

Staff was great!

No TV for movies.

Sat, Mar 17
ORD
CUN
3h 50m
Wed, Mar 21
CUN
ORD
4h 04m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Mon, Mar 19
ORD
CUN
3h 53m
Wed, Mar 21
CUN
ORD
4h 04m
Trip: 3 days
8.0ExcellentShow reviews
Overall 8.0 Excellent
Based on 1 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
MSP
TPA
Okay 4.6

Smooth flight. On time.

Very tight seating. Seat trays were the size of an iPhone. Seats didn’t recline. 30 rows with 6 per row. Had to pay for pop, water, and coffee.

SLC
DEN
Mediocre 2.0

It was cancelled d

DEN
BNA
Okay 5.6

I've had a number of enjoyable Frontier flights - the last two from DEN to BNA specifically haven't been among those.

In my most recent trip, we start with an announcement that the AC isn't working so we are in for a hot and stuffy flight. Great - what happens next - a kid two rows up from me pukes. Basically clockwork. The crew did as much as they could for the poor kid but there seems to be a consistent trend of maintenance issues or issues being late in my more recent flights with them.

MIA
BUF
Okay 4.0

Had the AC cranked. Asked for a blanket and the attendant laughed like airplanes never carry those.

CLT
TTN
Mediocre 2.6

Frontier's flight from Charlotte to Trenton was canceled due to equipment problems. Frontier gave us a $10 meal voucher, rebooked us on another flight, and gave us a voucher for a future flight.

The flight was scheduled to depart at 10 am but we had to wait till 2 pm before the flight was canceled. The rebooked flight took us to Newark. We then had to drive to Trenton to pick up our car.

Tue, Apr 10
ORD
CUN
3h 40m
Thu, Apr 19
CUN
ORD
3h 50m
Trip: 10 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 23 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.4
ORD
CUN
Good 6.3

Been on lots of planes super rough takeoff turbulence was awful landing was not good

ORD
CUN
Mediocre 2.0

Because we missed our connecting flight with United, we had to fly American from Dallas to Cancun.

ORD
CUN
Excellent 8.6

Comfort

No compleings

IAH
CUN
Mediocre 2.0

poor service, rude flight attendants, no leg room, dirty plane...

poor service, rude flight attendants, no leg room, dirty plane...

ORD
CUN
Excellent 10.0

Legroom coffee and snacks

Nothing

Tue, May 15
ORD
CUN
3h 35m
Wed, May 16
CUN
ORD
4h 00m
Trip: 2 days
9.3ExcellentShow reviews
Overall 9.3 Excellent
Based on 2 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.7
LAS
DFW
Excellent 8.0

Flight was punctual and service was good.

Gate change

DFW
FLL
Excellent 8.0

No issues at all

N/A

CLT
LGA
Excellent 10.0

Ability to upgrade to first class

Security taking forever

CLT
ILM
Mediocre 3.0

Three hours delay. I paid for a upgrade to first class. But because of the flight change i didn't get to keep my upgrade and I had to beg for a refund. I have had two trips in the past 5 days and all flights have been anywhere from 1 to 3 hours late. Worst experience with AA I have had in a long time.

ORD
CUN
Excellent 8.6

No entertainment. There wasn't even a drop down screen for a movie.

Tue, Feb 27
ORD
CUN
3h 30m
Thu, Mar 8
CUN
ORD
3h 48m
Trip: 10 days
4.3OkayShow reviews
Overall 4.3 Okay
Based on 1 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
LAS
SEA
Okay 4.6

It didn’t crash. Flight crew was great.

Delayed. Hidden fees. Uncomfortable. Sucky.

ATL
DFW
Good 7.3

I didnt have food or entertainment on the flight & yet that's not an option in this survey

give your survey a does not apply option to questions

IAH
SAN
Okay 5.5

Seats were awful. My shoulders were in so much pain after but I guess that's what you have to expect with Spirit

ORD
CUN
Okay 4.3

Not that many passengers so many of us got our own row! All the extra fees though? Just fly on a nicer airline, cost ends up being the same with better service.

Crew was loud and ubnoxious while we waited to board. On the unprofessional side. Flight attendants were going on about their social lives and my kids didn’t need to hear all that adult stuff. Fees?! Oh smack. Get ready! Take lots of extra $$

BOS
MCO
Excellent 10.0

Everything

Tue, May 1
ORD
CUN
3h 40m
Thu, May 10
CUN
ORD
3h 50m
Trip: 10 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 23 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.4
SFO
SNA
Okay 5.0

Cold, not enough space for carry on

ORD
CUN
Good 6.0

I made it to Cancun.

When I got to the gate in Chicago I asked if my seat could be moved next to my friend. The attendant said she would only be able to move me closer and the issued another ticket to me. It ended up being a different persons name from mine. I was afraid I wouldn't be able to board because big her mistake.

ORD
CUN
Excellent 8.3

Almost like normal seats, almost like normal flights. Ontime, helpful, professional, & courteous crew.

They don't recline.

GRR
IAH
Good 6.0

Pay for food, cold on plane entire time, everyone bundled up in blankets, jackets but staff friendly

ORD
CUN
Good 6.3

Been on lots of planes super rough takeoff turbulence was awful landing was not good

Fri, Feb 23
ORD
CUN
3h 50m
Thu, Mar 1
CUN
ORD
4h 05m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Fri, Feb 23
ORD
CUN
3h 30m
Sat, Mar 3
CUN
ORD
3h 48m
Trip: 9 days
4.3OkayShow reviews
Overall 4.3 Okay
Based on 1 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
LAX
IAH
Mediocre 2.6

Price is fair but the 50 pound regulation Should be enforced not 40 pounds

They lost my luggage and need my gear to work !!!!

BOS
MCO
Excellent 10.0

Everything

MYR
BOS
Good 6.5

Ticket price

Baggage fees are nearly double the cost of the ticket

MCO
ORD
Mediocre 3.6

Family of 5 of infant and toddler did not sit together.

ORD
CUN
Okay 4.3

Not that many passengers so many of us got our own row! All the extra fees though? Just fly on a nicer airline, cost ends up being the same with better service.

Crew was loud and ubnoxious while we waited to board. On the unprofessional side. Flight attendants were going on about their social lives and my kids didn’t need to hear all that adult stuff. Fees?! Oh smack. Get ready! Take lots of extra $$

Tue, Apr 3
ORD
CUN
14h 10m
Wed, Apr 11
CUN
ORD
11h 02m
Trip: 9 days
9.3ExcellentShow reviews
Overall 9.3 Excellent
Based on 2 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.7
LHR
ORD
Mediocre 2.0

Nothing really. I will never book from Kayak ever

Everything

SJU
MIA
Excellent 9.3

New onboard entertainment

DFW
FLL
Excellent 8.0

No issues at all

N/A

ORD
CLT
Mediocre 3.0

Three hours delay. I paid for a upgrade to first class. But because of the flight change i didn't get to keep my upgrade and I had to beg for a refund. I have had two trips in the past 5 days and all flights have been anywhere from 1 to 3 hours late. Worst experience with AA I have had in a long time.

CLT
ILM
Mediocre 3.0

Three hours delay. I paid for a upgrade to first class. But because of the flight change i didn't get to keep my upgrade and I had to beg for a refund. I have had two trips in the past 5 days and all flights have been anywhere from 1 to 3 hours late. Worst experience with AA I have had in a long time.

Sat, Mar 17
ORD
CUN
3h 50m
Thu, Mar 22
CUN
ORD
8h 30m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Feb 24
ORD
CUN
3h 30m
Fri, Mar 2
CUN
ORD
3h 48m
Trip: 7 days
4.3OkayShow reviews
Overall 4.3 Okay
Based on 1 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
MCO
ORD
Mediocre 3.6

Family of 5 of infant and toddler did not sit together.

LAX
IAH
Mediocre 2.6

Price is fair but the 50 pound regulation Should be enforced not 40 pounds

They lost my luggage and need my gear to work !!!!

ORD
CUN
Okay 4.3

Not that many passengers so many of us got our own row! All the extra fees though? Just fly on a nicer airline, cost ends up being the same with better service.

Crew was loud and ubnoxious while we waited to board. On the unprofessional side. Flight attendants were going on about their social lives and my kids didn’t need to hear all that adult stuff. Fees?! Oh smack. Get ready! Take lots of extra $$

BOS
PBI
Good 6.0

clean plane flight was on time and loading was prompt and orderly.

seats were way to tight and leg room was not nearly enough for a six footer

CLE
TPA
Mediocre 2.0

Sitting a small seat

5hour delay and ,50dollats for a bag is robbery

Show more results

Chicago to Cancun Flight Information

Avg. Flight Duration 3h 48m
Flights Arrive in Cancun
Flights Depart from Chicago
Flight Price $177
Distance 1441 miles
Airlines Aeromexico, Frontier, American Airlines, United, Spirit Airlines, Volaris, 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.