$90 Cheap flight deals from Chicago (CHI) to Isla Contoy (CUN)

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This Weekend's Flight Deals from Chicago to Isla Contoy

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Nov 15 - Fri, Nov 21
ORD
O'Hare Intl.
CUN
Cancun Intl.
$219 Roundtrip, just found
$219
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Nov 15 from O'Hare Intl. to Cancun Intl., returning Fri, Nov 21, priced at $219 just found
Sat, Nov 15 - Fri, Nov 21
MDW
Midway Intl.
CUN
Cancun Intl.
$332 Roundtrip, found 4 hours ago
$332
Roundtrip
found 4 hours ago
Select Delta flight, departing Sat, Nov 15 from Midway Intl. to Cancun Intl., returning Fri, Nov 21, priced at $332 found 4 hours ago
Fri, Nov 14 - Wed, Nov 19
RFD
Greater Rockford
CUN
Cancun Intl.
$460 Roundtrip, found 5 days ago
$460
Roundtrip
found 5 days ago
Select American Airlines flight, departing Fri, Nov 14 from Greater Rockford to Cancun Intl., returning Wed, Nov 19, priced at $460 found 5 days ago

Airfares from $90 One Way, $201 Round Trip from Chicago to Isla Contoy

Prices starting at $201 for return flights and $90 for one-way flights to Isla Contoy were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Mon, Jan 26 - Mon, Feb 2
ORD
Chicago
CUN
Cancun
$201 Roundtrip, just found
$201
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, Jan 26 from Chicago to Cancun, returning Mon, Feb 2, priced at $201 just found
Sun, Jan 11 - Thu, Jan 15
ORD
Chicago
CUN
Cancun
$210 Roundtrip, just found
$210
Roundtrip
just found
Select Spirit Airlines flight, departing Sun, Jan 11 from Chicago to Cancun, returning Thu, Jan 15, priced at $210 just found
Tue, Dec 9 - Fri, Dec 12
ORD
Chicago
CUN
Cancun
$229 Roundtrip, just found
$229
Roundtrip
just found
Select Funjet Vacations flight, departing Tue, Dec 9 from Chicago to Cancun, returning Fri, Dec 12, priced at $229 just found
Sun, Nov 30 - Wed, Dec 10
MDW
Chicago
CUN
Cancun
$262 Roundtrip, found 6 days ago
$262
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sun, Nov 30 from Chicago to Cancun, returning Wed, Dec 10, priced at $262 found 6 days ago
Tue, Dec 9 - Fri, Dec 12
ORD
Chicago
CUN
Cancun
$262 Roundtrip, just found
$262
Roundtrip
just found
Select United flight, departing Tue, Dec 9 from Chicago to Cancun, returning Fri, Dec 12, priced at $262 just found

Isla Contoy economy flight packages

Price found within the past 48 hours. Click for updated prices.
Naay Boutique Hotel
4.0-star property

Naay Boutique Hotel

8.4/10 Very Good! (192 reviews)

Dec 17 - Dec 23

6 night stay

Chicago (CHI) to Cancun (CUN)

Frontier Airlines • Coach

Cancun (CUN) to Chicago (CHI)

Spirit Airlines • Coach
Price was $1,703, price is now $613 per person
$613
per person
found 1 day ago
Amazing and beautiful property! Thank you!

Reviewed on Sep 3, 2024

Hotelito del Mar
3.0-star property

Hotelito del Mar

9/10 Wonderful! (67 reviews)

Dec 31 - Jan 7

7 night stay

Chicago (ORD) to Cancun (CUN)

Frontier Airlines • Coach

Cancun (CUN) to Chicago (ORD)

Spirit Airlines • Coach
Price was $2,191, price is now $811 per person
$811
per person
found 20 hours ago
Spacious rooms and roof top pool. Just a few blocks from 5th Avenue. Loved it and will be back!

Reviewed on Jul 26, 2019

The Sens Tulum Riviera By Oasis
4.0-star property

The Sens Tulum Riviera By Oasis

7.2/10 Good! (180 reviews)

Dec 15 - Dec 21

6 night stay

Chicago (CHI) to Cancun (CUN)

United • Coach

Cancun (CUN) to Chicago (CHI)

Spirit Airlines • Coach
Price was $2,101, price is now $948 per person
$948
per person
found 1 day ago
So far so good..Considering price as compared to other beachfront/ocean properties quite reasonable for services offered including restaurants pools, etc. Property needs some updating overall and addition of services and some standard amenities. Restroom additions closer to pool areas and beach areas would be helpful. Roving drink servers for pool bars & towels at each pool location would make life more pleasurable and convenient for guests. All in all we enjoyed stay and happy with our choice.

Reviewed on Apr 1, 2025

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Isla Contoy business class flight packages

Price found within the past 48 hours. Click for updated prices.
Hard Rock Hotel Cancun - All Inclusive
4.5-star property

Hard Rock Hotel Cancun - All Inclusive

7.8/10 Good! (1,307 reviews)

Jan 2 - Jan 6

4 night stay

Chicago (CHI) to Cancun (CUN)

American Airlines • Non-stop roundtrip • BusinessClass
Save 100% on your flight
Price was $3,417, price is now $1,969 per person
$1,969
per person
found 1 hour ago
Room was a little dated and worn. Staff were excellent.

Reviewed on Oct 29, 2025

Family 3 Bedroom Ocean Villa By Wyndham Grand Cancun
4.0-star property

Family 3 Bedroom Ocean Villa By Wyndham Grand Cancun

7.6/10 Good! (49 reviews)

Jan 2 - Jan 6

4 night stay

Chicago (CHI) to Cancun (CUN)

American Airlines • Non-stop roundtrip • BusinessClass
Price was $6,434, price is now $3,305 per person
$3,305
per person
found 1 hour ago
This property is not equipped to handle the amount of people staying here. Peope are running to the pool and beach at 7 a.m. to get lounge chairs bc there are not enough on the property. The dining facilities are not large enough. My party was turned away a few times bc the various reataurants were full or at capacity (only one restaurant takes a reservation which is a scramble to get at 8 a.m. each morning).The room was outdated and needs renovating and new decor. It was hard to get anyone to help with anything. Once, I did connect with someone he/she was nice, polite, and helpful. The hotel is understaffed and needs more lounge chairs and umbrellas.

Reviewed on Apr 11, 2022

Temptation at The Tower Cancún All Inclusive - Adults Only
4.5-star property

Temptation at The Tower Cancún All Inclusive - Adults Only

9/10 Wonderful! (591 reviews)

Jan 1 - Jan 4

3 night stay

Chicago (ORD) to Cancun (CUN)

American Airlines • Roundtrip • BusinessClass
Save 100% on your flight
Price was $4,931, price is now $2,799 per person
$2,799
per person
found 1 day ago
The resort was clean, pleasing, and plenty of space. The food however left something to be desired. I feel that quality was sacrificed for quantity. Even the "nicer" dining areas were somewhat of a disappointment. The Flame was a total disappointment. The grilled chicken wasn't grilled and was very dry. The Strip steak wasn't what a Strip steak should be and was mostly fat and gristle. The food at the grills at the pool and the party were fantastic. The staff was great.

Reviewed on Mar 19, 2023

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Isla Contoy first class flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Palace Kukulkan - Adults Only - All Inclusive
4.5-star property

Hotel Riu Palace Kukulkan - Adults Only - All Inclusive

9/10 Wonderful! (4,405 reviews)

Dec 28 - Jan 1

4 night stay

Chicago (ORD) to Cancun (CUN)

American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $4,313, price is now $2,506 per person
$2,506
per person
found 1 day ago
Very clean rooms, the staff was very friendly and accommodating, breakfast was great very delicious plenty of choices, Balcony was breath taking an amazing view to the ocean.

Reviewed on Oct 14, 2025

Temptation at The Tower Cancún All Inclusive - Adults Only
4.5-star property

Temptation at The Tower Cancún All Inclusive - Adults Only

9/10 Wonderful! (591 reviews)

Dec 30 - Jan 3

4 night stay

Chicago (ORD) to Cancun (CUN)

American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $6,508, price is now $3,460 per person
$3,460
per person
found 1 day ago
The resort was clean, pleasing, and plenty of space. The food however left something to be desired. I feel that quality was sacrificed for quantity. Even the "nicer" dining areas were somewhat of a disappointment. The Flame was a total disappointment. The grilled chicken wasn't grilled and was very dry. The Strip steak wasn't what a Strip steak should be and was mostly fat and gristle. The food at the grills at the pool and the party were fantastic. The staff was great.

Reviewed on Mar 19, 2023

Temptation Cancun Resort All Inclusive - Adults Only
4.5-star property

Temptation Cancun Resort All Inclusive - Adults Only

8.8/10 Excellent! (4,326 reviews)

Dec 30 - Jan 3

4 night stay

Chicago (ORD) to Cancun (CUN)

American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $4,546, price is now $2,610 per person
$2,610
per person
found 1 day ago
Service was great and professional. Friendly staff especially Sophia, Odales and Marlene. Amazing experience. Will book again very soon!

Reviewed on Oct 13, 2025

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More About Flying To Isla Contoy from Chicago

Route Information for Flights from Chicago to Isla Contoy

Origin Airport IATA Code
CHI
Destination Airport IATA Code
CUN
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Isla Contoy

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.