$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, found 1 hour ago
$219
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sat, Nov 15 from O'Hare Intl. to Cancun Intl., returning Fri, Nov 21, priced at $219 found 1 hour ago
Fri, Nov 14 - Thu, Nov 20
MDW
Midway Intl.
CUN
Cancun Intl.
$332 Roundtrip, found 1 hour ago
$332
Roundtrip
found 1 hour ago
Select Aeromexico flight, departing Fri, Nov 14 from Midway Intl. to Cancun Intl., returning Thu, Nov 20, priced at $332 found 1 hour ago
Fri, Nov 14 - Wed, Nov 19
RFD
Greater Rockford
CUN
Cancun Intl.
$460 Roundtrip, found 4 days ago
$460
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, Nov 14 from Greater Rockford to Cancun Intl., returning Wed, Nov 19, priced at $460 found 4 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, Feb 2 - Thu, Feb 5
ORD
Chicago
CUN
Cancun
$201 Roundtrip, just found
$201
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, Feb 2 from Chicago to Cancun, returning Thu, Feb 5, priced at $201 just found
Sat, Jan 10 - Sat, Jan 17
ORD
Chicago
CUN
Cancun
$210 Roundtrip, found 1 hour ago
$210
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sat, Jan 10 from Chicago to Cancun, returning Sat, Jan 17, priced at $210 found 1 hour ago
Fri, Jan 9 - Wed, Jan 14
ORD
Chicago
CUN
Cancun
$229 Roundtrip, just found
$229
Roundtrip
just found
Select Funjet Vacations flight, departing Fri, Jan 9 from Chicago to Cancun, returning Wed, Jan 14, priced at $229 just found
Sun, Nov 30 - Wed, Dec 10
MDW
Chicago
CUN
Cancun
$262 Roundtrip, found 5 days ago
$262
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Sun, Nov 30 from Chicago to Cancun, returning Wed, Dec 10, priced at $262 found 5 days ago
Sun, Jan 25 - Thu, Jan 29
ORD
Chicago
CUN
Cancun
$262 Roundtrip, found 5 hours ago
$262
Roundtrip
found 5 hours ago
Select United flight, departing Sun, Jan 25 from Chicago to Cancun, returning Thu, Jan 29, priced at $262 found 5 hours ago

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

Beachscape Kin ha Villas & Suites
3.5-star property

Beachscape Kin ha Villas & Suites

8.6/10 Excellent! (1,904 reviews)

Dec 20 - Dec 27

7 night stay

Chicago (CHI) to Cancun (CUN)

Spirit Airlines • Non-stop roundtrip • Coach
Price was $3,276, price is now $1,386 per person
$1,386
per person
found 1 day ago
Great location, close to restaurants and grocery store. Clean property and friendly staff. Food at the restaurant was good. Actual property not nearly as nice as the photos, very dated.

Reviewed on Jun 19, 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 20 - Dec 27

7 night stay

Chicago (CHI) to Cancun (CUN)

Spirit Airlines • Non-stop roundtrip • Coach
Price was $5,464, price is now $2,501 per person
$2,501
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 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 1 - Jan 4

3 night stay

Chicago (ORD) to Cancun (CUN)

American Airlines • Roundtrip • BusinessClass
Save 100% on your flight
Price was $3,699, price is now $2,406 per person
$2,406
per person
found 22 hours ago
Room was a little dated and worn. Staff were excellent.

Reviewed on Oct 29, 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)

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 22 hours 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

Finest Playa Mujeres by The Excellence Collection - All Inclusive
5.0-star property

Finest Playa Mujeres by The Excellence Collection - All Inclusive

9/10 Wonderful! (1,452 reviews)

Jan 1 - Jan 4

3 night stay

Chicago (ORD) to Cancun (CUN)

American Airlines • Roundtrip • BusinessClass
Save 100% on your flight
Price was $5,014, price is now $3,163 per person
$3,163
per person
found 22 hours ago
Beautiful property. Plenty of dining options, service is exceptional. Travelled with a toddler. Felt safe as a family. Room was dated, but mostly comfortable. Several different pools around the property. All were easy to access except the main pool which was challenging/near impossible to get seats at unless you claimed some before 10am. Beach was beautiful. Entertainment was fun.

Reviewed on May 14, 2025

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Isla Contoy first class flight packages

Price found within the past 48 hours. Click for updated prices.
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

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

Finest Playa Mujeres by The Excellence Collection - All Inclusive
5.0-star property

Finest Playa Mujeres by The Excellence Collection - All Inclusive

9/10 Wonderful! (1,452 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 $7,248, price is now $4,290 per person
$4,290
per person
found 1 day ago
Beautiful property. Plenty of dining options, service is exceptional. Travelled with a toddler. Felt safe as a family. Room was dated, but mostly comfortable. Several different pools around the property. All were easy to access except the main pool which was challenging/near impossible to get seats at unless you claimed some before 10am. Beach was beautiful. Entertainment was fun.

Reviewed on May 14, 2025

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See all available trips from Chicago to Isla Contoy
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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.