$147 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, Aug 15 - Thu, Aug 20
ORD
O'Hare Intl.
CUN
Cancun Intl.
$587 Roundtrip, found 3 hours ago
$587
Roundtrip
found 3 hours ago
Select Volaris flight, departing Sat, Aug 15 from O'Hare Intl. to Cancun Intl., returning Thu, Aug 20, priced at $587 found 3 hours ago
Sat, Aug 15 - Thu, Aug 20
MDW
Midway Intl.
CUN
Cancun Intl.
$611 Roundtrip, found 3 hours ago
$611
Roundtrip
found 3 hours ago
Select Aeromexico flight, departing Sat, Aug 15 from Midway Intl. to Cancun Intl., returning Thu, Aug 20, priced at $611 found 3 hours ago
Sun, Aug 16 - Sun, Aug 23
RFD
Greater Rockford
CUN
Cancun Intl.
$900 Roundtrip, found 4 days ago
$900
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sun, Aug 16 from Greater Rockford to Cancun Intl., returning Sun, Aug 23, priced at $900 found 4 days ago

Airfares from $147 One Way, $347 Round Trip from Chicago to Isla Contoy

Prices starting at $347 for return flights and $147 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, Nov 2 - Thu, Nov 19
ORD
Chicago
CUN
Cancun
$347 Roundtrip, found 3 hours ago
$347
Roundtrip
found 3 hours ago
Select Arajet flight, departing Mon, Nov 2 from Chicago to Cancun, returning Thu, Nov 19, priced at $347 found 3 hours ago
Mon, Nov 2 - Thu, Nov 12
ORD
Chicago
CUN
Cancun
$359 Roundtrip, found 3 hours ago
$359
Roundtrip
found 3 hours ago
Select Arajet flight, departing Mon, Nov 2 from Chicago to Cancun, returning Thu, Nov 12, priced at $359 found 3 hours ago
Thu, Feb 11 - Wed, Feb 17
ORD
Chicago
CUN
Cancun
$376 Roundtrip, found 17 hours ago
$376
Roundtrip
found 17 hours ago
Select Viva flight, departing Thu, Feb 11 from Chicago to Cancun, returning Wed, Feb 17, priced at $376 found 17 hours ago
Fri, Oct 23 - Mon, Oct 26
ORD
Chicago
CUN
Cancun
$392 Roundtrip, found 18 hours ago
$392
Roundtrip
found 18 hours ago
Select Air Canada flight, departing Fri, Oct 23 from Chicago to Cancun, returning Mon, Oct 26, priced at $392 found 18 hours ago
Wed, Dec 2 - Wed, Dec 9
ORD
Chicago
CUN
Cancun
$399 Roundtrip, just found
$399
Roundtrip
just found
Select Funjet Vacations flight, departing Wed, Dec 2 from Chicago to Cancun, returning Wed, Dec 9, priced at $399 just found

Isla Contoy economy flight packages

Price found within the past 48 hours. Click for updated prices.
Casa Gitano
3.5-star property

Casa Gitano

8.6/10 Excellent! (99 reviews)

Sep 8 - Sep 13

5 night stay

Chicago (CHI) to Cancun (CUN)

Aeromexico • Non-stop • Coach

Cancun (CUN) to Chicago (CHI)

American Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,958, price is now $905 per person
$905
per person
found 1 day ago

The Sens Cancun By Oasis
4.0-star property

The Sens Cancun By Oasis

7.4/10 Good! (672 reviews)

Sep 8 - Sep 15

7 night stay

Chicago (CHI) to Cancun (CUN)

Volaris • Non-stop roundtrip • Coach
Price was $2,399, price is now $1,091 per person
$1,091
per person
found 1 day ago

Palmaïa-The House of AïA: All Inclusive Wellness Resort
5.0-star property

Palmaïa-The House of AïA: All Inclusive Wellness Resort

9.8/10 Exceptional! (659 reviews)

Sep 8 - Sep 13

5 night stay

Chicago (CHI) to Cancun (CUN)

Aeromexico • Non-stop • Coach

Cancun (CUN) to Chicago (CHI)

American Airlines • Non-stop • Coach
Price was $5,009, price is now $2,377 per person
$2,377
per person
found 1 day ago
Wow! Easily the best resort we have stayed at. I am not Vegan but the best part of this trip was definitely the food. The all-inclusive is the best deal around by far. There are plenty of non-vegan options but honestly I mostly ate the vegan versions. Everything was top-shelf. Charlies Vegan Tacos were a highlight. And we actually lost some weight while we were there since its so healthy. The service was incredible. Everywhere we went we were greeted with smiles and hellos. We got to know by name many of the staff. The Pools are about the best I have seen and the beach (when there is not seaweed) is incredible. And they keep it cleaner than any other beach around. Every time we ventured out to try something different we came back to the hotel because it was just better. The free classes like Yoga were amazing as well. I feel this is a secret that will soon be out. But thank you to all the staff who were part of this experience.

Reviewed on Aug 8, 2026

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Isla Contoy business class flight packages

Price found within the past 48 hours. Click for updated prices.
The Sens Cancun By Oasis
4.0-star property

The Sens Cancun By Oasis

7.4/10 Good! (672 reviews)

Sep 28 - Oct 5

7 night stay

Chicago (ORD) to Cancun (CUN)

United • Roundtrip • BusinessClass
Save 100% on your flight
Price was $3,091, price is now $1,569 per person
$1,569
per person
found 19 hours ago

Palmaïa-The House of AïA: All Inclusive Wellness Resort
5.0-star property

Palmaïa-The House of AïA: All Inclusive Wellness Resort

9.8/10 Exceptional! (659 reviews)

Sep 26 - Oct 1

5 night stay

Chicago (CHI) to Cancun (CUN)

Frontier Airlines • Non-stop roundtrip • BusinessClass
Price was $4,947, price is now $2,303 per person
$2,303
per person
found 20 hours ago
Wow! Easily the best resort we have stayed at. I am not Vegan but the best part of this trip was definitely the food. The all-inclusive is the best deal around by far. There are plenty of non-vegan options but honestly I mostly ate the vegan versions. Everything was top-shelf. Charlies Vegan Tacos were a highlight. And we actually lost some weight while we were there since its so healthy. The service was incredible. Everywhere we went we were greeted with smiles and hellos. We got to know by name many of the staff. The Pools are about the best I have seen and the beach (when there is not seaweed) is incredible. And they keep it cleaner than any other beach around. Every time we ventured out to try something different we came back to the hotel because it was just better. The free classes like Yoga were amazing as well. I feel this is a secret that will soon be out. But thank you to all the staff who were part of this experience.

Reviewed on Aug 8, 2026

The Pyramid Cancun By Oasis - All Inclusive
4.0-star property

The Pyramid Cancun By Oasis - All Inclusive

7.4/10 Good! (1,809 reviews)

Sep 28 - Oct 5

7 night stay

Chicago (ORD) to Cancun (CUN)

United • Roundtrip • BusinessClass
Save 100% on your flight
Price was $3,095, price is now $1,589 per person
$1,589
per person
found 19 hours ago
Food is great Servers amazing Check in it’s ok We couldn’t book a reservation for any restaurant But the buffet was open and food was good

Reviewed on Aug 8, 2026

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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.