$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.

Sun, Aug 16 - Thu, Aug 20
MDW
Midway Intl.
CUN
Cancun Intl.
$548 Roundtrip, found 2 hours ago
$548
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sun, Aug 16 from Midway Intl. to Cancun Intl., returning Thu, Aug 20, priced at $548 found 2 hours ago
Fri, Aug 14 - Mon, Aug 17
ORD
O'Hare Intl.
CUN
Cancun Intl.
$572 Roundtrip, found 3 hours ago
$572
Roundtrip
found 3 hours ago
Select Arajet flight, departing Fri, Aug 14 from O'Hare Intl. to Cancun Intl., returning Mon, Aug 17, priced at $572 found 3 hours ago
Sun, Aug 16 - Sun, Aug 23
RFD
Greater Rockford
CUN
Cancun Intl.
$900 Roundtrip, found 5 days ago
$900
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sun, Aug 16 from Greater Rockford to Cancun Intl., returning Sun, Aug 23, priced at $900 found 5 days ago

Airfares from $147 One Way, $350 Round Trip from Chicago to Isla Contoy

Prices starting at $350 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 - Mon, Nov 9
ORD
Chicago
CUN
Cancun
$350 Roundtrip, found 3 hours ago
$350
Roundtrip
found 3 hours ago
Select Arajet flight, departing Mon, Nov 2 from Chicago to Cancun, returning Mon, Nov 9, priced at $350 found 3 hours ago
Mon, Nov 2 - Thu, Nov 12
ORD
Chicago
CUN
Cancun
$359 Roundtrip, found 16 hours ago
$359
Roundtrip
found 16 hours ago
Select Arajet flight, departing Mon, Nov 2 from Chicago to Cancun, returning Thu, Nov 12, priced at $359 found 16 hours ago
Thu, Jan 14 - Wed, Jan 20
ORD
Chicago
CUN
Cancun
$377 Roundtrip, just found
$377
Roundtrip
just found
Select Viva flight, departing Thu, Jan 14 from Chicago to Cancun, returning Wed, Jan 20, priced at $377 just found
Fri, Oct 23 - Mon, Oct 26
ORD
Chicago
CUN
Cancun
$387 Roundtrip, just found
$387
Roundtrip
just found
Select Air Canada flight, departing Fri, Oct 23 from Chicago to Cancun, returning Mon, Oct 26, priced at $387 just found
Sun, Oct 18 - Fri, Oct 23
ORD
Chicago
CUN
Cancun
$399 Roundtrip, found 3 hours ago
$399
Roundtrip
found 3 hours ago
Select Funjet Vacations flight, departing Sun, Oct 18 from Chicago to Cancun, returning Fri, Oct 23, priced at $399 found 3 hours ago

Isla Contoy economy flight packages

Price found within the past 48 hours. Click for updated prices.
Ocean Dream Cancun by GuruHotel
3.0-star property

Ocean Dream Cancun by GuruHotel

7.6/10 Good! (1,053 reviews)

Sep 30 - Oct 6

6 night stay

Chicago (CHI) to Cancun (CUN)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,663, price is now $770 per person
$770
per person
found 1 day ago
The hotel was really nice. We chose the ocean view and it was amazing waking up to the ocean. We went during the sargassum season so there was a lot on the beach. Overall it was a nice clean hotel and everyone was very helpful.

Reviewed on Aug 9, 2026

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! (50 reviews)

Sep 11 - Sep 17

6 night stay

Chicago (CHI) to Cancun (CUN)

United • Roundtrip • Coach
Price was $5,521, price is now $2,563 per person
$2,563
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 17 - Sep 21

4 night stay

Chicago (CHI) to Cancun (CUN)

Volaris • Non-stop roundtrip • Coach
Price was $3,784, price is now $1,779 per person
$1,779
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 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 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 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

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 1 day ago
Excellent

Reviewed on Aug 9, 2026

Don't see what you're looking for?
See all available trips from Chicago to Isla Contoy
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Isla Contoy first class flight packages

Price found within the past 48 hours. Click for updated prices.
Ocean Dream Cancun by GuruHotel
3.0-star property

Ocean Dream Cancun by GuruHotel

7.6/10 Good! (1,053 reviews)

Sep 26 - Oct 3

7 night stay

Chicago (CHI) to Cancun (CUN)

Frontier Airlines • Non-stop • FirstClass

Cancun (CUN) to Chicago (CHI)

American Airlines • Non-stop • FirstClass
Save 100% on your flight
Price was $2,076, price is now $1,057 per person
$1,057
per person
found 1 hour ago
The hotel was really nice. We chose the ocean view and it was amazing waking up to the ocean. We went during the sargassum season so there was a lot on the beach. Overall it was a nice clean hotel and everyone was very helpful.

Reviewed on Aug 9, 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 26 - Oct 3

7 night stay

Chicago (CHI) to Cancun (CUN)

Frontier Airlines • Non-stop • FirstClass

Cancun (CUN) to Chicago (CHI)

American Airlines • Non-stop • FirstClass
Save 100% on your flight
Price was $2,768, price is now $1,378 per person
$1,378
per person
found 1 hour ago
Excellent

Reviewed on Aug 9, 2026

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 24 - Sep 28

4 night stay

Chicago (CHI) to Cancun (CUN)

American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $4,612, price is now $2,394 per person
$2,394
per person
found 8 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

Don't see what you're looking for?
See all available trips from Chicago to Isla Contoy
View all trips

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.