$95 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, Mar 29 - Thu, Apr 2
ORD
O'Hare Intl.
CUN
Cancun Intl.
$419 Roundtrip, found 4 hours ago
$419
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sun, Mar 29 from O'Hare Intl. to Cancun Intl., returning Thu, Apr 2, priced at $419 found 4 hours ago
Sun, Mar 29 - Thu, Apr 2
MDW
Midway Intl.
CUN
Cancun Intl.
$464 Roundtrip, found 5 hours ago
$464
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Sun, Mar 29 from Midway Intl. to Cancun Intl., returning Thu, Apr 2, priced at $464 found 5 hours ago
Sat, Mar 28 - Thu, Apr 2
RFD
Greater Rockford
CUN
Cancun Intl.
$543 Roundtrip, found 5 days ago
$543
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Mar 28 from Greater Rockford to Cancun Intl., returning Thu, Apr 2, priced at $543 found 5 days ago

Airfares from $95 One Way, $202 Round Trip from Chicago to Isla Contoy

Prices starting at $202 for return flights and $95 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, Apr 13 - Thu, Apr 16
ORD
Chicago
CUN
Cancun
$202 Roundtrip, found 1 hour ago
$202
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Mon, Apr 13 from Chicago to Cancun, returning Thu, Apr 16, priced at $202 found 1 hour ago
Sat, Apr 4 - Tue, Apr 14
ORD
Chicago
CUN
Cancun
$225 Roundtrip, found 2 hours ago
$225
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Sat, Apr 4 from Chicago to Cancun, returning Tue, Apr 14, priced at $225 found 2 hours ago
Mon, Apr 13 - Thu, Apr 16
ORD
Chicago
CUN
Cancun
$229 Roundtrip, found 1 hour ago
$229
Roundtrip
found 1 hour ago
Select Funjet Vacations flight, departing Mon, Apr 13 from Chicago to Cancun, returning Thu, Apr 16, priced at $229 found 1 hour ago
Sat, Apr 4 - Sat, Apr 11
MDW
Chicago
CUN
Cancun
$241 Roundtrip, found 1 day ago
$241
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Apr 4 from Chicago to Cancun, returning Sat, Apr 11, priced at $241 found 1 day ago
Wed, May 6 - Wed, May 13
MDW
Chicago
CUN
Cancun
$315 Roundtrip, found 2 hours ago
$315
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Wed, May 6 from Chicago to Cancun, returning Wed, May 13, priced at $315 found 2 hours ago

Isla Contoy economy flight packages

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

Casa Gitano

8.4/10 Very Good! (86 reviews)

May 3 - May 8

5 night stay

Chicago (CHI) to Cancun (CUN)

Frontier Airlines • Roundtrip • Coach
Price was $1,793, price is now $665 per person
$665
per person
found 1 day ago
Tago Tulum by G Hotels
3.5-star property

Tago Tulum by G Hotels

9.2/10 Wonderful! (389 reviews)

May 1 - May 4

3 night stay

Chicago (CHI) to Cancun (CUN)

Spirit Airlines • Non-stop • Coach

Cancun (CUN) to Chicago (CHI)

Frontier Airlines • Non-stop • Coach
Price was $2,356, price is now $793 per person
$793
per person
found 1 day ago
Its all about the Staff here in addition to the splendid property and food!

Reviewed on Jun 23, 2024

Ocean Dream Cancun by GuruHotel
3.0-star property

Ocean Dream Cancun by GuruHotel

7.6/10 Good! (1,026 reviews)

May 17 - May 24

7 night stay

Chicago (CHI) to Cancun (CUN)

Spirit Airlines • Non-stop • Coach

Cancun (CUN) to Chicago (CHI)

Frontier Airlines • Non-stop • Coach
Price was $1,988, price is now $745 per person
$745
per person
found 1 day ago
Room service phone did not work, TVs are outdated and bathroom was clogged Other than that it was okay Loved that it’s very well located

Reviewed on Sep 16, 2025

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Isla Contoy business 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! (1,026 reviews)

May 14 - May 19

5 night stay

Chicago (ORD) to Cancun (CUN)

United • Roundtrip • BusinessClass
Save 100% on your flight
Price was $1,968, price is now $1,083 per person
$1,083
per person
found 1 day ago
Room service phone did not work, TVs are outdated and bathroom was clogged Other than that it was okay Loved that it’s very well located

Reviewed on Sep 16, 2025

Fiesta Americana Cancun Villas
4.0-star property

Fiesta Americana Cancun Villas

8.4/10 Very Good! (1,106 reviews)

May 14 - May 19

5 night stay

Chicago (ORD) to Cancun (CUN)

United • Roundtrip • BusinessClass
Save 100% on your flight
Price was $2,604, price is now $1,473 per person
$1,473
per person
found 1 day ago
The staff were always very helpful and kind. The breakfast buffet may seem expensive, but it's worth $30 for the variety of traditional Mexican foods and attentive service while enjoying a great view of the ocean. The property is well kept though a bit dated and rooms are spacious. You can access the ocean right in front of the resort by walking down concrete steps, but we walked a few minutes to the beach on either side of the property to enjoy a more traditional beachfront. It's an easy walk to many good restaurants and a grocery store. We cooked at least one meal a day in our little kitchen. One area that could be improved is pool cleanliness. The water looked stagnant in some areas in the mornings and our toddler kept on getting dirty streaks on his swimsuit, which I finally figured out was from some film on the side of the pool.

Reviewed on Mar 19, 2025

Excellence Riviera Cancun - Adults Only All Inclusive
5.0-star property

Excellence Riviera Cancun - Adults Only All Inclusive

9.4/10 Exceptional! (2,117 reviews)

May 14 - May 19

5 night stay

Chicago (ORD) to Cancun (CUN)

United • Roundtrip • BusinessClass
Save 100% on your flight
Price was $3,221, price is now $1,944 per person
$1,944
per person
found 1 day ago
Great food and drinks, great service, and very clean. The shows at night were also really good, almost Vegas quality. We had a great time and will definitely be back!

Reviewed on Dec 17, 2025

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Isla Contoy first class flight packages

Price found within the past 48 hours. Click for updated prices.
Allegro Playacar - All Inclusive
3.5-star property

Allegro Playacar - All Inclusive

7.8/10 Good! (1,009 reviews)

Apr 30 - May 5

5 night stay

Chicago (ORD) to Cancun (CUN)

American Airlines • Non-stop • FirstClass

Cancun (CUN) to Chicago (ORD)

United • Non-stop • FirstClass
Price was $2,218, price is now $1,421 per person
$1,421
per person
found 6 hours ago
Absolutely fabulous!

Reviewed on Jan 13, 2026

The Sens Riviera By Oasis
4.0-star property

The Sens Riviera By Oasis

7.2/10 Good! (187 reviews)

Apr 30 - May 5

5 night stay

Chicago (ORD) to Cancun (CUN)

American Airlines • Non-stop • FirstClass

Cancun (CUN) to Chicago (ORD)

United • Non-stop • FirstClass
Price was $2,438, price is now $1,589 per person
$1,589
per person
found 6 hours 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

Hotel Riu Playacar - All Inclusive
3.5-star property

Hotel Riu Playacar - All Inclusive

8.8/10 Excellent! (1,009 reviews)

Apr 30 - May 5

5 night stay

Chicago (ORD) to Cancun (CUN)

American Airlines • Non-stop • FirstClass

Cancun (CUN) to Chicago (ORD)

United • Non-stop • FirstClass
Price was $2,186, price is now $1,463 per person
$1,463
per person
found 6 hours ago
Loved the food close to down town playa del carmen walkable

Reviewed on Oct 6, 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.