$110 Cheap flight deals from Chicago (CHI) to Isla Contoy (CUN)

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

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, Feb 14 - Wed, Feb 18
RFD
Greater Rockford
CUN
Cancun Intl.
$399 Roundtrip, found 5 days ago
$399
Roundtrip
found 5 days ago
Select Funjet Vacations flight, departing Sat, Feb 14 from Greater Rockford to Cancun Intl., returning Wed, Feb 18, priced at $399 found 5 days ago
Sat, Feb 14 - Tue, Feb 17
ORD
O'Hare Intl.
CUN
Cancun Intl.
$408 Roundtrip, just found
$408
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Feb 14 from O'Hare Intl. to Cancun Intl., returning Tue, Feb 17, priced at $408 just found
Sat, Feb 14 - Thu, Feb 19
MDW
Midway Intl.
CUN
Cancun Intl.
$427 Roundtrip, found 1 hour ago
$427
Roundtrip
found 1 hour ago
Select Delta flight, departing Sat, Feb 14 from Midway Intl. to Cancun Intl., returning Thu, Feb 19, priced at $427 found 1 hour ago

Airfares from $110 One Way, $180 Round Trip from Chicago to Isla Contoy

Prices starting at $180 for return flights and $110 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.

Tue, Apr 7 - Tue, Apr 14
ORD
Chicago
CUN
Cancun
$180 Roundtrip, found 7 hours ago
$180
Roundtrip
found 7 hours ago
Select Funjet Vacations flight, departing Tue, Apr 7 from Chicago to Cancun, returning Tue, Apr 14, priced at $180 found 7 hours ago
Tue, Feb 10 - Wed, Feb 25
ORD
Chicago
CUN
Cancun
$206 Roundtrip, found 4 days ago
$206
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Feb 10 from Chicago to Cancun, returning Wed, Feb 25, priced at $206 found 4 days ago
Tue, Feb 10 - Wed, Feb 25
ORD
Chicago
CUN
Cancun
$218 Roundtrip, found 4 days ago
$218
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Tue, Feb 10 from Chicago to Cancun, returning Wed, Feb 25, priced at $218 found 4 days ago
Sat, Feb 28 - Sat, Mar 7
MDW
Chicago
CUN
Cancun
$256 Roundtrip, found 7 hours ago
$256
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Sat, Feb 28 from Chicago to Cancun, returning Sat, Mar 7, priced at $256 found 7 hours ago
Tue, Apr 7 - Wed, Apr 15
ORD
Chicago
CUN
Cancun
$285 Roundtrip, found 7 hours ago
$285
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Tue, Apr 7 from Chicago to Cancun, returning Wed, Apr 15, priced at $285 found 7 hours ago

Isla Contoy economy flight packages

Price found within the past 48 hours. Click for updated prices.
Wyndham Grand Cancun All Inclusive Resort & Villas
4.0-star property

Wyndham Grand Cancun All Inclusive Resort & Villas

8.4/10 Very Good! (3,498 reviews)

Mar 30 - Apr 4

5 night stay

Chicago (CHI) to Cancun (CUN)

Air Canada • Non-stop • Coach

Cancun (CUN) to Chicago (CHI)

Volaris • Non-stop • Coach
Price was $2,703, price is now $1,339 per person
$1,339
per person
found 1 day ago
Room was very clean and staff was so friendly, really enjoyed our time there. The food was good, alrhough was difficult to book reservations for some of the restaurants, the buffet option was always available, would go back

Reviewed on Feb 2, 2026

Seadust Cancún All Inclusive Family Resort
3.5-star property

Seadust Cancún All Inclusive Family Resort

7.6/10 Good! (2,675 reviews)

Mar 13 - Mar 20

7 night stay

Chicago (CHI) to Cancun (CUN)

Frontier Airlines • Non-stop • Coach

Cancun (CUN) to Chicago (CHI)

Viva Aerobus • Non-stop • Coach
Price was $3,511, price is now $1,654 per person
$1,654
per person
found 1 day ago
The staff members were exceptional. The rooms were clean. The restaurant staffs were exceptional. We had a beautiful view of the sea. Excellent choice for an adult or family all inclusive stay.

Reviewed on Jan 29, 2026

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

Isla Contoy packages with premium economy flights

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

7.4/10 Good! (1,000 reviews)

Apr 3 - Apr 8

5 night stay

Chicago (CHI) to Cancun (CUN)

Spirit Airlines • Non-stop • PremiumEconomy

Cancun (CUN) to Chicago (CHI)

Frontier Airlines • Non-stop • PremiumEconomy
Price was $2,118, price is now $1,068 per person
$1,068
per person
found 8 hours 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

Wyndham Grand Cancun All Inclusive Resort & Villas
4.0-star property

Wyndham Grand Cancun All Inclusive Resort & Villas

8.4/10 Very Good! (3,498 reviews)

Apr 3 - Apr 8

5 night stay

Chicago (CHI) to Cancun (CUN)

Spirit Airlines • Non-stop • PremiumEconomy

Cancun (CUN) to Chicago (CHI)

Frontier Airlines • Non-stop • PremiumEconomy
Price was $3,313, price is now $1,734 per person
$1,734
per person
found 8 hours ago
Room was very clean and staff was so friendly, really enjoyed our time there. The food was good, alrhough was difficult to book reservations for some of the restaurants, the buffet option was always available, would go back

Reviewed on Feb 2, 2026

Seadust Cancún All Inclusive Family Resort
3.5-star property

Seadust Cancún All Inclusive Family Resort

7.6/10 Good! (2,675 reviews)

Apr 3 - Apr 8

5 night stay

Chicago (CHI) to Cancun (CUN)

Spirit Airlines • Non-stop • PremiumEconomy

Cancun (CUN) to Chicago (CHI)

Frontier Airlines • Non-stop • PremiumEconomy
Price was $2,532, price is now $1,369 per person
$1,369
per person
found 8 hours ago
The staff members were exceptional. The rooms were clean. The restaurant staffs were exceptional. We had a beautiful view of the sea. Excellent choice for an adult or family all inclusive stay.

Reviewed on Jan 29, 2026

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

Isla Contoy business class flight packages

Price found within the past 48 hours. Click for updated prices.
Grand Riviera Princess - All Inclusive
5.0-star property

Grand Riviera Princess - All Inclusive

8/10 Very Good! (4,367 reviews)

Apr 1 - Apr 7

6 night stay

Chicago (ORD) to Cancun (CUN)

American Airlines • Non-stop roundtrip • BusinessClass
Save 100% on your flight
Price was $2,999, price is now $1,845 per person
$1,845
per person
found 8 hours ago
The property Is still under renovation and the rooms still need to be updated we had a 32in old school tv that stood on the dresser the jetted tub was not clean it had a rust ring around it as well as the jets had rust…room service is not included in your stay it’s an additional charge and if you don’t get reservations for a restaurant they get you a table if you buy a bottle…we basically ate at the buffets which was not bad the pasta and seafood options are good for those that do not eat meat like me…staff was friendly oh yea and the drinks are all watered down so make sure you buy a bottle at the hotel or order double shots on the side to add yourself

Reviewed on Oct 26, 2025

Hotel Riu Playacar - All Inclusive
3.5-star property

Hotel Riu Playacar - All Inclusive

8.8/10 Excellent! (1,002 reviews)

Apr 1 - Apr 7

6 night stay

Chicago (ORD) to Cancun (CUN)

American Airlines • Non-stop roundtrip • BusinessClass
Save 100% on your flight
Price was $3,408, price is now $1,939 per person
$1,939
per person
found 8 hours ago
Loved the food close to down town playa del carmen walkable

Reviewed on Oct 6, 2025

Hyatt Zilara Riviera Maya Adults Only All Inclusive
4.5-star property

Hyatt Zilara Riviera Maya Adults Only All Inclusive

8.8/10 Excellent! (1,000 reviews)

Apr 1 - Apr 7

6 night stay

Chicago (ORD) to Cancun (CUN)

American Airlines • Non-stop roundtrip • BusinessClass
Save 100% on your flight
Price was $3,437, price is now $2,079 per person
$2,079
per person
found 8 hours ago
Everything at the resort was amazing! We made our trip in July and I could not have been more impressed. The resort wasn’t very packed with people, and it was easy to get drinks and chairs by the pool. Most importantly the food was incredible at EVERY restaurant. We are so happy we chose to stay here, and we are looking forward to coming back.

Reviewed on Jul 19, 2025

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

Isla Contoy first class flight packages

Price found within the past 48 hours. Click for updated prices.
Wyndham Grand Cancun All Inclusive Resort & Villas
4.0-star property

Wyndham Grand Cancun All Inclusive Resort & Villas

8.4/10 Very Good! (3,498 reviews)

Mar 31 - Apr 5

5 night stay

Chicago (CHI) to Cancun (CUN)

American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $3,112, price is now $1,718 per person
$1,718
per person
found 1 day ago
Room was very clean and staff was so friendly, really enjoyed our time there. The food was good, alrhough was difficult to book reservations for some of the restaurants, the buffet option was always available, would go back

Reviewed on Feb 2, 2026

Seadust Cancún All Inclusive Family Resort
3.5-star property

Seadust Cancún All Inclusive Family Resort

7.6/10 Good! (2,675 reviews)

Mar 31 - Apr 5

5 night stay

Chicago (CHI) to Cancun (CUN)

American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $3,254, price is now $1,720 per person
$1,720
per person
found 1 day ago
The staff members were exceptional. The rooms were clean. The restaurant staffs were exceptional. We had a beautiful view of the sea. Excellent choice for an adult or family all inclusive stay.

Reviewed on Jan 29, 2026

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

Excellence Riviera Cancun - Adults Only All Inclusive

9.4/10 Exceptional! (1,915 reviews)

Mar 19 - Mar 26

7 night stay

Chicago (CHI) to Cancun (CUN)

Spirit Airlines • FirstClass

Cancun (CUN) to Chicago (CHI)

United • FirstClass
Price was $4,922, price is now $2,747 per person
$2,747
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

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

Book your trip through Orbitz for the best deals on Chicago to Isla Contoy flights. With our cutting-edge mobile tools, getting fantastic savings on international or domestic flights or updates on your flight status has never been easier. Find your low-priced flights from Chicago to Isla Contoy today with Orbitz.

Frequent Flyer Rewards

If you are a member of a frequent flyer program, Orbitz will ensure you get points or miles for your qualifying Chicago to Isla Contoy flights. Just provide your frequent flyer number or your loyalty program number when booking your flight online with Orbtiz.com.

Flight Deals on the Go

Never miss out on great savings! Get fantastic deals on flights from Chicago to Isla Contoy on your mobile device with our apps for iPhone, Android, and iPad, or use your mobile Web browser to access m.orbitz.com. Find big discounts on the hotels you want to stay at to go along with your Chicago to Isla Contoy flights. The app even gives you information for baggage claim and other important flight details.

Free Flight Alerts

With Orbitz, not do you get amazing low-cost deals on Chicago to Isla Contoy flights, but we can send you flight alerts to your mobile phone or email. Instantly learn about delays to your flights from Chicago to Isla Contoy, so you can plan ahead and make different travel arrangements if you need to.

Guaranteed low prices for Chicago to Isla Contoy flights makes Orbitz the perfect online budget travel source.

More Destinations

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.