$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, Dec 27 - Tue, Dec 30
ORD
O'Hare Intl.
CUN
Cancun Intl.
$466 Roundtrip, found 1 hour ago
$466
Roundtrip
found 1 hour ago
Select Aeromexico flight, departing Sat, Dec 27 from O'Hare Intl. to Cancun Intl., returning Tue, Dec 30, priced at $466 found 1 hour ago
Sat, Dec 27 - Wed, Dec 31
RFD
Greater Rockford
CUN
Cancun Intl.
$689 Roundtrip, found 6 days ago
$689
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, Dec 27 from Greater Rockford to Cancun Intl., returning Wed, Dec 31, priced at $689 found 6 days ago
Sat, Dec 27 - Sat, Jan 3
MDW
Midway Intl.
CUN
Cancun Intl.
$1,106 Roundtrip, found 4 hours ago
$1,106
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Sat, Dec 27 from Midway Intl. to Cancun Intl., returning Sat, Jan 3, priced at $1,106 found 4 hours ago

Airfares from $90 One Way, $199 Round Trip from Chicago to Isla Contoy

Prices starting at $199 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.

Sun, Jan 18 - Fri, Jan 23
ORD
Chicago
CUN
Cancun
$199 Roundtrip, found 8 hours ago
$199
Roundtrip
found 8 hours ago
Select Spirit Airlines flight, departing Sun, Jan 18 from Chicago to Cancun, returning Fri, Jan 23, priced at $199 found 8 hours ago
Mon, Feb 2 - Sat, Feb 7
ORD
Chicago
CUN
Cancun
$206 Roundtrip, found 4 hours ago
$206
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Mon, Feb 2 from Chicago to Cancun, returning Sat, Feb 7, priced at $206 found 4 hours ago
Thu, Jan 8 - Thu, Jan 15
ORD
Chicago
CUN
Cancun
$208 Roundtrip, found 1 hour ago
$208
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Thu, Jan 8 from Chicago to Cancun, returning Thu, Jan 15, priced at $208 found 1 hour ago
Tue, Jan 6 - Fri, Jan 16
ORD
Chicago
CUN
Cancun
$229 Roundtrip, found 8 hours ago
$229
Roundtrip
found 8 hours ago
Select Funjet Vacations flight, departing Tue, Jan 6 from Chicago to Cancun, returning Fri, Jan 16, priced at $229 found 8 hours ago
Mon, Jan 26 - Fri, Jan 30
ORD
Chicago
CUN
Cancun
$269 Roundtrip, found 9 hours ago
$269
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Mon, Jan 26 from Chicago to Cancun, returning Fri, Jan 30, priced at $269 found 9 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

7.4/10 Good! (1,000 reviews)

Feb 3 - Feb 9

6 night stay

Chicago (CHI) to Cancun (CUN)

Spirit Airlines • Roundtrip • Coach
Price was $1,664, price is now $640 per person
$640
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

Devossion By Live Aqua Playa del Carmen All Inclusive - Adults Only
5.0-star property

Devossion By Live Aqua Playa del Carmen All Inclusive - Adults Only

9.6/10 Exceptional! (47 reviews)

Jan 28 - Feb 1

4 night stay

Chicago (CHI) to Cancun (CUN)

Spirit Airlines • Non-stop roundtrip • Coach
Price was $3,551, price is now $1,399 per person
$1,399
per person
found 1 day ago
Beachfront Hotel Boutique DK
3.5-star property

Beachfront Hotel Boutique DK

9.6/10 Exceptional! (57 reviews)

Feb 8 - Feb 14

6 night stay

Chicago (CHI) to Cancun (CUN)

Frontier Airlines • Roundtrip • Coach
Price was $1,990, price is now $805 per person
$805
per person
found 13 hours ago
The property is beautiful and the beach in front of it amazing!

Reviewed on Aug 20, 2025

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Isla Contoy business class flight packages

Price found within the past 48 hours. Click for updated prices.
Devossion By Live Aqua Playa del Carmen All Inclusive - Adults Only
5.0-star property

Devossion By Live Aqua Playa del Carmen All Inclusive - Adults Only

9.6/10 Exceptional! (47 reviews)

Feb 6 - Feb 9

3 night stay

Chicago (CHI) to Cancun (CUN)

American Airlines • Non-stop roundtrip • BusinessClass
Save 100% on your flight
Price was $2,584, price is now $1,327 per person
$1,327
per person
found 1 day ago
Iberostar Selection Coral Cancún - Adults Only - All Inclusive
5.0-star property

Iberostar Selection Coral Cancún - Adults Only - All Inclusive

9/10 Wonderful! (1,002 reviews)

Feb 6 - Feb 9

3 night stay

Chicago (CHI) to Cancun (CUN)

American Airlines • Non-stop roundtrip • BusinessClass
Save 100% on your flight
Price was $2,924, price is now $1,707 per person
$1,707
per person
found 1 day ago
Loved my ocean view-the fact that it was adults only and had top shelf liquor as part of the all-inclusive package was a huge plus! Will definitely come back to this and other Iberostar properties

Reviewed on Oct 15, 2025

AVA Resort All Oceanfront - All Inclusive
5.0-star property

AVA Resort All Oceanfront - All Inclusive

8.4/10 Very Good! (633 reviews)

Feb 8 - Feb 11

3 night stay

Chicago (ORD) to Cancun (CUN)

American Airlines • Non-stop roundtrip • BusinessClass
Save 100% on your flight
Price was $2,855, price is now $1,673 per person
$1,673
per person
found 10 hours ago
Great open but food was average at best

Reviewed on Aug 15, 2025

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Isla Contoy first class flight packages

Price found within the past 48 hours. Click for updated prices.
Seadust Cancún All Inclusive Family Resort
3.5-star property

Seadust Cancún All Inclusive Family Resort

7.6/10 Good! (2,675 reviews)

Feb 7 - Feb 12

5 night stay

Chicago (CHI) to Cancun (CUN)

United • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $2,328, price is now $1,212 per person
$1,212
per person
found 1 day ago
kids area was down or close by 8 pm elevators were down not working

Reviewed on Nov 10, 2025

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! (49 reviews)

Feb 3 - Feb 8

5 night stay

Chicago (CHI) to Cancun (CUN)

United • Roundtrip • FirstClass
Price was $8,714, price is now $4,322 per person
$4,322
per person
found 1 day ago
This property is not equipped to handle the amount of people staying here. Peope are running to the pool and beach at 7 a.m. to get lounge chairs bc there are not enough on the property. The dining facilities are not large enough. My party was turned away a few times bc the various reataurants were full or at capacity (only one restaurant takes a reservation which is a scramble to get at 8 a.m. each morning).The room was outdated and needs renovating and new decor. It was hard to get anyone to help with anything. Once, I did connect with someone he/she was nice, polite, and helpful. The hotel is understaffed and needs more lounge chairs and umbrellas.

Reviewed on Apr 11, 2022

Platinum Yucatan Princess Adults Only - All Inclusive
5.0-star property

Platinum Yucatan Princess Adults Only - All Inclusive

8.4/10 Very Good! (2,903 reviews)

Feb 7 - Feb 12

5 night stay

Chicago (CHI) to Cancun (CUN)

United • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $2,929, price is now $1,584 per person
$1,584
per person
found 1 day ago
We had a very good stay. We stayed in the Platinum section in the Honeymoon suite. This room was very large, had a jacuzzi tub and a round king size bed. We had a swim out room that also had a jacuzzi tub on the patio although it was not in great shape. We also had a plastic chair outside that was broken almost in half. The staff was mostly nice with a few that just didn't seem to be happy to be there. We tipped generously, but that didn't seem to matter. On the Platinum side there are really only three dinner options. The sushi restaurant was great. We all loved the food. We did not try the hibachi. You need a reservation to do that portion. There was also an Italian restaurant that was very good as well. And a buffet for breakfast, lunch, and dinner options. We had a server named Brian for breakfast every day. He was the best. For pools that are adults only we had two. Our swim out room pools, and another larger pool. Both had bars. Drinks were hit or miss. They could make the normal stuff such as Pina Coladas and Dirty Monkeys. They could also make some mixed drinks such as rum and coke, etc. Not much else. We found a few shots that our group enjoyed, but most were full of their mixer that tasted more like lemon juice. Overall we enjoyed ourselves, but spoke to a few that had just horrible experiences. If you're looking for a cheap vacation, this could be it, but you get what you pay for here.

Reviewed on Sep 25, 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.

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