$89 Cheap flight deals from Chicago (CHI) to Isla Holbox (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 Holbox

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, May 19 - Thu, May 23
ORD
O'Hare Intl.
CUN
Cancun Intl.
$225 Roundtrip, found 1 hour ago
$225
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sun, May 19 from O'Hare Intl. to Cancun Intl., returning Thu, May 23, priced at $225 found 1 hour ago
Sat, May 18 - Wed, May 22
MDW
Midway Intl.
CUN
Cancun Intl.
$284 Roundtrip, found 2 hours ago
$284
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sat, May 18 from Midway Intl. to Cancun Intl., returning Wed, May 22, priced at $284 found 2 hours ago

Airfares from $89 One Way, $191 Round Trip from Chicago to Isla Holbox

Prices starting at $191 for return flights and $89 for one-way flights to Isla Holbox 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, Aug 27 - Tue, Sep 10
ORD
Chicago
CUN
Cancun
$191 Roundtrip, found 18 hours ago
$191
Roundtrip
found 18 hours ago
Select Spirit Airlines flight, departing Tue, Aug 27 from Chicago to Cancun, returning Tue, Sep 10, priced at $191 found 18 hours ago
Tue, Jul 23 - Thu, Jul 25
ORD
Chicago
CUN
Cancun
$193 Roundtrip, found 1 day ago
$193
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Jul 23 from Chicago to Cancun, returning Thu, Jul 25, priced at $193 found 1 day ago
Sun, Sep 8 - Thu, Sep 12
ORD
Chicago
CUN
Cancun
$196 Roundtrip, found 1 day ago
$196
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Sep 8 from Chicago to Cancun, returning Thu, Sep 12, priced at $196 found 1 day ago
Sat, May 18 - Tue, May 21
MDW
Chicago
CUN
Cancun
$235 Roundtrip, found 5 hours ago
$235
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Sat, May 18 from Chicago to Cancun, returning Tue, May 21, priced at $235 found 5 hours ago
Mon, Sep 2 - Wed, Sep 11
ORD
Chicago
CUN
Cancun
$235 Roundtrip, found 10 hours ago
$235
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Mon, Sep 2 from Chicago to Cancun, returning Wed, Sep 11, priced at $235 found 10 hours ago

Isla Holbox economy flight packages

Price found within the past 48 hours. Click for updated prices.
Ventus at Marina El Cid Spa & Beach Resort - All Inclusive
4.0-star property

Ventus at Marina El Cid Spa & Beach Resort - All Inclusive

8.4/10 Very Good! (1,049 reviews)

Jun 25 - Jun 30

5 night stay

Chicago (CHI) to Cancun (CUN)

Spirit Airlines • Coach

Cancun (CUN) to Chicago (CHI)

American Airlines • Coach
per person
Not everyone may like my opinion about this resort, but it depends on the people themselves what they are looking for. In my opinion, everything was great, the service staff was wonderful, the food was excellent everywhere. The place is great, maybe only the ocean itself, not so much more precisely the water soles, but you can see that they are trying to collect soles and sandy beach, but it is always difficult to get along with nature, everything else is the highest rating. Palm groves are arranged everywhere, you feel like you are in the most wonderful natural world, in the evenings it is incredibly quiet no one bothers you, you can enjoy the ocean breeze in peace.

Reviewed on Apr 28, 2024

The Tower by Temptation Cancun Resort - All Inclusive - Adults Only
4.5-star property

The Tower by Temptation Cancun Resort - All Inclusive - Adults Only

9/10 Wonderful! (384 reviews)

Jun 22 - Jun 29

7 night stay

Chicago (CHI) to Cancun (CUN)

Aeromexico • Non-stop • Coach

Cancun (CUN) to Chicago (CHI)

Spirit Airlines • Non-stop • Coach
per person
The resort was clean, pleasing, and plenty of space. The food however left something to be desired. I feel that quality was sacrificed for quantity. Even the "nicer" dining areas were somewhat of a disappointment. The Flame was a total disappointment. The grilled chicken wasn't grilled and was very dry. The Strip steak wasn't what a Strip steak should be and was mostly fat and gristle. The food at the grills at the pool and the party were fantastic. The staff was great.

Reviewed on Mar 19, 2023

Hidden Beach Resort Au Naturel Adults Only – More Inclusive
5.0-star property

Hidden Beach Resort Au Naturel Adults Only – More Inclusive

9.2/10 Wonderful! (13 reviews)

Jul 5 - Jul 9

4 night stay

Chicago (CHI) to Cancun (CUN)

Delta • Non-stop roundtrip • Coach
per person
Don't see what you're looking for?
See all available trips from Chicago to Isla Holbox
View all trips

Isla Holbox packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Grand Sirenis Riviera Maya Resort & Spa - All Inclusive
4.0-star property

Grand Sirenis Riviera Maya Resort & Spa - All Inclusive

8.2/10 Very Good! (3,055 reviews)

Jul 4 - Jul 9

5 night stay

Chicago (CHI) to Cancun (CUN)

Aeromexico • Non-stop • PremiumEconomy

Cancun (CUN) to Chicago (CHI)

United • Non-stop • PremiumEconomy
per person
Dining experience could be better. The restaurants had food that was under par. We tried different restaurants and the verdict was same, poor quality that missed the mark of the restaurant's theme.

Reviewed on Apr 4, 2024

The Sens Tulum Riviera By Oasis - All Inclusive
2.5-star property

The Sens Tulum Riviera By Oasis - All Inclusive

7.4/10 Good! (9 reviews)

Jul 4 - Jul 9

5 night stay

Chicago (CHI) to Cancun (CUN)

Aeromexico • Non-stop • PremiumEconomy

Cancun (CUN) to Chicago (CHI)

United • Non-stop • PremiumEconomy
Save 100% on your flight
per person
El Dorado Casitas Royale A Spa Resorts - More Inclusive
5.0-star property

El Dorado Casitas Royale A Spa Resorts - More Inclusive

8.2/10 Very Good! (20 reviews)

Jun 23 - Jun 28

5 night stay

Chicago (ORD) to Cancun (CUN)

Aeromexico • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
per person
I have stayed at this property 4 times. I am surprised of the many new rules since I understand new management has taken over, yet rooms ,including the Casitas are not as up to date as they used to be. They've taken away a lot of what was fun, close things down earlier, and make you have a reservation at every restaurant for dinner. The food really hasn't changed, and the room service menu has become lackluster, as has the regular food. I miss the craft beer options since the last time I was there. The follow up and follow through on customer service's end was not stellar this time around. I was considering becoming a member, but after even inquiring 3 times, nobody wanted to follow up to talk with me about it. Sadly, this may be my last time at such an amazing place I used to love and enjoy.

Reviewed on Jan 20, 2024

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

Isla Holbox first class flight packages

Price found within the past 48 hours. Click for updated prices.
Kinbe Deluxe Boutique Hotel
3.5-star property

Kinbe Deluxe Boutique Hotel

9/10 Wonderful! (56 reviews)

Jun 17 - Jun 21

4 night stay

Chicago (ORD) to Cancun (CUN)

American Airlines • Non-stop roundtrip • FirstClass
per person
This is a very cute hotel . Located in the heart of playa it’s close to everything you might want or need . Checking in was super easy and the staff were super friendly and helpful . The pool is very nice with a beautiful waterfall. Our room had a balcony overlooking the pool which was pretty cool . The room was spacious clean and cozy . This will be our go to place in playa from now on .

Reviewed on Aug 5, 2022

Hotel Ojo de Agua
3.0-star property

Hotel Ojo de Agua

7.6/10 Good! (1,002 reviews)

Jun 17 - Jun 21

4 night stay

Chicago (ORD) to Cancun (CUN)

American Airlines • Non-stop roundtrip • FirstClass
per person
Hotel Ojo de Agua was okay, I didn’t like that there was empty beer cans by the pool area. Some of the bed sheets were dirty and one of the ladies got mad because we asked for some towels. Then we got some towels that were ripped and with holes. Only one small garbage. But other than that the view was very beautiful right on the beach.

Reviewed on Jul 20, 2023

Anah Suites by Sunest
4.0-star property

Anah Suites by Sunest

8.4/10 Very Good! (287 reviews)

Jun 17 - Jun 21

4 night stay

Chicago (ORD) to Cancun (CUN)

American Airlines • Non-stop roundtrip • FirstClass
per person
No me gusto esta oferta de hospedaje, es de un particular, que renta una recamara. Prefiero un hotel con todos sus servicios y amenidades.

Reviewed on Aug 19, 2022

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

More About Flying To Isla Holbox from Chicago

Route Information for Flights from Chicago to Isla Holbox

Origin Airport IATA Code
CHI
Destination Airport IATA Code
CUN
Distance
1447 mi
Direct Flight Airlines
American Airlines, Frontier Airlines, Emirates, Southwest Airlines, United Airlines, Spirit Airlines
Earliest Flight Arrival
2:32PM UTC
Latest Flight Arrival
7:28PM UTC

Chicago to Isla Holbox

Low Cost Flights From Chicago to Isla Holbox

Tired of the endless online search for the cheapest flights from Chicago to Isla Holbox? Save the energy for your vacation by using Orbitz to plan your next air trip. Orbitz guarantees the lowest prices on Chicago to Isla Holbox flights, and our cutting-edge mobile tools mean you can search and book flights with your iPhone, Android phone, iPad, or tablet.

Book Discount Chicago to Isla Holbox Flights With Ease

Take advantage of amazing sales on international and domestic fares, including bargain flights from Chicago to Isla Holbox. Not only do you find cheap deals on Orbitz, we make researching and planning your trip online and booking your tickets a breeze. Our discount Chicago to Isla Holbox flights keep more money in your pocket for your travel adventures.

Plan Flights From Chicago to Isla Holbox Anywhere, Anytime

Planning your vacation has never been easier using the convenient Orbitz apps available for most mobile devices. If there are any changes or delays for Chicago to Isla Holbox flights, Orbitz customers receive instant free alerts via email or mobile phone text message. Change or cancel flights from Chicago to Isla Holbox anytime online or by calling our Customer Service representatives.

Frequent Flyer? Earn Miles and Points Through Orbitz!

Earn points or miles on your low fare Chicago to Isla Holbox flights with Orbitz, just as you would by booking directly with the airline. Be sure to include your frequent flyer details when you book qualifying flights from Chicago to Isla Holbox on the Orbitz website.

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.