$94 Cheap flight deals from Chicago (CHI) to Isla Holbox (CUN)

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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.

Sat, Sep 20 - Thu, Sep 25
ORD
O'Hare Intl.
CUN
Cancun Intl.
$351 Roundtrip, just found
$351
Roundtrip
just found
Select Air Canada flight, departing Sat, Sep 20 from O'Hare Intl. to Cancun Intl., returning Thu, Sep 25, priced at $351 just found
Sun, Sep 21 - Wed, Sep 24
MDW
Midway Intl.
CUN
Cancun Intl.
$381 Roundtrip, found 17 hours ago
$381
Roundtrip
found 17 hours ago
Select Southwest Airlines flight, departing Sun, Sep 21 from Midway Intl. to Cancun Intl., returning Wed, Sep 24, priced at $381 found 17 hours ago

Airfares from $94 One Way, $209 Round Trip from Chicago to Isla Holbox

Prices starting at $209 for return flights and $94 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.

Sun, Nov 16 - Wed, Nov 19
ORD
Chicago
CUN
Cancun
$209 Roundtrip, found 1 hour ago
$209
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sun, Nov 16 from Chicago to Cancun, returning Wed, Nov 19, priced at $209 found 1 hour ago
Sun, Nov 16 - Wed, Nov 19
ORD
Chicago
CUN
Cancun
$211 Roundtrip, found 1 hour ago
$211
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sun, Nov 16 from Chicago to Cancun, returning Wed, Nov 19, priced at $211 found 1 hour ago
Tue, Sep 23 - Sat, Sep 27
ORD
Chicago
CUN
Cancun
$220 Roundtrip, found 22 hours ago
$220
Roundtrip
found 22 hours ago
Select Spirit Airlines flight, departing Tue, Sep 23 from Chicago to Cancun, returning Sat, Sep 27, priced at $220 found 22 hours ago
Sat, Nov 29 - Wed, Dec 3
ORD
Chicago
CUN
Cancun
$229 Roundtrip, just found
$229
Roundtrip
just found
Select Funjet Vacations flight, departing Sat, Nov 29 from Chicago to Cancun, returning Wed, Dec 3, priced at $229 just found
Sun, Sep 28 - Fri, Oct 3
MDW
Chicago
CUN
Cancun
$261 Roundtrip, found 1 day ago
$261
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sun, Sep 28 from Chicago to Cancun, returning Fri, Oct 3, priced at $261 found 1 day ago

Isla Holbox economy 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! (548 reviews)

Nov 2 - Nov 7

5 night stay

Chicago (CHI) to Cancun (CUN)

United • Coach

Cancun (CUN) to Chicago (CHI)

Spirit Airlines • Coach
Price was $1,805, price is now $814 per person
$814
per person
found 1 day ago
Very nice small resort..! You have everything you need.

Reviewed on Jul 21, 2025

Chablé Maroma
5.0-star property

Chablé Maroma

9.4/10 Exceptional! (150 reviews)

Oct 31 - Nov 6

6 night stay

Chicago (CHI) to Cancun (CUN)

United • Coach

Cancun (CUN) to Chicago (CHI)

Frontier Airlines • Coach
Price was $5,685, price is now $2,555 per person
$2,555
per person
found 1 day ago
Everything was amazing! The daily breakfast that was included was absolutely delicious! We highly recommend the French fries and guacamole pool side as well. Luis, our pool side attendant and Aram, our concierge, were top notch, along with everyone else that works there! Our only challenge was we weren’t aware it was a cashless resort, so we weren’t able to break our big bills for individual tips. We recommend you bring small bills ($1’s and $5’s) for tipping purposes!

Reviewed on Jul 24, 2022

The Pyramid Cancun By Oasis - All Inclusive
4.0-star property

The Pyramid Cancun By Oasis - All Inclusive

7.2/10 Good! (1,480 reviews)

Nov 2 - Nov 7

5 night stay

Chicago (CHI) to Cancun (CUN)

United • Coach

Cancun (CUN) to Chicago (CHI)

Spirit Airlines • Coach
Price was $1,805, price is now $817 per person
$817
per person
found 1 day ago
No mentioned anywhere that I saw, property in under renovations . Staff is friendly with exemptions, frozen smiles

Reviewed on Jul 17, 2025

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Isla Holbox business class flight packages

Price found within the past 48 hours. Click for updated prices.
Temptation at The Tower Cancún All Inclusive - Adults Only
4.5-star property

Temptation at The Tower Cancún All Inclusive - Adults Only

9/10 Wonderful! (578 reviews)

Oct 23 - Oct 29

6 night stay

Chicago (CHI) to Cancun (CUN)

American Airlines • Non-stop roundtrip • BusinessClass
Price was $4,622, price is now $2,262 per person
$2,262
per person
found 1 day ago
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

Chablé Maroma
5.0-star property

Chablé Maroma

9.4/10 Exceptional! (150 reviews)

Oct 24 - Oct 31

7 night stay

Chicago (CHI) to Cancun (CUN)

United • Non-stop roundtrip • BusinessClass
Price was $6,299, price is now $3,098 per person
$3,098
per person
found 1 day ago
Everything was amazing! The daily breakfast that was included was absolutely delicious! We highly recommend the French fries and guacamole pool side as well. Luis, our pool side attendant and Aram, our concierge, were top notch, along with everyone else that works there! Our only challenge was we weren’t aware it was a cashless resort, so we weren’t able to break our big bills for individual tips. We recommend you bring small bills ($1’s and $5’s) for tipping purposes!

Reviewed on Jul 24, 2022

Temptation Cancun Resort All Inclusive - Adults Only
4.5-star property

Temptation Cancun Resort All Inclusive - Adults Only

8.8/10 Excellent! (4,206 reviews)

Oct 23 - Oct 29

6 night stay

Chicago (CHI) to Cancun (CUN)

American Airlines • Non-stop roundtrip • BusinessClass
Save 100% on your flight
Price was $4,520, price is now $2,368 per person
$2,368
per person
found 1 day ago
Wife and I went with a 3 other couples. Knowing what we read based of previous reviews, I’d say it was def interesting for sure. The theme nights are fun and entertaining for sure. As far as things to do, there isn’t much. Two small pools and few dining options. We made the best of it as we do anywhere we go. Overall, I’d give this place a 6.5/10.

Reviewed on Aug 8, 2025

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Isla Holbox first class flight packages

Price found within the past 48 hours. Click for updated prices.
Cancun Bay All Inclusive Hotel
3.5-star property

Cancun Bay All Inclusive Hotel

7.6/10 Good! (1,245 reviews)

Oct 31 - Nov 7

7 night stay

Chicago (CHI) to Cancun (CUN)

United • Roundtrip • FirstClass
Save 100% on your flight
Price was $2,972, price is now $1,435 per person
$1,435
per person
found 1 day ago
The staff was amazing, food was great and had a variety of foods available. The room was small but for the time we stayed, it was doable. The surrounding areas were beautiful and well maintained. They played games during the day and had entertainment at night, which was always fun. Small hotel, but you were never bored. I would definitely come back here.

Reviewed on Aug 1, 2025

Chablé Maroma
5.0-star property

Chablé Maroma

9.4/10 Exceptional! (150 reviews)

Oct 31 - Nov 7

7 night stay

Chicago (CHI) to Cancun (CUN)

United • Roundtrip • FirstClass
Price was $7,086, price is now $3,412 per person
$3,412
per person
found 1 day ago
Everything was amazing! The daily breakfast that was included was absolutely delicious! We highly recommend the French fries and guacamole pool side as well. Luis, our pool side attendant and Aram, our concierge, were top notch, along with everyone else that works there! Our only challenge was we weren’t aware it was a cashless resort, so we weren’t able to break our big bills for individual tips. We recommend you bring small bills ($1’s and $5’s) for tipping purposes!

Reviewed on Jul 24, 2022

Hotel NYX Cancun All Inclusive
3.5-star property

Hotel NYX Cancun All Inclusive

8.6/10 Excellent! (1,500 reviews)

Oct 31 - Nov 7

7 night stay

Chicago (CHI) to Cancun (CUN)

United • Roundtrip • FirstClass
Save 100% on your flight
Price was $3,704, price is now $1,855 per person
$1,855
per person
found 1 day ago
Efrain is a great server helpful person ! Nayely waitress captain is really sweet owesome person

Reviewed on Aug 27, 2025

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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
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Isla Holbox

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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.