$89 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, Nov 8 - Fri, Nov 21
ORD
O'Hare Intl.
CUN
Cancun Intl.
$210 Roundtrip, just found
$210
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Nov 8 from O'Hare Intl. to Cancun Intl., returning Fri, Nov 21, priced at $210 just found
Sun, Nov 9 - Thu, Nov 13
MDW
Midway Intl.
CUN
Cancun Intl.
$314 Roundtrip, found 1 day ago
$314
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sun, Nov 9 from Midway Intl. to Cancun Intl., returning Thu, Nov 13, priced at $314 found 1 day ago
Sun, Nov 9 - Thu, Nov 13
RFD
Greater Rockford
CUN
Cancun Intl.
$383 Roundtrip, found 3 days ago
$383
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sun, Nov 9 from Greater Rockford to Cancun Intl., returning Thu, Nov 13, priced at $383 found 3 days ago

Airfares from $89 One Way, $200 Round Trip from Chicago to Isla Holbox

Prices starting at $200 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.

Sat, Nov 15 - Thu, Nov 20
ORD
Chicago
CUN
Cancun
$200 Roundtrip, just found
$200
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Nov 15 from Chicago to Cancun, returning Thu, Nov 20, priced at $200 just found
Mon, Nov 24 - Sat, Dec 6
ORD
Chicago
CUN
Cancun
$213 Roundtrip, found 20 hours ago
$213
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Mon, Nov 24 from Chicago to Cancun, returning Sat, Dec 6, priced at $213 found 20 hours ago
Sun, Nov 9 - Thu, Nov 13
ORD
Chicago
CUN
Cancun
$229 Roundtrip, just found
$229
Roundtrip
just found
Select Funjet Vacations flight, departing Sun, Nov 9 from Chicago to Cancun, returning Thu, Nov 13, priced at $229 just found
Mon, Jan 26 - Thu, Jan 29
ORD
Chicago
CUN
Cancun
$252 Roundtrip, found 1 day ago
$252
Roundtrip
found 1 day ago
Select United flight, departing Mon, Jan 26 from Chicago to Cancun, returning Thu, Jan 29, priced at $252 found 1 day ago
Wed, Mar 11 - Tue, Mar 17
ORD
Chicago
CUN
Cancun
$262 Roundtrip, found 1 hour ago
$262
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Wed, Mar 11 from Chicago to Cancun, returning Tue, Mar 17, priced at $262 found 1 hour ago

Isla Holbox economy flight packages

Price found within the past 48 hours. Click for updated prices.
Naay Boutique Hotel
4.0-star property

Naay Boutique Hotel

8.4/10 Very Good! (192 reviews)

Dec 13 - Dec 17

4 night stay

Chicago (CHI) to Cancun (CUN)

Frontier Airlines • Roundtrip • Coach
Price was $1,079, price is now $416 per person
$416
per person
found 1 day ago
Amazing and beautiful property! Thank you!

Reviewed on Sep 3, 2024

AWA Holbox Hotel Boutique - Beach Front
4.0-star property

AWA Holbox Hotel Boutique - Beach Front

9.4/10 Exceptional! (349 reviews)

Dec 17 - Dec 24

7 night stay

Chicago (CHI) to Cancun (CUN)

Frontier Airlines • Roundtrip • Coach
Price was $2,744, price is now $1,157 per person
$1,157
per person
found 1 day ago
Edwardo was a great receptionist, the area of the property is amazing and the food was great.

Reviewed on Aug 3, 2024

Beachscape Kin ha Villas & Suites
3.5-star property

Beachscape Kin ha Villas & Suites

8.6/10 Excellent! (1,904 reviews)

Nov 30 - Dec 7

7 night stay

Chicago (CHI) to Cancun (CUN)

Frontier Airlines • Roundtrip • Coach
Price was $1,815, price is now $769 per person
$769
per person
found 1 day ago
Great location, close to restaurants and grocery store. Clean property and friendly staff. Food at the restaurant was good. Actual property not nearly as nice as the photos, very dated.

Reviewed on Jun 19, 2025

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Isla Holbox business class flight packages

Price found within the past 48 hours. Click for updated prices.
The Fives Oceanfront Riviera Maya - All Inclusive Optional
4.5-star property

The Fives Oceanfront Riviera Maya - All Inclusive Optional

8.8/10 Excellent! (417 reviews)

Dec 8 - Dec 16

8 night stay

Chicago (CHI) to Cancun (CUN)

American Airlines • Roundtrip • BusinessClass
Price was $6,198, price is now $2,408 per person
$2,408
per person
found 1 day ago
We were having an excellent experience. People like Andres in the Romarley restaurant made our stay incredibly special. The food is nice and the place is beautiful. Nevertheless staying there feels like a teenager staying at their parents' house. I invited a friend over to co-work and I was made to pay around $100 to grant her access to the hotel and despite being very clear we would work, and they have no suitable working space so we would be in my room to take some zoom calls, they came upstairs to insist that she should not be allowed in my room at all. Additionally, they provide no support in day care or recommending nannies, and when hiring a nanny to take care of your kids you will also be made to pay a fee. Basically they do not state this anywhere but if you go to this hotel you can forget about having guests unless you want a very harsh treatment and to be made to pay and still be harassed about it.

Reviewed on Aug 28, 2024

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)

Dec 8 - Dec 16

8 night stay

Chicago (CHI) to Cancun (CUN)

American Airlines • Roundtrip • BusinessClass
Price was $10,482, price is now $5,008 per person
$5,008
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

Chablé Maroma
5.0-star property

Chablé Maroma

9.4/10 Exceptional! (154 reviews)

Dec 8 - Dec 16

8 night stay

Chicago (CHI) to Cancun (CUN)

American Airlines • Roundtrip • BusinessClass
Price was $6,849, price is now $3,308 per person
$3,308
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

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Isla Holbox first class flight packages

Price found within the past 48 hours. Click for updated prices.
The Pyramid Cancun By Oasis - All Inclusive
4.0-star property

The Pyramid Cancun By Oasis - All Inclusive

7.2/10 Good! (1,513 reviews)

Dec 6 - Dec 13

7 night stay

Chicago (CHI) to Cancun (CUN)

American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $2,809, price is now $1,443 per person
$1,443
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

The Beachfront by The Fives Hotels - A la Carte All Inclusive Adults Only
4.0-star property

The Beachfront by The Fives Hotels - A la Carte All Inclusive Adults Only

9.6/10 Exceptional! (99 reviews)

Dec 5 - Dec 10

5 night stay

Chicago (ORD) to Cancun (CUN)

American Airlines • Non-stop roundtrip • FirstClass
Price was $6,279, price is now $1,814 per person
$1,814
per person
found 1 day ago
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)

Dec 1 - Dec 5

4 night stay

Chicago (ORD) to Cancun (CUN)

American Airlines • Roundtrip • FirstClass
Price was $5,421, price is now $2,761 per person
$2,761
per person
found 20 hours 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

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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.