$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.
ORD
O'Hare Intl.
CUN
Cancun Intl.
$199 Roundtrip, found 7 hours ago
$199
Roundtrip
found 7 hours ago
MDW
Midway Intl.
CUN
Cancun Intl.
$314 Roundtrip, found 1 day ago
$314
Roundtrip
found 1 day ago
RFD
Greater Rockford
CUN
Cancun Intl.
$383 Roundtrip, found 3 days ago
$383
Roundtrip
found 3 days ago
Airfares from $89 One Way, $199 Round Trip from Chicago to Isla Holbox
Prices starting at $199 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.
ORD
Chicago
CUN
Cancun
$199 Roundtrip, found 6 hours ago
$199
Roundtrip
found 6 hours ago
ORD
Chicago
CUN
Cancun
$200 Roundtrip, found 11 hours ago
$200
Roundtrip
found 11 hours ago
ORD
Chicago
CUN
Cancun
$229 Roundtrip, found 1 hour ago
$229
Roundtrip
found 1 hour ago
ORD
Chicago
CUN
Cancun
$252 Roundtrip, found 12 hours ago
$252
Roundtrip
found 12 hours ago
ORD
Chicago
CUN
Cancun
$252 Roundtrip, found 20 hours ago
$252
Roundtrip
found 20 hours ago
Isla Holbox economy flight packages
Price found within the past 48 hours. Click for updated prices.
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
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
3.5-star property
Beachfront Hotel Boutique DK
9.6/10 Exceptional! (54 reviews)
Dec 17 - Dec 24
7 night stay
Chicago (CHI) to Cancun (CUN)
Frontier Airlines • Roundtrip • Coach
Price was $1,819, price is now $811 per person
$811
per person
found 1 day ago
The property is beautiful and the beach in front of it amazing!
Reviewed on Aug 20, 2025
Isla Holbox packages with premium economy flights
Price found within the past 48 hours. Click for updated prices.
4.0-star property
GR Solaris Cancun & Spa - All Inclusive
8/10 Very Good! (4,661 reviews)
Dec 11 - Dec 18
7 night stay
Chicago (CHI) to Cancun (CUN)
American Airlines • PremiumEconomy
Cancun (CUN) to Chicago (CHI)
Spirit Airlines • PremiumEconomy
Save 100% on your flight
Price was $2,107, price is now $1,197 per person
$1,197
per person
found 1 day ago
The Air Conditioner Leaked water all over the floor daily
Reviewed on Oct 9, 2025
4.5-star property
Hard Rock Hotel Cancun - All Inclusive
7.8/10 Good! (1,307 reviews)
Dec 11 - Dec 18
7 night stay
Chicago (CHI) to Cancun (CUN)
American Airlines • PremiumEconomy
Cancun (CUN) to Chicago (CHI)
Spirit Airlines • PremiumEconomy
Save 100% on your flight
Price was $3,864, price is now $2,031 per person
$2,031
per person
found 1 day ago
Room was a little dated and worn. Staff were excellent.
Reviewed on Oct 29, 2025
5.0-star property
Finest Playa Mujeres by The Excellence Collection - All Inclusive
9/10 Wonderful! (1,452 reviews)
Dec 11 - Dec 18
7 night stay
Chicago (CHI) to Cancun (CUN)
American Airlines • PremiumEconomy
Cancun (CUN) to Chicago (CHI)
Spirit Airlines • PremiumEconomy
Save 100% on your flight
Price was $3,623, price is now $1,914 per person
$1,914
per person
found 1 day ago
Beautiful property. Plenty of dining options, service is exceptional. Travelled with a toddler. Felt safe as a family. Room was dated, but mostly comfortable. Several different pools around the property. All were easy to access except the main pool which was challenging/near impossible to get seats at unless you claimed some before 10am. Beach was beautiful. Entertainment was fun.
Reviewed on May 14, 2025
Isla Holbox business class flight packages
Price found within the past 48 hours. Click for updated prices.
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 18 hours 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
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 18 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
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 20 hours 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
Isla Holbox first class flight packages
Price found within the past 48 hours. Click for updated prices.
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
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 20 hours ago
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 12 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
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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Isla Holbox Airports
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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.