$93 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.
$209 Roundtrip, just found
$209
Roundtrip
just found
MDW
Midway Intl.
CUN
Cancun Intl.
$307 Roundtrip, found 4 hours ago
$307
Roundtrip
found 4 hours ago
RFD
Greater Rockford
CUN
Cancun Intl.
$405 Roundtrip, found 3 days ago
$405
Roundtrip
found 3 days ago
Airfares from $93 One Way, $200 Round Trip from Chicago to Isla Holbox
Prices starting at $200 for return flights and $93 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
$200 Roundtrip, just found
$200
Roundtrip
just found
ORD
Chicago
CUN
Cancun
$209 Roundtrip, found 1 day ago
$209
Roundtrip
found 1 day ago
ORD
Chicago
CUN
Cancun
$229 Roundtrip, found 2 hours ago
$229
Roundtrip
found 2 hours ago
MDW
Chicago
CUN
Cancun
$265 Roundtrip, found 1 day ago
$265
Roundtrip
found 1 day ago
ORD
Chicago
CUN
Cancun
$288 Roundtrip, found 1 day ago
$288
Roundtrip
found 1 day ago
Isla Holbox economy flight packages
Price found within the past 48 hours. Click for updated prices.
3.0-star property
Ocean Dream Cancun by GuruHotel
7.4/10 Good! (1,000 reviews)
Mar 7 - Mar 11
4 night stay
Chicago (CHI) to Cancun (CUN)
Spirit Airlines • Coach
Cancun (CUN) to Chicago (CHI)
Frontier Airlines • Coach
Price was $1,613, price is now $593 per person
$593
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Room service phone did not work, TVs are outdated and bathroom was clogged Other than that it was okay Loved that it’s very well located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
3.5-star property
Seadust Cancún All Inclusive Family Resort
7.6/10 Good! (2,675 reviews)
Mar 4 - Mar 9
5 night stay
Chicago (CHI) to Cancun (CUN)
Spirit Airlines • Non-stop roundtrip • Coach
Price was $2,138, price is now $949 per person
$949
per person
found 1 day ago
The staff members were exceptional. The rooms were clean. The restaurant staffs were exceptional. We had a beautiful view of the sea. Excellent choice for an adult or family all inclusive stay.
Reviewed on Jan 29, 2026
4.0-star property
Wyndham Grand Cancun All Inclusive Resort & Villas
8.4/10 Very Good! (3,498 reviews)
Mar 9 - Mar 14
5 night stay
Chicago (CHI) to Cancun (CUN)
Frontier Airlines • Roundtrip • Coach
Price was $2,702, price is now $1,233 per person
$1,233
per person
found 1 day ago
Clean rooms. Very courteous staff.
Excellent facilities.
Reviewed on Jan 1, 2026
Isla Holbox packages with premium economy flights
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Wyndham Grand Cancun All Inclusive Resort & Villas
8.4/10 Very Good! (3,498 reviews)
Mar 9 - Mar 13
4 night stay
Chicago (MDW) to Cancun (CUN)
Aeromexico • Non-stop roundtrip • PremiumEconomy
Price was $3,142, price is now $2,060 per person
$2,060
per person
found 6 hours ago
Clean rooms. Very courteous staff.
Excellent facilities.
Reviewed on Jan 1, 2026
5.0-star property
Excellence Riviera Cancun - Adults Only All Inclusive
9.4/10 Exceptional! (1,915 reviews)
Mar 9 - Mar 13
4 night stay
Chicago (MDW) to Cancun (CUN)
Aeromexico • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $5,302, price is now $3,232 per person
$3,232
per person
found 6 hours ago
Great food and drinks, great service, and very clean. The shows at night were also really good, almost Vegas quality. We had a great time and will definitely be back!
Reviewed on Dec 17, 2025
4.5-star property
Hotel Riu Palace Kukulkan - Adults Only - All Inclusive
9/10 Wonderful! (4,559 reviews)
Mar 9 - Mar 13
4 night stay
Chicago (MDW) to Cancun (CUN)
Aeromexico • Non-stop roundtrip • PremiumEconomy
Price was $3,657, price is now $2,374 per person
$2,374
per person
found 6 hours ago
Great stay - great location, food, beach, clean rooms, service and staff were amazing. They really do run a tight ship! Highly recommend :)
Reviewed on Jan 8, 2026
Isla Holbox business class flight packages
Price found within the past 48 hours. Click for updated prices.
5.0-star property
Grand Riviera Princess - All Inclusive
8/10 Very Good! (4,367 reviews)
Mar 8 - Mar 12
4 night stay
Chicago (CHI) to Cancun (CUN)
United • Roundtrip • BusinessClass
Save 100% on your flight
Price was $2,266, price is now $1,345 per person
$1,345
per person
found 1 day ago
The property Is still under renovation and the rooms still need to be updated we had a 32in old school tv that stood on the dresser the jetted tub was not clean it had a rust ring around it as well as the jets had rust…room service is not included in your stay it’s an additional charge and if you don’t get reservations for a restaurant they get you a table if you buy a bottle…we basically ate at the buffets which was not bad the pasta and seafood options are good for those that do not eat meat like me…staff was friendly oh yea and the drinks are all watered down so make sure you buy a bottle at the hotel or order double shots on the side to add yourself
Reviewed on Oct 26, 2025
3.5-star property
Hotel NYX Cancun All Inclusive
8.6/10 Excellent! (1,625 reviews)
Mar 11 - Mar 15
4 night stay
Chicago (ORD) to Cancun (CUN)
American Airlines • Roundtrip • BusinessClass
Save 100% on your flight
Price was $3,058, price is now $1,700 per person
$1,700
per person
found 1 day ago
The property and staff were great. The room decor was a bit off. Our room was pretty big and certainly could have held two chairs, just a place to sit other than the bed would be nice. Several properties surrounding the immediate area seemed to be vacant and in disrepair, not the fault of NYX, just sad to see.
Reviewed on Oct 22, 2025
Isla Holbox first class flight packages
Price found within the past 48 hours. Click for updated prices.
3.0-star property
Pelicano Inn Playa del Carmen - Beachfront Hotel
8.2/10 Very Good! (324 reviews)
Mar 10 - Mar 17
7 night stay
Chicago (ORD) to Cancun (CUN)
United • Roundtrip • FirstClass
Save 100% on your flight
Price was $2,412, price is now $1,263 per person
$1,263
per person
found 2 days ago
Great stay! My only critique is for the Hotel to implement that the 24-hr security guard have access to the master key to rooms in the event an hotel guest accidentally locks themselves out of their room. This happened to me one night after the front desk was closed (which was 11p) and I couldn’t get back into my room until the front desk reopened at 7a. Luckily, I had a friend who was staying nearby and I was able to sleep there but I would have much rather stayed in the room I paid for. Nonetheless, I thoroughly enjoyed my stay and recommend it.
Reviewed on Apr 10, 2025
3.5-star property
Allegro Playacar - All Inclusive
7.8/10 Good! (1,001 reviews)
Mar 10 - Mar 17
7 night stay
Chicago (ORD) to Cancun (CUN)
United • Roundtrip • FirstClass
Save 100% on your flight
Price was $3,350, price is now $1,763 per person
$1,763
per person
found 2 days ago
Absolutely fabulous!
Reviewed on Jan 13, 2026
3.5-star property
Hotel NYX Cancun All Inclusive
8.6/10 Excellent! (1,625 reviews)
Mar 19 - Mar 24
5 night stay
Chicago (ORD) to Cancun (CUN)
American Airlines • Roundtrip • FirstClass
Save 100% on your flight
Price was $3,953, price is now $2,160 per person
$2,160
per person
found 1 day ago
The property and staff were great. The room decor was a bit off. Our room was pretty big and certainly could have held two chairs, just a place to sit other than the bed would be nice. Several properties surrounding the immediate area seemed to be vacant and in disrepair, not the fault of NYX, just sad to see.
Reviewed on Oct 22, 2025
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.