$147 Cheap flight deals from Chicago (CHI) to Riviera Maya (CUN)

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This Weekend's Flight Deals from Chicago to Riviera Maya

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, Jun 27 - Wed, Jul 1
ORD
O'Hare Intl.
CUN
Cancun Intl.
$506 Roundtrip, found 9 hours ago
$506
Roundtrip
found 9 hours ago
Select Volaris flight, departing Sat, Jun 27 from O'Hare Intl. to Cancun Intl., returning Wed, Jul 1, priced at $506 found 9 hours ago
Sun, Jun 28 - Sun, Jul 26
MDW
Midway Intl.
CUN
Cancun Intl.
$552 Roundtrip, found 8 hours ago
$552
Roundtrip
found 8 hours ago
Select Southwest Airlines flight, departing Sun, Jun 28 from Midway Intl. to Cancun Intl., returning Sun, Jul 26, priced at $552 found 8 hours ago
Sat, Jun 27 - Fri, Jul 3
ORD
O'Hare Intl.
TQO
Tulum Intl. Airport
$577 Roundtrip, found 1 day ago
$577
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Jun 27 from O'Hare Intl. to Tulum Intl. Airport, returning Fri, Jul 3, priced at $577 found 1 day ago
Sat, Jun 27 - Mon, Jul 13
RFD
Greater Rockford
CUN
Cancun Intl.
$665 Roundtrip, found 6 days ago
$665
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, Jun 27 from Greater Rockford to Cancun Intl., returning Mon, Jul 13, priced at $665 found 6 days ago

Airfares from $147 One Way, $335 Round Trip from Chicago to Riviera Maya

Prices starting at $335 for return flights and $147 for one-way flights to Riviera Maya were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Aug 26 - Thu, Sep 3
ORD
Chicago
CUN
Cancun
$335 Roundtrip, found 8 hours ago
$335
Roundtrip
found 8 hours ago
Select Volaris flight, departing Wed, Aug 26 from Chicago to Cancun, returning Thu, Sep 3, priced at $335 found 8 hours ago
Tue, Aug 4 - Thu, Aug 13
ORD
Chicago
CUN
Cancun
$349 Roundtrip, found 11 hours ago
$349
Roundtrip
found 11 hours ago
Select Funjet Vacations flight, departing Tue, Aug 4 from Chicago to Cancun, returning Thu, Aug 13, priced at $349 found 11 hours ago
Thu, Feb 25 - Sun, Feb 28
ORD
Chicago
CUN
Cancun
$350 Roundtrip, found 2 hours ago
$350
Roundtrip
found 2 hours ago
Select Viva flight, departing Thu, Feb 25 from Chicago to Cancun, returning Sun, Feb 28, priced at $350 found 2 hours ago
Tue, Aug 11 - Thu, Aug 20
MDW
Chicago
CUN
Cancun
$372 Roundtrip, found 21 hours ago
$372
Roundtrip
found 21 hours ago
Select Southwest Airlines flight, departing Tue, Aug 11 from Chicago to Cancun, returning Thu, Aug 20, priced at $372 found 21 hours ago
Sat, Jan 23 - Sat, Feb 6
ORD
Chicago
CZM
Cozumel
$377 Roundtrip, found 1 day ago
$377
Roundtrip
found 1 day ago
Select Volaris flight, departing Sat, Jan 23 from Chicago to Cozumel, returning Sat, Feb 6, priced at $377 found 1 day ago

Riviera Maya economy flight packages

Price found within the past 48 hours. Click for updated prices.
Ocean Dream Cancun by GuruHotel
3.0-star property

Ocean Dream Cancun by GuruHotel

7.6/10 Good! (1,043 reviews)

Jul 24 - Jul 30

6 night stay

Chicago (CHI) to Cancun (CUN)

Roundtrip • Coach
Price was $2,162, price is now $821 per person
$821
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

Tago Tulum by G Hotels
3.5-star property

Tago Tulum by G Hotels

9.2/10 Wonderful! (422 reviews)

Aug 7 - Aug 15

8 night stay

Chicago (CHI) to Cancun (CUN)

Volaris • Non-stop roundtrip • Coach
Price was $4,029, price is now $1,521 per person
$1,521
per person
found 1 day ago
Its all about the Staff here in addition to the splendid property and food!

Reviewed on Jun 23, 2024

Azucar Hotel Tulum
4.0-star property

Azucar Hotel Tulum

9.6/10 Exceptional! (5 reviews)

Jul 30 - Aug 6

7 night stay

Chicago (ORD) to Cancun (CUN)

United • Roundtrip • Coach
Price was $2,676, price is now $1,166 per person
$1,166
per person
found 11 hours ago
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Riviera Maya packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Fiesta Americana Cancun Villas
4.0-star property

Fiesta Americana Cancun Villas

8.6/10 Excellent! (1,141 reviews)

Aug 2 - Aug 8

6 night stay

Chicago (ORD) to Cancun (CUN)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,760, price is now $1,045 per person
$1,045
per person
found 6 hours ago
Staff were very nice and polite. Pool was clean and weel maintained Room was spacious

Reviewed on May 20, 2026

Seadust Cancún Beach Resort All Inclusive
3.5-star property

Seadust Cancún Beach Resort All Inclusive

7.4/10 Good! (3,468 reviews)

Aug 2 - Aug 8

6 night stay

Chicago (ORD) to Cancun (CUN)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,773, price is now $1,531 per person
$1,531
per person
found 6 hours ago
I’m a real traveler from Arkansas went with a family of 4. I’ll start off with the good and then get into the real cons. The cleaning staff for the rooms was amazing. Cons- the kids play area advertised as indoor has no ac at all. It’s also under the hotel and barely any ventilation. There’s fans but they do not help the little ones. I was standing there sweating. The restaurants don’t open up till 6pm. Other than that you have the same buffet or the one restaurant open. There’s another restaurant that only opens from 12-4 which is crazy because family’s have different routines makes it a bit difficult. Lastly this reason is the one that I will not be coming back nor recommending this hotel. The infinity luxury scheme they have going on. They will reel you in and try to sell you on this travel the world package. Sales people were very pushy and make us feel so uncomfortable. It didn’t stop there they have these workers in blue shirts in the lobby 24/7 trying to set up appointments and reel you in to go get sold by the infinity luxury sales people. I couldn’t hang out in the lobby without being bothered by them. Oh did I mention they have this amazing breakfast restaurant exclusively if you become a infinity luxury membership? Yes seems like the hotel is in with the whole thing. It’s very unfortunate. Feels like they want to take advantage of us instead of make us feel relaxed on vacation. Will not be coming back.

Reviewed on Apr 24, 2026

Hotel Riu Palace Kukulkan - Adults Only - All Inclusive
4.5-star property

Hotel Riu Palace Kukulkan - Adults Only - All Inclusive

9.2/10 Wonderful! (5,077 reviews)

Jul 24 - Jul 28

4 night stay

Chicago (CHI) to Cancun (CUN)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,244, price is now $1,244 per person
$1,244
per person
found 1 day ago
Our stay was very elegant and so relaxing! The food was good each night, and the best part is that you could choose which restaurant you wanted to dine in and not just buffet. They have some type of entertainment ever night. An there pool area is great. There are several nights where they have parties away from your location to one of their other Riu resorts to have fun!!!!

Reviewed on Jun 19, 2026

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Riviera Maya business class flight packages

Price found within the past 48 hours. Click for updated prices.
Krystal Cancun All Inclusive
4.0-star property

Krystal Cancun All Inclusive

7.6/10 Good! (1,368 reviews)

Aug 3 - Aug 8

5 night stay

Chicago (CHI) to Cancun (CUN)

United • BusinessClass

Cancun (CUN) to Chicago (CHI)

Frontier Airlines • BusinessClass
Save 100% on your flight
Price was $2,231, price is now $1,290 per person
$1,290
per person
found 23 hours ago
Everything excellent

Reviewed on May 24, 2026

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)

Aug 4 - Aug 9

5 night stay

Chicago (ORD) to Cancun (CUN)

United • BusinessClass

Cancun (CUN) to Chicago (ORD)

Frontier Airlines • BusinessClass
Price was $5,633, price is now $2,625 per person
$2,625
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

Hotel Mousai Cancun Adults Only - All Inclusive
5.0-star property

Hotel Mousai Cancun Adults Only - All Inclusive

9.6/10 Exceptional! (118 reviews)

Aug 4 - Aug 9

5 night stay

Chicago (ORD) to Cancun (CUN)

United • BusinessClass

Cancun (CUN) to Chicago (ORD)

Frontier Airlines • BusinessClass
Save 100% on your flight
Price was $4,762, price is now $2,665 per person
$2,665
per person
found 18 hours ago
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Riviera Maya first class flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Palace Kukulkan - Adults Only - All Inclusive
4.5-star property

Hotel Riu Palace Kukulkan - Adults Only - All Inclusive

9.2/10 Wonderful! (5,077 reviews)

Aug 11 - Aug 17

6 night stay

Chicago (CHI) to Cancun (CUN)

United • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $3,263, price is now $1,775 per person
$1,775
per person
found 1 day ago
Our stay was very elegant and so relaxing! The food was good each night, and the best part is that you could choose which restaurant you wanted to dine in and not just buffet. They have some type of entertainment ever night. An there pool area is great. There are several nights where they have parties away from your location to one of their other Riu resorts to have fun!!!!

Reviewed on Jun 19, 2026

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)

Aug 11 - Aug 17

6 night stay

Chicago (CHI) to Cancun (CUN)

United • Non-stop roundtrip • FirstClass
Price was $6,458, price is now $3,041 per person
$3,041
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

Palmaïa-The House of AïA: All Inclusive Wellness Resort
5.0-star property

Palmaïa-The House of AïA: All Inclusive Wellness Resort

9.8/10 Exceptional! (640 reviews)

Aug 11 - Aug 17

6 night stay

Chicago (CHI) to Cancun (CUN)

United • Non-stop roundtrip • FirstClass
Price was $6,194, price is now $3,170 per person
$3,170
per person
found 1 day ago
Exceptional service from the minute I arrived at the reception, desk until the minute I left. I came here as a solo traveler over my birthday. This resort had been on my radar for a few years and I’m so glad I finally booked it - I have traveled the world and it’s such a unique and beautiful space. I have never been one to choose an all inclusive, but the reviews made me want to try it. And I hate to even use that term for a property of this caliber. The food and drinks are incredible. The property is serene and immaculate, and the beach is swimmable and gorgeous. Thanks to everyone. I’ll definitely be back!

Reviewed on Mar 17, 2025

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More About Flying To Riviera Maya from Chicago

Route Information for Flights from Chicago to Riviera Maya

Origin Airport IATA Code
CHI
Destination Airport IATA Code
CUN
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Riviera Maya

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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.