$99 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 7 - Thu, Jun 12
ORD
O'Hare Intl.
CUN
Cancun Intl.
$257 Roundtrip, just found
$257
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Jun 7 from O'Hare Intl. to Cancun Intl., returning Thu, Jun 12, priced at $257 just found
Sat, Jun 7 - Wed, Jun 11
ORD
O'Hare Intl.
TQO
Tulum Intl. Airport
$309 Roundtrip, found 9 hours ago
$309
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Sat, Jun 7 from O'Hare Intl. to Tulum Intl. Airport, returning Wed, Jun 11, priced at $309 found 9 hours ago
Sun, Jun 8 - Sun, Jun 15
MDW
Midway Intl.
CUN
Cancun Intl.
$329 Roundtrip, found 14 hours ago
$329
Roundtrip
found 14 hours ago
Select Southwest Airlines flight, departing Sun, Jun 8 from Midway Intl. to Cancun Intl., returning Sun, Jun 15, priced at $329 found 14 hours ago
Sun, Jun 8 - Sun, Jun 15
ORD
O'Hare Intl.
CZM
Cozumel Intl.
$680 Roundtrip, found 2 days ago
$680
Roundtrip
found 2 days ago
Select United flight, departing Sun, Jun 8 from O'Hare Intl. to Cozumel Intl., returning Sun, Jun 15, priced at $680 found 2 days ago

Airfares from $99 One Way, $225 Round Trip from Chicago to Riviera Maya

Prices starting at $225 for return flights and $99 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.

Sat, Jul 5 - Fri, Jul 11
ORD
Chicago
CUN
Cancun
$225 Roundtrip, just found
$225
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Jul 5 from Chicago to Cancun, returning Fri, Jul 11, priced at $225 just found
Sat, Jul 19 - Thu, Jul 24
ORD
Chicago
CUN
Cancun
$229 Roundtrip, found 1 hour ago
$229
Roundtrip
found 1 hour ago
Select Funjet Vacations flight, departing Sat, Jul 19 from Chicago to Cancun, returning Thu, Jul 24, priced at $229 found 1 hour ago
Sun, Jun 15 - Wed, Jun 18
MDW
Chicago
CUN
Cancun
$267 Roundtrip, found 4 hours ago
$267
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Sun, Jun 15 from Chicago to Cancun, returning Wed, Jun 18, priced at $267 found 4 hours ago
Fri, Sep 12 - Tue, Sep 16
ORD
Chicago
CUN
Cancun
$267 Roundtrip, found 5 hours ago
$267
Roundtrip
found 5 hours ago
Select United flight, departing Fri, Sep 12 from Chicago to Cancun, returning Tue, Sep 16, priced at $267 found 5 hours ago
Sun, Sep 7 - Fri, Sep 12
ORD
Chicago
CUN
Cancun
$269 Roundtrip, found 1 hour ago
$269
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Sun, Sep 7 from Chicago to Cancun, returning Fri, Sep 12, priced at $269 found 1 hour ago

Riviera Maya economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Royal Haciendas All Inclusive
4.0-star property

The Royal Haciendas All Inclusive

8.6/10 Excellent! (1,806 reviews)

Jul 18 - Jul 25

7 night stay

Chicago (CHI) to Cancun (CUN)

Southwest Airlines • Coach

Cancun (CUN) to Chicago (CHI)

Spirit Airlines • Coach
per person
found 1 day ago
Staff were welcoming, very friendly, and accommodating. Resort was clean and well Maintained. Variety of activities available.

Reviewed on Apr 12, 2025

Grand Palladium Kantenah Resort & Spa All Inclusive
4.0-star property

Grand Palladium Kantenah Resort & Spa All Inclusive

8/10 Very Good! (1,002 reviews)

Jul 18 - Jul 25

7 night stay

Chicago (CHI) to Cancun (CUN)

Southwest Airlines • Coach

Cancun (CUN) to Chicago (CHI)

Spirit Airlines • Coach
per person
found 1 day ago
1. Se necesita habilidad apagar la luz en baño. 2. Se necesita habilidad tapar la luz del termostato durante tiempo de dormir. 3. Ofrecer misa o servicios religiosos durante la semana. 4. Poner Biblias en las habitaciones.

Reviewed on Dec 31, 2024

Ventus at Marina El Cid Spa & Beach Resort - All Inclusive
4.0-star property

Ventus at Marina El Cid Spa & Beach Resort - All Inclusive

8.6/10 Excellent! (1,373 reviews)

Jul 18 - Jul 25

7 night stay

Chicago (CHI) to Cancun (CUN)

Southwest Airlines • Coach

Cancun (CUN) to Chicago (CHI)

Spirit Airlines • Coach
per person
found 1 day ago
Absolutely amazing stay, food was great, pools were great, staff was unbelievable.

Reviewed on May 19, 2025

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Riviera Maya packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
The Royal Cancun All Villas Resort - All Inclusive
4.0-star property

The Royal Cancun All Villas Resort - All Inclusive

8.8/10 Excellent! (1,029 reviews)

Jul 4 - Jul 9

5 night stay

Chicago (MDW) to Cancun (CUN)

Aeromexico • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
per person
found 1 day ago
Really liked that the beach is close to hotel. Not a Hugh sprawling resort which makes getting around easy. All the staff extremely kind. The bed was hard. No wave action.

Reviewed on May 19, 2025

Finest Playa Mujeres by The Excellence Collection - All Inclusive
5.0-star property

Finest Playa Mujeres by The Excellence Collection - All Inclusive

9/10 Wonderful! (1,194 reviews)

Jul 4 - Jul 9

5 night stay

Chicago (MDW) to Cancun (CUN)

Aeromexico • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
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

Villa del Palmar Cancun All Inclusive Beach Resort & Spa
4.5-star property

Villa del Palmar Cancun All Inclusive Beach Resort & Spa

8.8/10 Excellent! (1,528 reviews)

Jul 4 - Jul 9

5 night stay

Chicago (MDW) to Cancun (CUN)

Aeromexico • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
per person
found 1 day ago
The property was OK a few things that I didn’t like No welcome drink like other resorts or hotels as soon as you walk in, the buffet was very limited on food. The steak restaurant is very minimal had no taste at all. The Italian restaurant was fantastic. That was our best place for breakfast. We only did room service due to having an infant and not wanting to wake up early. When we were out at the beach, the waitress service was limited as well. They were not attentive as other waiters at other resorts. The food at the snack bar was minimal and OK. I like this resort just because it was far away from the others and the waters were great But out of 10 I will definitely rate this at a four compared to other resorts out there the ferry as well was a big thing why we got their clothes was because we can go to Isla‘s very faster, but that ferry is a cargo ferry and it’s only three times it leaves so keep in mind in that they do not advertise that part. There’s no shopping around. I wanted to do some shopping at least at different stores, but not a lot of nightlife so I figured this would be a good resort but definitely wrong. I kind of recommend it. I guess you would have to stay to take your own review.

Reviewed on May 16, 2025

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Riviera Maya business class flight packages

Price found within the past 48 hours. Click for updated prices.
Temptation Cancun Resort All Inclusive - Adults Only
4.5-star property

Temptation Cancun Resort All Inclusive - Adults Only

8.8/10 Excellent! (3,895 reviews)

Jul 7 - Jul 13

6 night stay

Chicago (ORD) to Cancun (CUN)

American Airlines • Roundtrip • BusinessClass
Save 100% on your flight
per person
found 1 hour ago
The food was good, the people in the hotel were very friendly, dinner was great and the show was very entertaining and it was fun to watch it….

Reviewed on Feb 18, 2025

Grand Fiesta Americana Coral Beach Cancun - All Inclusive
5.0-star property

Grand Fiesta Americana Coral Beach Cancun - All Inclusive

9.2/10 Wonderful! (3,668 reviews)

Jul 7 - Jul 13

6 night stay

Chicago (ORD) to Cancun (CUN)

American Airlines • Roundtrip • BusinessClass
per person
found 1 hour ago
The staff is super nice and the property is really clean. I did have some issues with the TV not working in my room, the safe did not work and the key fob would sometimes not open the door and making me walk across a pretty large hotel to the concierge. The fridge in my room was leaking and unfortunately it’s like a fight to try and make reservations for the restaurants which they don’t allow you to do until you arrive and we could not make all the reservations we wanted as they were already booked. I was finally able to get a reservation and I ate something that was not good and spend one full day in horrible pain vomiting and diarrhea. Hopefully the next person experience is better than mine.

Reviewed on May 21, 2025

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! (530 reviews)

Jul 7 - Jul 13

6 night stay

Chicago (ORD) to Cancun (CUN)

American Airlines • Roundtrip • BusinessClass
Save 100% on your flight
per person
found 1 hour 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

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Riviera Maya first class flight packages

Price found within the past 48 hours. Click for updated prices.
Grand Residences Riviera Cancún All Inclusive
5.0-star property

Grand Residences Riviera Cancún All Inclusive

9.4/10 Exceptional! (1,017 reviews)

Jul 14 - Jul 18

4 night stay

Chicago (ORD) to Cancun (CUN)

American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
per person
found 16 hours ago
This is a very quiet and elegant place. It VERY small, so if you’re wanting variety for your day or view… this is not the place to go. Just 1 big pool and a small beach and One main restaurant. But everything was awesome if that’s what you’re wanting.

Reviewed on Mar 22, 2025

Occidental at Xcaret Destination - All Inclusive
4.0-star property

Occidental at Xcaret Destination - All Inclusive

8.2/10 Very Good! (4,279 reviews)

Jul 2 - Jul 7

5 night stay

Chicago (ORD) to Cancun (CUN)

American Airlines • Non-stop roundtrip • FirstClass
per person
found 22 hours ago
The complex overall was very beautiful however, when we first arrived, the check-in service was very poor no signage they wouldn’t allow you to keep your car out front while you were checking in and then we had to go to another building to actually do the check-in which took about an hour the complex was so large and they had very few or poorly communicated signs to find your way around. It was easy to get lost and to get from one point to another point they had a shuttle, but only one and it would take 30 minutes to come by. they had many pools. The water was great. The amenities of the pool was great however, you had to have a card to get a towel but if you didn’t turn your towel in before six, you wouldn’t get your card back and you’d be charged for the towel finally constant pressure to buy a timeshare or spend your vacation touring and listening to them promote itself the hotel timeshare. It was annoying.

Reviewed on May 31, 2025

Finest Playa Mujeres by The Excellence Collection - All Inclusive
5.0-star property

Finest Playa Mujeres by The Excellence Collection - All Inclusive

9/10 Wonderful! (1,194 reviews)

Jul 14 - Jul 18

4 night stay

Chicago (ORD) to Cancun (CUN)

American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
per person
found 16 hours 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

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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.

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