$183 Cheap flight deals from Chicago (CHI) to Riviera Maya (TUY)

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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, Oct 31 - Tue, Nov 3
ORD
O'Hare Intl.
CUN
Cancun Intl.
$459 Roundtrip, just found
$459
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Oct 31 from O'Hare Intl. to Cancun Intl., returning Tue, Nov 3, priced at $459 just found
Sun, Nov 1 - Thu, Nov 5
MDW
Midway Intl.
CUN
Cancun Intl.
$496 Roundtrip, just found
$496
Roundtrip
just found
Select Frontier Airlines flight, departing Sun, Nov 1 from Midway Intl. to Cancun Intl., returning Thu, Nov 5, priced at $496 just found
Sat, Oct 31 - Sun, Nov 8
ORD
O'Hare Intl.
TQO
Tulum Intl. Airport
$508 Roundtrip, just found
$508
Roundtrip
just found
Select Air Canada flight, departing Sat, Oct 31 from O'Hare Intl. to Tulum Intl. Airport, returning Sun, Nov 8, priced at $508 just found
Sat, Oct 31 - Sat, Nov 7
ORD
O'Hare Intl.
CZM
Cozumel Intl.
$622 Roundtrip, found 2 days ago
$622
Roundtrip
found 2 days ago
Select Air Canada flight, departing Sat, Oct 31 from O'Hare Intl. to Cozumel Intl., returning Sat, Nov 7, priced at $622 found 2 days ago

Airfares from $183 One Way, $349 Round Trip from Chicago to Riviera Maya

Prices starting at $349 for return flights and $183 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.

Fri, Dec 11 - Thu, Dec 17
ORD
Chicago
CUN
Cancun
$349 Roundtrip, just found
$349
Roundtrip
just found
Select Funjet Vacations flight, departing Fri, Dec 11 from Chicago to Cancun, returning Thu, Dec 17, priced at $349 just found
Wed, Dec 9 - Sat, Dec 19
ORD
Chicago
CUN
Cancun
$356 Roundtrip, found 4 days ago
$356
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Wed, Dec 9 from Chicago to Cancun, returning Sat, Dec 19, priced at $356 found 4 days ago
Tue, May 4 - Tue, May 11
ORD
Chicago
CUN
Cancun
$370 Roundtrip, found 4 hours ago
$370
Roundtrip
found 4 hours ago
Select Viva flight, departing Tue, May 4 from Chicago to Cancun, returning Tue, May 11, priced at $370 found 4 hours ago
Sun, Nov 15 - Thu, Nov 19
MDW
Chicago
CUN
Cancun
$408 Roundtrip, found 1 day ago
$408
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Nov 15 from Chicago to Cancun, returning Thu, Nov 19, priced at $408 found 1 day ago
Wed, Jan 27 - Wed, Feb 3
ORD
Chicago
CUN
Cancun
$417 Roundtrip, found 1 hour ago
$417
Roundtrip
found 1 hour ago
Select Volaris flight, departing Wed, Jan 27 from Chicago to Cancun, returning Wed, Feb 3, priced at $417 found 1 hour ago

Riviera Maya economy flight packages

Price found within the past 48 hours. Click for updated prices.
Kanan Tulum Hotel & Spa Adults Only Playground
4.0-star property

Kanan Tulum Hotel & Spa Adults Only Playground

9/10 Wonderful! (431 reviews)

Dec 2 - Dec 6

4 night stay

Chicago (CHI) to Cancun (CUN)

Delta • Non-stop • Coach

Cancun (CUN) to Chicago (CHI)

Air Canada • Non-stop • Coach
Price was $2,498, price is now $1,179 per person
$1,179
per person
found 1 day ago
Overall, we had a good stay at Hotel Kanan, and our room was absolutely amazing. However, the hotel itself felt a bit neglected and could definitely use some maintenance and extra attention. I understand that tourism may be slower right now, but I actually think this is the perfect opportunity to take care of the property and make improvements. One of our biggest disappointments was the beach. I completely understand that sargassum is a natural issue and difficult to control. However, there is a difference between dealing with seaweed and simply not maintaining the beach. We noticed trash sitting in the same spots for several days, and while neighboring hotels were actively cleaning up the seaweed and keeping their beaches tidy, here it seemed to be simply ignored or worked around. Breakfast was another disappointment. The options were underwhelming, and the food was quite bland and lacked flavor. It's a shame because the hotel has so much potential, and our room was truly wonderful. With better maintenance, more attention to cleanliness, and improvements to the breakfast, this could be a fantastic place to stay.

Reviewed on Oct 22, 2026

Hotel Riu Palace Peninsula - All Inclusive
4.0-star property

Hotel Riu Palace Peninsula - All Inclusive

9/10 Wonderful! (4,733 reviews)

Dec 14 - Dec 21

7 night stay

Chicago (CHI) to Cancun (CUN)

Delta • Non-stop • Coach

Cancun (CUN) to Chicago (CHI)

American Airlines • Non-stop • Coach
Price was $3,893, price is now $1,674 per person
$1,674
per person
found 1 day ago

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

Hotel Mousai Cancun Adults Only - All Inclusive

9.8/10 Exceptional! (139 reviews)

Nov 27 - Dec 1

4 night stay

Chicago (CHI) to Cancun (CUN)

Frontier Airlines • Coach

Cancun (CUN) to Chicago (CHI)

Viva Aerobus • Coach
Price was $3,850, price is now $1,796 per person
$1,796
per person
found 1 day ago
This experience was mind blowing. Have visited multiple hotels but this one is one of its kind. Property, room, cleanliness, amenities were all top notch, but what really stood out was the staff and the food. Food is michelin star grade, without a question. Restaurants DAO, NOI, Bocados were out of this world… When talking abouts staff, i’m basically speechless. Intelligence paired with kindness, manner and they were all seeking to make every single of your moments unforgettable: special thanks to Marcia our concierge, Jose & Jesus the mixologists, and the best waiters EVER Manuel and Yamil on the rooftop, Fernando at NOI. Honestly, i could write this review for hours, was a lifetime exoerience for us to be there. Everything was way beyond our expectations. One thing to keep in mind though: beach is not the best, this is not your place if that is your point. But honestly, Isla mujeres is like 40min away from there, with Playa Norte which is one of the TOP beaches in Mexico. There is also a construction going on next to the hotel, they are bulding Lemuria their new property, but there were little to no discomcofrts about that. They even pay attention to crank up the music when there is noise.

Reviewed on Oct 22, 2026

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Riviera Maya packages with premium economy flights

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

Wyndham Grand Cancun All Inclusive Resort & Villas

8.4/10 Very Good! (3,506 reviews)

Nov 27 - Dec 4

7 night stay

Chicago (ORD) to Cancun (CUN)

Frontier Airlines • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $3,333, price is now $1,681 per person
$1,681
per person
found 3 hours ago
Service room was too fast , my rooms was always cleaned.

Reviewed on Oct 26, 2026

Hotel Riu Palace Peninsula - All Inclusive
4.0-star property

Hotel Riu Palace Peninsula - All Inclusive

9/10 Wonderful! (4,733 reviews)

Nov 27 - Dec 4

7 night stay

Chicago (ORD) to Cancun (CUN)

Frontier Airlines • Roundtrip • PremiumEconomy
Price was $4,757, price is now $2,160 per person
$2,160
per person
found 3 hours ago

Hotel Riu Palace Las Americas - Adults Only- All Inclusive
4.0-star property

Hotel Riu Palace Las Americas - Adults Only- All Inclusive

9.2/10 Wonderful! (5,769 reviews)

Nov 27 - Dec 4

7 night stay

Chicago (ORD) to Cancun (CUN)

Frontier Airlines • Roundtrip • PremiumEconomy
Price was $3,784, price is now $1,842 per person
$1,842
per person
found 3 hours ago

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Riviera Maya business class flight packages

Price found within the past 48 hours. Click for updated prices.
Ventus at Marina El Cid Spa & Beach Resort - All Inclusive
5.0-star property

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

8.8/10 Excellent! (1,459 reviews)

Nov 27 - Dec 4

7 night stay

Chicago (CHI) to Cancun (CUN)

Frontier Airlines • Roundtrip • BusinessClass
Save 100% on your flight
Price was $2,955, price is now $1,593 per person
$1,593
per person
found 1 day ago
Our check in experience was worst.. We paid an upgrade then they send us to platinum club.. Repeat everything same told to me at check in.. calls in a collegue who explains about investment and to book an appointment. Guest coming after travel should not be welcomed like this.. no drinks were offered not even water.. Spa is redicolous my wife and daugther went for nails aftwr 10-15 mins we were told none service is available( for nails and hairs).. Our buttlwr assigned Celine and Alberto were good they were in touch if anything needed.. Best restaurant is Hacinta (Mexican cuisine). Best servers Margarito and Alexandar.. Bar service can be improved with adding more servers depending on crowd.. At pool and bar table wait was too long if you need service at table.

Reviewed on Oct 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! (5,642 reviews)

Nov 27 - Dec 4

7 night stay

Chicago (CHI) to Cancun (CUN)

Frontier Airlines • Roundtrip • BusinessClass
Save 100% on your flight
Price was $4,792, price is now $2,550 per person
$2,550
per person
found 1 day ago
I love the property this was my second time visiting however the food wasn’t too good this time but it won’t stop me from returning .

Reviewed on Oct 26, 2026

Majestic Mirage Costa Mujeres, All Suite Resort - All Inclusive
5.0-star property

Majestic Mirage Costa Mujeres, All Suite Resort - All Inclusive

9/10 Wonderful! (547 reviews)

Nov 27 - Dec 4

7 night stay

Chicago (CHI) to Cancun (CUN)

Frontier Airlines • Roundtrip • BusinessClass
Save 100% on your flight
Price was $5,043, price is now $2,786 per person
$2,786
per person
found 1 day ago
Todo estuvo excelente. Un hotel para ir a descansar y desconectarte. La comida deliciosa si volveriamoa a ir.

Reviewed on Oct 25, 2026

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Riviera Maya first class flight packages

Price found within the past 48 hours. Click for updated prices.
Haven Riviera Cancun - All Inclusive - Adults Only
5.0-star property

Haven Riviera Cancun - All Inclusive - Adults Only

9.4/10 Exceptional! (5,061 reviews)

Dec 3 - Dec 7

4 night stay

Chicago (CHI) to Cancun (CUN)

United • FirstClass

Cancun (CUN) to Chicago (CHI)

American Airlines • FirstClass
Price was $3,434, price is now $2,334 per person
$2,334
per person
found 1 day ago
We had an amazing anniversary getaway here! Amazing service, food and drinks. Pools were perfect. Only downside is this area of cancun although quieter the ocean water is overflowing with smelly seaweed. But we were at the pools the most so it was not a big deal for us. The shows were fantastic as well. Loved the spa hydrotherapy and massage. Would definitely stay here again!

Reviewed on Oct 25, 2026

Family Villas By Wyndham Grand Cancún All Inclusive
4.0-star property

Family Villas By Wyndham Grand Cancún All Inclusive

7.6/10 Good! (51 reviews)

Dec 3 - Dec 7

4 night stay

Chicago (CHI) to Cancun (CUN)

United • FirstClass

Cancun (CUN) to Chicago (CHI)

American Airlines • FirstClass
Price was $4,010, price is now $2,588 per person
$2,588
per person
found 1 day ago

Ocean Maya Royale - Adults Only - All Inclusive
5.0-star property

Ocean Maya Royale - Adults Only - All Inclusive

8.8/10 Excellent! (2,869 reviews)

Nov 26 - Nov 30

4 night stay

Chicago (CHI) to Cancun (CUN)

United • Roundtrip • FirstClass
Price was $3,741, price is now $2,581 per person
$2,581
per person
found 1 day ago

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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
TUY
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.