$148 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, Oct 24 - Fri, Oct 30
ORD
O'Hare Intl.
CUN
Cancun Intl.
$432 Roundtrip, just found
$432
Roundtrip
just found
Select Air Canada flight, departing Sat, Oct 24 from O'Hare Intl. to Cancun Intl., returning Fri, Oct 30, priced at $432 just found
Sat, Oct 24 - Sun, Nov 1
ORD
O'Hare Intl.
CZM
Cozumel Intl.
$480 Roundtrip, found 4 days ago
$480
Roundtrip
found 4 days ago
Select Air Canada flight, departing Sat, Oct 24 from O'Hare Intl. to Cozumel Intl., returning Sun, Nov 1, priced at $480 found 4 days ago
Sat, Oct 24 - Fri, Oct 30
MDW
Midway Intl.
CUN
Cancun Intl.
$510 Roundtrip, just found
$510
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Oct 24 from Midway Intl. to Cancun Intl., returning Fri, Oct 30, priced at $510 just found
Fri, Oct 23 - Sun, Oct 25
ORD
O'Hare Intl.
TQO
Tulum Intl. Airport
$738 Roundtrip, found 1 day ago
$738
Roundtrip
found 1 day ago
Select Volaris flight, departing Fri, Oct 23 from O'Hare Intl. to Tulum Intl. Airport, returning Sun, Oct 25, priced at $738 found 1 day ago

Airfares from $148 One Way, $299 Round Trip from Chicago to Riviera Maya

Prices starting at $299 for return flights and $148 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.

Mon, Nov 2 - Fri, Nov 6
ORD
Chicago
CUN
Cancun
$299 Roundtrip, found 10 hours ago
$299
Roundtrip
found 10 hours ago
Select Funjet Vacations flight, departing Mon, Nov 2 from Chicago to Cancun, returning Fri, Nov 6, priced at $299 found 10 hours ago
Thu, Apr 8 - Mon, Apr 12
ORD
Chicago
CUN
Cancun
$370 Roundtrip, found 10 hours ago
$370
Roundtrip
found 10 hours ago
Select Viva flight, departing Thu, Apr 8 from Chicago to Cancun, returning Mon, Apr 12, priced at $370 found 10 hours ago
Sun, Dec 6 - Fri, Dec 11
ORD
Chicago
CUN
Cancun
$377 Roundtrip, found 9 hours ago
$377
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Sun, Dec 6 from Chicago to Cancun, returning Fri, Dec 11, priced at $377 found 9 hours ago
Mon, Nov 9 - Thu, Nov 19
ORD
Chicago
CUN
Cancun
$378 Roundtrip, found 1 day ago
$378
Roundtrip
found 1 day ago
Select Arajet flight, departing Mon, Nov 9 from Chicago to Cancun, returning Thu, Nov 19, priced at $378 found 1 day ago
Mon, Nov 9 - Fri, Nov 13
MDW
Chicago
CUN
Cancun
$408 Roundtrip, found 1 day ago
$408
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Nov 9 from Chicago to Cancun, returning Fri, Nov 13, priced at $408 found 1 day ago

Riviera Maya economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Sens Riviera By Oasis
4.0-star property

The Sens Riviera By Oasis

7.2/10 Good! (195 reviews)

Nov 30 - Dec 6

6 night stay

Chicago (CHI) to Cancun (CUN)

American Airlines • Coach

Cancun (CUN) to Chicago (CHI)

Viva Aerobus • Coach
Price was $2,264, price is now $939 per person
$939
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 21 - Nov 28

7 night stay

Chicago (CHI) to Cancun (CUN)

Viva Aerobus • Non-stop • Coach

Cancun (CUN) to Chicago (CHI)

Volaris • Non-stop • Coach
Save 100% on your flight
Price was $4,458, price is now $2,154 per person
$2,154
per person
found 1 day ago
Nice place to relax

Reviewed on Oct 19, 2026

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 26 - Nov 30

4 night stay

Chicago (CHI) to Cancun (CUN)

Southwest Airlines • Coach

Cancun (CUN) to Chicago (CHI)

Viva Aerobus • Coach
Price was $4,239, price is now $2,058 per person
$2,058
per person
found 1 day ago
Absolutely stunning property, stunning views, and the most accomodating staff! There were so many tiny details that made such a big difference, and people like me who appreciate those types of things will truly enjoy themselves here!

Reviewed on Oct 14, 2026

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Riviera Maya packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Platinum Yucatan Princess Adults Only - All Inclusive
5.0-star property

Platinum Yucatan Princess Adults Only - All Inclusive

8.6/10 Excellent! (3,134 reviews)

Dec 2 - Dec 6

4 night stay

Chicago (CHI) to Cancun (CUN)

Frontier Airlines • Roundtrip • PremiumEconomy
Price was $1,730, price is now $1,299 per person
$1,299
per person
found 21 hours ago
This was our second time here. We could not wait to go back because we wanted to stay in building 3 in a swim out since they go right into the main pool with the swim up bar. We sent several requests asking for building 3. Always received a response saying they have that in our notes. I know you can not always guarantee the building you request. However, the ENTIRE building 3 was closed for our entire stay. An email to let us know that we could not have our request would have been nice. It is a shame because we brought other people with us who were looking forward to these swim up rooms. We liked the food and the entertainment staff were amazing. Because of lack of communication, we most likely will not be back.

Reviewed on Oct 20, 2026

Iberostar Selection Cancún - All Inclusive
4.5-star property

Iberostar Selection Cancún - All Inclusive

8.4/10 Very Good! (1,232 reviews)

Dec 2 - Dec 6

4 night stay

Chicago (CHI) to Cancun (CUN)

Frontier Airlines • Roundtrip • PremiumEconomy
Price was $2,070, price is now $2,070 per person
$2,070
per person
found 21 hours ago
If you’re looking for an all inclusive resort in Cancun Mexico. This might not be it. First of all when I think all inclusive, I think everything is included. That would be the wrong assumption here. There was more to pay for than what you actually receive. Next they are trying to up Sell you before you get in the door. Next the room we received was very out dated and very dirty. Next limited selection on room service or breakfast. Yes, Breakfast was possibly the worst buffet breakfast I’ve had in years and Yes it was the only option. We had to leave the resort to actually get a decent meal. Now let be totally transparent, I was able to get a great meal one evening in the steak house when I did the up charged Cowboy steak. But other that that I was overwhelmed by the total package here. One morning I got up super early and went down to the pool and got a pretty good chair. Then the staff come over and asked if I would like to pay to sit there. Now we are talking at 7:30am and they wanted me to pay to sit at the pool. Like I said maybe you should rethink this place if you are looking for all inclusive.

Reviewed on Oct 19, 2026

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Riviera Maya first class flight packages

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

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

9/10 Wonderful! (1,452 reviews)

Nov 26 - Dec 3

7 night stay

Chicago (ORD) to Cancun (CUN)

American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $3,465, price is now $1,846 per person
$1,846
per person
found 1 day ago
the staff were amazing very helpful with booking extra activities and the pools were amazing

Reviewed on Oct 19, 2026

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 - Dec 3

7 night stay

Chicago (ORD) to Cancun (CUN)

American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $4,373, price is now $2,175 per person
$2,175
per person
found 1 day ago
Nice place to relax

Reviewed on Oct 19, 2026

Ocean Allure Costa Mujeres - Adults Only - All Inclusive
5.0-star property

Ocean Allure Costa Mujeres - Adults Only - All Inclusive

9/10 Wonderful! (762 reviews)

Nov 26 - Dec 3

7 night stay

Chicago (ORD) to Cancun (CUN)

American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $4,669, price is now $2,442 per person
$2,442
per person
found 1 day ago
Disappointing Stay at Ocean Allure Costa Mujeres Our stay at Ocean Allure Costa Mujeres fell well below expectations, particularly for a Master Suite booking. The biggest disappointment was our airport transfer. Despite receiving a booking confirmation and voucher, no transfer was arranged. After being advised by the hotel to take a taxi, with a promise of reimbursement, we paid USD 175. When we tried to resolve the issue, we were passed between departments, with neither the hotel nor management taking responsibility. The advertised butler service was also poor. We never met our butler, and WhatsApp responses were very slow. Our suite had several issues, including a malfunctioning main shower, visible damage and poor interior finishing. Even the welcome card was addressed to another family. Food and drinks were mediocre, and customer service throughout the resort was basic. Overall, the lack of attention to detail, poor service and failure to take responsibility for problems made our stay disappointing. The experience did not meet the standards expected of a luxury resort, and we would struggle to recommend it.

Reviewed on Oct 20, 2026

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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.

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