$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.

Fri, Aug 21 - Thu, Aug 27
ORD
O'Hare Intl.
CUN
Cancun Intl.
$493 Roundtrip, just found
$493
Roundtrip
just found
Select Volaris flight, departing Fri, Aug 21 from O'Hare Intl. to Cancun Intl., returning Thu, Aug 27, priced at $493 just found
Fri, Aug 21 - Mon, Aug 24
ORD
O'Hare Intl.
TQO
Tulum Intl. Airport
$499 Roundtrip, found 1 hour ago
$499
Roundtrip
found 1 hour ago
Select Volaris flight, departing Fri, Aug 21 from O'Hare Intl. to Tulum Intl. Airport, returning Mon, Aug 24, priced at $499 found 1 hour ago
Fri, Aug 21 - Wed, Aug 26
MDW
Midway Intl.
CUN
Cancun Intl.
$563 Roundtrip, just found
$563
Roundtrip
just found
Select Aeromexico flight, departing Fri, Aug 21 from Midway Intl. to Cancun Intl., returning Wed, Aug 26, priced at $563 just found
Sun, Aug 23 - Thu, Aug 27
MDW
Midway Intl.
TQO
Tulum Intl. Airport
$1,057 Roundtrip, found 1 hour ago
$1,057
Roundtrip
found 1 hour ago
Select Delta flight, departing Sun, Aug 23 from Midway Intl. to Tulum Intl. Airport, returning Thu, Aug 27, priced at $1,057 found 1 hour ago

Airfares from $147 One Way, $307 Round Trip from Chicago to Riviera Maya

Prices starting at $307 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.

Mon, Nov 2 - Fri, Nov 6
ORD
Chicago
CUN
Cancun
$307 Roundtrip, just found
$307
Roundtrip
just found
Select Arajet flight, departing Mon, Nov 2 from Chicago to Cancun, returning Fri, Nov 6, priced at $307 just found
Tue, Oct 13 - Tue, Oct 20
ORD
Chicago
CUN
Cancun
$349 Roundtrip, found 5 hours ago
$349
Roundtrip
found 5 hours ago
Select Funjet Vacations flight, departing Tue, Oct 13 from Chicago to Cancun, returning Tue, Oct 20, priced at $349 found 5 hours ago
Mon, Jan 25 - Thu, Jan 28
ORD
Chicago
TQO
Tulum
$377 Roundtrip, found 6 days ago
$377
Roundtrip
found 6 days ago
Select Viva flight, departing Mon, Jan 25 from Chicago to Tulum, returning Thu, Jan 28, priced at $377 found 6 days ago
Sat, Oct 24 - Fri, Oct 30
ORD
Chicago
TQO
Tulum
$384 Roundtrip, found 4 days ago
$384
Roundtrip
found 4 days ago
Select Air Canada flight, departing Sat, Oct 24 from Chicago to Tulum, returning Fri, Oct 30, priced at $384 found 4 days ago
Sun, Nov 1 - Fri, Nov 6
MDW
Chicago
CUN
Cancun
$394 Roundtrip, found 3 days ago
$394
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sun, Nov 1 from Chicago to Cancun, returning Fri, Nov 6, priced at $394 found 3 days ago

Riviera Maya economy 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! (1,468 reviews)

Oct 3 - Oct 9

6 night stay

Chicago (CHI) to Cancun (CUN)

American Airlines • Coach

Cancun (CUN) to Chicago (CHI)

Volaris • Coach
Price was $2,123, price is now $930 per person
$930
per person
found 1 day ago
We had an overall enjoyable stay at this all-inclusive resort. The staff was very friendly, welcoming, and helpful throughout our visit. The resort itself was clean and well maintained, and we thought the food was good with plenty of options to choose from. There were a couple of downsides that affected our experience. We had ants in our room, which was disappointing and definitely something that should be addressed. The biggest issue for us was the amount of sargassum/seagrass along the shoreline. Unfortunately, it made the beach pretty much unusable during our stay, which was disappointing since enjoying the beach was something we were really looking forward to. Overall, we still had a nice stay and appreciated the friendly staff, cleanliness of the resort, and good food. With better pest control in the rooms and improved management of the seaweed along the beach, the experience would have been much better.

Reviewed on Aug 16, 2026

The Sens Cancun By Oasis
4.0-star property

The Sens Cancun By Oasis

7.4/10 Good! (674 reviews)

Oct 3 - Oct 10

7 night stay

Chicago (CHI) to Cancun (CUN)

American Airlines • Coach

Cancun (CUN) to Chicago (CHI)

Volaris • Coach
Price was $2,633, price is now $1,064 per person
$1,064
per person
found 1 day ago

The Grand Oasis Cancun - All Inclusive
4.0-star property

The Grand Oasis Cancun - All Inclusive

6.2/10 (2,073 reviews)

Oct 3 - Oct 10

7 night stay

Chicago (CHI) to Cancun (CUN)

American Airlines • Coach

Cancun (CUN) to Chicago (CHI)

Volaris • Coach
Price was $2,357, price is now $1,035 per person
$1,035
per person
found 1 day ago

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Riviera Maya business 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! (5,258 reviews)

Sep 26 - Oct 1

5 night stay

Chicago (CHI) to Cancun (CUN)

Frontier Airlines • Non-stop roundtrip • BusinessClass
Save 100% on your flight
Price was $2,557, price is now $1,481 per person
$1,481
per person
found 1 day ago

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! (346 reviews)

Sep 18 - Sep 25

7 night stay

Chicago (CHI) to Cancun (CUN)

Frontier Airlines • Non-stop roundtrip • BusinessClass
Save 100% on your flight
Price was $3,164, price is now $1,818 per person
$1,818
per person
found 9 hours ago
Excellent experience we all came really happy about the hotel and service

Reviewed on Aug 17, 2026

Moon Palace Cancun - All-Inclusive
5.0-star property

Moon Palace Cancun - All-Inclusive

8.4/10 Very Good! (3,127 reviews)

Sep 26 - Oct 1

5 night stay

Chicago (CHI) to Cancun (CUN)

Frontier Airlines • Non-stop roundtrip • BusinessClass
Save 100% on your flight
Price was $5,379, price is now $3,093 per person
$3,093
per person
found 1 day ago
Rooms were clean, staff was somewhat helpful now the pool I saw them cleaning every day, but our swimsuits did have black stain from the tiles that were really dirty. Swim up bar was nice. Staff was a little irritated. You can say I mean you can tell they work very hard but sometimes they were a little rude.. Did room service several times we did an add-on to the room service and it never came. We contacted them. They kept on saying it was on its way on its way never came so we had to just cancel so I do recommend if you have kids make sure they eat because room service didn’t show up, but besides that overall hotel was great, clean, food is delicious,family friendly the only thing with the resort credits which I don’t really understand I was trying to use them at the store, but then they said I couldn’t use them so I had a remaining balance that I couldn’t use. To buy souvenirs. We did do a dolphin excursion. And that was nice. Been to Cancun many times the hotel zone this time we set up moon Palace. The only downfall is the beach. It is not clean what is out of their hands but everything else it’s great.

Reviewed on Aug 17, 2026

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Riviera Maya first class flight packages

Price found within the past 48 hours. Click for updated prices.
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! (50 reviews)

Sep 16 - Sep 20

4 night stay

Chicago (CHI) to Cancun (CUN)

United • Non-stop • FirstClass

Cancun (CUN) to Chicago (CHI)

Frontier Airlines • Non-stop • FirstClass
Save 100% on your flight
Price was $4,601, price is now $2,787 per person
$2,787
per person
found 17 hours ago

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! (662 reviews)

Sep 24 - Sep 28

4 night stay

Chicago (CHI) to Cancun (CUN)

American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $4,727, price is now $2,828 per person
$2,828
per person
found 1 day ago
Wow! Easily the best resort we have stayed at. I am not Vegan but the best part of this trip was definitely the food. The all-inclusive is the best deal around by far. There are plenty of non-vegan options but honestly I mostly ate the vegan versions. Everything was top-shelf. Charlies Vegan Tacos were a highlight. And we actually lost some weight while we were there since its so healthy. The service was incredible. Everywhere we went we were greeted with smiles and hellos. We got to know by name many of the staff. The Pools are about the best I have seen and the beach (when there is not seaweed) is incredible. And they keep it cleaner than any other beach around. Every time we ventured out to try something different we came back to the hotel because it was just better. The free classes like Yoga were amazing as well. I feel this is a secret that will soon be out. But thank you to all the staff who were part of this experience.

Reviewed on Aug 8, 2026

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

Hotel Mousai Cancun Adults Only - All Inclusive

9.6/10 Exceptional! (124 reviews)

Sep 16 - Sep 20

4 night stay

Chicago (CHI) to Cancun (CUN)

United • Non-stop • FirstClass

Cancun (CUN) to Chicago (CHI)

Frontier Airlines • Non-stop • FirstClass
Save 100% on your flight
Price was $4,464, price is now $2,813 per person
$2,813
per person
found 17 hours ago
The hotel was beyond clean and staff and food were amazing. Can say enough about the entire experience and can’t wait to go back. The art work is very strange, not sure what they were thinking but everything else was exceptional

Reviewed on Aug 16, 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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