$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.

Sun, Jul 19 - Tue, Jul 21
ORD
O'Hare Intl.
CUN
Cancun Intl.
$517 Roundtrip, just found
$517
Roundtrip
just found
Select Volaris flight, departing Sun, Jul 19 from O'Hare Intl. to Cancun Intl., returning Tue, Jul 21, priced at $517 just found
Sun, Jul 19 - Fri, Jul 24
ORD
O'Hare Intl.
TQO
Tulum Intl. Airport
$565 Roundtrip, found 18 hours ago
$565
Roundtrip
found 18 hours ago
Select Volaris flight, departing Sun, Jul 19 from O'Hare Intl. to Tulum Intl. Airport, returning Fri, Jul 24, priced at $565 found 18 hours ago
Sat, Jul 18 - Tue, Jul 21
MDW
Midway Intl.
CUN
Cancun Intl.
$625 Roundtrip, found 4 hours ago
$625
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Sat, Jul 18 from Midway Intl. to Cancun Intl., returning Tue, Jul 21, priced at $625 found 4 hours ago
Sat, Jul 18 - Mon, Jul 20
ORD
O'Hare Intl.
CZM
Cozumel Intl.
$675 Roundtrip, found 6 days ago
$675
Roundtrip
found 6 days ago
Select Volaris flight, departing Sat, Jul 18 from O'Hare Intl. to Cozumel Intl., returning Mon, Jul 20, priced at $675 found 6 days ago

Airfares from $147 One Way, $305 Round Trip from Chicago to Riviera Maya

Prices starting at $305 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.

Fri, Sep 11 - Thu, Sep 17
ORD
Chicago
CUN
Cancun
$305 Roundtrip, found 1 hour ago
$305
Roundtrip
found 1 hour ago
Select Arajet flight, departing Fri, Sep 11 from Chicago to Cancun, returning Thu, Sep 17, priced at $305 found 1 hour ago
Tue, Nov 10 - Tue, Nov 17
ORD
Chicago
CUN
Cancun
$349 Roundtrip, found 12 hours ago
$349
Roundtrip
found 12 hours ago
Select Funjet Vacations flight, departing Tue, Nov 10 from Chicago to Cancun, returning Tue, Nov 17, priced at $349 found 12 hours ago
Sun, Aug 23 - Wed, Aug 26
MDW
Chicago
CUN
Cancun
$373 Roundtrip, found 4 days ago
$373
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Sun, Aug 23 from Chicago to Cancun, returning Wed, Aug 26, priced at $373 found 4 days ago
Mon, Feb 22 - Thu, Feb 25
ORD
Chicago
CZM
Cozumel
$384 Roundtrip, found 7 hours ago
$384
Roundtrip
found 7 hours ago
Select Volaris flight, departing Mon, Feb 22 from Chicago to Cozumel, returning Thu, Feb 25, priced at $384 found 7 hours ago
Wed, Aug 26 - Fri, Aug 28
ORD
Chicago
TQO
Tulum
$405 Roundtrip, found 5 days ago
$405
Roundtrip
found 5 days ago
Select Volaris flight, departing Wed, Aug 26 from Chicago to Tulum, returning Fri, Aug 28, priced at $405 found 5 days 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! (1,036 reviews)

Aug 29 - Sep 4

6 night stay

Chicago (CHI) to Cancun (CUN)

American Airlines • Coach

Cancun (CUN) to Chicago (CHI)

Volaris • Coach
Price was $1,579, price is now $685 per person
$685
per person
found 1 day ago
This was by far the worst hotel I’ve ever stayed at in Cancun. The rooms were dirty, the furniture was old, worn out, and broken, and we found roaches in both the bedroom and the bathroom. The overall condition of the hotel was unacceptable, and it did not match the standards that were advertised. I would not recommend staying here and definitely would not return.

Reviewed on Jul 14, 2026

Delek Holbox
4.0-star property

Delek Holbox

8.8/10 Excellent! (283 reviews)

Aug 21 - Aug 27

6 night stay

Chicago (CHI) to Cancun (CUN)

Volaris • Non-stop roundtrip • Coach
Price was $2,241, price is now $757 per person
$757
per person
found 1 day ago
We had a wonderful stay at Delek Holbox. The staff was very friendly, helpful, and welcoming throughout our visit. The beach and beach bar were beautiful and perfect for relaxing, and the rooms were clean, comfortable, and very nice. We would happily stay here again

Reviewed on Jun 28, 2026

Delek Tulum
4.0-star property

Delek Tulum

9.2/10 Wonderful! (368 reviews)

Aug 16 - Aug 20

4 night stay

Chicago (CHI) to Cancun (CUN)

Southwest Airlines • Coach

Cancun (CUN) to Chicago (CHI)

Volaris • Coach
Price was $1,758, price is now $772 per person
$772
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.
Tago Tulum by G Hotels
3.5-star property

Tago Tulum by G Hotels

9.2/10 Wonderful! (429 reviews)

Aug 21 - Aug 26

5 night stay

Chicago (CHI) to Cancun (CUN)

United • Roundtrip • BusinessClass
Price was $2,892, price is now $1,292 per person
$1,292
per person
found 24 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! (646 reviews)

Aug 22 - Aug 27

5 night stay

Chicago (CHI) to Cancun (CUN)

Frontier Airlines • Non-stop roundtrip • BusinessClass
Price was $5,238, price is now $2,497 per person
$2,497
per person
found 1 day ago
Palmaia was such a peaceful paradise! We went in mid June and it was pretty quiet so we felt like we had so much space to ourselves. Our nomadic guide Karen was helpful with all of our questions and checked in with us each day to see if we needed anything. We really appreciated her! Edgar gave us a tour when we first arrived and helped us get to the store at Sandos when we needed to get electrolytes (I got dehydrated the first day!) But what helped even more was when room service brought us fresh coconuts and a natural electrolyte drink. They literally saved our vacation because I felt better within an hour after that. The food was so good too! As vegetarians it was nice to not have to wonder what we could pick from the menu, and everything we chose was fresh and delicious. Our favorite restaurant was Ume- their sushi, pho, and desserts were our favorite dishes! Another highlight for us was the coffee shop, Plantissa. The interior design is out of a high end magazine and their bakery and drinks were a yummy mid day snack! We also attended some of the daily activities like yoga, a sound bath, breath work and an art class. It all felt like a dream, doing these things with such beautiful scenery around us! The teachers were kind and patient and we really appreciated the whole experience. We keep looking back at pictures and wanting to book again soon, it’s was so worth it!

Reviewed on Jul 14, 2026

Haven Riviera Cancun - All Inclusive - Adults Only
5.0-star property

Haven Riviera Cancun - All Inclusive - Adults Only

9.2/10 Wonderful! (5,108 reviews)

Aug 22 - Aug 27

5 night stay

Chicago (CHI) to Cancun (CUN)

Frontier Airlines • Non-stop roundtrip • BusinessClass
Save 100% on your flight
Price was $3,152, price is now $1,709 per person
$1,709
per person
found 1 day ago
Staff was very friendly and accommodating. They upgraded us to a junior suite with ocean view. The only downside was some of the restaurants were closed certain nights and we had to eat at the same place a couple of times.

Reviewed on Jul 15, 2026

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Riviera Maya first class flight packages

Price found within the past 48 hours. Click for updated prices.
AVA Resort Cancun - All Inclusive
5.0-star property

AVA Resort Cancun - All Inclusive

8.6/10 Excellent! (1,266 reviews)

Aug 20 - Aug 24

4 night stay

Chicago (CHI) to Cancun (CUN)

Frontier Airlines • Non-stop • FirstClass

Cancun (CUN) to Chicago (CHI)

United • Non-stop • FirstClass
Save 100% on your flight
Price was $2,844, price is now $1,793 per person
$1,793
per person
found 10 hours ago
Excellent experience with 2 kids ages 4 and 6. The lagoon is fairly shallow and the kids had a blast. Like others have states the beach is basically inaccessible but we didn't miss it with the lagoon. Lots for kids to do including a paid arcade, kids club is awesome, food is on the higher end for all inclusive but will definitely need salt / seasoning. Room cleaning and turndown were impeccable and room service was surprisingly quick. Definitely will return for a laid back experience. We had a concierge and he was extremely responsive. They also provide a daily schedule of activities to help plan your day. We ended up leaving the resort for an excursion on one of the days but definitely didn't feel like we needed to.

Reviewed on Jul 14, 2026

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! (646 reviews)

Sep 3 - Sep 7

4 night stay

Chicago (CHI) to Cancun (CUN)

American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $4,827, price is now $2,611 per person
$2,611
per person
found 1 day ago
Palmaia was such a peaceful paradise! We went in mid June and it was pretty quiet so we felt like we had so much space to ourselves. Our nomadic guide Karen was helpful with all of our questions and checked in with us each day to see if we needed anything. We really appreciated her! Edgar gave us a tour when we first arrived and helped us get to the store at Sandos when we needed to get electrolytes (I got dehydrated the first day!) But what helped even more was when room service brought us fresh coconuts and a natural electrolyte drink. They literally saved our vacation because I felt better within an hour after that. The food was so good too! As vegetarians it was nice to not have to wonder what we could pick from the menu, and everything we chose was fresh and delicious. Our favorite restaurant was Ume- their sushi, pho, and desserts were our favorite dishes! Another highlight for us was the coffee shop, Plantissa. The interior design is out of a high end magazine and their bakery and drinks were a yummy mid day snack! We also attended some of the daily activities like yoga, a sound bath, breath work and an art class. It all felt like a dream, doing these things with such beautiful scenery around us! The teachers were kind and patient and we really appreciated the whole experience. We keep looking back at pictures and wanting to book again soon, it’s was so worth it!

Reviewed on Jul 14, 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)

Sep 3 - Sep 7

4 night stay

Chicago (ORD) to Cancun (CUN)

United • FirstClass

Cancun (CUN) to Chicago (ORD)

American Airlines • FirstClass
Price was $4,608, price is now $2,680 per person
$2,680
per person
found 11 hours ago
It was great value. Clean and convenient. Food was delicious . People were friendly. A/C didn’t work well in one bedroom and we couldn’t get TV’s to connect to any streaming service and could not cast.

Reviewed on Sep 6, 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.