$95 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, Dec 7 - Mon, Dec 15
ORD
O'Hare Intl.
CUN
Cancun Intl.
$286 Roundtrip, just found
$286
Roundtrip
just found
Select Spirit Airlines flight, departing Sun, Dec 7 from O'Hare Intl. to Cancun Intl., returning Mon, Dec 15, priced at $286 just found
Sat, Dec 6 - Wed, Dec 10
MDW
Midway Intl.
CUN
Cancun Intl.
$329 Roundtrip, just found
$329
Roundtrip
just found
Select Aeromexico flight, departing Sat, Dec 6 from Midway Intl. to Cancun Intl., returning Wed, Dec 10, priced at $329 just found
Sun, Dec 7 - Wed, Dec 17
ORD
O'Hare Intl.
TQO
Tulum Intl. Airport
$345 Roundtrip, found 16 hours ago
$345
Roundtrip
found 16 hours ago
Select Delta flight, departing Sun, Dec 7 from O'Hare Intl. to Tulum Intl. Airport, returning Wed, Dec 17, priced at $345 found 16 hours ago
Sat, Dec 6 - Tue, Dec 9
RFD
Greater Rockford
CUN
Cancun Intl.
$349 Roundtrip, found 2 days ago
$349
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Dec 6 from Greater Rockford to Cancun Intl., returning Tue, Dec 9, priced at $349 found 2 days ago

Airfares from $95 One Way, $203 Round Trip from Chicago to Riviera Maya

Prices starting at $203 for return flights and $95 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.

Sun, Dec 7 - Tue, Dec 23
ORD
Chicago
CUN
Cancun
$203 Roundtrip, found 4 days ago
$203
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sun, Dec 7 from Chicago to Cancun, returning Tue, Dec 23, priced at $203 found 4 days ago
Sun, Feb 22 - Wed, Feb 25
ORD
Chicago
CUN
Cancun
$210 Roundtrip, just found
$210
Roundtrip
just found
Select Spirit Airlines flight, departing Sun, Feb 22 from Chicago to Cancun, returning Wed, Feb 25, priced at $210 just found
Thu, Jan 29 - Thu, Feb 5
MDW
Chicago
CUN
Cancun
$300 Roundtrip, found 3 days ago
$300
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Jan 29 from Chicago to Cancun, returning Thu, Feb 5, priced at $300 found 3 days ago
Thu, Mar 5 - Sun, Mar 8
ORD
Chicago
TQO
Tulum
$306 Roundtrip, found 5 hours ago
$306
Roundtrip
found 5 hours ago
Select Aeromexico flight, departing Thu, Mar 5 from Chicago to Tulum, returning Sun, Mar 8, priced at $306 found 5 hours ago
Mon, Dec 8 - Fri, Dec 12
MDW
Chicago
TQO
Tulum
$314 Roundtrip, found 6 days ago
$314
Roundtrip
found 6 days ago
Select Aeromexico flight, departing Mon, Dec 8 from Chicago to Tulum, returning Fri, Dec 12, priced at $314 found 6 days ago

Riviera Maya economy flight packages

Price found within the past 48 hours. Click for updated prices.
Naay Boutique Hotel
4.0-star property

Naay Boutique Hotel

8.6/10 Excellent! (199 reviews)

Jan 9 - Jan 13

4 night stay

Chicago (CHI) to Cancun (CUN)

Spirit Airlines • Coach

Cancun (CUN) to Chicago (CHI)

Frontier Airlines • Coach
Price was $1,649, price is now $498 per person
$498
per person
found 22 hours ago
Amazing and beautiful property! Thank you!

Reviewed on Sep 3, 2024

The Beachfront by The Fives Hotels - A la Carte All Inclusive Adults Only
4.0-star property

The Beachfront by The Fives Hotels - A la Carte All Inclusive Adults Only

9.6/10 Exceptional! (108 reviews)

Jan 14 - Jan 18

4 night stay

Chicago (CHI) to Cancun (CUN)

Volaris • Non-stop roundtrip • Coach
Price was $5,729, price is now $1,651 per person
$1,651
per person
found 1 day ago
AVA Resort All Oceanfront - All Inclusive
5.0-star property

AVA Resort All Oceanfront - All Inclusive

8.4/10 Very Good! (633 reviews)

Dec 30 - Jan 6

7 night stay

Chicago (CHI) to Cancun (CUN)

Frontier Airlines • Non-stop • Coach

Cancun (CUN) to Chicago (CHI)

Sterling Blue • Non-stop • Coach
Price was $8,607, price is now $3,032 per person
$3,032
per person
found 1 day ago
Great open but food was average at best

Reviewed on Aug 15, 2025

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Riviera Maya packages with premium economy flights

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

9.2/10 Wonderful! (4,815 reviews)

Jan 21 - Jan 25

4 night stay

Chicago (CHI) to Cancun (CUN)

Aeromexico • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $3,781, price is now $1,855 per person
$1,855
per person
found 7 hours ago
The resoet was fabulous. Seaweed was a problem but the pools were fantastic! Service was amazing!

Reviewed on Sep 30, 2025

Valentin Imperial Rivera Maya All Inclusive - Adult Only
4.5-star property

Valentin Imperial Rivera Maya All Inclusive - Adult Only

9.4/10 Exceptional! (1,630 reviews)

Jan 21 - Jan 25

4 night stay

Chicago (CHI) to Cancun (CUN)

Aeromexico • Non-stop roundtrip • PremiumEconomy
Price was $5,433, price is now $2,209 per person
$2,209
per person
found 7 hours ago
This is our 5th visit and we had an amazing visit as always. The staff is so accommodating and friendly! Room service was super fast with our morning orders. The food is excellent. We love the fillet minion at the French restaurant, chef specials at Ginger and everything at Mar Tierra breakfast, Lunch and dinner! The pool was beautiful and entertainment staff works very well with guests. The grounds are beautiful and the evening walks with lights along pathways along with soft music was a romantic.

Reviewed on Jun 25, 2025

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)

Jan 17 - Jan 21

4 night stay

Chicago (CHI) to Cancun (CUN)

Spirit Airlines • PremiumEconomy

Cancun (CUN) to Chicago (CHI)

American Airlines • PremiumEconomy
Price was $5,391, price is now $2,614 per person
$2,614
per person
just found
This property is not equipped to handle the amount of people staying here. Peope are running to the pool and beach at 7 a.m. to get lounge chairs bc there are not enough on the property. The dining facilities are not large enough. My party was turned away a few times bc the various reataurants were full or at capacity (only one restaurant takes a reservation which is a scramble to get at 8 a.m. each morning).The room was outdated and needs renovating and new decor. It was hard to get anyone to help with anything. Once, I did connect with someone he/she was nice, polite, and helpful. The hotel is understaffed and needs more lounge chairs and umbrellas.

Reviewed on Apr 11, 2022

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Riviera Maya first class flight packages

Price found within the past 48 hours. Click for updated prices.
Areia Playa del Carmen-Beach front Hotel
3.0-star property

Areia Playa del Carmen-Beach front Hotel

7.4/10 Good! (62 reviews)

Dec 31 - Jan 4

4 night stay

Chicago (ORD) to Cancun (CUN)

United • Roundtrip • FirstClass
Price was $2,871, price is now $1,948 per person
$1,948
per person
found 18 hours ago
Was pretty good and the costumer service was great and else people are so frenly

Reviewed on May 15, 2025

Playacar Palace All Inclusive
4.5-star property

Playacar Palace All Inclusive

8.8/10 Excellent! (1,000 reviews)

Dec 31 - Jan 4

4 night stay

Chicago (ORD) to Cancun (CUN)

United • Roundtrip • FirstClass
Save 100% on your flight
Price was $6,796, price is now $4,037 per person
$4,037
per person
found 18 hours ago
Our stay was lovely. The activities are wonderful with staff that really provides fun….yoga, pool volleyball were great. Daniel the head of Wellness is superb, professional and super fun. The buffet was great offering food that is fresh (fresh grilled fish) and many options. The restaurants are lovely as well. The spa is definitely a 5 star experience and stunning. The hotel is the closest right next door to the town center and super cute outside mall and boutique shops. If you are looking for expansive beach this is not your place as there’s little beach area in front - however amazing to sit at the pool overlooking the sea - and the beach water is easy to access and lovely.

Reviewed on Feb 24, 2025

Dreams Natura Resort & Spa - All Inclusive
4.5-star property

Dreams Natura Resort & Spa - All Inclusive

8.2/10 Very Good! (1,400 reviews)

Dec 31 - Jan 4

4 night stay

Chicago (ORD) to Cancun (CUN)

United • Roundtrip • FirstClass
Price was $3,776, price is now $2,621 per person
$2,621
per person
found 18 hours ago
We have stayed at many Dreams properties, and this one is nice with the lazy river and newer facility. Food was good. At times, certain areas seemed to be a bit understaffed. Only one bartender working the pool bar, entertainment staff didn’t invite us to activities, only one bellboy when multiples needed, and the activity and restaurant options were sometimes limited or didn’t match what was published on the app. We still had a great time and the staff that was working was pleasant and hard working. The seaweed on the beach was unfortunate, but staff worked hard to keep it clean. The 4th of July party was great! Not sure it was worth the larger price tag compared with other dreams resort.

Reviewed on Jul 7, 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.