$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.

Sat, Dec 6 - Sat, Dec 13
ORD
O'Hare Intl.
CUN
Cancun Intl.
$210 Roundtrip, just found
$210
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Dec 6 from O'Hare Intl. to Cancun Intl., returning Sat, Dec 13, priced at $210 just found
Sat, Dec 6 - Sat, Dec 13
MDW
Midway Intl.
CUN
Cancun Intl.
$328 Roundtrip, just found
$328
Roundtrip
just found
Select Aeromexico flight, departing Sat, Dec 6 from Midway Intl. to Cancun Intl., returning Sat, Dec 13, priced at $328 just found
Sat, Dec 6 - Tue, Dec 9
RFD
Greater Rockford
CUN
Cancun Intl.
$349 Roundtrip, found 5 days ago
$349
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Dec 6 from Greater Rockford to Cancun Intl., returning Tue, Dec 9, priced at $349 found 5 days ago
Fri, Dec 5 - Tue, Dec 16
ORD
O'Hare Intl.
TQO
Tulum Intl. Airport
$396 Roundtrip, found 5 hours ago
$396
Roundtrip
found 5 hours ago
Select Air Canada flight, departing Fri, Dec 5 from O'Hare Intl. to Tulum Intl. Airport, returning Tue, Dec 16, priced at $396 found 5 hours ago

Airfares from $95 One Way, $201 Round Trip from Chicago to Riviera Maya

Prices starting at $201 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.

Wed, Dec 31 - Thu, Feb 12
ORD
Chicago
CUN
Cancun
$201 Roundtrip, found 14 hours ago
$201
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Wed, Dec 31 from Chicago to Cancun, returning Thu, Feb 12, priced at $201 found 14 hours ago
Sat, Jan 10 - Sat, Jan 17
ORD
Chicago
CUN
Cancun
$204 Roundtrip, found 3 hours ago
$204
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Sat, Jan 10 from Chicago to Cancun, returning Sat, Jan 17, priced at $204 found 3 hours ago
Fri, Jan 30 - Wed, Feb 4
MDW
Chicago
TQO
Tulum
$256 Roundtrip, found 2 days ago
$256
Roundtrip
found 2 days ago
Select Aeromexico flight, departing Fri, Jan 30 from Chicago to Tulum, returning Wed, Feb 4, priced at $256 found 2 days ago
Fri, Jan 30 - Wed, Feb 4
MDW
Chicago
CUN
Cancun
$269 Roundtrip, found 2 days ago
$269
Roundtrip
found 2 days ago
Select Aeromexico flight, departing Fri, Jan 30 from Chicago to Cancun, returning Wed, Feb 4, priced at $269 found 2 days ago
Thu, Jan 29 - Tue, Feb 3
ORD
Chicago
TQO
Tulum
$304 Roundtrip, found 2 days ago
$304
Roundtrip
found 2 days ago
Select Air Canada flight, departing Thu, Jan 29 from Chicago to Tulum, returning Tue, Feb 3, priced at $304 found 2 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 14 - Jan 18

4 night stay

Chicago (CHI) to Cancun (CUN)

Spirit Airlines • Non-stop roundtrip • Coach
Price was $1,686, price is now $535 per person
$535
per person
found 1 day ago
Amazing and beautiful property! Thank you!

Reviewed on Sep 3, 2024

AVA Resort All Oceanfront - All Inclusive
5.0-star property

AVA Resort All Oceanfront - All Inclusive

8.4/10 Very Good! (633 reviews)

Jan 4 - Jan 9

5 night stay

Chicago (CHI) to Cancun (CUN)

Spirit Airlines • Roundtrip • Coach
Price was $4,951, price is now $1,740 per person
$1,740
per person
found 1 day ago
Great open but food was average at best

Reviewed on Aug 15, 2025

Ocean Dream Cancun by GuruHotel
3.0-star property

Ocean Dream Cancun by GuruHotel

7.4/10 Good! (1,000 reviews)

Jan 2 - Jan 5

3 night stay

Chicago (CHI) to Cancun (CUN)

United • Coach

Cancun (CUN) to Chicago (CHI)

JetBlue Airways • Coach
Price was $3,104, price is now $1,188 per person
$1,188
per person
found 1 day ago
Room service phone did not work, TVs are outdated and bathroom was clogged Other than that it was okay Loved that it’s very well located

Reviewed on Sep 16, 2025

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Riviera Maya packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Mahekal Beach Front Resort & Spa
4.0-star property

Mahekal Beach Front Resort & Spa

8.8/10 Excellent! (1,001 reviews)

Jan 12 - Jan 16

4 night stay

Chicago (CHI) to Cancun (CUN)

Spirit Airlines • PremiumEconomy

Cancun (CUN) to Chicago (CHI)

American Airlines • PremiumEconomy
Save 100% on your flight
Price was $1,453, price is now $818 per person
$818
per person
found 1 day ago
Staff clean room was perfect viewof sea

Reviewed on May 26, 2025

Chablé Maroma
5.0-star property

Chablé Maroma

9.4/10 Exceptional! (156 reviews)

Jan 12 - Jan 16

4 night stay

Chicago (CHI) to Cancun (CUN)

Spirit Airlines • PremiumEconomy

Cancun (CUN) to Chicago (CHI)

American Airlines • PremiumEconomy
Price was $4,587, price is now $2,288 per person
$2,288
per person
found 1 day ago
Everything was amazing! The daily breakfast that was included was absolutely delicious! We highly recommend the French fries and guacamole pool side as well. Luis, our pool side attendant and Aram, our concierge, were top notch, along with everyone else that works there! Our only challenge was we weren’t aware it was a cashless resort, so we weren’t able to break our big bills for individual tips. We recommend you bring small bills ($1’s and $5’s) for tipping purposes!

Reviewed on Jul 24, 2022

Hotel Riu Playacar - All Inclusive
3.5-star property

Hotel Riu Playacar - All Inclusive

8.8/10 Excellent! (1,002 reviews)

Jan 12 - Jan 16

4 night stay

Chicago (CHI) to Cancun (CUN)

Spirit Airlines • PremiumEconomy

Cancun (CUN) to Chicago (CHI)

American Airlines • PremiumEconomy
Save 100% on your flight
Price was $1,799, price is now $1,008 per person
$1,008
per person
found 1 day ago
Loved the food close to down town playa del carmen walkable

Reviewed on Oct 6, 2025

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Riviera Maya business class flight packages

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

AVA Resort All Oceanfront - All Inclusive

8.4/10 Very Good! (633 reviews)

Jan 21 - Jan 25

4 night stay

Chicago (CHI) to Cancun (CUN)

American Airlines • Non-stop roundtrip • BusinessClass
Price was $4,414, price is now $1,927 per person
$1,927
per person
found 22 hours ago
Great open but food was average at best

Reviewed on Aug 15, 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)

American Airlines • Non-stop roundtrip • BusinessClass
Price was $5,325, price is now $2,396 per person
$2,396
per person
found 22 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

Temptation at The Tower Cancún All Inclusive - Adults Only
4.5-star property

Temptation at The Tower Cancún All Inclusive - Adults Only

9/10 Wonderful! (597 reviews)

Jan 21 - Jan 25

4 night stay

Chicago (CHI) to Cancun (CUN)

American Airlines • Non-stop roundtrip • BusinessClass
Price was $4,332, price is now $2,138 per person
$2,138
per person
found 22 hours ago
The resort was clean, pleasing, and plenty of space. The food however left something to be desired. I feel that quality was sacrificed for quantity. Even the "nicer" dining areas were somewhat of a disappointment. The Flame was a total disappointment. The grilled chicken wasn't grilled and was very dry. The Strip steak wasn't what a Strip steak should be and was mostly fat and gristle. The food at the grills at the pool and the party were fantastic. The staff was great.

Reviewed on Mar 19, 2023

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Riviera Maya first class flight packages

Price found within the past 48 hours. Click for updated prices.
Seadust Cancún All Inclusive Family Resort
3.5-star property

Seadust Cancún All Inclusive Family Resort

7.6/10 Good! (2,675 reviews)

Jan 6 - Jan 13

7 night stay

Chicago (ORD) to Cancun (CUN)

United • FirstClass

Cancun (CUN) to Chicago (ORD)

American Airlines • FirstClass
Save 100% on your flight
Price was $2,967, price is now $1,404 per person
$1,404
per person
found 1 day ago
kids area was down or close by 8 pm elevators were down not working

Reviewed on Nov 10, 2025

AVA Resort All Oceanfront - All Inclusive
5.0-star property

AVA Resort All Oceanfront - All Inclusive

8.4/10 Very Good! (633 reviews)

Jan 6 - Jan 13

7 night stay

Chicago (ORD) to Cancun (CUN)

United • FirstClass

Cancun (CUN) to Chicago (ORD)

American Airlines • FirstClass
Price was $7,227, price is now $2,783 per person
$2,783
per person
found 1 day ago
Great open but food was average at best

Reviewed on Aug 15, 2025

Temptation at The Tower Cancún All Inclusive - Adults Only
4.5-star property

Temptation at The Tower Cancún All Inclusive - Adults Only

9/10 Wonderful! (597 reviews)

Jan 6 - Jan 13

7 night stay

Chicago (ORD) to Cancun (CUN)

United • FirstClass

Cancun (CUN) to Chicago (ORD)

American Airlines • FirstClass
Price was $6,589, price is now $2,958 per person
$2,958
per person
found 24 hours ago
The resort was clean, pleasing, and plenty of space. The food however left something to be desired. I feel that quality was sacrificed for quantity. Even the "nicer" dining areas were somewhat of a disappointment. The Flame was a total disappointment. The grilled chicken wasn't grilled and was very dry. The Strip steak wasn't what a Strip steak should be and was mostly fat and gristle. The food at the grills at the pool and the party were fantastic. The staff was great.

Reviewed on Mar 19, 2023

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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.