$117 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, Feb 22 - Thu, Mar 5
ORD
O'Hare Intl.
CUN
Cancun Intl.
$327 Roundtrip, just found
$327
Roundtrip
just found
Select Aeromexico flight, departing Sun, Feb 22 from O'Hare Intl. to Cancun Intl., returning Thu, Mar 5, priced at $327 just found
Sat, Feb 21 - Thu, Feb 26
MDW
Midway Intl.
CUN
Cancun Intl.
$370 Roundtrip, found 6 hours ago
$370
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Sat, Feb 21 from Midway Intl. to Cancun Intl., returning Thu, Feb 26, priced at $370 found 6 hours ago
Sat, Feb 21 - Wed, Feb 25
ORD
O'Hare Intl.
TQO
Tulum Intl. Airport
$452 Roundtrip, found 1 day ago
$452
Roundtrip
found 1 day ago
Select Volaris flight, departing Sat, Feb 21 from O'Hare Intl. to Tulum Intl. Airport, returning Wed, Feb 25, priced at $452 found 1 day ago
Fri, Feb 20 - Fri, Feb 27
ORD
O'Hare Intl.
CZM
Cozumel Intl.
$464 Roundtrip, found 2 days ago
$464
Roundtrip
found 2 days ago
Select Volaris flight, departing Fri, Feb 20 from O'Hare Intl. to Cozumel Intl., returning Fri, Feb 27, priced at $464 found 2 days ago

Airfares from $117 One Way, $249 Round Trip from Chicago to Riviera Maya

Prices starting at $249 for return flights and $117 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.

Tue, Mar 3 - Wed, Mar 4
ORD
Chicago
CUN
Cancun
$249 Roundtrip, found 1 day ago
$249
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Mar 3 from Chicago to Cancun, returning Wed, Mar 4, priced at $249 found 1 day ago
Mon, Mar 9 - Mon, Mar 16
ORD
Chicago
CUN
Cancun
$250 Roundtrip, found 6 hours ago
$250
Roundtrip
found 6 hours ago
Select Funjet Vacations flight, departing Mon, Mar 9 from Chicago to Cancun, returning Mon, Mar 16, priced at $250 found 6 hours ago
Sun, Mar 8 - Fri, Mar 13
MDW
Chicago
CUN
Cancun
$293 Roundtrip, found 1 day ago
$293
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sun, Mar 8 from Chicago to Cancun, returning Fri, Mar 13, priced at $293 found 1 day ago
Mon, Feb 23 - Sat, Feb 28
RFD
Rockford
CUN
Cancun
$299 Roundtrip, found 9 hours ago
$299
Roundtrip
found 9 hours ago
Select Funjet Vacations flight, departing Mon, Feb 23 from Rockford to Cancun, returning Sat, Feb 28, priced at $299 found 9 hours ago
Mon, Mar 2 - Thu, Mar 5
MDW
Chicago
TQO
Tulum
$325 Roundtrip, found 5 days ago
$325
Roundtrip
found 5 days ago
Select Aeromexico flight, departing Mon, Mar 2 from Chicago to Tulum, returning Thu, Mar 5, priced at $325 found 5 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)

Apr 8 - Apr 12

4 night stay

Chicago (CHI) to Cancun (CUN)

American Airlines • Non-stop • Coach

Cancun (CUN) to Chicago (CHI)

Air Canada • Non-stop • Coach
Price was $1,767, price is now $786 per person
$786
per person
found 1 day ago
Amazing and beautiful property! Thank you!

Reviewed on Sep 3, 2024

Seadust Cancún All Inclusive Family Resort
3.5-star property

Seadust Cancún All Inclusive Family Resort

7.6/10 Good! (2,675 reviews)

Apr 1 - Apr 9

8 night stay

Chicago (CHI) to Cancun (CUN)

Spirit Airlines • Non-stop • Coach

Cancun (CUN) to Chicago (CHI)

Delta • Non-stop • Coach
Price was $4,040, price is now $1,762 per person
$1,762
per person
found 1 day ago
The staff members were exceptional. The rooms were clean. The restaurant staffs were exceptional. We had a beautiful view of the sea. Excellent choice for an adult or family all inclusive stay.

Reviewed on Jan 29, 2026

Wyndham Grand Cancun All Inclusive Resort & Villas
4.0-star property

Wyndham Grand Cancun All Inclusive Resort & Villas

8.4/10 Very Good! (3,498 reviews)

Mar 16 - Mar 22

6 night stay

Chicago (CHI) to Cancun (CUN)

Roundtrip • Coach
Price was $4,272, price is now $1,932 per person
$1,932
per person
found 1 day ago
Room was very clean and staff was so friendly, really enjoyed our time there. The food was good, alrhough was difficult to book reservations for some of the restaurants, the buffet option was always available, would go back

Reviewed on Feb 2, 2026

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Riviera Maya packages with premium economy flights

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! (180 reviews)

Mar 23 - Mar 27

4 night stay

Chicago (ORD) to Cancun (CUN)

Aeromexico • Non-stop roundtrip • PremiumEconomy
Price was $2,045, price is now $1,524 per person
$1,524
per person
found 1 day ago
So far so good..Considering price as compared to other beachfront/ocean properties quite reasonable for services offered including restaurants pools, etc. Property needs some updating overall and addition of services and some standard amenities. Restroom additions closer to pool areas and beach areas would be helpful. Roving drink servers for pool bars & towels at each pool location would make life more pleasurable and convenient for guests. All in all we enjoyed stay and happy with our choice.

Reviewed on Apr 1, 2025

Bahia Principe Grand Tulum - All Inclusive
4.0-star property

Bahia Principe Grand Tulum - All Inclusive

8.4/10 Very Good! (1,388 reviews)

Mar 23 - Mar 27

4 night stay

Chicago (ORD) to Cancun (CUN)

Aeromexico • Non-stop roundtrip • PremiumEconomy
Price was $2,392, price is now $1,813 per person
$1,813
per person
found 1 day ago
The room is in need of a renovation. The room door and shower needs repairing. The staff was very attentive but the food was a little lackluster and at most times cold.

Reviewed on Nov 28, 2025

Bahia Principe Luxury Akumal - All Inclusive
4.5-star property

Bahia Principe Luxury Akumal - All Inclusive

8.4/10 Very Good! (1,145 reviews)

Mar 23 - Mar 27

4 night stay

Chicago (ORD) to Cancun (CUN)

Aeromexico • Non-stop roundtrip • PremiumEconomy
Price was $2,384, price is now $1,809 per person
$1,809
per person
found 1 day ago
Bernabe was the best bartender. Always smiling and hard-working. Once the renovations are complete, this place will be fantastic.

Reviewed on May 31, 2025

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Riviera Maya business class flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel NYX Cancun - Near La Isla Shopping Mall
3.5-star property

Hotel NYX Cancun - Near La Isla Shopping Mall

7.6/10 Good! (1,002 reviews)

Apr 10 - Apr 15

5 night stay

Chicago (CHI) to Cancun (CUN)

American Airlines • Non-stop roundtrip • BusinessClass
Save 100% on your flight
Price was $2,935, price is now $1,668 per person
$1,668
per person
found 1 day ago
Service was excellent. Please be prepared to tip all helpful staff, they were really amazing! Drinks were a bit disappointing and most of the food was good.

Reviewed on Mar 15, 2021

Hotel Riu Palace Costa Mujeres - All Inclusive
4.0-star property

Hotel Riu Palace Costa Mujeres - All Inclusive

8.8/10 Excellent! (1,305 reviews)

Mar 28 - Apr 2

5 night stay

Chicago (CHI) to Cancun (CUN)

Spirit Airlines • Non-stop • BusinessClass

Cancun (CUN) to Chicago (CHI)

American Airlines • Non-stop • BusinessClass
Price was $4,168, price is now $2,437 per person
$2,437
per person
found 1 day ago
Room was nice and clean. Excellent food choices! Pool was amazing!

Reviewed on Oct 28, 2025

Wyndham Grand Cancun All Inclusive Resort & Villas
4.0-star property

Wyndham Grand Cancun All Inclusive Resort & Villas

8.4/10 Very Good! (3,498 reviews)

Mar 28 - Apr 2

5 night stay

Chicago (CHI) to Cancun (CUN)

Spirit Airlines • Non-stop • BusinessClass

Cancun (CUN) to Chicago (CHI)

American Airlines • Non-stop • BusinessClass
Price was $3,176, price is now $1,870 per person
$1,870
per person
found 1 day ago
Room was very clean and staff was so friendly, really enjoyed our time there. The food was good, alrhough was difficult to book reservations for some of the restaurants, the buffet option was always available, would go back

Reviewed on Feb 2, 2026

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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)

Apr 3 - Apr 10

7 night stay

Chicago (CHI) to Cancun (CUN)

American Airlines • Non-stop • FirstClass

Cancun (CUN) to Chicago (CHI)

United • Non-stop • FirstClass
Price was $4,141, price is now $2,137 per person
$2,137
per person
found 7 hours ago
The staff members were exceptional. The rooms were clean. The restaurant staffs were exceptional. We had a beautiful view of the sea. Excellent choice for an adult or family all inclusive stay.

Reviewed on Jan 29, 2026

Wyndham Grand Cancun All Inclusive Resort & Villas
4.0-star property

Wyndham Grand Cancun All Inclusive Resort & Villas

8.4/10 Very Good! (3,498 reviews)

Apr 3 - Apr 10

7 night stay

Chicago (CHI) to Cancun (CUN)

American Airlines • Non-stop • FirstClass

Cancun (CUN) to Chicago (CHI)

United • Non-stop • FirstClass
Price was $5,083, price is now $2,582 per person
$2,582
per person
found 7 hours ago
Room was very clean and staff was so friendly, really enjoyed our time there. The food was good, alrhough was difficult to book reservations for some of the restaurants, the buffet option was always available, would go back

Reviewed on Feb 2, 2026

Hotel Riu Palace Kukulkan - Adults Only - All Inclusive
4.5-star property

Hotel Riu Palace Kukulkan - Adults Only - All Inclusive

9/10 Wonderful! (4,559 reviews)

Apr 3 - Apr 10

7 night stay

Chicago (CHI) to Cancun (CUN)

American Airlines • Non-stop • FirstClass

Cancun (CUN) to Chicago (CHI)

United • Non-stop • FirstClass
Price was $4,526, price is now $2,377 per person
$2,377
per person
found 7 hours ago
Clean rooms, staff great , just a nice place

Reviewed on Feb 12, 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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Get Package Savings by Booking Flights and Hotels at the Same Time

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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.