$110 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 15 - Thu, Feb 19
ORD
O'Hare Intl.
CUN
Cancun Intl.
$273 Roundtrip, just found
$273
Roundtrip
just found
Select Spirit Airlines flight, departing Sun, Feb 15 from O'Hare Intl. to Cancun Intl., returning Thu, Feb 19, priced at $273 just found
Sat, Feb 14 - Wed, Feb 18
RFD
Greater Rockford
CUN
Cancun Intl.
$399 Roundtrip, found 4 days ago
$399
Roundtrip
found 4 days ago
Select Funjet Vacations flight, departing Sat, Feb 14 from Greater Rockford to Cancun Intl., returning Wed, Feb 18, priced at $399 found 4 days ago
Sat, Feb 14 - Wed, Feb 18
MDW
Midway Intl.
CUN
Cancun Intl.
$431 Roundtrip, found 3 hours ago
$431
Roundtrip
found 3 hours ago
Select Delta flight, departing Sat, Feb 14 from Midway Intl. to Cancun Intl., returning Wed, Feb 18, priced at $431 found 3 hours ago
Sun, Feb 15 - Fri, Feb 20
ORD
O'Hare Intl.
CZM
Cozumel Intl.
$447 Roundtrip, found 1 day ago
$447
Roundtrip
found 1 day ago
Select Volaris flight, departing Sun, Feb 15 from O'Hare Intl. to Cozumel Intl., returning Fri, Feb 20, priced at $447 found 1 day ago

Airfares from $110 One Way, $200 Round Trip from Chicago to Riviera Maya

Prices starting at $200 for return flights and $110 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, Apr 29 - Wed, May 6
ORD
Chicago
CUN
Cancun
$200 Roundtrip, found 8 hours ago
$200
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Wed, Apr 29 from Chicago to Cancun, returning Wed, May 6, priced at $200 found 8 hours ago
Tue, Feb 10 - Wed, Feb 25
ORD
Chicago
CUN
Cancun
$218 Roundtrip, found 3 days ago
$218
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Tue, Feb 10 from Chicago to Cancun, returning Wed, Feb 25, priced at $218 found 3 days ago
Sat, Mar 7 - Sat, Mar 14
MDW
Chicago
CUN
Cancun
$259 Roundtrip, just found
$259
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Mar 7 from Chicago to Cancun, returning Sat, Mar 14, priced at $259 just found
Wed, Mar 25 - Wed, Apr 1
RFD
Rockford
CUN
Cancun
$300 Roundtrip, found 15 hours ago
$300
Roundtrip
found 15 hours ago
Select Funjet Vacations flight, departing Wed, Mar 25 from Rockford to Cancun, returning Wed, Apr 1, priced at $300 found 15 hours ago
Sat, Feb 28 - Wed, Mar 4
ORD
Chicago
TQO
Tulum
$305 Roundtrip, found 17 hours ago
$305
Roundtrip
found 17 hours ago
Select United flight, departing Sat, Feb 28 from Chicago to Tulum, returning Wed, Mar 4, priced at $305 found 17 hours ago

Riviera Maya economy flight packages

Price found within the past 48 hours. Click for updated prices.
Fiesta Americana Cancun Villas
4.0-star property

Fiesta Americana Cancun Villas

8.4/10 Very Good! (1,027 reviews)

Mar 12 - Mar 18

6 night stay

Chicago (CHI) to Cancun (CUN)

Spirit Airlines • Non-stop roundtrip • Coach
Price was $2,517, price is now $1,160 per person
$1,160
per person
found 1 day ago
The staff were always very helpful and kind. The breakfast buffet may seem expensive, but it's worth $30 for the variety of traditional Mexican foods and attentive service while enjoying a great view of the ocean. The property is well kept though a bit dated and rooms are spacious. You can access the ocean right in front of the resort by walking down concrete steps, but we walked a few minutes to the beach on either side of the property to enjoy a more traditional beachfront. It's an easy walk to many good restaurants and a grocery store. We cooked at least one meal a day in our little kitchen. One area that could be improved is pool cleanliness. The water looked stagnant in some areas in the mornings and our toddler kept on getting dirty streaks on his swimsuit, which I finally figured out was from some film on the side of the pool.

Reviewed on Mar 19, 2025

Seadust Cancún All Inclusive Family Resort
3.5-star property

Seadust Cancún All Inclusive Family Resort

7.6/10 Good! (2,675 reviews)

Mar 12 - Mar 18

6 night stay

Chicago (CHI) to Cancun (CUN)

Spirit Airlines • Non-stop roundtrip • Coach
Price was $2,842, price is now $1,265 per person
$1,265
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 12 - Mar 18

6 night stay

Chicago (CHI) to Cancun (CUN)

Spirit Airlines • Non-stop roundtrip • Coach
Price was $3,411, price is now $1,548 per person
$1,548
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.
Allegro Playacar - All Inclusive
3.5-star property

Allegro Playacar - All Inclusive

7.8/10 Good! (1,001 reviews)

Mar 8 - Mar 12

4 night stay

Chicago (MDW) to Cancun (CUN)

Aeromexico • Non-stop roundtrip • PremiumEconomy
Price was $2,886, price is now $1,971 per person
$1,971
per person
found 1 day ago
Absolutely fabulous!

Reviewed on Jan 13, 2026

Grand Sunset Princess - All Inclusive
5.0-star property

Grand Sunset Princess - All Inclusive

8.2/10 Very Good! (2,559 reviews)

Mar 8 - Mar 12

4 night stay

Chicago (MDW) to Cancun (CUN)

Aeromexico • Non-stop roundtrip • PremiumEconomy
Price was $2,923, price is now $2,003 per person
$2,003
per person
found 1 day ago
Grand Riviera Princess - All Inclusive
5.0-star property

Grand Riviera Princess - All Inclusive

8/10 Very Good! (4,367 reviews)

Mar 8 - Mar 12

4 night stay

Chicago (MDW) to Cancun (CUN)

Aeromexico • Non-stop roundtrip • PremiumEconomy
Price was $2,943, price is now $2,023 per person
$2,023
per person
found 1 day ago
The property Is still under renovation and the rooms still need to be updated we had a 32in old school tv that stood on the dresser the jetted tub was not clean it had a rust ring around it as well as the jets had rust…room service is not included in your stay it’s an additional charge and if you don’t get reservations for a restaurant they get you a table if you buy a bottle…we basically ate at the buffets which was not bad the pasta and seafood options are good for those that do not eat meat like me…staff was friendly oh yea and the drinks are all watered down so make sure you buy a bottle at the hotel or order double shots on the side to add yourself

Reviewed on Oct 26, 2025

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Riviera Maya business 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)

Mar 8 - Mar 12

4 night stay

Chicago (MDW) to Cancun (CUN)

Aeromexico • Non-stop • BusinessClass

Cancun (CUN) to Chicago (MDW)

Delta • Non-stop • BusinessClass
Price was $3,152, price is now $2,147 per person
$2,147
per person
found 3 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)

Mar 8 - Mar 12

4 night stay

Chicago (MDW) to Cancun (CUN)

Aeromexico • Non-stop • BusinessClass

Cancun (CUN) to Chicago (MDW)

Delta • Non-stop • BusinessClass
Price was $3,577, price is now $2,352 per person
$2,352
per person
found 3 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)

Mar 8 - Mar 12

4 night stay

Chicago (MDW) to Cancun (CUN)

Aeromexico • Non-stop • BusinessClass

Cancun (CUN) to Chicago (MDW)

Delta • Non-stop • BusinessClass
Price was $3,826, price is now $2,560 per person
$2,560
per person
found 3 hours ago
Great stay - great location, food, beach, clean rooms, service and staff were amazing. They really do run a tight ship! Highly recommend :)

Reviewed on Jan 8, 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)

Mar 29 - Apr 2

4 night stay

Chicago (ORD) to Cancun (CUN)

Spirit Airlines • Roundtrip • FirstClass
Price was $2,824, price is now $1,849 per person
$1,849
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

Hotel NYX Cancun All Inclusive
3.5-star property

Hotel NYX Cancun All Inclusive

8.6/10 Excellent! (1,625 reviews)

Mar 29 - Apr 2

4 night stay

Chicago (ORD) to Cancun (CUN)

Spirit Airlines • Roundtrip • FirstClass
Save 100% on your flight
Price was $4,623, price is now $2,878 per person
$2,878
per person
found 1 day ago
The property and staff were great. The room decor was a bit off. Our room was pretty big and certainly could have held two chairs, just a place to sit other than the bed would be nice. Several properties surrounding the immediate area seemed to be vacant and in disrepair, not the fault of NYX, just sad to see.

Reviewed on Oct 22, 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 29 - Apr 2

4 night stay

Chicago (ORD) to Cancun (CUN)

Spirit Airlines • Roundtrip • FirstClass
Price was $3,086, price is now $2,013 per person
$2,013
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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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.