$124 Cheap flight deals from Chicago (CHI) to Riviera Maya (CUN)

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

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 5 - Fri, Jul 10
ORD
O'Hare Intl.
CUN
Cancun Intl.
$439 Roundtrip, found 4 hours ago
$439
Roundtrip
found 4 hours ago
Select Volaris flight, departing Sun, Jul 5 from O'Hare Intl. to Cancun Intl., returning Fri, Jul 10, priced at $439 found 4 hours ago
Sun, Jul 5 - Sat, Jul 11
ORD
O'Hare Intl.
TQO
Tulum Intl. Airport
$501 Roundtrip, found 3 days ago
$501
Roundtrip
found 3 days ago
Select Volaris flight, departing Sun, Jul 5 from O'Hare Intl. to Tulum Intl. Airport, returning Sat, Jul 11, priced at $501 found 3 days ago
Sat, Jul 4 - Sat, Jul 25
ORD
O'Hare Intl.
CZM
Cozumel Intl.
$517 Roundtrip, found 15 hours ago
$517
Roundtrip
found 15 hours ago
Select Air Canada flight, departing Sat, Jul 4 from O'Hare Intl. to Cozumel Intl., returning Sat, Jul 25, priced at $517 found 15 hours ago
Fri, Jul 3 - Fri, Jul 10
MDW
Midway Intl.
CUN
Cancun Intl.
$567 Roundtrip, found 15 hours ago
$567
Roundtrip
found 15 hours ago
Select Volaris flight, departing Fri, Jul 3 from Midway Intl. to Cancun Intl., returning Fri, Jul 10, priced at $567 found 15 hours ago

Airfares from $124 One Way, $293 Round Trip from Chicago to Riviera Maya

Prices starting at $293 for return flights and $124 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, Oct 16 - Fri, Oct 23
ORD
Chicago
CUN
Cancun
$293 Roundtrip, found 5 hours ago
$293
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Fri, Oct 16 from Chicago to Cancun, returning Fri, Oct 23, priced at $293 found 5 hours ago
Thu, Aug 6 - Thu, Aug 13
ORD
Chicago
CUN
Cancun
$349 Roundtrip, found 8 hours ago
$349
Roundtrip
found 8 hours ago
Select Funjet Vacations flight, departing Thu, Aug 6 from Chicago to Cancun, returning Thu, Aug 13, priced at $349 found 8 hours ago
Sat, Feb 27 - Sat, Mar 6
ORD
Chicago
CZM
Cozumel
$374 Roundtrip, found 21 hours ago
$374
Roundtrip
found 21 hours ago
Select Volaris flight, departing Sat, Feb 27 from Chicago to Cozumel, returning Sat, Mar 6, priced at $374 found 21 hours ago
Sat, Aug 1 - Wed, Aug 5
MDW
Chicago
CUN
Cancun
$377 Roundtrip, found 4 hours ago
$377
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sat, Aug 1 from Chicago to Cancun, returning Wed, Aug 5, priced at $377 found 4 hours ago
Wed, Aug 26 - Mon, Aug 31
ORD
Chicago
TQO
Tulum
$411 Roundtrip, found 5 hours ago
$411
Roundtrip
found 5 hours ago
Select Volaris flight, departing Wed, Aug 26 from Chicago to Tulum, returning Mon, Aug 31, priced at $411 found 5 hours ago

Riviera Maya economy flight packages

Price found within the past 48 hours. Click for updated prices.
Terasu Riviera Maya Hotel & Spa Luxury Edition, en Xcaret
4.0-star property

Terasu Riviera Maya Hotel & Spa Luxury Edition, en Xcaret

9.4/10 Exceptional! (208 reviews)

Aug 12 - Aug 19

7 night stay

Chicago (CHI) to Cancun (CUN)

Volaris • Non-stop • Coach

Cancun (CUN) to Chicago (CHI)

American Airlines • Non-stop • Coach
Price was $2,129, price is now $908 per person
$908
per person
found 1 day ago
This 9 bedroom tropical boutique hotel, nestled between its natural beauty of jungle and exotic animals does not fall short of luxury and comfort. Bedrooms exceed in ammenities, comfortable beds, pillows, snacks, mini bar. Onsite kitchen, offering limited but tasteful options. The staff is great, always willing to keep you entertained with conversation and very helpful. It is an adorable property, we enjoyed the spider monkeys and iguanas plus more animals we’d never seen. Landscaping is in its natural habitat and gorgeous. It was a relaxing and comfortable stay. Barrowd the bikes and pedaled to Go Mart for snacks and beverages. Getting to Xcaret was easy. Fernando, Rocio, Evon and the chefs are absolute gems.

Reviewed on Jun 21, 2026

Tago Tulum by G Hotels
3.5-star property

Tago Tulum by G Hotels

9/10 Wonderful! (424 reviews)

Aug 2 - Aug 7

5 night stay

Chicago (CHI) to Cancun (CUN)

American Airlines • Coach

Cancun (CUN) to Chicago (CHI)

Frontier Airlines • Coach
Price was $2,559, price is now $1,097 per person
$1,097
per person
found 1 day ago
The property is gorgeous and housekeeping was on point every single day. Big shoutout to Angel, Giovanny, and Blanca — they were genuinely great and made the trip feel special. I had arranged a birthday decoration setup for my boyfriend prior to arrival and it was beautifully done — and housekeeping kept it maintained throughout the rest of our stay. We had complimentary breakfast every morning which was a great perk — always fresh and a nice way to start the day. Food overall is on the pricier side, but honestly that’s just Tulum — coming from someone who lives in Los Angeles , it’s comparable. That said, a few things worth knowing before you book. We had no hot water for 4 out of 7 days, which was frustrating because honestly the shower was a highlight, once we had hot water. Also — the balcony pool never got warm the entire stay. We basically couldn’t use it, so don’t let that be a selling point for you. The most frustrating part was checkout. We tipped cash for room service every time AND were signing receipts, but when we asked what the receipts were for, staff brushed it off with “oh it’s nothing.” Then at the end of the trip, room service charges showed up on our bill. We had to go back and explain that we’d already been tipping in cash the whole time. Angel sorted it out, but it was an annoying situation that could’ve been avoided with just a little transparency upfront. If you order room service, ask questions before you sign anything. Bring pesos !

Reviewed on Jun 23, 2026

El Dorado Royale, All & More Inclusive Adults Only
5.0-star property

El Dorado Royale, All & More Inclusive Adults Only

8.6/10 Excellent! (640 reviews)

Aug 22 - Aug 26

4 night stay

Chicago (CHI) to Cancun (CUN)

American Airlines • Coach

Cancun (CUN) to Chicago (CHI)

Volaris • Coach
Price was $2,228, price is now $960 per person
$960
per person
found 1 day ago
We visited here in 2009 and had the best experience ever, well 17 years later we hoped it would be much of the same. I can’t say our stay was horrible because it definitely was not. We were able to relax and enjoy ourselves, but it was quite a different experience this time around. A lot of restaurants closed on certain days, and even only being at 30% capacity we waited nearly 45 minutes at a restaurant the concierge made us reservations at, but they didn’t have it on the books. The seaweed made it impossible to even step foot on the beach. The clear blue water days are over, unfortunately. While we enjoyed our time, it just wasn’t what we remembered years ago. I’m not sure if they have gotten so big they are spreading themselves thin or if it truly is that they are so short staffed due to being 44% down on tourism. I don’t want be entirely negative of the resort - Kampai and Jade were our most favorite places to eat. Most of the service was excellent. Again, we can to relax after many stressful days at work, and that’s what we got.

Reviewed on Jun 26, 2026

Don't see what you're looking for?
See all available trips from Chicago to Riviera Maya
View all trips

Riviera Maya business class flight packages

Price found within the past 48 hours. Click for updated prices.
El Dorado Royale, All & More Inclusive Adults Only
5.0-star property

El Dorado Royale, All & More Inclusive Adults Only

8.6/10 Excellent! (640 reviews)

Aug 10 - Aug 14

4 night stay

Chicago (CHI) to Cancun (CUN)

United • BusinessClass

Cancun (CUN) to Chicago (CHI)

Frontier Airlines • BusinessClass
Save 100% on your flight
Price was $2,572, price is now $1,332 per person
$1,332
per person
found 9 hours ago
We visited here in 2009 and had the best experience ever, well 17 years later we hoped it would be much of the same. I can’t say our stay was horrible because it definitely was not. We were able to relax and enjoy ourselves, but it was quite a different experience this time around. A lot of restaurants closed on certain days, and even only being at 30% capacity we waited nearly 45 minutes at a restaurant the concierge made us reservations at, but they didn’t have it on the books. The seaweed made it impossible to even step foot on the beach. The clear blue water days are over, unfortunately. While we enjoyed our time, it just wasn’t what we remembered years ago. I’m not sure if they have gotten so big they are spreading themselves thin or if it truly is that they are so short staffed due to being 44% down on tourism. I don’t want be entirely negative of the resort - Kampai and Jade were our most favorite places to eat. Most of the service was excellent. Again, we can to relax after many stressful days at work, and that’s what we got.

Reviewed on Jun 26, 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)

Aug 10 - Aug 14

4 night stay

Chicago (CHI) to Cancun (CUN)

United • BusinessClass

Cancun (CUN) to Chicago (CHI)

Frontier Airlines • BusinessClass
Save 100% on your flight
Price was $4,786, price is now $2,600 per person
$2,600
per person
found 9 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

Hotel Mousai Cancun Adults Only - All Inclusive
5.0-star property

Hotel Mousai Cancun Adults Only - All Inclusive

9.6/10 Exceptional! (118 reviews)

Aug 10 - Aug 14

4 night stay

Chicago (CHI) to Cancun (CUN)

United • BusinessClass

Cancun (CUN) to Chicago (CHI)

Frontier Airlines • BusinessClass
Save 100% on your flight
Price was $4,097, price is now $2,463 per person
$2,463
per person
found 9 hours ago
Amazing staff. Amazing property. If you want absolute luxury and comfort this is your hotel. From the heated toilets with built in bidets to the amazing stone jacuzzis, from the fantastic hammocks to the pool lounge chairs and umbrellas, absolutely no expense was spared here. If you want an all inclusive with gourmet food and fantastic attentive service, look no further than Hotel Mousai.

Reviewed on Jun 11, 2026

Don't see what you're looking for?
See all available trips from Chicago to Riviera Maya
View all trips

Riviera Maya first class flight packages

Price found within the past 48 hours. Click for updated prices.
The Pyramid Cancun By Oasis - All Inclusive
4.0-star property

The Pyramid Cancun By Oasis - All Inclusive

7.2/10 Good! (1,785 reviews)

Aug 12 - Aug 19

7 night stay

Chicago (ORD) to Cancun (CUN)

Frontier Airlines • Non-stop • FirstClass

Cancun (CUN) to Chicago (ORD)

United • Non-stop • FirstClass
Save 100% on your flight
Price was $3,202, price is now $1,785 per person
$1,785
per person
found 1 day ago
Room was clean but two of our 5 days they gave us no wash rags to wash after a hot day buffet food was not that great most drinks wateres down besides in reservation restaurants. I booked honey moon sweet for a 10 year anniversary at time of booking I requested out door jacuzzi room we were on 6th floor above all jacuzzi rooms and could see not one person was on them balconies our whole stay yet we were put in a diff room told them rooms are booked definitely not pool almost to warm to be refreshing staff was very nice helpful mostly we definitely still had a great trip fun 1st time in cancun oh yeah and one of the nights staff was chanting very loudly at 3am in the main lobby waking my husband and I up as well

Reviewed on Jun 30, 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)

Aug 12 - Aug 19

7 night stay

Chicago (ORD) to Cancun (CUN)

Frontier Airlines • Non-stop • FirstClass

Cancun (CUN) to Chicago (ORD)

United • Non-stop • FirstClass
Price was $7,266, price is now $3,576 per person
$3,576
per person
found 1 day 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

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

Hotel Riu Palace Kukulkan - Adults Only - All Inclusive

9.2/10 Wonderful! (5,069 reviews)

Aug 12 - Aug 19

7 night stay

Chicago (ORD) to Cancun (CUN)

Frontier Airlines • Non-stop • FirstClass

Cancun (CUN) to Chicago (ORD)

United • Non-stop • FirstClass
Save 100% on your flight
Price was $3,544, price is now $1,965 per person
$1,965
per person
found 1 day ago
Everything was wonderful.

Reviewed on Jun 30, 2026

Don't see what you're looking for?
See all available trips from Chicago to Riviera Maya
View all trips

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

Finding cheap flights from Chicago to Riviera Maya need never be a problem again when you put your faith in Orbitz, the online leader in discounted travel arrangements. You’ll get guaranteed low prices every time you book and be able to choose from a great selection of hotels, flight, cruises, and more.

Orbitz deals in bargains

You can have total confidence in Orbitz to help you find spectacular deals on Chicago to Riviera Maya flights at bargain prices. We also display quality accommodations at unbelievable rates, leaving you with spare cash for a little extra indulgence in Riviera Maya.

Mix flights for a perfect schedule

Orbitz helps you find that low fare time and again whether you are looking at domestic or international tickets for leisure or business. Our extensive search capabilities let you select alternative airlines for your departure and return on your flights from Chicago to Riviera Maya to give you the best deals that suit your schedule.

Cutting-edge mobile apps

Finding budget flights from Chicago to Riviera Maya is easier with cutting-edge mobile tools as our app that allows you to check flight availabilities on the move using your smartphone or tablet. We can even send you free alerts to your email and mobile phone to inform you of any delays to your Chicago to Riviera Maya flights.

Orbitz adds value to your search for bargain Chicago to Riviera Maya flights

If value is what you are after, let Orbitz take care of you. Your low cost Chicago to Riviera Maya flights along with our great bargains on hotels and car rentals will make your trip all the more memorable.

More Destinations

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.