HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Riviera Maya

$109+ Cheap flights from Chicago (CHI) to Riviera Maya

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CUN
Apr 29 — May 61
Tue 4/29
Tue 5/6
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Riviera Maya with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Chicago to Riviera Maya

Keep the following information in mind while searching for Chicago to Riviera Maya flight deals. Data was last updated April 24, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$240
(CheapOair)

One-way from

$110
(Cheapflightsfares)

Popular in

March

Cheapest in

September

Average price

$402
Provider with most accurate pricing for Chicago (CHI)-Cancun flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Cancun flights.
Search Deals
From Chicago (CHI) to Riviera Maya
Search Deals
One-way flight from Chicago (CHI) to Riviera Maya
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($32 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals

Find flight deals from Chicago to Riviera Maya

Cheapest flights from Chicago to Riviera Maya
Explore the most affordable flight options available from Chicago to Riviera Maya. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 24, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/46:00 amORD - CUN
Nonstop3h 41mSpirit Airlines
Sat 5/1010:52 amCUN - ORD
Nonstop3h 57mSpirit Airlines
Deal found 4/21$234
This Frontier deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/37:15 amORD - CUN
Nonstop3h 59mFrontier
Thu 5/810:37 amCUN - ORD
Nonstop4h 01mFrontier
Deal found 4/22$235
This CheapOair deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/267:05 amORD - CUN
Nonstop4h 02mMultiple Airlines
Sat 5/312:16 pmCUN - ORD
1 stop12h 42mMultiple Airlines
Deal found 4/23$240
This Southwest deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/1110:45 amMDW - CUN
Nonstop3h 40mSouthwest
Thu 5/159:00 amCUN - MDW
Nonstop3h 40mSouthwest
Deal found 4/23$246
This Trip.com deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/66:04 amMDW - CUN
1 stop6h 46mAeromexico
Tue 5/138:00 amCUN - MDW
1 stop7h 30mAeromexico
Deal found 4/22$299
This United Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/610:42 amORD - CUN
Nonstop3h 46mUnited Airlines
Wed 6/1112:20 pmCUN - ORD
Nonstop4h 02mUnited Airlines
Deal found 4/22$300
This Aeromexico deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/296:24 amORD - CUN
2 stops15h 05mAeromexico
Tue 6/36:01 amCUN - ORD
1 stop8h 09mAeromexico
Deal found 4/22$311
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/712:48 pmMDW - CUN
1 stop7h 32mDelta
Sat 6/148:30 amCUN - MDW
2 stops13h 15mDelta
Deal found 4/23$321
This Delta deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/198:55 amORD - CUN
2 stops11h 03mDelta
Mon 7/2812:30 pmCUN - ORD
1 stop8h 04mDelta
Deal found 4/22$325
This Kiwi.com deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1212:48 pmMDW - CUN
1 stop7h 32mMultiple Airlines
Fri 5/1612:39 pmCUN - MDW
1 stop9h 34mMultiple Airlines
Deal found 4/23$339
This American Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/118:40 amORD - CUN
Nonstop3h 45mAmerican Airlines
Thu 5/151:25 pmCUN - ORD
Nonstop4h 00mAmerican Airlines
Deal found 4/22$344
This CheapOair deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1012:45 pmORD - CUN
1 stop9h 04mVolaris
Tue 10/144:00 pmCUN - ORD
1 stop13h 42mVolaris
Deal found 4/23$360

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago to Riviera Maya that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 24, 2025.
Use the filters below to find and compare flights from Chicago to Riviera Maya that are best for you.

Fly from

Chicago

Fly to

Riviera Maya

Route

Depart

Return

Price

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sun 5/4

6:00 am-9:41 am

Nonstop3h 41m

Cancun

Sat 5/10

10:52 am-2:49 pm

Nonstop3h 57m

$234

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sat 5/3

7:15 am-11:14 am

Nonstop3h 59m

Cancun

Thu 5/8

10:37 am-2:38 pm

Nonstop4h 01m

$235

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Tue 5/6

7:15 am-11:22 am

Nonstop4h 07m

Cancun

Tue 5/13

12:18 pm-11:04 pm

1 stop10h 46m

$240

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 5/11

10:45 am-2:25 pm

Nonstop3h 40m

Cancun

Thu 5/15

9:00 am-12:40 pm

Nonstop3h 40m

$246

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 5/6

6:04 am-12:50 pm

1 stop6h 46m

Cancun

Tue 5/13

8:00 am-3:30 pm

1 stop7h 30m

$299

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Tue 5/6

10:42 am-2:28 pm

Nonstop3h 46m

Cancun

Wed 6/11

12:20 pm-4:22 pm

Nonstop4h 02m

$300

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Tue 6/24

9:49 am-11:32 pm

2 stops13h 43m

Cancun

Fri 6/27

9:38 am-9:24 pm

2 stops11h 46m

$305

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 6/7

6:00 am-5:30 pm

2 stops11h 30m

Cancun

Sat 6/14

9:15 am-9:45 pm

2 stops12h 30m

$321

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Tue 5/6

7:05 am-2:01 pm

1 stop6h 56m

Cancun

Thu 5/8

9:55 am-4:47 pm

1 stop6h 52m

$321

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 5/12

12:48 pm-8:20 pm

1 stop7h 32m

Cancun

Fri 5/16

12:39 pm-10:13 pm

1 stop9h 34m

$339

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

Showing 1-10 of 50 results
1
2
3
...
5

Best time to book a flight from Chicago to Riviera Maya

Have a flexible travel schedule? Discover the best time to fly to Riviera Maya from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Riviera Maya

What is the cheapest month to book a flight from Chicago to Riviera Maya?

Currently, January is the cheapest month in which you can book a flight from Chicago to Riviera Maya (average of $360). Flying from Chicago to Riviera Maya in March is currently the most expensive (average of $492). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to ETW?

Find hourly flight availability from Chicago to Riviera Maya. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 24, 2025.

When flying from Chicago to Riviera Maya, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Chicago to Riviera Maya

Explore weekly flight availability from Chicago to Riviera Maya. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated April 24, 2025.

The most flights from CHI to zzETW are scheduled on a Monday (9 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (7 on average).

Rainfall in Riviera Maya by month

Plan your trip to Riviera Maya by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Riviera Maya ranges from 1.1 - 11.1 inches per month. October is typically the wettest month, when rainfall can reach 11.1 in. April is typically the driest time to visit Riviera Maya when rainfall is around 1.1 in.

Temperature in Riviera Maya by month

Plan your trip to Riviera Maya by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Riviera Maya, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 86.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 75.2 F).

Reviews of airlines servicing Riviera Maya

Get insights into the airlines that provide service to Riviera Maya. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Riviera Maya. Reviews last updated April 24, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest and Delta from Chicago to Riviera Maya to help guide your decision. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,918 reviews

Overall

8.0

Food

7.1

Comfort

7.9

Entertainment

7.1

Crew

8.5

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,918 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Overall

8.0

Food

7.1

Comfort

7.9

Entertainment

7.1

Crew

8.5

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very good
4,286 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Overall

8.0

Food

7.1

Comfort

7.9

Entertainment

7.1

Crew

8.5

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,920 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Overall

8.0

Food

7.1

Comfort

7.9

Entertainment

7.1

Crew

8.5

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Aeromexico
7.5
Good
1,700 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Overall

8.0

Food

7.1

Comfort

7.9

Entertainment

7.1

Crew

8.5

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,685 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Overall

8.0

Food

7.1

Comfort

7.9

Entertainment

7.1

Crew

8.5

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

Related info for your journey

Find useful and relevant information for your journey from Chicago to Riviera Maya. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Chicago to Riviera Maya one-way?

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $110. Users have also found prices from $111 and $111 on Southwest and Spirit Airlines, respectively.

  • What are the most popular routes from Chicago to Riviera Maya?

    The most popular flight routes from Chicago to Riviera Maya are Chicago O'Hare Intl - Cancun, Chicago Midway - Cancun and Chicago O'Hare Intl - Cozumel.

  • What are the most reliable airlines from Chicago to Riviera Maya?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago to Riviera Maya on time: United Airlines (81%), Emirates (80%), Spirit Airlines (76%).

  • What are the cheapest flights from Chicago to Riviera Maya?

    Looking for the cheapest flight from Chicago to Riviera Maya? While on average our users pay $707, our data indicates the cheapest price to be $94. The most popular route (Chicago O'Hare Intl - Cancun), is priced around $225.

  • Can I find deals for flights from Chicago to Riviera Maya that include hotel bookings?

    Yes. In addition to deals on Chicago to Riviera Maya flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Riviera Maya?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Riviera Maya.

  • Can I find deals for business class flights from Chicago to Riviera Maya?

    Yes. Cheapflights offers flight deals from Chicago to Riviera Maya by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Riviera Maya?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Riviera Maya (average of $360). Flying from Chicago to Riviera Maya in March is currently the most expensive (average of $492). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Top 10 airlines flying from Chicago to Riviera Maya

Discover the top 10 airlines that operate flights from Chicago to Riviera Maya. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$120Average$321FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$161Average$502FlexibilityNo cancel feeOn-time69%
FrontierCheapest$161Average$390FlexibilityNo cancel feeOn-time62%
VolarisCheapest$179Average$556FlexibilityNo cancel feeOn-time79%
VivaCheapest$251Average$323FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$279Average$955FlexibilityNo cancel feeOn-time67%
AeromexicoCheapest$287Average$518FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$310Average$578FlexibilityNo cancel feeOn-time71%
DeltaCheapest$320Average$529FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$340Average$694FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.