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Riviera Maya

$104+ 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 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CUN
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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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 July 31, 2025.

Round-trip from

$255
(Cheapflightsfares)

One-way from

$104
(Mytrip)

Popular in

March

Cheapest in

September

Average price

$389
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. 6% potential increase in price ($29 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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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 July 31, 2025.

This SmartFares deal was found by Cheapflights users on 7/31. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/165:17 pmORD - CUN
1 stop14h 54mSpirit Airlines
Fri 9/199:16 amCUN - ORD
1 stop12h 42mSpirit Airlines
Deal found 7/31$255
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
Sat 9/136:10 amORD - CUN
Nonstop3h 37mMultiple Airlines
Sun 9/2111:34 amCUN - ORD
Nonstop4h 09mMultiple Airlines
Deal found 7/30$257
This Frontier deal was found by Cheapflights users on 7/30. 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.
Mon 8/187:35 amORD - CUN
Nonstop3h 55mFrontier
Sun 8/2411:51 amCUN - ORD
Nonstop4h 01mFrontier
Deal found 7/30$262
This Southwest deal was found by Cheapflights users on 7/31. 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.
Sat 11/83:40 pmMDW - CUN
Nonstop3h 45mSouthwest
Sat 11/1511:55 amCUN - MDW
Nonstop3h 50mSouthwest
Deal found 7/31$270
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
Thu 9/117:25 amORD - CUN
1 stop13h 38mVolaris
Thu 9/1811:34 amCUN - ORD
Nonstop4h 09mVolaris
Deal found 7/30$277
This United Airlines deal was found by Cheapflights users on 7/28. 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.
Wed 10/298:43 amORD - CUN
Nonstop3h 50mUnited Airlines
Mon 11/34:20 pmCUN - ORD
1 stop8h 39mUnited Airlines
Deal found 7/28$296
This SmartFares deal was found by Cheapflights users on 7/29. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/66:00 amMDW - CUN
1 stop5h 30mAeromexico
Thu 9/1112:25 pmCUN - MDW
1 stop9h 11mAeromexico
Deal found 7/29$303
This Mytrip deal was found by Cheapflights users on 7/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/51:40 amORD - CZM
1 stop16h 12mVolaris
Sat 9/135:42 pmCZM - ORD
1 stop11h 00mVolaris
Deal found 7/29$312
This Delta deal was found by Cheapflights users on 7/29. 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.
Sun 10/2610:35 amMDW - CUN
1 stop9h 45mDelta
Sat 11/18:00 amCUN - MDW
1 stop14h 14mDelta
Deal found 7/29$324
This Frontier deal was found by Cheapflights users on 7/30. 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 9/136:15 amMDW - CUN
1 stop6h 25mFrontier
Sat 9/201:55 pmCUN - MDW
1 stop9h 22mFrontier
Deal found 7/30$331
This Priceline deal was found by Cheapflights users on 7/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/86:00 amMDW - CUN
1 stop14h 20mMultiple Airlines
Sat 11/152:41 pmCUN - MDW
1 stop9h 28mMultiple Airlines
Deal found 7/29$341
This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
Sat 8/3012:45 pmORD - CZM
2 stops25h 02mMultiple Airlines
Fri 9/58:00 pmCZM - ORD
1 stop17h 49mMultiple Airlines
Deal found 7/29$402

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 July 31, 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

Tue 9/16

5:17 pm-8:11 am

1 stop14h 54m

Cancun

Fri 9/19

9:16 am-9:58 pm

1 stop12h 42m

$255

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sat 9/13

6:10 am-9:47 am

Nonstop3h 37m

Cancun

Sun 9/21

11:34 am-3:43 pm

Nonstop4h 09m

$257

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Mon 8/18

7:35 am-11:30 am

Nonstop3h 55m

Cancun

Sun 8/24

11:51 am-3:52 pm

Nonstop4h 01m

$262

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 10/26

10:40 am-2:15 pm

Nonstop3h 35m

Cancun

Thu 10/30

3:20 pm-6:55 pm

Nonstop3h 35m

$270

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Thu 9/11

7:25 am-9:03 pm

1 stop13h 38m

Cancun

Thu 9/18

11:34 am-3:43 pm

Nonstop4h 09m

$277

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Wed 10/29

8:43 am-12:33 pm

Nonstop3h 50m

Cancun

Mon 11/3

4:20 pm-11:59 pm

1 stop8h 39m

$296

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 9/6

6:00 am-11:30 am

1 stop5h 30m

Cancun

Thu 9/11

12:25 pm-9:36 pm

1 stop9h 11m

$303

ChicagoCozumel

ORD - CZM

ORDCZM

Chicago O'Hare Intl

Fri 9/5

1:40 am-4:52 pm

1 stop16h 12m

Cozumel

Sat 9/13

5:42 pm-5:42 am

1 stop11h 00m

$312

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 10/26

10:35 am-8:20 pm

1 stop9h 45m

Cancun

Sat 11/1

8:00 am-10:14 pm

1 stop14h 14m

$324

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 9/13

6:15 am-12:40 pm

1 stop6h 25m

Cancun

Sat 9/20

1:55 pm-11:17 pm

1 stop9h 22m

$331

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 33 results
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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 July 31, 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 July 31, 2025.

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

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 July 31, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and Aeromexico from Chicago to Riviera Maya by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Aeromexico
7.5
Good
1,721 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,900 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Viva
7.0
Good
788 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 Viva. According to our data, you can fly for as low as $104. Users have also found prices from $108 and $113 on Volaris 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: Emirates (91%), United Airlines (91%), Frontier (85%).

  • 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 $752, our data indicates the cheapest price to be $107. The most popular route (Chicago O'Hare Intl - Cancun), is priced around $216.

  • 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

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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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$124Average$326FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$161Average$522FlexibilityNo cancel feeOn-time69%
FrontierCheapest$167Average$398FlexibilityNo cancel feeOn-time62%
DeltaCheapest$168Average$554FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$181Average$546FlexibilityNo cancel feeOn-time79%
AeromexicoCheapest$191Average$496FlexibilityNo cancel feeOn-timeN/A
VivaCheapest$251Average$322FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$266Average$639FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$331Average$587FlexibilityNo cancel feeOn-time71%
AviancaCheapest$552Average$896FlexibilityNo cancel feeOn-time71%

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