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Riviera Maya

$99+ 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 4/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CUN
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$215
(Kiwi.com)

One-way from

$99
(Cheapflightsfares)

Popular in

March

Cheapest in

September

Average price

$382
Provider with most accurate pricing for Chicago (CHI)-Cancun flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Cancun flights.
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From Chicago (CHI) to Riviera Maya
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One-way flight from Chicago (CHI) to Riviera Maya
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Highest demand for flights based on searches. 4% potential increase in price ($17 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 20, 2025.

This Kiwi.com deal was found by Cheapflights users on 2/20. 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 3/106:00 amORD - CUN
Nonstop3h 48mMultiple Airlines
Sat 3/1510:40 amCUN - ORD
Nonstop4h 03mMultiple Airlines
Deal found 2/20$215
This Cheapflightsfares deal was found by Cheapflights users on 2/20. 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 3/96:00 amORD - CUN
Nonstop3h 48mSpirit Airlines
Tue 3/119:21 amCUN - ORD
1 stop15h 38mSpirit Airlines
Deal found 2/20$216
This Kiwi.com deal was found by Cheapflights users on 2/20. 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.
Sun 3/26:00 amORD - CUN
Nonstop4h 06mFrontier
Wed 3/1210:40 amCUN - ORD
Nonstop4h 03mFrontier
Deal found 2/20$220
This Viva deal was found by Cheapflights users on 2/20. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/102:25 amORD - CUN
1 stop11h 15mViva
Fri 3/1411:25 amCUN - ORD
1 stop13h 05mViva
Deal found 2/20$234
This Kiwi.com deal was found by Cheapflights users on 2/19. 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.
Tue 4/12:45 pmMDW - CUN
1 stop21h 20mFrontier
Tue 4/810:40 amCUN - MDW
1 stop9h 11mFrontier
Deal found 2/19$247
This Kiwi.com deal was found by Cheapflights users on 2/19. 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.
Tue 4/14:40 pmMDW - CUN
1 stop15h 33mMultiple Airlines
Thu 4/1010:30 amCUN - MDW
1 stop11h 57mMultiple Airlines
Deal found 2/19$266
This CheapOair deal was found by Cheapflights users on 2/20. 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.
Mon 3/311:40 amORD - CUN
1 stop8h 23mVolaris
Tue 4/810:00 pmCUN - ORD
1 stop7h 42mVolaris
Deal found 2/20$287
This Viva deal was found by Cheapflights users on 2/20. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/15:05 pmORD - CZM
1 stop29h 50mViva
Thu 11/610:40 pmCZM - ORD
1 stop15h 55mViva
Deal found 2/20$293
This United Airlines deal was found by Cheapflights users on 2/20. 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.
Sun 2/238:42 amORD - CUN
Nonstop3h 51mUnited Airlines
Tue 2/251:27 pmCUN - ORD
Nonstop3h 56mUnited Airlines
Deal found 2/20$305
This Southwest deal was found by Cheapflights users on 2/20. 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.
Wed 5/78:45 amMDW - CUN
1 stop6h 05mSouthwest
Wed 5/149:00 amCUN - MDW
Nonstop3h 40mSouthwest
Deal found 2/20$307
This American Airlines deal was found by Cheapflights users on 2/20. 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 2/235:10 amORD - CUN
1 stop8h 17mAmerican Airlines
Fri 2/2811:32 amCUN - ORD
1 stop9h 18mAmerican Airlines
Deal found 2/20$320
This CheapOair deal was found by Cheapflights users on 2/19. 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 4/41:40 amORD - CZM
1 stop16h 12mVolaris
Wed 4/95:42 pmCZM - ORD
1 stop11h 00mVolaris
Deal found 2/19$367

Find flights from Chicago to Riviera Maya within your budget

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 February 20, 2025.

Fly from

Chicago

Fly to

Riviera Maya

Route

Depart

Return

Price

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Mon 3/10

6:00 am-9:48 am

Nonstop3h 48m

Cancun

Sat 3/15

10:40 am-2:43 pm

Nonstop4h 03m

$215

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sun 3/9

6:00 am-9:48 am

Nonstop3h 48m

Cancun

Tue 3/11

9:21 am-12:59 am

1 stop15h 38m

$216

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sun 3/2

6:00 am-11:06 am

Nonstop4h 06m

Cancun

Wed 3/12

10:40 am-2:43 pm

Nonstop4h 03m

$220

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Mon 3/10

2:25 am-9:10 pm

1 stop18h 45m

Cancun

Wed 3/19

4:05 pm-12:30 am

1 stop8h 25m

$234

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 4/1

2:45 pm-12:05 pm

1 stop21h 20m

Cancun

Tue 4/8

10:40 am-7:51 pm

1 stop9h 11m

$247

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 4/1

4:40 pm-8:13 am

1 stop15h 33m

Cancun

Thu 4/10

10:30 am-10:27 pm

1 stop11h 57m

$266

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Mon 3/31

1:40 am-10:03 am

1 stop8h 23m

Cancun

Tue 4/8

10:00 pm-5:42 am

1 stop7h 42m

$287

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sun 2/23

8:42 am-1:33 pm

Nonstop3h 51m

Cancun

Tue 2/25

1:27 pm-4:23 pm

Nonstop3h 56m

$305

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 5/7

8:45 am-2:50 pm

1 stop6h 05m

Cancun

Wed 5/14

9:00 am-12:40 pm

Nonstop3h 40m

$307

ChicagoCozumel

ORD - CZM

ORDCZM

Chicago O'Hare Intl

Wed 4/2

12:35 pm-5:30 pm

1 stop29h 55m

Cozumel

Sun 4/13

8:25 pm-11:40 pm

1 stop26h 15m

$310

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 54 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.

Travel insights for flights from Chicago to Riviera Maya

Get recent, data-driven insights about flights from Chicago to Riviera Maya including ideal travel times, pricing trends, and more.

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 February 20, 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 February 20, 2025.

The most flights from CHI to zzETW are scheduled on a Monday (11 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (9 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 February 20, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and KLM 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.
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

KLM
7.8
Good
1,333 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Aeromexico
7.5
Good
1,771 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 Spirit Airlines. According to our data, you can fly for as low as $99. Users have also found prices from $100 and $106 on Viva and Frontier, 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: American Airlines (80%), Spirit Airlines (77%), Emirates (77%).

  • 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 $734, our data indicates the cheapest price to be $96. The most popular route (Chicago O'Hare Intl - Cancun), is priced around $210.

  • 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$28Average$311FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$113Average$351FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$174Average$464FlexibilityNo cancel feeOn-time69%
VolarisCheapest$177Average$550FlexibilityNo cancel feeOn-time79%
VivaCheapest$251Average$321FlexibilityNo cancel feeOn-timeN/A
AeromexicoCheapest$286Average$513FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$298Average$552FlexibilityNo cancel feeOn-time71%
DeltaCheapest$335Average$529FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$340Average$686FlexibilityNo cancel feeOn-time63%
AviancaCheapest$672Average$896FlexibilityNo cancel feeOn-time71%
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