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Riviera Maya

$93+ 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 9/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CUN
oct. 16 — oct. 231
jue. 10/16
jue. 10/23
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 septiembre 16, 2025.

Round-trip from

$233
(Kiwi.com)

One-way from

$93
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$347
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. 5% potential increase in price ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in September 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 septiembre 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
mar. 12/95:05 amORD - CUN
1 stop6h 22mMultiple Airlines
vie. 12/1211:38 amCUN - ORD
Nonstop4h 03mMultiple Airlines
Deal found 9/16$233
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
dom. 10/196:30 amORD - CUN
Nonstop3h 45mMultiple Airlines
mar. 10/289:09 amCUN - ORD
1 stop7h 14mMultiple Airlines
Deal found 9/14$234
This Spirit deal was found by Cheapflights users on 9/14. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 9/215:05 amORD - CUN
1 stop7h 54mSpirit Airlines
mar. 9/239:16 amCUN - ORD
1 stop12h 42mSpirit Airlines
Deal found 9/14$235
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
mar. 10/216:30 amORD - CUN
Nonstop3h 45mMultiple Airlines
mar. 11/410:09 amCUN - ORD
1 stop12h 24mMultiple Airlines
Deal found 9/14$236
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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.
sáb. 11/15:28 pmORD - CUN
1 stop15h 36mSpirit Airlines
sáb. 11/810:37 amCUN - ORD
1 stop9h 39mSpirit Airlines
Deal found 9/13$238
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
vie. 12/56:00 amORD - CUN
Nonstop3h 37mMultiple Airlines
vie. 12/1211:38 amCUN - ORD
Nonstop4h 03mMultiple Airlines
Deal found 9/16$240
This Expedia deal was found by Cheapflights users on 9/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/295:05 amORD - CUN
1 stop7h 39mSpirit Airlines
mié. 11/51:35 pmCUN - ORD
1 stop8h 25mSpirit Airlines
Deal found 9/14$241
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
sáb. 11/86:00 amORD - CUN
Nonstop3h 37mSpirit Airlines
sáb. 11/1511:42 amCUN - ORD
Nonstop4h 08mSpirit Airlines
Deal found 9/14$242
This Booking.com deal was found by Cheapflights users on 9/14. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/1012:25 pmORD - CUN
1 stop9h 50mMultiple Airlines
mié. 10/159:09 amCUN - ORD
1 stop8h 44mMultiple Airlines
Deal found 9/14$243
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
sáb. 11/86:00 amORD - CUN
Nonstop3h 37mSpirit Airlines
mié. 11/121:35 pmCUN - ORD
1 stop11h 07mSpirit Airlines
Deal found 9/14$244
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
dom. 9/215:05 amORD - CUN
1 stop7h 54mSpirit Airlines
jue. 9/259:16 amCUN - ORD
1 stop6h 56mSpirit Airlines
Deal found 9/14$245
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
vie. 11/147:30 pmORD - CUN
1 stop14h 12mSpirit Airlines
mié. 11/1911:42 amCUN - ORD
Nonstop4h 08mSpirit Airlines
Deal found 9/14$246

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 septiembre 16, 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

MDW - CUN

MDWCUN

Chicago Midway

sáb. 12/6

3:40 pm-8:25 pm

Nonstop3h 45m

Cancun

vie. 12/12

2:15 pm-5:00 pm

Nonstop3h 45m

$270

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

dom. 9/28

10:35 am-2:10 pm

Nonstop3h 35m

Cancun

jue. 10/2

3:20 pm-6:55 pm

Nonstop3h 35m

$281

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

sáb. 11/15

5:50 am-4:05 pm

2 stops9h 15m

Cancun

mié. 11/19

1:45 pm-4:30 pm

Nonstop3h 45m

$285

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

mar. 1/13

8:43 am-1:33 pm

Nonstop3h 50m

Cancun

mar. 2/10

4:20 pm-11:59 pm

1 stop8h 39m

$291

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

mié. 10/29

8:43 am-12:33 pm

Nonstop3h 50m

Cancun

mié. 11/5

3:18 pm-6:09 pm

Nonstop3h 51m

$304

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

mar. 11/11

5:25 am-3:25 pm

1 stop9h 00m

Cancun

sáb. 11/15

8:10 am-4:40 pm

1 stop9h 30m

$314

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

vie. 11/28

6:45 am-3:34 pm

1 stop7h 49m

Cancun

mar. 12/2

6:00 am-1:12 pm

1 stop8h 12m

$315

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

sáb. 1/17

7:00 am-9:10 pm

2 stops13h 10m

Cancun

jue. 1/22

6:00 am-12:48 pm

1 stop7h 48m

$320

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

lun. 10/27

8:55 am-8:20 pm

2 stops11h 25m

Cancun

jue. 10/30

6:00 am-2:12 pm

1 stop8h 12m

$320

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

dom. 1/18

7:00 am-9:10 pm

2 stops13h 10m

Cancun

jue. 1/22

6:00 am-12:48 pm

1 stop7h 48m

$320

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 60 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 septiembre 16, 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 septiembre 16, 2025.

The most flights from CHI to zzETW are scheduled on a Thursday (7 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (5 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 septiembre 16, 2025.
Get a feel of what it's like to fly with Southwest, United Airlines, and American Airlines 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
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,924 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,019 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,174 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • How long is the flight from Chicago to Riviera Maya?

    Airlines like Southwest, United Airlines, and Delta fly from Chicago to Riviera Maya in about 3h 45m. The time it takes to get you to your destination can typically vary by up to 4h 04m. The distance between Chicago and Riviera Maya is about 1434 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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: Spirit Airlines (100%), Frontier (80%), Emirates (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 $513, our data indicates the cheapest price to be $90. The most popular route (Chicago O'Hare Intl - Cancun), is priced around $220.

  • 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 septiembre 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$132Average$332FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$161Average$532FlexibilityNo cancel feeOn-time69%
DeltaCheapest$168Average$534FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$172Average$457FlexibilityNo cancel feeOn-time62%
VolarisCheapest$180Average$546FlexibilityNo cancel feeOn-time79%
AeromexicoCheapest$191Average$456FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$205Average$685FlexibilityNo cancel feeOn-time67%
VivaCheapest$251Average$322FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$266Average$608FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$338Average$580FlexibilityNo cancel feeOn-time71%

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