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Riviera Maya

$115+ 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 6/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CUN
Jun 15 — Jun 221
Mon 6/15
Mon 6/22
1 adult, Economy
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Cheap 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 May 16, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/12. 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 7/46:00 am
ORD
-
CUN
Nonstop4h 01m
Frontier
Thu 7/911:00 am
CUN
-
ORD
Nonstop4h 09m
Frontier
Deal found 5/12$253
This Frontier deal was found by Cheapflights users on 5/12. 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 6/296:00 am
ORD
-
CUN
Nonstop4h 01m
Frontier
Thu 7/211:00 am
CUN
-
ORD
Nonstop4h 17m
Frontier
Deal found 5/12$254
This Super.com deal was found by Cheapflights users on 5/12. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/46:00 am
ORD
-
CUN
Nonstop4h 01m
Frontier
Sat 7/1111:00 am
CUN
-
ORD
Nonstop4h 09m
Frontier
Deal found 5/12$256
This FlightHub deal was found by Cheapflights users on 5/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/71:40 am
ORD
-
CUN
1 stop12h 48m
Multiple Airlines
Wed 7/1511:00 am
CUN
-
ORD
Nonstop4h 09m
Multiple Airlines
Deal found 5/13$259
This Kissandfly.com deal was found by Cheapflights users on 5/13. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/71:59 am
ORD
-
CUN
1 stop8h 32m
Multiple Airlines
Wed 6/1711:00 am
CUN
-
ORD
Nonstop4h 17m
Multiple Airlines
Deal found 5/13$261
This Expedia deal was found by Cheapflights users on 5/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/76:00 am
ORD
-
CUN
Nonstop3h 49m
Frontier
Thu 7/1611:00 am
CUN
-
ORD
Nonstop4h 09m
Frontier
Deal found 5/13$262
This Kiwi.com deal was found by Cheapflights users on 5/12. 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 7/131:40 am
ORD
-
CUN
1 stop8h 23m
Multiple Airlines
Thu 7/1611:00 am
CUN
-
ORD
Nonstop4h 09m
Multiple Airlines
Deal found 5/12$263
This Justfly.com deal was found by Cheapflights users on 5/12. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/317:35 am
ORD
-
CUN
1 stop13h 28m
Multiple Airlines
Thu 6/410:25 am
CUN
-
ORD
Nonstop4h 10m
Multiple Airlines
Deal found 5/12$267
This Kiwi.com deal was found by Cheapflights users on 5/12. 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 7/142:53 am
ORD
-
CUN
1 stop9h 01m
Multiple Airlines
Thu 7/1611:00 am
CUN
-
ORD
Nonstop4h 09m
Multiple Airlines
Deal found 5/12$268
This Kiwi.com deal was found by Cheapflights users on 5/12. 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.
Fri 7/102:53 am
ORD
-
CUN
1 stop9h 01m
Multiple Airlines
Thu 7/1611:00 am
CUN
-
ORD
Nonstop4h 09m
Multiple Airlines
Deal found 5/12$269
This FlightHub deal was found by Cheapflights users on 5/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/148:23 pm
MDW
-
CUN
1 stop13h 32m
Volaris
Wed 6/1710:40 am
CUN
-
MDW
1 stop8h 24m
Volaris
Deal found 5/13$341
This FlightHub deal was found by Cheapflights users on 5/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/158:23 pm
MDW
-
CUN
1 stop13h 32m
Volaris
Thu 6/1810:40 am
CUN
-
MDW
1 stop8h 54m
Volaris
Deal found 5/13$348

Find 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 May 16, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$253
(Kiwi.com)

One-way from

$115
(Super.com)

Popular in

December

Cheapest in

September

Average price

$436
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. 4% potential increase in price ($20 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 May 2026
Search Deals

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 May 16, 2026.
Use the filters below to find and compare flights from Chicago to Riviera Maya that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sat 6/27

1:49 pm-8:25 pm

1 stop6h 36m

Cancun

Tue 6/30

1:40 pm-12:08 am

1 stop10h 28m

$388

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 7/30

11:05 am-8:15 pm

1 stop9h 10m

Cancun

Thu 8/6

3:32 pm-10:36 pm

1 stop7h 04m

$398

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Fri 6/5

6:24 am-7:35 pm

2 stops13h 11m

Cancun

Wed 6/10

10:55 am-8:32 pm

1 stop9h 37m

$398

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sat 6/27

6:30 am-6:37 pm

2 stops12h 07m

Cancun

Thu 7/2

8:00 am-8:31 pm

2 stops12h 31m

$403

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Thu 8/6

6:25 am-12:56 pm

1 stop6h 31m

Cancun

Tue 8/11

8:05 am-8:22 pm

2 stops12h 17m

$403

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 7/28

12:41 pm-8:15 pm

1 stop7h 34m

Cancun

Mon 8/3

2:10 pm-10:36 pm

1 stop8h 26m

$408

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Wed 5/27

7:00 am-8:16 pm

2 stops13h 16m

Cancun

Sat 6/6

7:03 am-12:07 am

1 stop17h 04m

$423

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 5/29

10:59 am-8:16 pm

1 stop9h 17m

Cancun

Wed 6/3

8:09 am-9:09 pm

2 stops13h 00m

$428

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 5/31

10:59 am-8:16 pm

1 stop9h 17m

Cancun

Fri 6/5

8:00 am-9:09 pm

1 stop13h 09m

$428

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Wed 5/27

6:31 pm-11:40 am

1 stop17h 09m

Cancun

Tue 6/2

6:07 am-6:41 pm

2 stops12h 34m

$428

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/15

Showing 1-10 of 60 resultsSorted by cheapest first
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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

How far ahead should I book a flight from Chicago to Riviera Maya?

The price you pay for your flight from Chicago to Riviera Maya may vary depending on when you book. For the best chance of a lower fare, look to book 16 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, July is the cheapest month in which you can book a flight from Chicago to Riviera Maya (average of $385). Flying from Chicago to Riviera Maya in March is currently the most expensive (average of $582). 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 May 16, 2026.

A simple way to save on the total cost of your ticket is to fly from Chicago to Riviera Maya in the afternoon. If you’re flexible enough to do this you can expect to save up to 25% on your trip compared to booking a flight at noon.

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 May 16, 2026.

The most flights from CHI to zzETW are scheduled on a Monday (12 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (10 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 May 16, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andAmerican 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
4,294 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,729 reviews
Southwest
8.0
Very good
4,294 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,662 reviews
Southwest
8.0
Very good
4,294 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Spirit Airlines
6.2
Okay
8,625 reviews
Southwest
8.0
Very good
4,294 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.7
Fair
2,949 reviews
Southwest
8.0
Very good
4,294 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 Delta, Viva, and United Airlines fly from Chicago to Riviera Maya in about 6h 36m. The time it takes to get you to your destination can typically vary by up to 12h 44m. The distance between Chicago and Riviera Maya is about 1447 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 $64. Users have also found prices from $87 and $95 on Frontier and Volaris, 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: Spirit Airlines (79%), Emirates (67%), United Airlines (66%).

  • 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 $576, our data indicates the cheapest price to be $93. The most popular route (Chicago O'Hare Intl - Cancun), is priced around $308.

  • 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, July is the cheapest month in which you can book a flight from Chicago to Riviera Maya (average of $385). Flying from Chicago to Riviera Maya in March is currently the most expensive (average of $582). 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

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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 May 16, 2026.
AirlineCheapestAverageFlexibilityOn-time
VolarisCheapest$112Average$312FlexibilityNo cancel feeOn-time79%
Spirit AirlinesCheapest$145Average$351FlexibilityNo cancel feeOn-time65%
DeltaCheapest$155Average$2,020FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$189Average$430FlexibilityNo cancel feeOn-time62%
AeromexicoCheapest$190Average$390FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$262Average$480FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$289Average$583FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$293Average$497FlexibilityNo cancel feeOn-time63%
VivaCheapest$317Average$515FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$319Average$539FlexibilityNo cancel feeOn-time71%

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