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Riviera Maya

$91+ 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 2/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CUN
Jan 30 — Feb 61
Fri 1/30
Fri 2/6
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 December 31, 2025.

This Aeromexico deal was found by Cheapflights users on 12/28. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3110:46 amORD - CUN
1 stop9h 34mAeromexico
Sat 1/318:00 amCUN - ORD
1 stop6h 49mAeromexico
Deal found 12/28$327
This Expedia deal was found by Cheapflights users on 12/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:55 pmORD - CUN
1 stop17h 55mMultiple Airlines
Sat 1/3111:59 amCUN - ORD
Nonstop3h 54mMultiple Airlines
Deal found 12/28$330
This Kiwi.com deal was found by Cheapflights users on 12/29. 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.
Wed 12/3110:37 amORD - CUN
Nonstop4h 11mMultiple Airlines
Thu 1/810:13 amCUN - ORD
1 stop10h 28mMultiple Airlines
Deal found 12/29$338
This Kiwi.com deal was found by Cheapflights users on 12/29. 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.
Wed 12/3110:37 amORD - CUN
Nonstop4h 11mMultiple Airlines
Mon 1/1211:59 amCUN - ORD
Nonstop3h 54mMultiple Airlines
Deal found 12/29$339
This Kiwi.com deal was found by Cheapflights users on 12/30. 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.
Wed 12/3110:37 amORD - CUN
Nonstop4h 11mMultiple Airlines
Fri 1/91:21 pmCUN - ORD
1 stop8h 42mMultiple Airlines
Deal found 12/30$349
This Frontier deal was found by Cheapflights users on 12/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3110:37 amORD - CUN
Nonstop4h 11mFrontier
Mon 1/123:24 pmCUN - ORD
1 stop8h 15mFrontier
Deal found 12/29$373
This Aeromexico deal was found by Cheapflights users on 12/30. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:30 amORD - CUN
1 stop10h 07mAeromexico
Sat 1/31:37 pmCUN - ORD
1 stop9h 34mAeromexico
Deal found 12/30$379
This Frontier deal was found by Cheapflights users on 12/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3110:37 amORD - CUN
Nonstop4h 11mFrontier
Thu 1/83:14 pmCUN - ORD
1 stop8h 25mFrontier
Deal found 12/31$390
This CheapOair deal was found by Cheapflights users on 12/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3110:37 amORD - CUN
Nonstop4h 11mFrontier
Wed 1/72:04 pmCUN - ORD
1 stop25h 18mFrontier
Deal found 12/30$391
This Aeromexico deal was found by Cheapflights users on 12/29. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:00 amMDW - CUN
1 stop6h 46mAeromexico
Wed 1/74:40 pmCUN - MDW
1 stop6h 27mAeromexico
Deal found 12/29$394
This Delta deal was found by Cheapflights users on 12/29. 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.
Tue 12/305:59 pmMDW - CUN
1 stop17h 11mDelta
Thu 1/84:40 pmCUN - MDW
1 stop6h 27mDelta
Deal found 12/29$404
This Gotogate deal was found by Cheapflights users on 12/29. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:54 pmMDW - CUN
1 stop13h 54mMultiple Airlines
Wed 1/73:14 pmCUN - MDW
1 stop8h 03mMultiple Airlines
Deal found 12/29$434

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 December 31, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$214
(Cheapflightsfares)

One-way from

$91
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$513
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. 5% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 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 1/20

7:34 am-12:30 pm

Nonstop3h 56m

Cancun

Sat 1/24

4:47 pm-7:47 pm

Nonstop4h 00m

$314

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sun 2/15

1:11 am-8:02 pm

1 stop17h 51m

Cancun

Wed 2/18

6:01 am-12:55 pm

1 stop7h 54m

$319

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sun 3/1

6:15 am-6:47 pm

2 stops11h 32m

Cancun

Thu 3/5

1:33 pm-11:00 pm

1 stop10h 27m

$323

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sat 2/7

7:05 am-8:02 pm

2 stops11h 57m

Cancun

Tue 2/10

6:01 am-12:55 pm

1 stop7h 54m

$323

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sat 2/7

7:05 am-8:02 pm

2 stops11h 57m

Cancun

Sat 2/14

3:35 pm-11:00 pm

1 stop8h 25m

$323

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Mon 2/9

7:05 am-8:02 pm

2 stops11h 57m

Cancun

Sat 2/14

4:20 pm-11:00 pm

1 stop7h 40m

$323

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sun 2/1

6:15 am-8:00 pm

2 stops12h 45m

Cancun

Wed 2/4

12:35 pm-11:00 pm

1 stop11h 25m

$323

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Wed 1/21

6:50 am-4:35 pm

2 stops8h 45m

Cancun

Wed 1/28

11:18 am-11:00 pm

1 stop12h 42m

$328

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sat 2/28

6:30 am-9:11 pm

2 stops13h 41m

Cancun

Wed 3/4

7:00 am-11:00 pm

1 stop17h 00m

$328

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Mon 3/23

1:58 am-11:40 am

1 stop9h 42m

Cancun

Mon 3/30

12:28 pm-8:14 pm

1 stop7h 46m

$329

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/31

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 $138). Flying from Chicago to Riviera Maya in July is currently the most expensive (average of $218). 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 December 31, 2025.

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 22% 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 December 31, 2025.

The most flights from CHI to zzETW are scheduled on a Monday (14 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (13 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 December 31, 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
4,252 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,252 reviews
Southwest
8.0
Very good
4,252 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,129 reviews
Southwest
8.0
Very good
4,252 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,069 reviews
Southwest
8.0
Very good
4,252 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Spirit Airlines
6.3
Okay
8,253 reviews
Southwest
8.0
Very good
4,252 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.7
Fair
3,066 reviews
Southwest
8.0
Very good
4,252 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 United Airlines, Delta, and Aeromexico fly from Chicago to Riviera Maya in about 3h 56m. The time it takes to get you to your destination can typically vary by up to 13h 55m. 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 Frontier. According to our data, you can fly for as low as $83. Users have also found prices from $88 and $91 on Viva 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 (78%), United Airlines (78%), American Airlines (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 $697, our data indicates the cheapest price to be $92. The most popular route (Chicago O'Hare Intl - Cancun), is priced around $195.

  • 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 $138). Flying from Chicago to Riviera Maya in July is currently the most expensive (average of $218). 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 December 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
AeromexicoCheapest$145Average$388FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$161Average$511FlexibilityNo cancel feeOn-time69%
DeltaCheapest$168Average$1,512FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$170Average$398FlexibilityNo cancel feeOn-time79%
Spirit AirlinesCheapest$171Average$349FlexibilityNo cancel feeOn-time65%
FrontierCheapest$188Average$446FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$250Average$417FlexibilityNo cancel feeOn-time62%
VivaCheapest$255Average$331FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$266Average$549FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$339Average$563FlexibilityNo cancel feeOn-time71%

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