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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 2/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CUN
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
1 adult, Economy
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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 November 6, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 11/6. 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.
Mon 12/16:00 amORD - CUN
Nonstop3h 44mSpirit Airlines
Fri 12/52:36 pmCUN - ORD
1 stop10h 33mSpirit Airlines
Deal found 11/6$228
This Trip.com deal was found by Cheapflights users on 11/6. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/156:00 amORD - CUN
Nonstop3h 44mSpirit Airlines
Sat 11/2210:12 amCUN - ORD
1 stop13h 54mSpirit Airlines
Deal found 11/6$229
This Super.com deal was found by Cheapflights users on 11/5. 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.
Mon 11/175:57 pmORD - CUN
1 stop16h 39mSpirit Airlines
Thu 11/202:44 pmCUN - ORD
1 stop9h 29mSpirit Airlines
Deal found 11/5$230
This Super.com deal was found by Cheapflights users on 11/5. 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.
Tue 11/185:10 amORD - CUN
1 stop7h 25mSpirit Airlines
Sat 11/2210:12 amCUN - ORD
1 stop13h 54mSpirit Airlines
Deal found 11/5$232
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 12/155:00 amORD - CUN
1 stop7h 13mMultiple Airlines
Tue 12/236:22 pmCUN - ORD
Nonstop4h 10mMultiple Airlines
Deal found 11/5$233
This Frontier deal was found by Cheapflights users on 11/5. 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 11/157:25 amORD - CUN
Nonstop3h 53mFrontier
Wed 11/194:45 pmCUN - ORD
Nonstop4h 03mFrontier
Deal found 11/5$234
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 12/1411:43 amORD - CUN
Nonstop4h 09mFrontier
Thu 12/256:22 pmCUN - ORD
Nonstop4h 10mFrontier
Deal found 11/5$235
This Super.com deal was found by Cheapflights users on 11/6. 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.
Sun 11/165:10 amORD - CUN
1 stop7h 25mSpirit Airlines
Thu 11/202:44 pmCUN - ORD
1 stop9h 29mSpirit Airlines
Deal found 11/6$236
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 12/155:00 amORD - CUN
1 stop7h 13mSpirit Airlines
Sat 12/2011:50 amCUN - ORD
Nonstop4h 03mSpirit Airlines
Deal found 11/6$237
This Cheapflightsfares deal was found by Cheapflights users on 11/5. 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 11/165:10 amORD - CUN
1 stop7h 25mSpirit Airlines
Wed 11/192:44 pmCUN - ORD
1 stop6h 43mSpirit Airlines
Deal found 11/5$238
This Cheapflightsfares deal was found by Cheapflights users on 11/5. 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.
Fri 12/129:14 pmORD - CUN
1 stop13h 22mSpirit Airlines
Fri 12/1911:50 amCUN - ORD
Nonstop4h 03mSpirit Airlines
Deal found 11/5$239
This Cheapflightsfares deal was found by Cheapflights users on 11/6. 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.
Sat 12/69:14 pmORD - CUN
1 stop13h 22mSpirit Airlines
Sat 12/1311:50 amCUN - ORD
Nonstop4h 03mSpirit Airlines
Deal found 11/6$240

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 November 6, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$228
(Cheapflightsfares)

One-way from

$104
(CheapOair)

Popular in

March

Cheapest in

September

Average price

$446
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 ($26 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 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 November 6, 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 2/10

1:00 am-9:00 pm

1 stop19h 00m

Cancun

Sun 2/15

7:00 am-11:50 pm

1 stop17h 50m

$317

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Tue 2/17

5:25 am-6:47 pm

2 stops12h 22m

Cancun

Wed 2/25

4:20 pm-11:00 pm

1 stop7h 40m

$317

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sat 2/7

12:49 am-12:45 pm

1 stop10h 56m

Cancun

Thu 2/12

4:15 pm-11:00 pm

1 stop7h 45m

$322

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 1/9

6:45 am-3:30 pm

1 stop7h 45m

Cancun

Tue 1/13

8:00 am-4:31 pm

1 stop9h 31m

$327

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 1/23

6:00 am-4:45 pm

1 stop9h 45m

Cancun

Wed 1/28

12:15 pm-5:32 pm

1 stop6h 17m

$327

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 1/29

12:48 pm-9:11 pm

1 stop7h 23m

Cancun

Mon 2/2

8:00 am-5:32 pm

1 stop10h 32m

$327

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Mon 3/2

5:53 pm-10:00 am

1 stop15h 07m

Cancun

Wed 3/4

5:30 pm-8:38 am

1 stop16h 08m

$327

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Fri 1/30

5:33 am-12:30 pm

1 stop5h 57m

Cancun

Mon 2/2

5:25 pm-8:40 am

1 stop16h 15m

$327

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Fri 1/23

7:05 am-8:00 pm

2 stops11h 55m

Cancun

Wed 1/28

8:38 am-7:21 pm

2 stops11h 43m

$327

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 1/5

6:45 am-9:11 pm

1 stop13h 26m

Cancun

Fri 1/9

12:05 pm-10:09 pm

2 stops11h 04m

$331

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

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 $129). Flying from Chicago to Riviera Maya in July is currently the most expensive (average of $217). 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 November 6, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to Riviera Maya at noon. If you’re flexible enough to do this you can expect to save up to 43% on your trip compared to booking a flight in the evening.

What is the cheapest day to fly from Chicago to Riviera Maya?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Riviera Maya. Price data was last updated on November 2, 2025.

Travelers seeking maximum savings on their Chicago to Riviera Maya flight should consider departing on Wednesday at noon when fares are most often at their lowest. Thursday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 November 6, 2025.

The most flights from CHI to zzETW are scheduled on a Thursday (9 on average). You will have fewer flight options on Wednesday, 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 November 6, 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
4,240 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

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
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

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
9,007 reviews
Southwest
8.0
Very good
4,240 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

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
11,040 reviews
Southwest
8.0
Very good
4,240 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

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
8,123 reviews
Southwest
8.0
Very good
4,240 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

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
3,115 reviews
Southwest
8.0
Very good
4,240 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

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 Viva, Delta, and Aeromexico fly from Chicago to Riviera Maya in about 8h 17m. The time it takes to get you to your destination can typically vary by up to 10h 43m. The distance between Chicago and Riviera Maya is about 1483 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 $114. Users have also found prices from $125 and $150 on United Airlines and Delta, 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 (89%), Frontier (89%), American Airlines (80%).

  • 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 $571, our data indicates the cheapest price to be $93. The most popular route (Chicago O'Hare Intl - Cancun), is priced around $202.

  • 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 $129). Flying from Chicago to Riviera Maya in July is currently the most expensive (average of $217). 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 November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
AeromexicoCheapest$145Average$446FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$152Average$342FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$161Average$539FlexibilityNo cancel feeOn-time69%
DeltaCheapest$168Average$516FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$176Average$465FlexibilityNo cancel feeOn-time62%
VolarisCheapest$178Average$548FlexibilityNo cancel feeOn-time79%
VivaCheapest$251Average$324FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$266Average$585FlexibilityNo cancel feeOn-time63%
Air CanadaCheapest$279Average$492FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$340Average$530FlexibilityNo cancel feeOn-time71%

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