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Riviera Maya

$108+ 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 5/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CUN
Apr 9 — Apr 161
Wed 4/9
Wed 4/16
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 April 4, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$225
(Cheapflightsfares)

One-way from

$108
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$361
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. 6% potential increase in price ($28 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 April 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 April 4, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/4. 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 4/286:00 amORD - CUN
Nonstop3h 41mSpirit Airlines
Wed 5/712:18 pmCUN - ORD
1 stop10h 46mSpirit Airlines
Deal found 4/4$225
This Southwest deal was found by Cheapflights users on 4/3. 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.
Sun 6/295:25 pmMDW - CUN
Nonstop3h 35mSouthwest
Wed 7/28:30 amCUN - MDW
Nonstop3h 35mSouthwest
Deal found 4/3$246
This American Airlines deal was found by Cheapflights users on 4/3. 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 5/119:59 amORD - CUN
Nonstop3h 45mAmerican Airlines
Thu 5/151:25 pmCUN - ORD
Nonstop4h 00mAmerican Airlines
Deal found 4/3$256
This Kiwi.com deal was found by Cheapflights users on 4/3. 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 5/47:25 amORD - CUN
1 stop13h 38mMultiple Airlines
Thu 5/89:12 amCUN - ORD
1 stop10h 51mMultiple Airlines
Deal found 4/3$264
This CheapTickets deal was found by Cheapflights users on 4/4. 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 CheapTickets is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1212:48 pmMDW - CUN
1 stop7h 32mAeromexico
Tue 5/138:00 amCUN - MDW
1 stop7h 30mAeromexico
Deal found 4/4$301
This Aeromexico deal was found by Cheapflights users on 4/4. 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.
Thu 4/102:21 pmORD - CUN
1 stop10h 34mAeromexico
Tue 4/1511:03 amCUN - ORD
1 stop7h 57mAeromexico
Deal found 4/4$316
This Delta deal was found by Cheapflights users on 4/3. 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.
Thu 5/1512:48 pmMDW - CUN
1 stop7h 32mDelta
Tue 5/208:31 amCUN - MDW
2 stops12h 56mDelta
Deal found 4/3$321
This Delta deal was found by Cheapflights users on 4/4. 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.
Sat 5/3111:05 amORD - CUN
1 stop9h 15mDelta
Tue 6/38:00 amCUN - ORD
1 stop10h 48mDelta
Deal found 4/4$321
This Kissandfly.com deal was found by Cheapflights users on 4/4. 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.
Fri 4/116:20 amORD - CUN
Nonstop4h 03mVolaris
Tue 4/1512:20 pmCUN - ORD
Nonstop4h 02mVolaris
Deal found 4/4$374
This Expedia deal was found by Cheapflights users on 4/3. 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.
Thu 4/104:31 pmMDW - CUN
1 stop17h 09mMultiple Airlines
Thu 4/1710:00 amCUN - MDW
1 stop6h 12mMultiple Airlines
Deal found 4/3$376
This eDestinos deal was found by Cheapflights users on 4/3. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/187:25 amORD - CZM
1 stop10h 27mVolaris
Thu 5/295:42 pmCZM - ORD
1 stop11h 00mVolaris
Deal found 4/3$378
This Kiwi.com deal was found by Cheapflights users on 4/3. 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 4/184:36 pmMDW - CUN
1 stop16h 24mFrontier
Thu 4/243:35 pmCUN - MDW
1 stop27h 31mFrontier
Deal found 4/3$395

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 April 4, 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

Mon 4/28

6:00 am-9:41 am

Nonstop3h 41m

Cancun

Sat 5/3

10:46 am-2:49 pm

Nonstop4h 03m

$225

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 6/29

5:25 pm-9:00 pm

Nonstop3h 35m

Cancun

Wed 7/2

8:30 am-12:05 pm

Nonstop3h 35m

$246

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sun 5/11

9:59 am-1:44 pm

Nonstop3h 45m

Cancun

Thu 5/15

1:25 pm-5:25 pm

Nonstop4h 00m

$256

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Fri 5/9

6:34 pm-10:00 pm

1 stop27h 26m

Cancun

Tue 5/13

12:18 pm-11:04 pm

1 stop10h 46m

$259

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 5/12

12:48 pm-8:20 pm

1 stop7h 32m

Cancun

Tue 5/13

8:00 am-3:30 pm

1 stop7h 30m

$301

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Fri 8/15

4:29 pm-1:42 am

1 stop9h 13m

Cancun

Tue 8/19

1:45 pm-9:21 pm

1 stop7h 36m

$316

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 5/15

12:48 pm-8:20 pm

1 stop7h 32m

Cancun

Tue 5/20

8:31 am-9:27 pm

2 stops12h 56m

$321

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sat 5/3

6:45 am-8:02 pm

2 stops13h 17m

Cancun

Wed 5/14

3:35 pm-11:58 pm

1 stop8h 23m

$325

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 4/10

4:31 pm-9:40 am

1 stop17h 09m

Cancun

Thu 4/17

10:00 am-4:12 pm

1 stop6h 12m

$376

ChicagoCozumel

ORD - CZM

ORDCZM

Chicago O'Hare Intl

Sun 5/18

7:25 am-4:52 pm

1 stop10h 27m

Cozumel

Thu 5/29

5:42 pm-5:42 am

1 stop11h 00m

$378

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/3

Showing 1-10 of 49 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 April 4, 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 April 4, 2025.

The most flights from CHI to zzETW are scheduled on a Friday (11 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (7 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 April 4, 2025.
Peruse reviews from past customers who have flown with Delta, Southwest and Aeromexico 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.
Delta
8.0
Very good
7,897 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,897 reviews
Delta
8.0
Very good
7,897 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Southwest
8.0
Very good
4,276 reviews
Delta
8.0
Very good
7,897 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Aeromexico
7.5
Good
1,701 reviews
Delta
8.0
Very good
7,897 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
United Airlines
7.4
Good
8,618 reviews
Delta
8.0
Very good
7,897 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
JetBlue
7.3
Good
2,919 reviews
Delta
8.0
Very good
7,897 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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 Southwest. According to our data, you can fly for as low as $111. Users have also found prices from $111 and $112 on United Airlines 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: United Airlines (82%), Emirates (82%), American Airlines (81%).

  • 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 $572, our data indicates the cheapest price to be $94. The most popular route (Chicago O'Hare Intl - Cancun), is priced around $225.

  • 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 April 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$116Average$319FlexibilityNo cancel feeOn-time65%
FrontierCheapest$149Average$386FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$173Average$480FlexibilityNo cancel feeOn-time69%
VolarisCheapest$180Average$556FlexibilityNo cancel feeOn-time79%
VivaCheapest$251Average$321FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$279Average$955FlexibilityNo cancel feeOn-time67%
AeromexicoCheapest$287Average$530FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$307Average$573FlexibilityNo cancel feeOn-time71%
DeltaCheapest$320Average$534FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$340Average$695FlexibilityNo cancel feeOn-time63%

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