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$136+ Cheap flights from Riviera Maya to Chicago (CHI)

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 9/17. Fares are subject to change and may not be available on all flights or dates of travel.
CUN — CHI
Jun 21 — Jun 281
Sat 6/21
Sat 6/28
1 adult, Economy
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Cheap flight deals from Riviera Maya to Chicago

Keep the following information in mind while searching for Riviera Maya to Chicago flight deals. Data was last updated June 16, 2025.

Round-trip from

$225
(Cheapflightsfares)

One-way from

$137
(Cheapflightsfares)

Popular in

June

Cheapest in

January

Average price

$344
From Riviera Maya to Chicago (CHI)
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One-way flight from Riviera Maya to Chicago (CHI)
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Highest demand for flights based on searches. 11% potential increase in price ($33 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Find flight deals from Riviera Maya to Chicago

Cheapest flights from Riviera Maya to Chicago
Explore the most affordable flight options available from Riviera Maya to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 16, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 6/15. 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 9/510:39 amCUN - ORD
Nonstop4h 03mSpirit Airlines
Mon 9/86:00 amORD - CUN
Nonstop3h 31mSpirit Airlines
Deal found 6/15$225
This United Airlines deal was found by Cheapflights users on 6/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1112:20 pmCUN - ORD
Nonstop3h 58mUnited Airlines
Sat 9/209:29 amORD - CUN
Nonstop3h 45mUnited Airlines
Deal found 6/14$229
This American Airlines deal was found by Cheapflights users on 6/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/112:50 pmCUN - ORD
Nonstop4h 00mAmerican Airlines
Sat 9/208:34 pmORD - CUN
1 stop13h 19mAmerican Airlines
Deal found 6/14$254
This Priceline deal was found by Cheapflights users on 6/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1112:35 pmCUN - MDW
1 stop11h 16mFrontier
Sat 7/128:05 amMDW - CUN
1 stop7h 51mFrontier
Deal found 6/13$259
This Delta deal was found by Cheapflights users on 6/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/212:16 pmCUN - ORD
1 stop11h 39mDelta
Tue 10/710:35 amORD - CUN
2 stops9h 29mDelta
Deal found 6/16$270
This Southwest deal was found by Cheapflights users on 6/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/268:30 amCUN - MDW
Nonstop3h 35mSouthwest
Sun 6/295:25 pmMDW - CUN
Nonstop3h 35mSouthwest
Deal found 6/16$272
This Kiwi.com deal was found by Cheapflights users on 6/15. 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 7/29:13 amCUN - ORD
1 stop9h 31mMultiple Airlines
Fri 7/116:30 amORD - CUN
1 stop7h 42mMultiple Airlines
Deal found 6/15$273
This Delta deal was found by Cheapflights users on 6/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/168:00 amCUN - MDW
1 stop7h 28mDelta
Wed 8/206:04 amMDW - CUN
1 stop8h 06mDelta
Deal found 6/14$275
This Priceline deal was found by Cheapflights users on 6/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/311:05 amCUN - ORD
Nonstop3h 59mFrontier
Thu 7/105:40 amORD - CUN
1 stop10h 40mFrontier
Deal found 6/14$321
This Aeromexico deal was found by Cheapflights users on 6/14. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1712:42 pmCUN - ORD
2 stops11h 11mAeromexico
Sat 10/181:16 pmORD - CUN
1 stop6h 53mAeromexico
Deal found 6/14$329
This Aeromexico deal was found by Cheapflights users on 6/16. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/143:10 pmCUN - MDW
1 stop6h 39mAeromexico
Tue 8/196:04 amMDW - CUN
1 stop8h 06mAeromexico
Deal found 6/16$340
This Cheapflightsfares deal was found by Cheapflights users on 6/14. 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.
Fri 9/1910:50 amCUN - ORD
1 stop12h 42mVolaris
Sat 9/271:40 amORD - CUN
1 stop8h 23mVolaris
Deal found 6/14$375

Cheapflights Fare Finder

Customize your flight search to find flights from Riviera Maya to Chicago 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 June 16, 2025.
Use the filters below to find and compare flights from Riviera Maya to Chicago that are best for you.

Fly from

Riviera Maya

Fly to

Chicago

Route

Depart

Return

Price

CancúnChicago

CUN - ORD

CUNORD

Cancun

Fri 9/5

10:39 am-2:42 pm

Nonstop4h 03m

Chicago O'Hare Intl

Mon 9/8

6:00 am-9:31 am

Nonstop3h 31m

$225

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 9/11

12:20 pm-4:18 pm

Nonstop3h 58m

Chicago O'Hare Intl

Sat 9/20

9:29 am-1:14 pm

Nonstop3h 45m

$229

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 9/11

2:50 pm-6:50 pm

Nonstop4h 00m

Chicago O'Hare Intl

Sat 9/20

8:34 pm-9:53 am

1 stop13h 19m

$254

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 7/11

12:35 pm-11:51 pm

1 stop11h 16m

Chicago Midway

Sat 7/12

8:05 am-3:56 pm

1 stop7h 51m

$259

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 10/2

12:16 pm-11:55 pm

1 stop11h 39m

Chicago O'Hare Intl

Tue 10/7

10:35 am-8:04 pm

2 stops9h 29m

$270

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 6/26

8:30 am-12:05 pm

Nonstop3h 35m

Chicago Midway

Sun 6/29

5:25 pm-9:00 pm

Nonstop3h 35m

$272

CancúnChicago

CUN - ORD

CUNORD

Cancun

Wed 7/2

9:13 am-6:44 pm

1 stop9h 31m

Chicago O'Hare Intl

Fri 7/11

6:30 am-2:12 pm

1 stop7h 42m

$273

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sat 8/16

8:00 am-3:28 pm

1 stop7h 28m

Chicago Midway

Wed 8/20

6:04 am-2:10 pm

1 stop8h 06m

$275

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 7/3

11:05 am-3:04 pm

Nonstop3h 59m

Chicago O'Hare Intl

Thu 7/10

5:40 am-4:20 pm

1 stop10h 40m

$321

CancúnChicago

CUN - ORD

CUNORD

Cancun

Fri 10/17

12:42 pm-11:53 pm

2 stops11h 11m

Chicago O'Hare Intl

Sat 10/18

1:16 pm-8:09 pm

1 stop6h 53m

$329

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/14

Showing 1-10 of 45 results
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Best time to book a flight from Riviera Maya to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Riviera Maya 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 Riviera Maya to Chicago

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

Currently, August is the cheapest month in which you can book a flight from Riviera Maya to Chicago (average of $245). Flying from Riviera Maya to Chicago in March is currently the most expensive (average of $321). 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 ETW to CHI?

Find hourly flight availability from Riviera Maya to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 16, 2025.

When flying from Riviera Maya to Chicago, 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 Riviera Maya to Chicago

Explore weekly flight availability from Riviera Maya to Chicago. 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 June 16, 2025.

The most flights from zzETW to CHI are scheduled on a Saturday (15 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (10 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated June 16, 2025.
Get a feel of what it's like to fly with Delta, Alaska Airlines and Southwest from Riviera Maya to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,963 reviews

Comfort

7.9

Food

7.3

Crew

8.5

Entertainment

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,963 reviews
Delta
8.0
Very good
7,963 reviews

Comfort

7.9

Food

7.3

Crew

8.5

Entertainment

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Alaska Airlines
8.0
Very good
10,000 reviews
Delta
8.0
Very good
7,963 reviews

Comfort

7.9

Food

7.3

Crew

8.5

Entertainment

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Southwest
8.0
Very good
4,278 reviews
Delta
8.0
Very good
7,963 reviews

Comfort

7.9

Food

7.3

Crew

8.5

Entertainment

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Aeromexico
7.5
Good
1,711 reviews
Delta
8.0
Very good
7,963 reviews

Comfort

7.9

Food

7.3

Crew

8.5

Entertainment

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,801 reviews
Delta
8.0
Very good
7,963 reviews

Comfort

7.9

Food

7.3

Crew

8.5

Entertainment

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

Find useful and relevant information for your journey from Riviera Maya to Chicago. 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 Riviera Maya to Chicago one-way?

    To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $137. Southwest flights start at $148 while deals on American Airlines start at $148 one-way.

  • What are the most popular routes from Riviera Maya to Chicago?

    When deciding which route to take from Riviera Maya to Chicago consider Cancun - Chicago O'Hare Intl, Cancun - Chicago Midway or Cozumel - Chicago O'Hare Intl as they are the most popular.

  • What are the most reliable airlines from Riviera Maya to Chicago?

    Consider Qatar Airways (90%), American Airlines (87%) or Emirates (81%) when booking your flight. These represent the most reliable airlines when flying from Riviera Maya to Chicago.

  • What are the cheapest flights from Riviera Maya to Chicago?

    The cheapest flight price from Riviera Maya to Chicago is $111. On average you can expect to pay $336. The most popular route, (Cancun - Chicago O'Hare Intl), can usually be booked for $225.

  • Can I find deals for flights from Riviera Maya to Chicago that include hotel bookings?

    Yes. In addition to deals on Riviera Maya to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Riviera Maya to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Riviera Maya to Chicago.

  • Can I find deals for business class flights from Riviera Maya to Chicago?

    Yes. Cheapflights offers flight deals from Riviera Maya to Chicago 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 Riviera Maya to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Riviera Maya to Chicago (average of $245). Flying from Riviera Maya to Chicago in March is currently the most expensive (average of $321). 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

Traveling to a place near Riviera Maya?

Book flights to Riviera Maya if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Riviera Maya to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Cancún to O'Hare Intl flights
Cancún to Midway flights
Cozumel to O'Hare Intl flights
Cancún to St. Louis flights
Cozumel to St. Louis flights

Top 4 airlines flying from Riviera Maya to Chicago

Discover the top 4 airlines that operate flights from Riviera Maya to Chicago. 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 June 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$124Average$170FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$177Average$241FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$212Average$319FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$310Average$428FlexibilityNo cancel feeOn-time71%

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