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$131+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
CUN — CHI
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
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 September 16, 2025.

Round-trip from

$158
(Frontier)

One-way from

$131
(Cheapflightsfares)

Popular in

June

Cheapest in

January

Average price

$337
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. 10% potential increase in price ($32 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 16, 2025.

This Frontier deal was found by Cheapflights users on 9/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/511:38 amCUN - ORD
Nonstop4h 03mFrontier
Tue 12/96:45 amORD - CUN
Nonstop4h 01mFrontier
Deal found 9/15$158
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Thu 10/1611:25 amCUN - ORD
Nonstop3h 55mFrontier
Tue 10/216:30 amORD - CUN
Nonstop3h 45mFrontier
Deal found 9/15$170
This eDestinos deal was found by Cheapflights users on 9/14. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/269:16 amCUN - ORD
1 stop12h 42mSpirit Airlines
Tue 9/305:05 amORD - CUN
1 stop7h 54mSpirit Airlines
Deal found 9/14$199
This eDestinos deal was found by Cheapflights users on 9/14. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/249:16 amCUN - ORD
1 stop12h 42mSpirit Airlines
Sat 9/276:10 amORD - CUN
Nonstop3h 37mSpirit Airlines
Deal found 9/14$217
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
Sat 12/611:42 amCUN - ORD
Nonstop4h 08mSpirit Airlines
Mon 12/85:05 amORD - CUN
1 stop6h 22mSpirit Airlines
Deal found 9/14$219
This United Airlines deal was found by Cheapflights users on 9/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/61:27 pmCUN - ORD
Nonstop4h 00mUnited Airlines
Tue 11/117:10 amORD - CUN
1 stop7h 49mUnited Airlines
Deal found 9/16$220
This United Airlines deal was found by Cheapflights users on 9/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/131:27 pmCUN - ORD
Nonstop4h 00mUnited Airlines
Tue 11/187:10 amORD - CUN
1 stop7h 49mUnited Airlines
Deal found 9/16$221
This Expedia deal was found by Cheapflights users on 9/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/119:09 amCUN - ORD
1 stop8h 44mMultiple Airlines
Sun 10/196:30 amORD - CUN
Nonstop3h 45mMultiple Airlines
Deal found 9/15$224
This Orbitz deal was found by Cheapflights users on 9/15. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1611:25 amCUN - ORD
Nonstop3h 55mMultiple Airlines
Tue 10/215:05 amORD - CUN
1 stop7h 39mMultiple Airlines
Deal found 9/15$225
This United Airlines deal was found by Cheapflights users on 9/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/167:51 amCUN - ORD
1 stop16h 23mUnited Airlines
Mon 10/205:01 amORD - CUN
1 stop7h 59mUnited Airlines
Deal found 9/15$226
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 10/1012:11 pmCUN - ORD
1 stop8h 00mSpirit Airlines
Tue 10/146:58 pmORD - CUN
1 stop13h 06mSpirit Airlines
Deal found 9/14$227
This Frontier deal was found by Cheapflights users on 9/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2411:16 amCUN - MDW
1 stop12h 04mFrontier
Fri 10/316:20 amMDW - CUN
1 stop5h 59mFrontier
Deal found 9/14$270

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 September 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 12/5

11:38 am-2:41 pm

Nonstop4h 03m

Chicago O'Hare Intl

Tue 12/9

6:45 am-11:46 am

Nonstop4h 01m

$158

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 11/6

1:27 pm-4:27 pm

Nonstop4h 00m

Chicago O'Hare Intl

Tue 11/11

7:10 am-3:59 pm

1 stop7h 49m

$220

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 11/13

1:27 pm-4:27 pm

Nonstop4h 00m

Chicago O'Hare Intl

Tue 11/18

7:10 am-3:59 pm

1 stop7h 49m

$221

CancúnChicago

CUN - ORD

CUNORD

Cancun

Fri 11/14

4:51 pm-12:15 am

1 stop8h 24m

Chicago O'Hare Intl

Wed 11/19

7:10 am-8:18 pm

1 stop12h 08m

$226

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 10/16

7:51 am-12:14 am

1 stop16h 23m

Chicago O'Hare Intl

Mon 10/20

5:01 am-1:00 pm

1 stop7h 59m

$226

CancúnChicago

CUN - ORD

CUNORD

Cancun

Fri 9/26

9:16 am-9:58 pm

1 stop12h 42m

Chicago O'Hare Intl

Tue 9/30

5:05 am-12:59 pm

1 stop7h 54m

$228

CancúnChicago

CUN - ORD

CUNORD

Cancun

Wed 12/24

4:47 pm-7:47 pm

Nonstop4h 00m

Chicago O'Hare Intl

Sat 1/3

10:35 am-3:35 pm

Nonstop4h 00m

$231

CancúnChicago

CUN - ORD

CUNORD

Cancun

Fri 2/13

5:55 pm-12:30 am

1 stop7h 35m

Chicago O'Hare Intl

Tue 2/17

7:34 am-12:30 pm

Nonstop3h 56m

$247

CancúnChicago

CUN - ORD

CUNORD

Cancun

Fri 10/10

3:38 pm-7:36 pm

Nonstop3h 58m

Chicago O'Hare Intl

Sun 10/19

10:43 am-2:28 pm

Nonstop3h 45m

$252

CancúnChicago

CUN - ORD

CUNORD

Cancun

Sat 10/4

9:16 am-9:58 pm

1 stop12h 42m

Chicago O'Hare Intl

Sat 10/11

7:43 pm-12:44 pm

1 stop17h 01m

$255

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 55 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 September 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 September 16, 2025.

The most flights from zzETW to CHI are scheduled on a Thursday (7 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (5 on average).

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 September 16, 2025.
See what other customers who have flown with Southwest, United Airlines, and Spirit Airlines from Riviera Maya to Chicago have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

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
8,924 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

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
8,019 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

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
3,174 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

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 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.

  • How long is the flight from Riviera Maya to Chicago?

    There are many flights that can get you from Riviera Maya to Chicago in 4h. Fly via Frontier, United Airlines, or Delta to get the fastest option. Airlines will cover a distance of 1447 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Riviera Maya to Chicago one-way?

    To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $144. United Airlines flights start at $144 while deals on Volaris start at $304 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 (79%), American Airlines (75%) or Emirates (75%) 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 $110. On average you can expect to pay $347. The most popular route, (Cancun - Chicago O'Hare Intl), can usually be booked for $221.

  • 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 Chicago?

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

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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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$167Average$202FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$194Average$283FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$212Average$320FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$272Average$352FlexibilityNo cancel feeOn-time71%

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