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$132+ 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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
CUN — CHI
dic. 6 — dic. 131
sáb. 12/6
sáb. 12/13
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 noviembre 6, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$144
(Frontier)

One-way from

$132
(Cheapflightsfares)

Popular in

September

Cheapest in

January

Average price

$239
Provider with most accurate pricing for Cancun-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Cancun-Chicago (CHI) flights.
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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. 15% potential increase in price ($51 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in November 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 noviembre 6, 2025.

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.
vie. 12/56:02 pmCUN - ORD
Nonstop4h 10mFrontier
mar. 12/911:43 amORD - CUN
Nonstop4h 09mFrontier
Deal found 11/5$144
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.
jue. 12/256:22 pmCUN - ORD
Nonstop4h 10mFrontier
lun. 1/510:37 amORD - CUN
Nonstop4h 11mFrontier
Deal found 11/5$145
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/56:02 pmCUN - ORD
Nonstop4h 10mFrontier
lun. 12/811:33 amORD - CUN
Nonstop4h 09mFrontier
Deal found 11/6$146
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/46:02 pmCUN - ORD
Nonstop4h 10mFrontier
mié. 12/1011:43 amORD - CUN
Nonstop4h 09mFrontier
Deal found 11/6$157
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/56:02 pmCUN - ORD
Nonstop4h 10mFrontier
dom. 12/711:43 amORD - CUN
Nonstop4h 09mFrontier
Deal found 11/6$161
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/126:02 pmCUN - ORD
Nonstop4h 10mFrontier
lun. 12/1511:33 amORD - CUN
Nonstop4h 09mFrontier
Deal found 11/5$181
This Flightnetwork 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/131:28 pmCUN - ORD
Nonstop4h 08mMultiple Airlines
lun. 11/175:57 pmORD - CUN
1 stop16h 39mMultiple Airlines
Deal found 11/6$214
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/126:02 pmCUN - ORD
Nonstop4h 10mMultiple Airlines
lun. 12/155:00 amORD - CUN
1 stop7h 13mMultiple Airlines
Deal found 11/5$215
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.
vie. 12/56:02 pmCUN - ORD
Nonstop4h 10mMultiple Airlines
dom. 12/79:14 pmORD - CUN
1 stop13h 22mMultiple Airlines
Deal found 11/6$218
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/52:36 pmCUN - ORD
1 stop10h 33mMultiple Airlines
mar. 12/911:43 amORD - CUN
Nonstop4h 09mMultiple Airlines
Deal found 11/6$219
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.
vie. 11/2111:53 amCUN - ORD
Nonstop4h 00mSpirit Airlines
lun. 11/245:00 amORD - CUN
1 stop7h 35mSpirit Airlines
Deal found 11/6$222
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.
jue. 12/2512:46 pmCUN - ORD
1 stop8h 18mSpirit Airlines
lun. 1/56:05 amORD - CUN
Nonstop3h 50mSpirit Airlines
Deal found 11/5$224

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 noviembre 6, 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

mié. 2/18

12:39 pm-3:47 pm

Nonstop4h 08m

Chicago O'Hare Intl

dom. 2/22

6:45 am-11:46 am

Nonstop4h 01m

$144

CancúnChicago

CUN - ORD

CUNORD

Cancun

vie. 2/13

12:28 pm-9:28 pm

1 stop10h 00m

Chicago O'Hare Intl

mar. 2/17

7:35 am-3:59 pm

1 stop7h 24m

$224

CancúnChicago

CUN - ORD

CUNORD

Cancun

dom. 1/11

12:06 pm-3:07 pm

Nonstop4h 01m

Chicago O'Hare Intl

dom. 1/11

7:52 pm-12:12 pm

1 stop15h 20m

$240

CancúnChicago

CUN - ORD

CUNORD

Cancun

vie. 2/13

12:27 pm-11:00 pm

1 stop11h 33m

Chicago O'Hare Intl

mar. 2/17

5:25 am-12:30 pm

1 stop6h 05m

$268

CancúnChicago

CUN - ORD

CUNORD

Cancun

jue. 2/19

12:27 pm-11:00 pm

1 stop11h 33m

Chicago O'Hare Intl

lun. 2/23

7:54 pm-10:00 am

1 stop13h 06m

$268

CancúnChicago

CUN - ORD

CUNORD

Cancun

mié. 1/21

6:01 am-12:40 pm

1 stop7h 39m

Chicago O'Hare Intl

lun. 1/26

7:05 am-3:30 pm

1 stop7h 25m

$269

CancúnChicago

CUN - ORD

CUNORD

Cancun

vie. 12/5

6:00 am-1:12 pm

1 stop8h 12m

Chicago O'Hare Intl

vie. 12/12

8:55 am-9:20 pm

2 stops11h 25m

$269

CancúnChicago

CUN - ORD

CUNORD

Cancun

vie. 12/5

6:00 am-1:12 pm

1 stop8h 12m

Chicago O'Hare Intl

mar. 12/9

6:00 am-3:15 pm

1 stop8h 15m

$269

CancúnChicago

CUN - ORD

CUNORD

Cancun

sáb. 2/14

8:39 am-12:26 am

1 stop16h 47m

Chicago O'Hare Intl

lun. 2/16

9:05 pm-2:18 pm

1 stop16h 13m

$270

CancúnChicago

CUN - ORD

CUNORD

Cancun

vie. 12/5

6:00 am-1:12 pm

1 stop8h 12m

Chicago O'Hare Intl

dom. 12/7

8:55 am-9:20 pm

2 stops11h 25m

$270

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

Showing 1-10 of 56 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 $78). Flying from Riviera Maya to Chicago in June is currently the most expensive (average of $248). 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 noviembre 6, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 58% on flights from Riviera Maya to Chicago by exploring options for tickets in the evening.

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 noviembre 6, 2025.

The most flights from zzETW to CHI are scheduled on a Thursday (10 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 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 noviembre 6, 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
4,241 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

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
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

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
4,241 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

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
8,122 reviews
Southwest
8.0
Very good
4,241 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

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
3,116 reviews
Southwest
8.0
Very good
4,241 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

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 01m. Fly via Frontier, United Airlines, or Spirit Airlines 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 Spirit Airlines, which is currently one of the cheapest options available, starting at $135. Southwest flights start at $144 while deals on United Airlines start at $149 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 Spirit Airlines (100%), Emirates (87%) or Qatar Airways (86%) 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 $114. On average you can expect to pay $368. The most popular route, (Cancun - Chicago O'Hare Intl), can usually be booked for $240.

  • 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 $78). Flying from Riviera Maya to Chicago in June is currently the most expensive (average of $248). 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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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 noviembre 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$142Average$202FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$194Average$283FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$209Average$352FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$272Average$352FlexibilityNo cancel feeOn-time71%

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