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$138+ 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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
CUN — CHI
feb. 25 — mar. 41
mar. 2/25
mar. 3/4
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 febrero 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$181
(Frontier)

One-way from

$138
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$188
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. 9% potential increase in price ($24 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in February 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 febrero 20, 2025.

This Frontier deal was found by Cheapflights users on 2/19. 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.
mar. 4/2210:43 amCUN - ORD
Nonstop4h 08mFrontier
mar. 4/297:05 amORD - CUN
Nonstop4h 02mFrontier
Deal found 2/19$181
This eDestinos deal was found by Cheapflights users on 2/20. 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.
jue. 3/611:53 amCUN - ORD
Nonstop4h 03mSpirit Airlines
lun. 3/106:00 amORD - CUN
Nonstop3h 48mSpirit Airlines
Deal found 2/20$196
This Mytrip deal was found by Cheapflights users on 2/20. 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. 2/2711:40 amCUN - ORD
Nonstop4h 06mMultiple Airlines
mié. 3/53:45 pmORD - CUN
1 stop16h 31mMultiple Airlines
Deal found 2/20$212
This Viva deal was found by Cheapflights users on 2/20. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 3/67:05 amCUN - ORD
1 stop8h 20mViva
dom. 3/92:25 amORD - CUN
1 stop18h 45mViva
Deal found 2/20$246
This Southwest deal was found by Cheapflights users on 2/20. 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.
jue. 3/69:20 amCUN - MDW
Nonstop3h 40mSouthwest
lun. 3/104:30 pmMDW - CUN
Nonstop3h 55mSouthwest
Deal found 2/20$249
This American Airlines deal was found by Cheapflights users on 2/20. 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.
mar. 4/2212:45 pmCUN - ORD
1 stop8h 13mAmerican Airlines
lun. 4/289:55 amORD - CUN
Nonstop3h 50mAmerican Airlines
Deal found 2/20$253
This Kiwi.com deal was found by Cheapflights users on 2/19. 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.
mié. 3/53:49 pmCUN - MDW
1 stop9h 28mFrontier
mié. 3/125:58 pmMDW - CUN
1 stop14h 18mFrontier
Deal found 2/19$276
This Kiwi.com deal was found by Cheapflights users on 2/19. 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. 2/281:12 pmCUN - MDW
1 stop7h 07mMultiple Airlines
mié. 3/51:16 pmMDW - CUN
2 stops22h 04mMultiple Airlines
Deal found 2/19$314
This Aeromexico deal was found by Cheapflights users on 2/20. 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.
mié. 7/212:17 pmCUN - ORD
1 stop12h 12mAeromexico
mié. 7/91:16 pmORD - CUN
1 stop6h 42mAeromexico
Deal found 2/20$342
This Delta deal was found by Cheapflights users on 2/20. 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.
jue. 2/278:00 amCUN - MDW
1 stop9h 20mDelta
mié. 3/510:57 amMDW - CUN
1 stop9h 08mDelta
Deal found 2/20$347
This Delta deal was found by Cheapflights users on 2/19. 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.
sáb. 3/18:15 amCUN - ORD
2 stops14h 00mDelta
mié. 3/510:05 amORD - CUN
1 stop10h 40mDelta
Deal found 2/19$347
This Cheapflightsfares deal was found by Cheapflights users on 2/20. 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. 6/1910:40 amCUN - ORD
Nonstop4h 06mVolaris
lun. 6/237:25 amORD - CUN
1 stop13h 38mVolaris
Deal found 2/20$355

Find flights from Riviera Maya to Chicago within your budget

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 febrero 20, 2025.

Fly from

Riviera Maya

Fly to

Chicago

Route

Depart

Return

Price

CancúnChicago

CUN - ORD

CUNORD

Cancun

mar. 4/22

10:43 am-2:51 pm

Nonstop4h 08m

Chicago O'Hare Intl

mar. 4/29

7:05 am-11:07 am

Nonstop4h 02m

$181

CancúnChicago

CUN - ORD

CUNORD

Cancun

jue. 3/6

11:53 am-2:56 pm

Nonstop4h 03m

Chicago O'Hare Intl

lun. 3/10

6:00 am-9:48 am

Nonstop3h 48m

$196

CancúnChicago

CUN - ORD

CUNORD

Cancun

jue. 3/6

11:40 am-2:46 pm

Nonstop4h 06m

Chicago O'Hare Intl

lun. 3/10

6:30 pm-9:28 am

1 stop14h 58m

$212

CancúnChicago

CUN - ORD

CUNORD

Cancun

jue. 3/6

7:05 am-2:25 pm

1 stop8h 20m

Chicago O'Hare Intl

dom. 3/9

2:25 am-9:10 pm

1 stop18h 45m

$246

CancúnChicago

CUN - MDW

CUNMDW

Cancun

jue. 3/6

9:20 am-12:00 pm

Nonstop3h 40m

Chicago Midway

lun. 3/10

4:30 pm-8:25 pm

Nonstop3h 55m

$249

CancúnChicago

CUN - ORD

CUNORD

Cancun

mar. 4/22

12:45 pm-8:58 pm

1 stop8h 13m

Chicago O'Hare Intl

lun. 4/28

9:55 am-1:45 pm

Nonstop3h 50m

$253

CancúnChicago

CUN - MDW

CUNMDW

Cancun

mié. 3/5

3:49 pm-12:17 am

1 stop9h 28m

Chicago Midway

mié. 3/12

5:58 pm-8:16 am

1 stop14h 18m

$276

CancúnChicago

CUN - ORD

CUNORD

Cancun

mié. 7/2

12:17 pm-12:29 am

1 stop12h 12m

Chicago O'Hare Intl

mié. 7/9

1:16 pm-7:58 pm

1 stop6h 42m

$342

CancúnChicago

CUN - MDW

CUNMDW

Cancun

mié. 3/19

11:05 am-6:02 pm

1 stop6h 57m

Chicago Midway

mié. 3/26

9:54 am-8:00 pm

1 stop10h 06m

$347

CancúnChicago

CUN - ORD

CUNORD

Cancun

mié. 4/23

12:35 pm-6:58 pm

1 stop6h 23m

Chicago O'Hare Intl

vie. 4/25

5:30 am-5:32 pm

2 stops12h 02m

$347

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 48 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.

Travel insights for flights from Riviera Maya to Chicago

Get recent, data-driven insights about flights from Riviera Maya to Chicago including ideal travel times, pricing trends, and more.

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 febrero 20, 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 febrero 20, 2025.

The most flights from zzETW to CHI are scheduled on a Monday (11 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (9 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 febrero 20, 2025.
Get a feel of what it's like to fly with Southwest, Delta and Alaska Airlines 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.
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,219 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,697 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

LATAM Airlines
7.5
Good
1,795 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Aeromexico
7.5
Good
1,771 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 Frontier, which is currently one of the cheapest options available, starting at $138. Volaris flights start at $140 while deals on Spirit Airlines start at $145 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 American Airlines (84%), Frontier (80%) or Spirit Airlines (80%) 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 $645. The most popular route, (Cancun - Chicago O'Hare Intl), can usually be booked for $216.

  • 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
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 febrero 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$124Average$162FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$163Average$197FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$215Average$299FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$262Average$426FlexibilityNo cancel feeOn-time71%
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