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$134+ 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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
CUN — CHI
may. 6 — may. 131
mar. 5/6
mar. 5/13
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 mayo 1, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$204
(eDestinos)

One-way from

$134
(Cheapflightsfares)

Popular in

June

Cheapest in

January

Average price

$226
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. 6% potential increase in price ($17 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 May 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 mayo 1, 2025.

This eDestinos deal was found by Cheapflights users on 4/30. 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.
vie. 5/1612:18 pmCUN - ORD
1 stop11h 47mSpirit Airlines
lun. 5/196:10 amORD - CUN
Nonstop3h 34mSpirit Airlines
Deal found 4/30$204
This Booking.com deal was found by Cheapflights users on 4/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 6/511:05 amCUN - ORD
Nonstop3h 59mFrontier
mar. 6/107:33 amORD - CUN
Nonstop3h 57mFrontier
Deal found 4/30$205
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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.
mar. 5/1311:05 amCUN - ORD
Nonstop3h 57mMultiple Airlines
vie. 5/166:10 amORD - CUN
Nonstop3h 34mMultiple Airlines
Deal found 4/30$213
This United Airlines deal was found by Cheapflights users on 4/30. 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.
sáb. 5/312:20 pmCUN - ORD
Nonstop4h 02mUnited Airlines
dom. 5/119:21 amORD - CUN
Nonstop3h 53mUnited Airlines
Deal found 4/30$222
This Southwest deal was found by Cheapflights users on 4/29. 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. 7/318:15 amCUN - MDW
Nonstop3h 35mSouthwest
dom. 8/35:25 pmMDW - CUN
Nonstop3h 35mSouthwest
Deal found 4/29$249
This American Airlines deal was found by Cheapflights users on 4/30. 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.
mié. 5/710:35 amCUN - ORD
1 stop10h 50mAmerican Airlines
dom. 5/119:59 amORD - CUN
Nonstop3h 45mAmerican Airlines
Deal found 4/30$258
This Delta deal was found by Cheapflights users on 4/30. 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. 5/33:11 pmCUN - MDW
1 stop7h 11mDelta
sáb. 5/106:00 amMDW - CUN
1 stop8h 25mDelta
Deal found 4/30$274
This Delta deal was found by Cheapflights users on 4/30. 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. 5/311:03 amCUN - ORD
1 stop7h 57mDelta
sáb. 5/1011:05 amORD - CUN
2 stops9h 15mDelta
Deal found 4/30$274
This Aeromexico deal was found by Cheapflights users on 5/1. 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.
lun. 6/91:01 amCUN - ORD
2 stops17h 48mAeromexico
mar. 6/171:45 pmORD - CUN
1 stop6h 35mAeromexico
Deal found 5/1$317
This Aeromexico deal was found by Cheapflights users on 4/30. 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.
sáb. 5/312:35 pmCUN - MDW
1 stop9h 47mAeromexico
lun. 5/1212:48 pmMDW - CUN
2 stops10h 57mAeromexico
Deal found 4/30$326
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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.
sáb. 8/163:19 pmCUN - ORD
1 stop13h 32mVolaris
sáb. 8/237:25 amORD - CUN
1 stop13h 38mVolaris
Deal found 4/30$339
This Kiwi.com deal was found by Cheapflights users on 5/1. 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. 5/3011:43 amCUN - MDW
1 stop8h 00mMultiple Airlines
sáb. 5/319:12 pmMDW - CUN
1 stop11h 04mMultiple Airlines
Deal found 5/1$384

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 mayo 1, 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

vie. 5/16

12:18 pm-12:05 am

1 stop11h 47m

Chicago O'Hare Intl

lun. 5/19

6:10 am-9:44 am

Nonstop3h 34m

$204

CancúnChicago

CUN - ORD

CUNORD

Cancun

jue. 6/5

11:05 am-3:04 pm

Nonstop3h 59m

Chicago O'Hare Intl

mar. 6/10

7:33 am-11:30 am

Nonstop3h 57m

$205

CancúnChicago

CUN - ORD

CUNORD

Cancun

mar. 5/13

11:05 am-3:02 pm

Nonstop3h 57m

Chicago O'Hare Intl

vie. 5/16

6:10 am-9:44 am

Nonstop3h 34m

$213

CancúnChicago

CUN - MDW

CUNMDW

Cancun

jue. 7/31

8:15 am-11:50 am

Nonstop3h 35m

Chicago Midway

dom. 8/3

5:25 pm-9:00 pm

Nonstop3h 35m

$249

CancúnChicago

CUN - MDW

CUNMDW

Cancun

mié. 5/14

9:55 am-6:45 pm

2 stops8h 50m

Chicago Midway

sáb. 5/17

12:48 pm-8:20 pm

1 stop7h 32m

$274

CancúnChicago

CUN - ORD

CUNORD

Cancun

jue. 6/5

11:00 am-9:20 pm

1 stop10h 20m

Chicago O'Hare Intl

mar. 6/10

11:20 am-8:20 pm

1 stop9h 00m

$274

CancúnChicago

CUN - ORD

CUNORD

Cancun

vie. 6/13

8:35 am-11:58 pm

2 stops15h 23m

Chicago O'Hare Intl

mar. 6/17

9:49 am-1:17 am

2 stops15h 28m

$279

CancúnChicago

CUN - ORD

CUNORD

Cancun

sáb. 8/16

3:19 pm-4:51 am

1 stop13h 32m

Chicago O'Hare Intl

sáb. 8/23

7:25 am-9:03 pm

1 stop13h 38m

$339

CancúnChicago

CUN - ORD

CUNORD

Cancun

mar. 6/10

12:20 pm-4:22 pm

Nonstop4h 02m

Chicago O'Hare Intl

mar. 6/17

12:45 pm-7:20 pm

1 stop6h 35m

$358

CancúnChicago

CUN - ORD

CUNORD

Cancun

mié. 10/8

2:50 pm-7:00 pm

Nonstop4h 10m

Chicago O'Hare Intl

mar. 10/14

5:00 am-2:24 pm

1 stop9h 24m

$382

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/1

Showing 1-10 of 47 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 mayo 1, 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 mayo 1, 2025.

The most flights from zzETW to CHI are scheduled on a Thursday (10 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 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 mayo 1, 2025.
Get a feel of what it's like to fly with Southwest, Delta and Aeromexico 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
8.0
Very good
4,293 reviews

Crew

8.6

Overall

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,293 reviews
Southwest
8.0
Very good
4,293 reviews

Crew

8.6

Overall

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,293 reviews

Crew

8.6

Overall

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Aeromexico
7.5
Good
1,698 reviews
Southwest
8.0
Very good
4,293 reviews

Crew

8.6

Overall

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,696 reviews
Southwest
8.0
Very good
4,293 reviews

Crew

8.6

Overall

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,293 reviews

Crew

8.6

Overall

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 $134. Southwest flights start at $137 while deals on Frontier start at $137 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 (74%), American Airlines (72%) or Spirit Airlines (69%) 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 $135. On average you can expect to pay $302. The most popular route, (Cancun - Chicago O'Hare Intl), can usually be booked for $265.

  • 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
Hammond
Benton Harbor
Porter
Lansing
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 mayo 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$124Average$167FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$177Average$246FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$212Average$309FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$262Average$426FlexibilityNo cancel feeOn-time71%

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