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$139+ 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 1/23. Fares are subject to change and may not be available on all flights or dates of travel.
CUN — CHI
Jan 27 — Feb 31
Tue 1/27
Tue 2/3
1 adult, Economy
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Cheap 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 December 28, 2025.

This Frontier deal was found by Cheapflights users on 12/26. 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.
Mon 12/296:22 pmCUN - ORD
Nonstop4h 10mFrontier
Mon 1/510:37 amORD - CUN
Nonstop4h 11mFrontier
Deal found 12/26$174
This Frontier deal was found by Cheapflights users on 12/26. 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.
Mon 12/296:22 pmCUN - ORD
Nonstop4h 10mFrontier
Thu 1/110:37 amORD - CUN
Nonstop4h 11mFrontier
Deal found 12/26$202
This Frontier deal was found by Cheapflights users on 12/26. 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.
Mon 12/296:22 pmCUN - ORD
Nonstop4h 10mFrontier
Sat 1/310:37 amORD - CUN
Nonstop4h 11mFrontier
Deal found 12/26$223
This Super.com deal was found by Cheapflights users on 12/26. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2911:50 amCUN - ORD
Nonstop4h 03mSpirit Airlines
Mon 1/56:05 amORD - CUN
Nonstop3h 50mSpirit Airlines
Deal found 12/26$226
This Frontier deal was found by Cheapflights users on 12/26. 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.
Mon 12/296:22 pmCUN - ORD
Nonstop4h 10mFrontier
Sun 1/410:37 amORD - CUN
Nonstop4h 11mFrontier
Deal found 12/26$231
This Kiwi.com deal was found by Cheapflights users on 12/26. 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.
Sun 12/2811:50 amCUN - ORD
Nonstop4h 03mMultiple Airlines
Mon 1/510:37 amORD - CUN
Nonstop4h 11mMultiple Airlines
Deal found 12/26$252
This Frontier deal was found by Cheapflights users on 12/26. 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 12/266:22 pmCUN - ORD
Nonstop4h 10mFrontier
Tue 1/610:37 amORD - CUN
Nonstop4h 11mFrontier
Deal found 12/26$258
This Frontier deal was found by Cheapflights users on 12/26. 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.
Tue 12/306:22 pmCUN - ORD
Nonstop4h 10mFrontier
Mon 1/510:37 amORD - CUN
Nonstop4h 11mFrontier
Deal found 12/26$264
This American Airlines deal was found by Cheapflights users on 12/27. 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.
Wed 12/312:34 pmCUN - ORD
Nonstop4h 05mAmerican Airlines
Sat 1/35:00 amORD - CUN
1 stop6h 13mAmerican Airlines
Deal found 12/27$267
This Kiwi.com deal was found by Cheapflights users on 12/26. 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.
Sun 12/2811:50 amCUN - ORD
Nonstop4h 03mSpirit Airlines
Fri 1/26:05 amORD - CUN
Nonstop3h 50mSpirit Airlines
Deal found 12/26$271
This Delta deal was found by Cheapflights users on 12/26. 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.
Mon 12/294:30 pmCUN - MDW
1 stop6h 52mDelta
Mon 1/56:45 amMDW - CUN
1 stop13h 26mDelta
Deal found 12/26$278
This Aeromexico deal was found by Cheapflights users on 12/26. 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 12/268:00 amCUN - MDW
1 stop15h 22mAeromexico
Sun 1/49:50 amMDW - CUN
1 stop5h 40mAeromexico
Deal found 12/26$348

Find 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 December 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$155
(Frontier)

One-way from

$139
(Kiwi.com)

Popular in

September

Cheapest in

January

Average price

$271
Provider with most accurate pricing for Cancun-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Cancun-Chicago (CHI) flights.
Search Deals
From Riviera Maya to Chicago (CHI)
Search Deals
One-way flight from Riviera Maya to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($51 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 28, 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

Thu 1/15

11:40 am-2:49 pm

Nonstop4h 09m

Chicago O'Hare Intl

Sun 1/18

6:45 am-11:49 am

Nonstop4h 04m

$179

CancúnChicago

CUN - ORD

CUNORD

Cancun

Fri 1/16

11:59 am-2:53 pm

Nonstop3h 54m

Chicago O'Hare Intl

Tue 1/20

5:15 am-12:16 pm

1 stop6h 01m

$223

CancúnChicago

CUN - ORD

CUNORD

Cancun

Wed 1/28

1:21 pm-11:46 pm

1 stop11h 25m

Chicago O'Hare Intl

Wed 2/4

6:05 am-10:54 am

Nonstop3h 49m

$223

CancúnChicago

CUN - ORD

CUNORD

Cancun

Sun 1/25

11:59 am-2:53 pm

Nonstop3h 54m

Chicago O'Hare Intl

Sun 2/1

6:05 am-10:54 am

Nonstop3h 49m

$228

CancúnChicago

CUN - ORD

CUNORD

Cancun

Wed 2/11

10:13 am-9:44 pm

1 stop12h 31m

Chicago O'Hare Intl

Sun 2/15

8:42 pm-12:00 pm

1 stop14h 18m

$236

CancúnChicago

CUN - ORD

CUNORD

Cancun

Wed 2/11

7:19 pm-10:28 pm

Nonstop4h 09m

Chicago O'Hare Intl

Sun 2/15

6:10 am-11:14 am

Nonstop4h 04m

$245

CancúnChicago

CUN - ORD

CUNORD

Cancun

Wed 1/28

3:18 pm-6:09 pm

Nonstop3h 51m

Chicago O'Hare Intl

Tue 2/3

10:35 am-3:35 pm

Nonstop4h 00m

$252

CancúnChicago

CUN - ORD

CUNORD

Cancun

Wed 1/21

4:47 pm-7:47 pm

Nonstop4h 00m

Chicago O'Hare Intl

Fri 1/30

10:35 am-3:35 pm

Nonstop4h 00m

$252

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 1/22

3:18 pm-6:09 pm

Nonstop3h 51m

Chicago O'Hare Intl

Fri 1/30

10:35 am-3:35 pm

Nonstop4h 00m

$252

CancúnChicago

CUN - ORD

CUNORD

Cancun

Tue 1/27

3:18 pm-6:09 pm

Nonstop3h 51m

Chicago O'Hare Intl

Mon 2/2

10:35 am-3:35 pm

Nonstop4h 00m

$252

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/27

Showing 1-10 of 60 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 $254). 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 December 28, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 64% 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 December 28, 2025.

The most flights from zzETW to CHI are scheduled on a Saturday (17 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (14 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 December 28, 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
4,250 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,250 reviews
Southwest
8.0
Very good
4,250 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,114 reviews
Southwest
8.0
Very good
4,250 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Spirit Airlines
6.3
Okay
8,212 reviews
Southwest
8.0
Very good
4,250 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.8
Fair
3,064 reviews
Southwest
8.0
Very good
4,250 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 3h 54m. Fly via Frontier, Spirit 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 Frontier, which is currently one of the cheapest options available, starting at $107. Spirit Airlines flights start at $113 while deals on United Airlines start at $125 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 (85%), American Airlines (80%) or Frontier (76%) 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 $116. On average you can expect to pay $299. The most popular route, (Cancun - Chicago O'Hare Intl), can usually be booked for $204.

  • 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 $254). 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
Merrillville
Hammond
Porter
Benton Harbor

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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 Midway flights
Cancún to O'Hare Intl 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 December 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$142Average$198FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$194Average$292FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$209Average$322FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$271Average$352FlexibilityNo cancel feeOn-time71%

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