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Riviera Maya

$119+ Cheap flights from Midway (MDW) to Riviera Maya

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 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
Oct 25 — Nov 11
Sat 10/25
Sat 11/1
1 adult, Economy
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Cheap flight deals from Midway to Riviera Maya

Keep the following information in mind while searching for Midway to Riviera Maya flight deals. Data was last updated September 25, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$261
(Southwest)

One-way from

$119
(Southwest)

Popular in

March

Cheapest in

September

Average price

$347
Provider with most accurate pricing for Chicago (CHI)-Cancun flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Cancun flights.
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From Chicago Midway to Riviera Maya
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One-way flight from Chicago Midway to Riviera Maya
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Highest demand for flights based on searches. 5% potential increase in price ($26 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($9 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 Midway to Riviera Maya

Cheapest flights from Midway to Riviera Maya
Explore the most affordable flight options available from Midway to Riviera Maya. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 25, 2025.

This Southwest deal was found by Cheapflights users on 9/25. 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.
Sun 10/268:25 amMDW - CUN
Nonstop3h 40mSouthwest
Thu 10/303:20 pmCUN - MDW
Nonstop3h 35mSouthwest
Deal found 9/25$261
This Southwest deal was found by Cheapflights users on 9/25. 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.
Sat 10/259:40 amMDW - CUN
Nonstop3h 35mSouthwest
Fri 10/313:15 pmCUN - MDW
Nonstop3h 35mSouthwest
Deal found 9/25$266
This Southwest deal was found by Cheapflights users on 9/23. 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.
Sun 12/1410:40 amMDW - CUN
Nonstop3h 45mSouthwest
Mon 12/222:30 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 9/23$270
This Southwest deal was found by Cheapflights users on 9/25. 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.
Sat 12/63:40 pmMDW - CUN
Nonstop3h 45mSouthwest
Sat 12/133:10 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 9/25$271
This Southwest deal was found by Cheapflights users on 9/25. 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.
Sat 10/256:30 amMDW - CUN
1 stop7h 10mSouthwest
Thu 10/303:20 pmCUN - MDW
Nonstop3h 35mSouthwest
Deal found 9/25$280
This Southwest deal was found by Cheapflights users on 9/25. 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.
Mon 10/69:40 amMDW - CUN
Nonstop3h 35mSouthwest
Thu 10/93:20 pmCUN - MDW
Nonstop3h 35mSouthwest
Deal found 9/25$281
This Southwest deal was found by Cheapflights users on 9/25. 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.
Sat 10/257:00 amMDW - CUN
1 stop6h 10mSouthwest
Sat 11/12:00 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 9/25$285
This Southwest deal was found by Cheapflights users on 9/25. 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.
Tue 11/118:40 amMDW - CUN
Nonstop3h 45mSouthwest
Sat 11/1511:20 amCUN - MDW
2 stops8h 45mSouthwest
Deal found 9/25$286
This Southwest deal was found by Cheapflights users on 9/25. 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.
Mon 9/299:55 amMDW - CUN
Nonstop3h 35mSouthwest
Wed 10/13:10 pmCUN - MDW
Nonstop3h 40mSouthwest
Deal found 9/25$301
This Mytrip deal was found by Cheapflights users on 9/24. 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.
Fri 10/245:28 pmMDW - CUN
1 stop16h 58mFrontier
Fri 11/72:30 pmCUN - MDW
1 stop8h 38mFrontier
Deal found 9/24$302
This Delta deal was found by Cheapflights users on 9/25. 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.
Thu 12/256:00 amMDW - CZM
1 stop8h 15mDelta
Tue 1/63:15 pmCZM - MDW
1 stop6h 31mDelta
Deal found 9/25$698
This Delta deal was found by Cheapflights users on 9/25. 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.
Thu 12/256:00 amMDW - CZM
1 stop8h 15mDelta
Mon 1/53:20 pmCZM - MDW
2 stops17h 30mDelta
Deal found 9/25$722

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Riviera Maya 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 25, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Riviera Maya that are best for you.

Fly from

Midway

Fly to

Riviera Maya

Route

Depart

Return

Price

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 11/11

8:40 am-1:25 pm

Nonstop3h 45m

Cancun

Sat 11/15

8:40 am-4:45 pm

1 stop9h 05m

$301

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 1/17

6:00 am-4:31 pm

1 stop9h 31m

Cancun

Wed 1/21

3:03 pm-9:46 pm

1 stop7h 43m

$326

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 12/3

9:34 am-9:20 pm

2 stops10h 46m

Cancun

Wed 12/17

8:00 am-6:00 pm

2 stops11h 00m

$330

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 1/11

6:00 am-4:31 pm

1 stop9h 31m

Cancun

Fri 1/16

12:15 pm-6:34 pm

1 stop7h 19m

$341

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 11/8

4:23 pm-12:35 pm

2 stops19h 12m

Cancun

Fri 11/14

8:00 am-4:38 pm

1 stop9h 38m

$345

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 11/10

9:34 am-9:20 pm

2 stops10h 46m

Cancun

Fri 11/14

8:00 am-6:08 pm

2 stops11h 08m

$345

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 12/3

9:20 am-8:25 pm

1 stop10h 05m

Cancun

Wed 12/17

2:15 pm-10:55 pm

1 stop9h 40m

$356

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 2/8

6:00 am-1:36 pm

1 stop6h 36m

Cancun

Sat 2/14

2:51 pm-11:25 pm

1 stop9h 34m

$374

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 1/12

10:35 am-9:10 pm

1 stop9h 35m

Cancun

Mon 1/26

4:25 pm-9:46 pm

1 stop6h 21m

$381

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 11/17

10:47 am-9:20 pm

1 stop9h 33m

Cancun

Sat 11/22

6:00 am-3:43 pm

2 stops10h 43m

$386

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/25

Showing 1-10 of 42 results
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Best time to book a flight from Midway to Riviera Maya

Have a flexible travel schedule? Discover the best time to fly to Riviera Maya from Midway 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 Chicago Midway Airport to Riviera Maya

What is the cheapest month to book a flight from Chicago Midway Airport to Riviera Maya?

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Riviera Maya (average of $360). Flying from Chicago Midway Airport to Riviera Maya in March is currently the most expensive (average of $492). 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 MDW to ETW?

Find hourly flight availability from Midway to Riviera Maya. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 25, 2025.

When flying from Chicago Midway Airport to Riviera Maya, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Riviera Maya

Get insights into the airlines that provide service to Riviera Maya. 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 Riviera Maya. Reviews last updated September 25, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and LATAM Airlines from Chicago Midway Airport to Riviera Maya by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

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
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

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
Delta
8.0
Very good
7,973 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

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
LATAM Airlines
7.5
Good
1,855 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

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
Aeromexico
7.5
Good
1,693 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

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
Volaris
6.7
Okay
1,152 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

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 Midway to Riviera Maya. 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 Chicago Midway Airport to Riviera Maya?

    Departing from Chicago Midway Airport to Riviera Maya will take you 3h 45m. The distance between Chicago Midway Airport and Riviera Maya is about 1434 mi. This flight may include one or multiple stops.

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

    The cheapest airlines for a one-way flight from Chicago Midway Airport to Riviera Maya are Southwest ($119), Aeromexico ($269), and Delta ($269).

  • What are the cheapest flights from Chicago Midway Airport to Riviera Maya?

    The cheapest flight price from Chicago Midway Airport to Riviera Maya is $124. On average you can expect to pay $315. The most popular route, (Chicago Midway - Cancun), can usually be booked for $280.

  • Can I find deals for flights from Midway to Riviera Maya that include hotel bookings?

    Yes. In addition to deals on Midway to Riviera Maya flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Riviera Maya?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Riviera Maya.

  • Can I find deals for business class flights from Midway to Riviera Maya?

    Yes. Cheapflights offers flight deals from Midway to Riviera Maya 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 Chicago Midway Airport to Riviera Maya?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Riviera Maya (average of $360). Flying from Chicago Midway Airport to Riviera Maya in March is currently the most expensive (average of $492). 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

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Alternative routes for Midway to Riviera Maya

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Cancún flights
Midway to Cancún flights
O'Hare Intl to Cozumel flights
Midway to Cozumel flights
O'Hare Intl to Chetumal flights

Top 7 airlines flying from Midway to Riviera Maya

Discover the top 7 airlines that operate flights from Midway to Riviera Maya. 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 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$161Average$419FlexibilityNo cancel feeOn-time69%
AeromexicoCheapest$312Average$494FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$345Average$575FlexibilityNo cancel feeOn-time63%
FrontierCheapest$362Average$565FlexibilityNo cancel feeOn-time62%
DeltaCheapest$380Average$609FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$486Average$872FlexibilityNo cancel feeOn-time79%
LATAM AirlinesCheapest$3,369Average$3,369FlexibilityNo cancel feeOn-time81%

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