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Riviera Maya

$125+ 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 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
Aug 16 — Aug 231
Sat 8/16
Sat 8/23
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 August 11, 2025.

Round-trip from

$271
(Southwest)

One-way from

$125
(Southwest)

Popular in

March

Cheapest in

September

Average price

$413
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. 6% potential increase in price ($27 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 August 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 August 11, 2025.

This Southwest deal was found by Cheapflights users on 8/10. 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 9/69:15 amMDW - CUN
Nonstop3h 35mSouthwest
Sat 9/132:25 pmCUN - MDW
Nonstop3h 40mSouthwest
Deal found 8/10$271
This Southwest deal was found by Cheapflights users on 8/11. 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 9/1410:35 amMDW - CUN
Nonstop3h 35mSouthwest
Thu 9/183:10 pmCUN - MDW
Nonstop3h 40mSouthwest
Deal found 8/11$281
This Southwest deal was found by Cheapflights users on 8/10. 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
Sat 10/411:35 amCUN - MDW
1 stop7h 30mSouthwest
Deal found 8/10$286
This Southwest deal was found by Cheapflights users on 8/10. 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
Tue 11/181:45 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 8/10$301
This SmartFares deal was found by Cheapflights users on 8/10. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/66:00 amMDW - CUN
1 stop5h 30mAeromexico
Sat 9/1312:35 pmCUN - MDW
1 stop8h 35mAeromexico
Deal found 8/10$305
This Southwest deal was found by Cheapflights users on 8/10. 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 11/311:25 amMDW - CUN
1 stop7h 20mSouthwest
Tue 11/41:45 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 8/10$306
This Southwest deal was found by Cheapflights users on 8/9. 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 11/37:05 amMDW - CUN
2 stops8h 55mSouthwest
Sat 11/811:55 amCUN - MDW
Nonstop3h 50mSouthwest
Deal found 8/9$310
This Southwest deal was found by Cheapflights users on 8/9. 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 9/78:00 amMDW - CUN
2 stops7h 30mSouthwest
Fri 9/123:10 pmCUN - MDW
Nonstop3h 40mSouthwest
Deal found 8/9$315
This Southwest deal was found by Cheapflights users on 8/11. 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 8/317:10 amMDW - CUN
1 stop6h 40mSouthwest
Sat 9/61:15 pmCUN - MDW
1 stop7h 30mSouthwest
Deal found 8/11$316
This Delta deal was found by Cheapflights users on 8/9. 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.
Sat 9/66:00 amMDW - CUN
1 stop5h 30mDelta
Sat 9/138:00 amCUN - MDW
1 stop7h 26mDelta
Deal found 8/9$317
This Delta deal was found by Cheapflights users on 8/9. 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 12/296:00 amMDW - CZM
1 stop8h 00mDelta
Wed 1/74:28 pmCZM - MDW
1 stop16h 26mDelta
Deal found 8/9$498
This Delta deal was found by Cheapflights users on 8/9. 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 12/296:00 amMDW - CZM
1 stop8h 00mDelta
Fri 1/93:15 pmCZM - MDW
2 stops17h 35mDelta
Deal found 8/9$502

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 August 11, 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

Sat 9/6

9:15 am-12:50 pm

Nonstop3h 35m

Cancun

Sat 9/13

2:25 pm-6:05 pm

Nonstop3h 40m

$271

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 9/14

10:35 am-2:10 pm

Nonstop3h 35m

Cancun

Thu 9/18

3:10 pm-6:50 pm

Nonstop3h 40m

$281

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 9/29

9:55 am-1:30 pm

Nonstop3h 35m

Cancun

Sat 10/4

11:35 am-7:05 pm

1 stop7h 30m

$286

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 9/6

6:00 am-11:30 am

1 stop5h 30m

Cancun

Sat 9/13

12:35 pm-9:10 pm

1 stop8h 35m

$305

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 11/3

11:25 am-7:45 pm

1 stop7h 20m

Cancun

Sat 11/8

3:10 pm-5:55 pm

Nonstop3h 45m

$306

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 9/7

8:00 am-3:30 pm

2 stops7h 30m

Cancun

Fri 9/12

3:10 pm-6:50 pm

Nonstop3h 40m

$315

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 8/31

7:10 am-1:50 pm

1 stop6h 40m

Cancun

Sat 9/6

1:15 pm-8:45 pm

1 stop7h 30m

$316

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 9/6

6:00 am-11:30 am

1 stop5h 30m

Cancun

Sat 9/13

8:00 am-3:26 pm

1 stop7h 26m

$317

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 9/3

6:00 am-2:10 pm

1 stop8h 10m

Cancun

Sat 9/6

8:00 am-3:28 pm

1 stop7h 28m

$318

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Thu 9/25

8:39 pm-4:52 pm

2 stops21h 13m

Cozumel

Thu 10/2

5:42 pm-7:16 pm

2 stops24h 34m

$892

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/9

Showing 1-10 of 41 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 August 11, 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.

Weekly flight availability from Chicago Midway Airport to Riviera Maya

Explore weekly flight availability from Midway to Riviera Maya. 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 August 11, 2025.

The most flights from MDW to zzETW are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).

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 August 11, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and Aeromexico 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

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,978 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Aeromexico
7.5
Good
1,724 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Volaris
6.6
Okay
1,163 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Frontier
5.8
Fair
3,222 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

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

    The cheapest flight price from Chicago Midway Airport to Riviera Maya is $123. On average you can expect to pay $316. The most popular route, (Chicago Midway - Cancun), can usually be booked for $271.

  • 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 8 airlines flying from Midway to Riviera Maya

Discover the top 8 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 August 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$161Average$419FlexibilityNo cancel feeOn-time69%
FrontierCheapest$198Average$565FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$241Average$333FlexibilityNo cancel feeOn-time65%
AeromexicoCheapest$312Average$506FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$345Average$577FlexibilityNo cancel feeOn-time63%
DeltaCheapest$380Average$612FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$486Average$872FlexibilityNo cancel feeOn-time79%
LATAM AirlinesCheapest$3,369Average$3,369FlexibilityNo cancel feeOn-time81%

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