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Riviera Maya

$111+ 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 7/28. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
Apr 9 — Apr 161
Wed 4/9
Wed 4/16
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 April 4, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$246
(Southwest)

One-way from

$111
(Southwest)

Popular in

March

Cheapest in

September

Average price

$401
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. 7% potential increase in price ($33 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 4, 2025.

This Southwest deal was found by Cheapflights users on 4/3. 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 6/295:25 pmMDW - CUN
Nonstop3h 35mSouthwest
Wed 7/28:30 amCUN - MDW
Nonstop3h 35mSouthwest
Deal found 4/3$246
This Trip.com deal was found by Cheapflights users on 4/4. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1212:48 pmMDW - CUN
1 stop7h 32mAeromexico
Tue 5/138:00 amCUN - MDW
1 stop7h 30mAeromexico
Deal found 4/4$291
This Delta deal was found by Cheapflights users on 4/4. 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 5/109:16 amMDW - CUN
2 stops11h 04mDelta
Sat 5/248:00 amCUN - MDW
1 stop7h 20mDelta
Deal found 4/4$325
This Kiwi.com deal was found by Cheapflights users on 4/4. 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.
Mon 5/1212:48 pmMDW - CUN
1 stop7h 32mMultiple Airlines
Fri 5/1612:39 pmCUN - MDW
1 stop9h 34mMultiple Airlines
Deal found 4/4$339
This Kiwi.com deal was found by Cheapflights users on 4/3. 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.
Fri 4/184:36 pmMDW - CUN
1 stop16h 24mFrontier
Thu 4/243:35 pmCUN - MDW
1 stop27h 31mFrontier
Deal found 4/3$395
This Booking.com deal was found by Cheapflights users on 4/3. 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.
Thu 8/148:39 pmMDW - CUN
1 stop14h 24mVolaris
Tue 8/198:00 amCUN - MDW
1 stop11h 16mVolaris
Deal found 4/3$432
This Mytrip deal was found by Cheapflights users on 4/3. 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.
Sat 5/38:39 pmMDW - CZM
2 stops21h 13mVolaris
Sat 5/105:42 pmCZM - MDW
2 stops24h 24mVolaris
Deal found 4/3$591
This Aeromexico deal was found by Cheapflights users on 4/4. 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.
Sat 4/266:04 amMDW - CZM
1 stop7h 56mAeromexico
Sat 5/32:25 pmCZM - MDW
1 stop6h 57mAeromexico
Deal found 4/4$628
This Mytrip deal was found by Cheapflights users on 4/4. 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.
Sun 5/188:39 pmMDW - CZM
2 stops18h 30mMultiple Airlines
Thu 5/295:42 pmCZM - MDW
2 stops24h 24mMultiple Airlines
Deal found 4/4$748
This Delta deal was found by Cheapflights users on 4/3. 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
Tue 1/63:15 pmCZM - MDW
1 stop6h 31mDelta
Deal found 4/3$828
This WestJet deal was found by Cheapflights users on 4/3. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/310:36 amMDW - CZM
2 stops51h 20mWestJet
Thu 4/101:50 pmCZM - MDW
2 stops27h 28mWestJet
Deal found 4/3$3,221

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 April 4, 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

Sun 6/29

5:25 pm-9:00 pm

Nonstop3h 35m

Cancun

Wed 7/2

8:30 am-12:05 pm

Nonstop3h 35m

$246

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 5/12

12:48 pm-8:20 pm

1 stop7h 32m

Cancun

Tue 5/13

8:00 am-3:30 pm

1 stop7h 30m

$291

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 5/15

12:48 pm-8:20 pm

1 stop7h 32m

Cancun

Tue 5/20

8:31 am-9:27 pm

2 stops12h 56m

$321

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 5/12

12:48 pm-8:20 pm

1 stop7h 32m

Cancun

Fri 5/16

12:39 pm-10:13 pm

1 stop9h 34m

$339

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 4/18

4:36 pm-9:00 am

1 stop16h 24m

Cancun

Thu 4/24

3:35 pm-7:06 pm

1 stop27h 31m

$395

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 8/14

8:39 pm-11:03 am

1 stop14h 24m

Cancun

Tue 8/19

8:00 am-7:16 pm

1 stop11h 16m

$432

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Sat 5/3

8:39 pm-4:52 pm

2 stops21h 13m

Cozumel

Sat 5/10

5:42 pm-7:06 pm

2 stops24h 24m

$591

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Sat 4/26

6:04 am-1:00 pm

1 stop7h 56m

Cozumel

Sat 5/3

2:25 pm-10:22 pm

1 stop6h 57m

$628

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Sun 5/18

8:39 pm-2:09 pm

2 stops18h 30m

Cozumel

Thu 5/29

5:42 pm-7:06 pm

2 stops24h 24m

$748

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Sat 5/3

6:04 am-1:00 pm

1 stop7h 56m

Cozumel

Mon 5/12

4:23 pm-3:30 pm

2 stops22h 07m

$848

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/4

Showing 1-10 of 21 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 April 4, 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.

Rainfall in Riviera Maya by month

Plan your trip to Riviera Maya by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Riviera Maya ranges from 1.1 - 11.1 inches per month. October is typically the wettest month, when rainfall can reach 11.1 in. April is typically the driest time to visit Riviera Maya when rainfall is around 1.1 in.

Temperature in Riviera Maya by month

Plan your trip to Riviera Maya by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Riviera Maya, 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 86.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 75.2 F).

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 April 4, 2025.
Get a feel of what it's like to fly with Southwest, Delta and Aeromexico from Chicago to Riviera Maya by reading reviews from past customers. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,276 reviews

Entertainment

7.6

Crew

8.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,276 reviews
Southwest
8.0
Very good
4,276 reviews

Entertainment

7.6

Crew

8.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,899 reviews
Southwest
8.0
Very good
4,276 reviews

Entertainment

7.6

Crew

8.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Aeromexico
7.5
Good
1,701 reviews
Southwest
8.0
Very good
4,276 reviews

Entertainment

7.6

Crew

8.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
WestJet
7.2
Good
2,795 reviews
Southwest
8.0
Very good
4,276 reviews

Entertainment

7.6

Crew

8.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Volaris
6.7
Okay
1,169 reviews
Southwest
8.0
Very good
4,276 reviews

Entertainment

7.6

Crew

8.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 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 ($111), Frontier ($138), and Delta ($146).

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

    The cheapest flight price from Chicago Midway Airport to Riviera Maya is $110. On average you can expect to pay $500. The most popular route, (Chicago Midway - Cancun), can usually be booked for $309.

  • 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 April 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$175Average$393FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$183Average$333FlexibilityNo cancel feeOn-time65%
FrontierCheapest$198Average$443FlexibilityNo cancel feeOn-time62%
AeromexicoCheapest$368Average$537FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$380Average$538FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$433Average$693FlexibilityNo cancel feeOn-time63%
VolarisCheapest$486Average$872FlexibilityNo cancel feeOn-time79%
LATAM AirlinesCheapest$3,369Average$3,369FlexibilityNo cancel feeOn-time81%

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