HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
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 6/10. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Riviera Maya with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 May 1, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$299
(Southwest)

One-way from

$111
(Southwest)

Popular in

March

Cheapest in

September

Average price

$387
Provider with most accurate pricing for Chicago (CHI)-Cancun flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Cancun flights.
Search Deals
From Chicago Midway to Riviera Maya
Search Deals
One-way flight from Chicago Midway to Riviera Maya
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($31 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2025
Search Deals

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 May 1, 2025.

This Southwest deal was found by Cheapflights users on 4/28. 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 5/1110:45 amMDW - CUN
Nonstop3h 40mSouthwest
Thu 5/159:00 amCUN - MDW
Nonstop3h 40mSouthwest
Deal found 4/28$246
This SmartFares 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/512:44 pmMDW - CUN
1 stop7h 36mAeromexico
Thu 7/1011:00 amCUN - MDW
1 stop7h 02mAeromexico
Deal found 4/29$306
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/66:04 amMDW - CUN
1 stop7h 57mDelta
Tue 5/1311:00 amCUN - MDW
1 stop10h 28mDelta
Deal found 4/29$321
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/2812:44 pmMDW - CUN
1 stop7h 36mMultiple Airlines
Thu 7/33:05 pmCUN - MDW
1 stop20h 35mMultiple Airlines
Deal found 4/30$362
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/36:40 amMDW - CUN
1 stop6h 20mFrontier
Sat 6/79:09 amCUN - MDW
1 stop10h 16mFrontier
Deal found 4/29$417
This Aeromexico 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:00 amMDW - CZM
1 stop8h 00mAeromexico
Tue 12/303:20 pmCZM - MDW
1 stop6h 45mAeromexico
Deal found 4/29$1,003
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/210:25 amMDW - CZM
2 stops28h 46mDelta
Tue 6/104:33 pmCZM - MDW
2 stops28h 12mDelta
Deal found 4/29$1,118
This WestJet 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/219:20 amMDW - CZM
2 stops28h 41mWestJet
Sat 11/292:50 pmCZM - MDW
2 stops27h 08mWestJet
Deal found 4/30$3,529

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 May 1, 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

Mon 5/19

5:10 am-1:20 pm

1 stop8h 10m

Cancun

Thu 5/22

9:00 am-12:40 pm

Nonstop3h 40m

$299

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 6/10

12:44 pm-8:20 pm

1 stop7h 36m

Cancun

Wed 6/11

2:00 pm-9:45 pm

1 stop7h 45m

$309

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 6/6

12:48 pm-8:20 pm

1 stop7h 32m

Cancun

Wed 6/11

12:35 pm-9:45 pm

1 stop9h 10m

$321

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 6/28

12:44 pm-8:20 pm

1 stop7h 36m

Cancun

Thu 7/3

3:05 pm-11:40 am

1 stop20h 35m

$362

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 6/3

6:40 am-1:00 pm

1 stop6h 20m

Cancun

Sat 6/7

9:09 am-7:25 pm

1 stop10h 16m

$417

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Thu 9/25

6:00 am-1:11 pm

2 stops32h 11m

Cozumel

Mon 9/29

1:59 pm-9:44 pm

2 stops30h 45m

$1,038

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Mon 6/2

10:25 am-2:11 pm

2 stops28h 46m

Cozumel

Tue 6/10

4:33 pm-9:45 pm

2 stops28h 12m

$1,118

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 6/10

4:30 pm-8:05 pm

Nonstop3h 35m

$111

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 6/30

9:12 pm-8:12 am

1 stop11h 00m

$143

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 6/26

10:26 am-8:20 pm

1 stop9h 54m

$144

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 17 results
1
2

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 May 1, 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 May 1, 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
4,294 reviews

Comfort

8.0

Food

7.1

Entertainment

7.6

Overall

8.0

Boarding

8.2

Crew

8.6

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
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Comfort

8.0

Food

7.1

Entertainment

7.6

Overall

8.0

Boarding

8.2

Crew

8.6

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
4,294 reviews

Comfort

8.0

Food

7.1

Entertainment

7.6

Overall

8.0

Boarding

8.2

Crew

8.6

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
4,294 reviews

Comfort

8.0

Food

7.1

Entertainment

7.6

Overall

8.0

Boarding

8.2

Crew

8.6

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!
WestJet
7.2
Good
2,826 reviews
Southwest
8.0
Very good
4,294 reviews

Comfort

8.0

Food

7.1

Entertainment

7.6

Overall

8.0

Boarding

8.2

Crew

8.6

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!
Volaris
6.7
Okay
1,174 reviews
Southwest
8.0
Very good
4,294 reviews

Comfort

8.0

Food

7.1

Entertainment

7.6

Overall

8.0

Boarding

8.2

Crew

8.6

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 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), Aeromexico ($144), 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 $111. On average you can expect to pay $370. The most popular route, (Chicago Midway - Cancun), can usually be booked for $246.

  • 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$161Average$419FlexibilityNo cancel feeOn-time69%
FrontierCheapest$198Average$445FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$241Average$333FlexibilityNo cancel feeOn-time65%
AeromexicoCheapest$320Average$526FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$380Average$536FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$429Average$686FlexibilityNo cancel feeOn-time63%
VolarisCheapest$486Average$872FlexibilityNo cancel feeOn-time79%
LATAM AirlinesCheapest$3,369Average$3,369FlexibilityNo cancel feeOn-time81%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.