HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Riviera Maya

$120+ 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 1/20. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
Dec 10 — Dec 171
Wed 12/10
Wed 12/17
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.

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 November 10, 2025.

This Aeromexico deal was found by Cheapflights users on 11/8. 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.
Mon 12/16:00 amMDW - CUN
1 stop8h 34mAeromexico
Wed 12/108:00 amCUN - MDW
1 stop9h 34mAeromexico
Deal found 11/8$319
This Delta deal was found by Cheapflights users on 11/9. 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.
Tue 12/912:50 pmMDW - CUN
1 stop7h 30mDelta
Thu 12/111:33 pmCUN - MDW
1 stop11h 14mDelta
Deal found 11/9$327
This Delta deal was found by Cheapflights users on 11/9. 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.
Fri 11/289:34 amMDW - CUN
2 stops10h 46mDelta
Sat 12/68:00 amCUN - MDW
2 stops11h 06mDelta
Deal found 11/9$331
This Aeromexico deal was found by Cheapflights users on 11/8. 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 11/1210:47 amMDW - CUN
1 stop9h 33mAeromexico
Sat 11/158:00 amCUN - MDW
1 stop8h 43mAeromexico
Deal found 11/8$337
This Southwest deal was found by Cheapflights users on 11/8. 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 11/153:40 pmMDW - CUN
Nonstop3h 45mSouthwest
Fri 11/212:15 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 11/8$342
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/136:00 amMDW - CUN
2 stops30h 13mMultiple Airlines
Sat 12/201:54 pmCUN - MDW
1 stop25h 05mMultiple Airlines
Deal found 11/9$343
This Delta deal was found by Cheapflights users on 11/8. 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.
Fri 12/1212:50 pmMDW - CUN
1 stop7h 30mDelta
Tue 12/168:00 amCUN - MDW
1 stop9h 44mDelta
Deal found 11/8$347
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/276:15 pmMDW - CUN
1 stop16h 01mMultiple Airlines
Tue 12/22:44 pmCUN - MDW
2 stops19h 02mMultiple Airlines
Deal found 11/10$349
This Delta deal was found by Cheapflights users on 11/8. 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 12/169:34 amMDW - CUN
2 stops10h 46mDelta
Mon 12/228:00 amCUN - MDW
1 stop15h 22mDelta
Deal found 11/8$351
This Southwest deal was found by Cheapflights users on 11/7. 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
Thu 11/132:15 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 11/7$352
This Kiwi.com deal was found by Cheapflights users on 11/8. 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 11/228:29 pmMDW - CUN
2 stops16h 06mMultiple Airlines
Wed 11/265:56 pmCUN - MDW
1 stop29h 47mMultiple Airlines
Deal found 11/8$354
This Southwest deal was found by Cheapflights users on 11/10. 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 12/155:35 amMDW - CUN
1 stop9h 50mSouthwest
Thu 12/182:15 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 11/10$357

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 November 10, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$262
(Southwest)

One-way from

$120
(Southwest)

Popular in

March

Cheapest in

September

Average price

$464
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. 5% potential increase in price ($25 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 November 10, 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 1/17

11:21 am-9:11 pm

1 stop8h 50m

Cancun

Wed 1/21

8:00 am-5:32 pm

1 stop10h 32m

$327

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 1/29

12:48 pm-9:11 pm

1 stop7h 23m

Cancun

Tue 2/3

1:40 pm-10:26 pm

1 stop9h 46m

$327

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 1/29

12:48 pm-9:11 pm

1 stop7h 23m

Cancun

Thu 2/5

8:00 am-5:32 pm

1 stop10h 32m

$327

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 12/12

10:49 am-9:20 pm

1 stop9h 31m

Cancun

Tue 12/16

8:00 am-6:00 pm

2 stops11h 00m

$331

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 1/19

6:00 am-9:11 pm

1 stop14h 11m

Cancun

Mon 1/26

12:05 pm-10:26 pm

2 stops11h 21m

$331

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 11/15

3:40 pm-8:25 pm

Nonstop3h 45m

Cancun

Fri 11/21

2:15 pm-5:00 pm

Nonstop3h 45m

$342

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 11/27

10:47 am-9:20 pm

1 stop9h 33m

Cancun

Tue 12/2

8:00 am-4:18 pm

1 stop9h 18m

$347

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 11/29

6:00 am-3:34 pm

1 stop8h 34m

Cancun

Sat 12/6

8:00 am-6:06 pm

2 stops11h 06m

$351

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 12/7

9:34 am-9:20 pm

2 stops10h 46m

Cancun

Wed 12/10

8:00 am-4:34 pm

1 stop9h 34m

$351

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 12/15

6:20 am-5:00 pm

2 stops9h 40m

Cancun

Sat 12/20

4:25 pm-7:10 pm

Nonstop3h 45m

$361

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/9

Showing 1-10 of 41 results
1
2
3
...
5

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, April is the cheapest month in which you can book a flight from Chicago Midway Airport to Riviera Maya (average of $253). Flying from Chicago Midway Airport to Riviera Maya in January is currently the most expensive (average of $430). 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 November 10, 2025.

It’s typically best to fly out from Chicago Midway Airport to Riviera Maya in the afternoon. Doing so could potentially save you 27% on the flight price compared to flying at noon, which is usually more expensive.

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 November 10, 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
4,235 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

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
4,235 reviews
Southwest
8.0
Very good
4,235 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

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
7.9
Good
8,006 reviews
Southwest
8.0
Very good
4,235 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

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
1,872 reviews
Southwest
8.0
Very good
4,235 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

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
7.4
Good
1,672 reviews
Southwest
8.0
Very good
4,235 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

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
4,235 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

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 8h 50m. The distance between Chicago Midway Airport and Riviera Maya is about 1434 mi.

  • 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 ($120), Delta ($146), and Aeromexico ($270).

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

    The cheapest flight price from Chicago Midway Airport to Riviera Maya is $114. On average you can expect to pay $324. The most popular route, (Chicago Midway - Cancun), can usually be booked for $314.

  • 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, April is the cheapest month in which you can book a flight from Chicago Midway Airport to Riviera Maya (average of $253). Flying from Chicago Midway Airport to Riviera Maya in January is currently the most expensive (average of $430). 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 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 November 10, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$161Average$490FlexibilityNo cancel feeOn-time69%
AeromexicoCheapest$312Average$510FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$345Average$572FlexibilityNo cancel feeOn-time63%
FrontierCheapest$362Average$567FlexibilityNo cancel feeOn-time62%
DeltaCheapest$380Average$618FlexibilityNo cancel feeOn-timeN/A
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.