How many flights depart from Chicago Midway Airport to Riviera Maya on average per week?

As of July 2026, 8 flights take off from Chicago Midway Airport and land in Riviera Maya each week. The most common flight departure day for this route is Mon, with 25% of weekly flights taking off on this day.

How many flights depart from Chicago Midway Airport to Riviera Maya on average per day?

1 flights are operational daily from Chicago Midway Airport to Riviera Maya as of July 2026. The most popular departure time for this route is 6:00AM, with 100% of flights per day taking off at noon.

What airlines fly to Riviera Maya?

Southwest, Frontier and Aeromexico are the top three most popular airlines that fly to Riviera Maya from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 71% of people opting to fly with this airline when traveling to Riviera Maya. Keep in mind that there are 4 different airlines that fly to Riviera Maya on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Chicago Midway to Riviera Maya?

Delta and Volaris are the most popular carriers operating from Chicago Midway to Riviera Maya

When did momondo last update prices for flights from Chicago Midway Airport to Riviera Maya?

Prices for flights from Chicago Midway Airport to Riviera Maya were last updated today.

How many operators does momondo search for flights from Chicago Midway Airport to Riviera Maya?

There are 4 operators available for flights from Chicago Midway Airport to Riviera Maya as of July 2026.

How old do you have to be to fly from Chicago Midway Airport to Riviera Maya?

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to Riviera Maya.

What documentation or ID do you need to fly to Riviera Maya?

The necessary travel and health documents for your Riviera Maya trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$125 Cheap Flights from Chicago Midway Airport to Riviera Maya in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago Midway Airport to Riviera Maya

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:23 pm - 9:55 am

MDW

CUN

13h 32m

1 stop

10:40 am - 7:04 pm

CUN

MDW

8h 24m

1 stop

$337Volaris

Fri, Aug 28 - Mon, Aug 31

8:23 pm - 9:55 am

MDW

CUN

13h 32m

1 stop

10:40 am - 7:04 pm

CUN

MDW

8h 24m

1 stop

$338Volaris

Fri, Aug 28 - Mon, Aug 31

8:23 pm - 9:55 am

MDW

CUN

13h 32m

1 stop

10:40 am - 7:04 pm

CUN

MDW

8h 24m

1 stop

$352Volaris

Fri, Oct 2 - Sun, Oct 11

8:23 pm - 9:55 am

MDW

CUN

13h 32m

1 stop

10:40 am - 7:04 pm

CUN

MDW

8h 24m

1 stop

$353Volaris

Mon, Aug 24 - Mon, Aug 31

8:23 pm - 9:55 am

MDW

CUN

13h 32m

1 stop

10:40 am - 7:04 pm

CUN

MDW

8h 24m

1 stop

$354Volaris

Fri, Oct 16 - Fri, Oct 23

8:23 pm - 9:55 am

MDW

CUN

13h 32m

1 stop

10:40 am - 7:04 pm

CUN

MDW

8h 24m

1 stop

$358Volaris

Mon, Oct 5 - Mon, Oct 19

6:00 am - 2:05 pm

MDW

CZM

7h 05m

1 stop

3:05 pm - 10:10 pm

CZM

MDW

8h 05m

1 stop

$837Delta

Tue, Dec 29 - Tue, Jan 5

6:00 am - 2:05 pm

MDW

CZM

7h 05m

1 stop

3:05 pm - 8:45 am

CZM

MDW

18h 40m

2 stops

$842Delta

Tue, Dec 29 - Tue, Jan 5

5:53 pm - 3:37 pm

MDW

CZM

21h 44m

2 stops

4:47 pm - 7:04 pm

CZM

MDW

26h 17m

3 stops

$845Multiple Airlines

Thu, Aug 20 - Thu, Aug 27

6:00 am - 2:05 pm

MDW

CZM

7h 05m

1 stop

3:05 pm - 10:10 pm

CZM

MDW

8h 05m

1 stop

$867Delta

Thu, Dec 31 - Tue, Jan 5

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Frontier flights from Chicago Midway Airport to Riviera Maya

Our best Frontier deals on Chicago Midway Airport to Riviera Maya flight tickets

Frontier

Aug 22

MDW11:45 amChicago Midway

21h 28m

2 stops

CUN9:13 amCancun

Aug 29

CUN3:06 pmCancun

7h 41m

1 stop

MDW10:47 pmChicago Midway

$419

Frontier

Jul 21

MDW6:05 amChicago Midway

7h 41m

1 stop

CUN1:46 pmCancun

Jul 29

CUN11:10 amCancun

10h 53m

2 stops

MDW10:03 pmChicago Midway

$481

Frontier

Jul 21

MDW6:05 amChicago Midway

7h 41m

1 stop

CUN1:46 pmCancun

Aug 4

CUN3:31 pmCancun

18h 20m

2 stops

MDW9:51 amChicago Midway

$504

Volaris flights from Chicago Midway Airport to Riviera Maya

Our best Volaris deals on Chicago Midway Airport to Riviera Maya flight tickets

Volaris

Aug 28

MDW8:23 pmChicago Midway

13h 32m

1 stop

CUN9:55 amCancun

Aug 31

CUN10:40 amCancun

8h 24m

1 stop

MDW7:04 pmChicago Midway

$337

Volaris

Aug 28

MDW8:23 pmChicago Midway

13h 32m

1 stop

CUN9:55 amCancun

Aug 31

CUN10:40 amCancun

8h 24m

1 stop

MDW7:04 pmChicago Midway

$338

Volaris

Jul 20

MDW8:23 pmChicago Midway

14h 32m

1 stop

CUN10:55 amCancun

Aug 26

CUN10:40 amCancun

8h 24m

1 stop

MDW7:04 pmChicago Midway

$342

momondo Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Riviera Maya that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 8/28

8:23 pm-9:55 am

1 stop13h 32m

Cancun

Mon 8/31

10:40 am-7:04 pm

1 stop8h 24m

$337

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 8/28

8:23 pm-9:55 am

1 stop13h 32m

Cancun

Mon 8/31

10:40 am-7:04 pm

1 stop8h 24m

$338

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 10/2

8:23 pm-9:55 am

1 stop13h 32m

Cancun

Sun 10/11

10:40 am-7:04 pm

1 stop8h 24m

$352

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 8/24

8:23 pm-9:55 am

1 stop13h 32m

Cancun

Mon 8/31

10:40 am-7:04 pm

1 stop8h 24m

$353

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 10/16

8:23 pm-9:55 am

1 stop13h 32m

Cancun

Fri 10/23

10:40 am-7:04 pm

1 stop8h 24m

$354

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 10/5

8:23 pm-9:55 am

1 stop13h 32m

Cancun

Mon 10/19

10:40 am-7:04 pm

1 stop8h 24m

$358

Quickest round-trip

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Tue 12/29

6:00 am-2:05 pm

1 stop7h 05m

Cozumel Intl

Tue 1/5

3:05 pm-10:10 pm

1 stop8h 05m

$837

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Tue 12/29

6:00 am-2:05 pm

1 stop7h 05m

Cozumel Intl

Tue 1/5

3:05 pm-8:45 am

2 stops18h 40m

$842

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Thu 8/20

5:53 pm-3:37 pm

2 stops21h 44m

Cozumel Intl

Thu 8/27

4:47 pm-7:04 pm

3 stops26h 17m

$845

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Thu 12/31

6:00 am-2:05 pm

1 stop7h 05m

Cozumel Intl

Tue 1/5

3:05 pm-10:10 pm

1 stop8h 05m

$867

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago Midway Airport to Riviera Maya

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest month to fly to Riviera Maya?

The cheapest month to fly to Riviera Maya from Chicago Midway Airport is in August. Flight prices, which tend to average around $194, are often lower during this time because this is during the off-season. If you’re not able to fly to Riviera Maya in August, then February is your next best option. Flight prices from Chicago Midway Airport to Riviera Maya during February average around $198.

What is the cheapest day to depart on your flight to Riviera Maya?

Our data shows that Tuesday is the least expensive day to fly to Riviera Maya. Tickets to fly out on this day can be as low as $419. Flights from Chicago Midway Airport to Riviera Maya on a Saturday will generally be more expensive and average around $506. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Riviera Maya?

Our data shows that the cheapest Chicago Midway Airport to Riviera Maya flights are usually those with departure times in the afternoon. Our users have found flights to Riviera Maya in the afternoon for as low as $483. At noon is when there is more demand to fly to Riviera Maya, so prices are often more expensive at around $664 per ticket.

What is the cheapest Chicago Midway to Riviera Maya flight route?

Fly from Chicago Midway to Cancun for the best Chicago Midway - Riviera Maya flight prices

How far in advance should I book a flight from Chicago Midway Airport to Riviera Maya?

You are more likely to see cheaper flights to Riviera Maya from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Riviera Maya for around $490 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Riviera Maya from Chicago Midway Airport for as low as $413 on momondo.

What cabin class options are available on Chicago Midway Airport to Riviera Maya flights?

There are 2 cabin classes available to choose from on Chicago Midway Airport to Riviera Maya flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago Midway Airport to Riviera Maya flights?

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to Riviera Maya.

Cheap Chicago Midway Airport to Riviera Maya flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Riviera Maya

Fastest flight time	3h 35m
Direct flights	Every day
Airports in Riviera Maya	3 airports

The fastest flight from Chicago Midway Airport to Riviera Maya takes 3h 35m

Direct flights go from Chicago Midway Airport to Riviera Maya every day.

There are 3 airports in Riviera Maya. From Chicago Midway Airport there are direct flights to Cancun (CUN).

Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Riviera Maya

When did momondo last update prices for flights from Chicago Midway Airport to Riviera Maya?
Prices for flights from Chicago Midway Airport to Riviera Maya were last updated today.
How many operators does momondo search for flights from Chicago Midway Airport to Riviera Maya?
There are 4 operators available for flights from Chicago Midway Airport to Riviera Maya as of July 2026.
How old do you have to be to fly from Chicago Midway Airport to Riviera Maya?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to Riviera Maya.
What documentation or ID do you need to fly to Riviera Maya?
The necessary travel and health documents for your Riviera Maya trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago Midway Airport to Riviera Maya?
Based on momondo bookings for flights between Chicago Midway Airport and Riviera Maya, the leading plane model is Boeing 737 MAX 8, making up 16.96% of the total bookings. Other popular models include Boeing 737-800 with 12.44%, Boeing 737-800 Passenger/BBJ2 (winglets) with 10.95%, and Airbus A320-100/200 with 9.62%.

Best airlines flying from Chicago Midway Airport to Riviera Maya

Compare and see reviews for airlines that fly from Chicago Midway Airport to Riviera Maya with momondo

Airline	Rating	Free Cancellation	Price
Aeromexico	PriceFrom $194	Free Cancellation	Rating 7.4 1,480 reviews	Search Aeromexico flights
Frontier	PriceFrom $198	Free Cancellation	Rating 5.6 2,835 reviews	Search Frontier flights
Southwest	PriceFrom $312	Free Cancellation	Rating 7.9 4,249 reviews	Search Southwest flights
Delta	PriceFrom $327	Free Cancellation	Rating 7.8 8,453 reviews	Search Delta flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Riviera Maya?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Riviera Maya. momondo saves you time and could save you money on your trip.

Can I find flights from Chicago to Riviera Maya with flexible booking policies on momondo?

Flights from Chicago to Riviera Maya with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Chicago to Riviera Maya?

momondo helps you find the best flight between Chicago and Riviera Maya by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Chicago to Riviera Maya right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Riviera Maya, momondo offers a useful price alert feature which will track prices for flights to Riviera Maya from Chicago and alert you when they change.