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

As of April 2026, 4 flights take off from Chicago Midway Airport and land in Riviera Maya each week. The most common flight departure day for this route is Sat, with 100% of weekly flights taking off on this day.

What airlines fly to Riviera Maya?

Southwest, Delta and Frontier 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 83% 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 Southwest 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 April 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.

$106 Cheap Flights from Chicago Midway Airport to Riviera Maya in 2026

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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.

6:00 am - 2:56 pm

MDW

CUN

8h 56m

1 stop

2:09 pm - 10:14 pm

CUN

MDW

8h 05m

1 stop

$261Frontier

Mon, Apr 27 - Sat, May 2

6:15 am - 2:56 pm

MDW

CUN

8h 41m

1 stop

1:25 pm - 10:14 pm

CUN

MDW

8h 49m

1 stop

$264Frontier

Wed, Apr 22 - Sat, Apr 25

6:00 am - 12:46 pm

MDW

CUN

6h 46m

1 stop

1:25 pm - 10:14 pm

CUN

MDW

8h 49m

1 stop

$270Frontier

Sat, Apr 18 - Sat, Apr 25

6:00 am - 12:46 pm

MDW

CUN

6h 46m

1 stop

1:25 pm - 10:14 pm

CUN

MDW

8h 49m

1 stop

$271Frontier

Sat, Apr 18 - Sat, Apr 25

6:10 am - 2:56 pm

MDW

CUN

8h 46m

1 stop

1:25 pm - 10:14 pm

CUN

MDW

8h 49m

1 stop

$272Frontier

Tue, Apr 14 - Sat, Apr 18

8:23 pm - 3:57 pm

MDW

CZM

20h 34m

2 stops

4:47 pm - 7:20 pm

CZM

MDW

25h 33m

2 stops

$734Volaris

Fri, May 15 - Fri, May 22

6:00 am - 12:57 pm

MDW

CZM

7h 57m

1 stop

2:14 pm - 10:28 pm

CZM

MDW

7h 14m

1 stop

$743Delta

Sat, Apr 25 - Sat, May 2

8:23 pm - 3:57 pm

MDW

CZM

20h 34m

2 stops

4:47 pm - 7:20 pm

CZM

MDW

25h 33m

3 stops

$745Volaris

Fri, May 15 - Fri, May 22

6:00 am - 12:57 pm

MDW

CZM

7h 57m

1 stop

2:14 pm - 10:28 pm

CZM

MDW

7h 14m

1 stop

$866Aeromexico

Sat, Apr 18 - Sat, Apr 25

5:21 pm - 3:19 pm

MDW

CZM

22h 58m

2 stops

2:14 pm - 10:28 pm

CZM

MDW

7h 14m

1 stop

$958Delta

Wed, Apr 15 - Sat, Apr 18

Frontier flights from Chicago Midway Airport to Riviera Maya

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

Frontier

Apr 11

MDW8:30 amChicago Midway

3h 50m

CUN12:20 pmCancun

Apr 18

CUN1:25 pmCancun

8h 49m

1 stop

MDW10:14 pmChicago Midway

$257

Frontier

Apr 11

MDW8:30 amChicago Midway

3h 50m

CUN12:20 pmCancun

Apr 16

CUN12:04 pmCancun

10h 18m

1 stop

MDW10:22 pmChicago Midway

$258

Frontier

Apr 11

MDW8:30 amChicago Midway

3h 50m

CUN12:20 pmCancun

Apr 18

CUN1:25 pmCancun

8h 49m

1 stop

MDW10:14 pmChicago Midway

$259

Southwest flights from Chicago Midway Airport to Riviera Maya

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

Southwest

Apr 19

MDW11:00 amChicago Midway

3h 35m

CUN2:35 pmCancun

Apr 28

CUN3:15 pmCancun

3h 40m

MDW6:55 pmChicago Midway

$313

Southwest

Apr 20

MDW9:35 amChicago Midway

3h 35m

CUN1:10 pmCancun

May 20

CUN3:15 pmCancun

3h 40m

MDW6:55 pmChicago Midway

$315

Southwest

Apr 20

MDW5:30 amChicago Midway

8h 30m

1 stop

CUN2:00 pmCancun

May 20

CUN3:15 pmCancun

3h 40m

MDW6:55 pmChicago Midway

$319

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

Mon 4/27

6:00 am-2:56 pm

1 stop8h 56m

Cancun

Sat 5/2

2:09 pm-10:14 pm

1 stop8h 05m

$261

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 4/22

6:15 am-2:56 pm

1 stop8h 41m

Cancun

Sat 4/25

1:25 pm-10:14 pm

1 stop8h 49m

$264

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 4/18

6:00 am-12:46 pm

1 stop6h 46m

Cancun

Sat 4/25

1:25 pm-10:14 pm

1 stop8h 49m

$270

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 4/18

6:00 am-12:46 pm

1 stop6h 46m

Cancun

Sat 4/25

1:25 pm-10:14 pm

1 stop8h 49m

$271

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 4/14

6:10 am-2:56 pm

1 stop8h 46m

Cancun

Sat 4/18

1:25 pm-10:14 pm

1 stop8h 49m

$272

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Fri 5/15

8:23 pm-3:57 pm

2 stops20h 34m

Cozumel

Fri 5/22

4:47 pm-7:20 pm

2 stops25h 33m

$734

Quickest round-trip

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Sat 4/25

6:00 am-12:57 pm

1 stop7h 57m

Cozumel

Sat 5/2

2:14 pm-10:28 pm

1 stop7h 14m

$743

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Fri 5/15

8:23 pm-3:57 pm

2 stops20h 34m

Cozumel

Fri 5/22

4:47 pm-7:20 pm

3 stops25h 33m

$745

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Sat 4/18

6:00 am-12:57 pm

1 stop7h 57m

Cozumel

Sat 4/25

2:14 pm-10:28 pm

1 stop7h 14m

$866

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Wed 4/15

5:21 pm-3:19 pm

2 stops22h 58m

Cozumel

Sat 4/18

2:14 pm-10:28 pm

1 stop7h 14m

$958

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 October. Flight prices, which tend to average around $313, are often lower during this time because this is during the off-season. If you’re not able to fly to Riviera Maya in October, then February is your next best option. Flight prices from Chicago Midway Airport to Riviera Maya during February average around $356.

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 $395. Flights from Chicago Midway Airport to Riviera Maya on a Saturday will generally be more expensive and average around $501. 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 $427. 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 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 $495 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 $432 on momondo.

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

There is only 1 cabin class available to choose from on Chicago Midway 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 30m
Direct flights	Every day
Airports in Riviera Maya	3 airports

The fastest flight from Chicago Midway Airport to Riviera Maya takes 3h 30m

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 April 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 16.06% of the total bookings. Other popular models include Boeing 737-800 Passenger/BBJ2 (winglets) with 12.42%, Airbus A320neo with 11.34%, and Airbus A321neo with 11.01%.

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
Frontier	PriceFrom $198	Free Cancellation	Rating 5.7 3,001 reviews	Search Frontier flights
Southwest	PriceFrom $291	Free Cancellation	Rating 8.0 4,344 reviews	Search Southwest flights
Aeromexico	PriceFrom $308	Free Cancellation	Rating 7.4 1,550 reviews	Search Aeromexico flights
Delta	PriceFrom $358	Free Cancellation	Rating 7.9 8,379 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.