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

Southwest, Delta, and Aeromexico are the most popular carriers operating from Chicago Midway to Riviera Maya

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 84% 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.

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

As of February 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 Mon, with 25% of weekly flights taking off on this day.

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 February 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.

$102 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.

9:00 am - 2:02 pm

MDW

CUN

4h 02mnonstop

3:07 pm - 7:13 pm

CUN

MDW

4h 06mnonstop

$245Frontier

Sat, Mar 7 - Sat, Mar 14

9:00 am - 2:02 pm

MDW

CUN

4h 02mnonstop

3:07 pm - 7:13 pm

CUN

MDW

4h 06mnonstop

$246Frontier

Sat, Mar 7 - Sat, Mar 14

9:00 am - 2:02 pm

MDW

CUN

4h 02mnonstop

3:07 pm - 7:13 pm

CUN

MDW

4h 06mnonstop

$248Frontier

Sat, Mar 7 - Sat, Mar 14

9:00 am - 2:02 pm

MDW

CUN

4h 02mnonstop

3:07 pm - 7:13 pm

CUN

MDW

4h 06mnonstop

$249Frontier

Sat, Mar 7 - Sat, Mar 14

6:54 pm - 9:48 am

MDW

CUN

13h 54m

1 stop

3:07 pm - 7:13 pm

CUN

MDW

4h 06mnonstop

$260Multiple Airlines

Sat, Mar 7 - Sat, Mar 14

6:54 pm - 9:48 am

MDW

CUN

13h 54m

1 stop

3:07 pm - 7:13 pm

CUN

MDW

4h 06mnonstop

$261Multiple Airlines

Sat, Mar 7 - Sat, Mar 14

6:00 am - 12:45 pm

MDW

CZM

7h 45m

1 stop

2:00 pm - 10:31 pm

CZM

MDW

7h 31m

1 stop

$542Aeromexico

Tue, Mar 24 - Tue, Mar 31

6:00 am - 1:55 pm

MDW

CZM

7h 55m

1 stop

3:10 pm - 10:31 pm

CZM

MDW

7h 21m

1 stop

$544Delta

Sun, Feb 22 - Thu, Feb 26

6:17 pm - 2:57 pm

MDW

CZM

20h 40m

2 stops

3:10 pm - 10:31 pm

CZM

MDW

7h 21m

1 stop

$548Delta

Sun, Feb 22 - Thu, Feb 26

6:00 am - 1:55 pm

MDW

CZM

7h 55m

1 stop

3:10 pm - 10:31 pm

CZM

MDW

7h 21m

1 stop

$554Aeromexico

Mon, Feb 23 - Thu, Feb 26

Aeromexico flights from Chicago Midway Airport to Riviera Maya

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

Aeromexico

Feb 23

MDW6:00 amChicago Midway

9h 45m

1 stop

CUN4:45 pmCancun

Feb 26

CUN4:45 pmCancun

6h 46m

1 stop

MDW10:31 pmChicago Midway

$304

Aeromexico

Feb 24

MDW6:00 amChicago Midway

7h 03m

1 stop

CUN2:03 pmCancun

Feb 27

CUN8:00 amCancun

10h 45m

1 stop

MDW5:45 pmChicago Midway

$328

Aeromexico

Feb 20

MDW6:00 amChicago Midway

9h 45m

1 stop

CUN4:45 pmCancun

Feb 24

CUN4:45 pmCancun

6h 48m

1 stop

MDW10:33 pmChicago Midway

$418

Frontier flights from Chicago Midway Airport to Riviera Maya

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

Frontier

Mar 7

MDW9:00 amChicago Midway

4h 02m

CUN2:02 pmCancun

Mar 14

CUN3:07 pmCancun

4h 06m

MDW7:13 pmChicago Midway

$245

Frontier

Mar 7

MDW9:00 amChicago Midway

4h 02m

CUN2:02 pmCancun

Mar 14

CUN3:07 pmCancun

4h 06m

MDW7:13 pmChicago Midway

$246

Frontier

Mar 7

MDW9:00 amChicago Midway

4h 02m

CUN2:02 pmCancun

Mar 14

CUN3:07 pmCancun

4h 06m

MDW7:13 pmChicago Midway

$250

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

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 3/7

9:00 am-2:02 pm

Nonstop4h 02m

Cancun

Sat 3/14

3:07 pm-7:13 pm

Nonstop4h 06m

$245

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 3/7

9:00 am-2:02 pm

Nonstop4h 02m

Cancun

Sat 3/14

3:07 pm-7:13 pm

Nonstop4h 06m

$246

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 3/7

9:00 am-2:02 pm

Nonstop4h 02m

Cancun

Sat 3/14

3:07 pm-7:13 pm

Nonstop4h 06m

$248

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 3/7

9:00 am-2:02 pm

Nonstop4h 02m

Cancun

Sat 3/14

3:07 pm-7:13 pm

Nonstop4h 06m

$249

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 3/7

6:54 pm-9:48 am

1 stop13h 54m

Cancun

Sat 3/14

3:07 pm-7:13 pm

Nonstop4h 06m

$260

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 3/7

6:54 pm-9:48 am

1 stop13h 54m

Cancun

Sat 3/14

3:07 pm-7:13 pm

Nonstop4h 06m

$261

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Tue 3/24

6:00 am-12:45 pm

1 stop7h 45m

Cozumel

Tue 3/31

2:00 pm-10:31 pm

1 stop7h 31m

$542

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Sun 2/22

6:00 am-1:55 pm

1 stop7h 55m

Cozumel

Thu 2/26

3:10 pm-10:31 pm

1 stop7h 21m

$544

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Sun 2/22

6:17 pm-2:57 pm

2 stops20h 40m

Cozumel

Thu 2/26

3:10 pm-10:31 pm

1 stop7h 21m

$548

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Mon 2/23

6:00 am-1:55 pm

1 stop7h 55m

Cozumel

Thu 2/26

3:10 pm-10:31 pm

1 stop7h 21m

$554

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 September. Flight prices, which tend to average around $371, are often lower during this time because this is during the off-season. If you’re not able to fly to Riviera Maya in September, then February is your next best option. Flight prices from Chicago Midway Airport to Riviera Maya during February average around $402.

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

Our data shows that Monday is the least expensive day to fly to Riviera Maya. Tickets to fly out on this day can be as low as $389. Flights from Chicago Midway Airport to Riviera Maya on a Saturday will generally be more expensive and average around $500. 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 $431. At noon is when there is more demand to fly to Riviera Maya, so prices are often more expensive at around $693 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 $510 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 $431 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

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 February 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 15.22% of the total bookings. Other popular models include Boeing 737-800 Passenger/BBJ2 (winglets) with 12.00%, Airbus A320neo with 11.83%, and Airbus A321neo with 10.34%.

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 3,052 reviews	Search Frontier flights
Southwest	PriceFrom $293	Free Cancellation	Rating 8.0 4,280 reviews	Search Southwest flights
Aeromexico	PriceFrom $309	Free Cancellation	Rating 7.4 1,577 reviews	Search Aeromexico flights
Delta	PriceFrom $358	Free Cancellation	Rating 7.9 8,180 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.