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 72% 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

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

As of August 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 August 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.

$171 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.

6:25 am - 12:37 pmMDW Chicago Midway-CUN Cancun

6h 12m1 stop Atlanta Hartsfield-Jackson

1:51 pm - 11:44 pmCUN Cancun-MDW Chicago Midway

9h 53m1 stop Atlanta Hartsfield-Jackson

$366Frontier

Mon, Sep 21 - Fri, Sep 25

6:25 am - 12:37 pmMDW Chicago Midway-CUN Cancun

6h 12m1 stop Atlanta Hartsfield-Jackson

1:51 pm - 11:43 pmCUN Cancun-MDW Chicago Midway

9h 52m1 stop Atlanta Hartsfield-Jackson

$366Frontier

Mon, Oct 5 - Thu, Oct 8

8:23 pm - 9:55 amMDW Chicago Midway-CUN Cancun

13h 32m1 stop Guadalajara Miguel Hidal

1:51 pm - 11:44 pmCUN Cancun-MDW Chicago Midway

9h 53m1 stop Atlanta Hartsfield-Jackson

$368Multiple Airlines

Mon, Sep 7 - Thu, Sep 17

8:23 pm - 9:55 amMDW Chicago Midway-CUN Cancun

13h 32m1 stop Guadalajara Miguel Hidal

1:51 pm - 11:44 pmCUN Cancun-MDW Chicago Midway

9h 53m1 stop Atlanta Hartsfield-Jackson

$376Multiple Airlines

Mon, Sep 7 - Fri, Sep 11

8:20 am - 1:05 pmMDW Chicago Midway-CUN Cancun

3h 45mnonstop

2:10 pm - 4:50 pmCUN Cancun-MDW Chicago Midway

3h 40mnonstop

$452Southwest

Mon, Nov 16 - Fri, Nov 20

8:25 am - 12:00 pmMDW Chicago Midway-CUN Cancun

3h 35mnonstop

1:05 pm - 4:40 pmCUN Cancun-MDW Chicago Midway

3h 35mnonstop

$452Southwest

Mon, Sep 21 - Thu, Sep 24

6:05 am - 1:00 pmMDW Chicago Midway-CUN Cancun

6h 55m1 stop Atlanta Hartsfield-Jackson

8:00 am - 4:14 pmCUN Cancun-MDW Chicago Midway

8h 14m1 stop Atlanta Hartsfield-Jackson

$453Aeromexico

Mon, Oct 5 - Wed, Oct 14

9:29 am - 8:55 pmMDW Chicago Midway-CUN Cancun

10h 26m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson

4:35 pm - 10:56 pmCUN Cancun-MDW Chicago Midway

7h 21m1 stop Atlanta Hartsfield-Jackson

$457Delta

Tue, Nov 3 - Wed, Nov 11

9:29 am - 8:55 pmMDW Chicago Midway-CUN Cancun

10h 26m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson

4:35 pm - 10:56 pmCUN Cancun-MDW Chicago Midway

7h 21m1 stop Atlanta Hartsfield-Jackson

$457Delta

Tue, Nov 3 - Thu, Nov 12

1:00 pm - 7:50 pmMDW Chicago Midway-CUN Cancun

6h 50m1 stop Atlanta Hartsfield-Jackson

8:00 am - 4:14 pmCUN Cancun-MDW Chicago Midway

8h 14m1 stop Atlanta Hartsfield-Jackson

$460Aeromexico

Mon, Sep 28 - Tue, Oct 6

Cheap last minute flights

Enter your travel dates to find the best prices.

8:23 pm - 9:55 amMDW Chicago Midway-CUN Cancun

13h 32m1 stop Guadalajara Miguel Hidal

10:40 am - 7:04 pmCUN Cancun-MDW Chicago Midway

8h 24m1 stop Guadalajara Miguel Hidal

$455Volaris

Fri, Aug 28 - Mon, Aug 31

8:23 pm - 9:55 amMDW Chicago Midway-CUN Cancun

13h 32m1 stop Guadalajara Miguel Hidal

10:40 am - 7:04 pmCUN Cancun-MDW Chicago Midway

8h 24m1 stop Guadalajara Miguel Hidal

$456Volaris

Fri, Aug 28 - Mon, Aug 31

9:26 pm - 10:00 amMDW Chicago Midway-CUN Cancun

12h 34m1 stop Dallas/Fort Worth

3:06 pm - 10:47 pmCUN Cancun-MDW Chicago Midway

7h 41m1 stop Atlanta Hartsfield-Jackson

$486Frontier

Thu, Aug 27 - Thu, Sep 3

9:26 pm - 10:00 amMDW Chicago Midway-CUN Cancun

12h 34m1 stop Dallas/Fort Worth

11:10 am - 8:31 pmCUN Cancun-MDW Chicago Midway

9h 21m1 stop Dallas/Fort Worth

$514Frontier

Thu, Aug 27 - Sun, Aug 30

10:54 am - 8:05 pmMDW Chicago Midway-CUN Cancun

9h 11m1 stop Atlanta Hartsfield-Jackson

8:05 am - 3:44 pmCUN Cancun-MDW Chicago Midway

7h 39m1 stop Atlanta Hartsfield-Jackson

$538Aeromexico

Wed, Aug 26 - Wed, Sep 2

6:05 am - 11:25 amMDW Chicago Midway-CUN Cancun

5h 20m1 stop Atlanta Hartsfield-Jackson

8:00 am - 10:36 pmCUN Cancun-MDW Chicago Midway

14h 36m2 stops Mexico City Benito Juarez Atlanta Hartsfield-Jackson

$538Delta

Wed, Aug 26 - Wed, Sep 2

10:54 am - 8:05 pmMDW Chicago Midway-CUN Cancun

9h 11m1 stop Atlanta Hartsfield-Jackson

2:10 pm - 10:36 pmCUN Cancun-MDW Chicago Midway

8h 26m1 stop Atlanta Hartsfield-Jackson

$538Delta

Wed, Aug 26 - Wed, Sep 2

8:25 am - 12:00 pmMDW Chicago Midway-CUN Cancun

3h 35mnonstop

1:05 pm - 4:40 pmCUN Cancun-MDW Chicago Midway

3h 35mnonstop

$547Southwest

Mon, Aug 24 - Thu, Aug 27

8:25 am - 12:00 pmMDW Chicago Midway-CUN Cancun

3h 35mnonstop

1:05 pm - 4:40 pmCUN Cancun-MDW Chicago Midway

3h 35mnonstop

$547Southwest

Mon, Aug 24 - Fri, Aug 28

10:54 am - 1:30 amMDW Chicago Midway-CUN Cancun

14h 36m2 stops Atlanta Hartsfield-Jackson Mexico City Benito Juarez

3:22 pm - 10:36 pmCUN Cancun-MDW Chicago Midway

7h 14m1 stop Atlanta Hartsfield-Jackson

$1,093Aeromexico

Wed, Aug 26 - Sun, Aug 30

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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

Oct 4

MDW6:25 amChicago Midway

6h 12m

1 stop

CUN12:37 pmCancun

Oct 8

CUN1:51 pmCancun

9h 52m

1 stop

MDW11:43 pmChicago Midway

$366

Frontier

Oct 19

MDW6:15 amChicago Midway

6h 26m

1 stop

CUN12:41 pmCancun

Oct 23

CUN1:51 pmCancun

9h 52m

1 stop

MDW11:43 pmChicago Midway

$369

Frontier

Nov 2

MDW7:25 amChicago Midway

5h 49m

1 stop

CUN2:14 pmCancun

Nov 6

CUN3:24 pmCancun

7h 29m

1 stop

MDW9:53 pmChicago Midway

$379

Volaris flights from Chicago Midway Airport to Riviera Maya

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

Volaris

Sep 16

MDW8:23 pmChicago Midway

13h 32m

1 stop

CUN9:55 amCancun

Sep 23

CUN10:40 amCancun

8h 24m

1 stop

MDW7:04 pmChicago Midway

$408

Volaris

Oct 9

MDW8:23 pmChicago Midway

13h 32m

1 stop

CUN9:55 amCancun

Oct 14

CUN10:40 amCancun

8h 24m

1 stop

MDW7:04 pmChicago Midway

$409

Volaris

Aug 30

MDW8:23 pmChicago Midway

13h 32m

1 stop

CUN9:55 amCancun

Oct 7

CUN10:40 amCancun

8h 24m

1 stop

MDW7:04 pmChicago Midway

$415

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 Chicago Midway - CUN Cancun

MDWCUN

Chicago Midway

Mon 9/21

6:25 am-12:37 pm

1 stop6h 12m

Cancun

Fri 9/25

1:51 pm-11:44 pm

1 stop9h 53m

$366

ChicagoCancún

MDW Chicago Midway - CUN Cancun

MDWCUN

Chicago Midway

Mon 10/5

6:25 am-12:37 pm

1 stop6h 12m

Cancun

Thu 10/8

1:51 pm-11:43 pm

1 stop9h 52m

$366

ChicagoCancún

MDW Chicago Midway - CUN Cancun

MDWCUN

Chicago Midway

Mon 9/7

8:23 pm-9:55 am

1 stop13h 32m

Cancun

Thu 9/17

1:51 pm-11:44 pm

1 stop9h 53m

$368

ChicagoCancún

MDW Chicago Midway - CUN Cancun

MDWCUN

Chicago Midway

Mon 9/7

8:23 pm-9:55 am

1 stop13h 32m

Cancun

Fri 9/11

1:51 pm-11:44 pm

1 stop9h 53m

$376

ChicagoCancún

MDW Chicago Midway - CUN Cancun

MDWCUN

Chicago Midway

Mon 11/16

8:20 am-1:05 pm

Nonstop3h 45m

Cancun

Fri 11/20

2:10 pm-4:50 pm

Nonstop3h 40m

$452

Quickest round-trip

ChicagoCancún

MDW Chicago Midway - CUN Cancun

MDWCUN

Chicago Midway

Mon 9/21

8:25 am-12:00 pm

Nonstop3h 35m

Cancun

Thu 9/24

1:05 pm-4:40 pm

Nonstop3h 35m

$452

ChicagoCancún

MDW Chicago Midway - CUN Cancun

MDWCUN

Chicago Midway

Mon 10/5

6:05 am-1:00 pm

1 stop6h 55m

Cancun

Wed 10/14

8:00 am-4:14 pm

1 stop8h 14m

$453

ChicagoCancún

MDW Chicago Midway - CUN Cancun

MDWCUN

Chicago Midway

Tue 11/3

9:29 am-8:55 pm

2 stops10h 26m

Cancun

Wed 11/11

4:35 pm-10:56 pm

1 stop7h 21m

$457

ChicagoCancún

MDW Chicago Midway - CUN Cancun

MDWCUN

Chicago Midway

Tue 11/3

9:29 am-8:55 pm

2 stops10h 26m

Cancun

Thu 11/12

4:35 pm-10:56 pm

1 stop7h 21m

$457

ChicagoCancún

MDW Chicago Midway - CUN Cancun

MDWCUN

Chicago Midway

Mon 9/28

1:00 pm-7:50 pm

1 stop6h 50m

Cancun

Tue 10/6

8:00 am-4:14 pm

1 stop8h 14m

$460

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 February. Flight prices, which tend to average around $356, are often lower during this time because this is during the off-season. If you’re not able to fly to Riviera Maya in February, then August is your next best option. Flight prices from Chicago Midway Airport to Riviera Maya during August average around $486.

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 $447. Flights from Chicago Midway Airport to Riviera Maya on a Wednesday will generally be more expensive and average around $555. 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 morning. Our users have found flights to Riviera Maya in the morning for as low as $494. 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 $543 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 $438 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

Best Price Found	$171
Fastest flight time	3h 35m
Direct flights	Every day
Airports in Riviera Maya	3 airports

The best one-way flight to Riviera Maya from Chicago Midway Airport in the past 72 hours is $171. The best round-trip flight deal from Chicago Midway Airport to Riviera Maya found on momondo in the last 72 hours is $366.

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 August 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 17.15% of the total bookings. Other popular models include Boeing 737-800 Passenger/BBJ2 (winglets) with 11.54%, Boeing 737-800 with 11.49%, and Airbus A320-100/200 with 10.76%.

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 1,471 reviews	Search Aeromexico flights
Frontier	PriceFrom $198	Free Cancellation	Rating 5.6 2,653 reviews	Search Frontier flights
Delta	PriceFrom $327	Free Cancellation	Rating 7.8 8,516 reviews	Search Delta flights
Southwest	PriceFrom $336	Free Cancellation	Rating 8.0 4,212 reviews	Search Southwest 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.