What airlines fly to Riviera Maya?

American Airlines, United Airlines and Frontier are the top three most popular airlines that fly to Riviera Maya from Chicago according to our data. American Airlines is the first choice among our users, with 32% of people opting to fly with this airline when traveling to Riviera Maya. Keep in mind that there are 11 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 to Riviera Maya on average per week?

64 flights are operational weekly from Chicago to Riviera Maya as of May 2026. The most popular departure day for this route is Mon, with 17% of flights per week taking off on this day.

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

The number of flights available between Chicago and Riviera Maya is 9 per day as of May 2026. The most frequent departure time is 10:00AM, with 100% of daily flights leaving at noon.

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

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

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

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

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

There are 11 operators available for flights from Chicago to Riviera Maya as of May 2026.

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

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Riviera Maya.

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

The travel and health documents you'll need for your trip to Riviera Maya may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Riviera Maya. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$113 Cheap Flights from Chicago to Riviera Maya in 2026

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Find the cheapest flights from Chicago to Riviera Maya

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:40 pm - 9:15 pm

ORD

CUN

24h 35m

1 stop

11:15 pm - 11:00 am

CUN

ORD

11h 45m

1 stop

$261Viva

Sat, Sep 5 - Sat, Sep 12

12:25 pm - 9:20 pm

ORD

CUN

8h 55m

1 stop

1:10 am - 10:55 am

CUN

ORD

9h 45m

1 stop

$262Viva

Thu, Aug 27 - Sat, Aug 29

7:35 am - 9:03 pm

ORD

CUN

13h 28m

1 stop

3:55 pm - 4:54 am

CUN

ORD

12h 59m

1 stop

$263Volaris

Sun, Aug 23 - Sat, Aug 29

1:35 am - 2:15 am

ORD

CUN

24h 40m

1 stop

9:40 am - 10:45 pm

CUN

ORD

14h 05m

1 stop

$267Viva

Tue, Oct 20 - Wed, Nov 4

8:40 pm - 9:15 pm

ORD

CUN

24h 35m

1 stop

11:15 pm - 11:00 am

CUN

ORD

11h 45m

1 stop

$270Viva

Sat, Sep 5 - Sat, Sep 12

1:30 am - 10:20 pm

ORD

CUN

20h 50m

1 stop

7:00 am - 11:45 pm

CUN

ORD

16h 45m

1 stop

$274Viva

Thu, Oct 8 - Mon, Oct 12

1:40 am - 10:03 am

ORD

CUN

8h 23m

1 stop

10:30 am - 11:55 pm

CUN

ORD

13h 25m

1 stop

$277Multiple Airlines

Sun, Jun 7 - Wed, Jun 10

1:59 am - 10:31 am

ORD

CUN

8h 32m

1 stop

11:55 am - 11:55 pm

CUN

ORD

12h 00m

1 stop

$278Multiple Airlines

Sun, Jun 7 - Wed, Jun 10

8:23 pm - 9:55 am

MDW

CUN

13h 32m

1 stop

10:40 am - 7:34 pm

CUN

MDW

8h 54m

1 stop

$350Volaris

Mon, Jun 8 - Thu, Jun 11

10:54 am - 2:11 pm

MDW

CZM

27h 17m

2 stops

4:18 pm - 10:36 pm

CZM

MDW

30h 18m

2 stops

$1,100Aeromexico

Mon, Aug 24 - Wed, Aug 26

Southwest flights from Chicago to Riviera Maya

Our best Southwest deals on Chicago to Riviera Maya flight tickets

Southwest

Jun 21

MDW7:30 amChicago Midway

3h 35m

CUN11:05 amCancun

Jun 30

CUN3:05 pmCancun

3h 30m

MDW6:35 pmChicago Midway

$394

Southwest

Aug 17

MDW8:25 amChicago Midway

3h 35m

CUN12:00 pmCancun

Aug 20

CUN1:05 pmCancun

3h 35m

MDW4:40 pmChicago Midway

$406

Southwest

Jun 9

MDW10:05 amChicago Midway

3h 35m

CUN1:40 pmCancun

Jun 17

CUN3:05 pmCancun

3h 30m

MDW6:35 pmChicago Midway

$504

Delta flights from Chicago to Riviera Maya

Our best Delta deals on Chicago to Riviera Maya flight tickets

Delta

Jun 24

MDW11:05 amChicago Midway

9h 20m

1 stop

CUN8:25 pmCancun

Jul 1

CUN8:00 amCancun

14h 17m

1 stop

MDW10:17 pmChicago Midway

$398

Delta

Jul 4

MDW10:55 amChicago Midway

9h 30m

1 stop

CUN8:25 pmCancun

Jul 11

CUN8:00 amCancun

7h 37m

1 stop

MDW3:37 pmChicago Midway

$408

Delta

May 30

MDW6:23 amChicago Midway

13h 53m

1 stop

CUN8:16 pmCancun

Jun 24

CUN8:00 amCancun

14h 17m

1 stop

MDW10:17 pmChicago Midway

$438

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sat 9/5

8:40 pm-9:15 pm

1 stop24h 35m

Cancun

Sat 9/12

11:15 pm-11:00 am

1 stop11h 45m

$261

Quickest round-trip

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Thu 8/27

12:25 pm-9:20 pm

1 stop8h 55m

Cancun

Sat 8/29

1:10 am-10:55 am

1 stop9h 45m

$262

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sun 8/23

7:35 am-9:03 pm

1 stop13h 28m

Cancun

Sat 8/29

3:55 pm-4:54 am

1 stop12h 59m

$263

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Tue 10/20

1:35 am-2:15 am

1 stop24h 40m

Cancun

Wed 11/4

9:40 am-10:45 pm

1 stop14h 05m

$267

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sat 9/5

8:40 pm-9:15 pm

1 stop24h 35m

Cancun

Sat 9/12

11:15 pm-11:00 am

1 stop11h 45m

$270

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Thu 10/8

1:30 am-10:20 pm

1 stop20h 50m

Cancun

Mon 10/12

7:00 am-11:45 pm

1 stop16h 45m

$274

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sun 6/7

1:40 am-10:03 am

1 stop8h 23m

Cancun

Wed 6/10

10:30 am-11:55 pm

1 stop13h 25m

$277

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sun 6/7

1:59 am-10:31 am

1 stop8h 32m

Cancun

Wed 6/10

11:55 am-11:55 pm

1 stop12h 00m

$278

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 6/8

8:23 pm-9:55 am

1 stop13h 32m

Cancun

Thu 6/11

10:40 am-7:34 pm

1 stop8h 54m

$350

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Mon 8/24

10:54 am-2:11 pm

2 stops27h 17m

Cozumel Intl

Wed 8/26

4:18 pm-10:36 pm

2 stops30h 18m

$1,100

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 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 is in July. Flight prices, which tend to average around $387, are often lower during this time because this is during the off-season. If you’re not able to fly to Riviera Maya in July, then May is your next best option. Flight prices from Chicago to Riviera Maya during May average around $389.

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 $434. Flights from Chicago to Riviera Maya on a Thursday will generally be more expensive and average around $495. 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 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 $466. In the afternoon is when there is more demand to fly to Riviera Maya, so prices are often more expensive at around $554 per ticket.

What is the cheapest Chicago to Riviera Maya flight route?

Fly from Chicago O'Hare Intl to Cancun for the best Chicago - Riviera Maya flight prices

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

You are more likely to see cheaper flights to Riviera Maya from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Riviera Maya for around $455 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 for as low as $359 on momondo.

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

There are 4 cabin classes available to choose from on Chicago 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 to Riviera Maya flights?

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

Cheap Chicago to Riviera Maya flight deals and tips

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

Fastest flight time	3h 30m
Direct flights	Every day
Airports in Riviera Maya	3 airports

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

Direct flights go from Chicago to Riviera Maya every day.

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

Search flight deals

Frequently asked questions about flying from Chicago to Riviera Maya

When did momondo last update prices for flights from Chicago to Riviera Maya?
Prices for flights from Chicago to Riviera Maya were last updated today.
How many operators does momondo search for flights from Chicago to Riviera Maya?
There are 11 operators available for flights from Chicago to Riviera Maya as of May 2026.
How old do you have to be to fly from Chicago to Riviera Maya?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Riviera Maya.
What documentation or ID do you need to fly to Riviera Maya?
The travel and health documents you'll need for your trip to Riviera Maya may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Riviera Maya. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago to Riviera Maya?
Based on momondo bookings for flights between Chicago and Riviera Maya, the leading plane model is Boeing 737-800, making up 17.85% of the total bookings. Other popular models include Airbus A321neo with 15.56%, Boeing 737-900 with 8.93%, and Airbus A321-100/200 with 7.91%.

Best airlines flying from Chicago to Riviera Maya

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

Airline	Rating	Free Cancellation	Price
Volaris	PriceFrom $112	Free Cancellation	Rating 6.6 1,160 reviews	Search Volaris flights
Spirit Airlines	PriceFrom $148	Free Cancellation	Rating 6.2	Search Spirit Airlines flights
Delta	PriceFrom $158	Free Cancellation	Rating 7.9 8,427 reviews	Search Delta flights
Aeromexico	PriceFrom $190	Free Cancellation	Rating 7.4 1,503 reviews	Search Aeromexico flights
Frontier	PriceFrom $191	Free Cancellation	Rating 5.6 2,933 reviews	Search Frontier flights
JetBlue	PriceFrom $262	Free Cancellation	Rating 7.1 2,982 reviews	Search JetBlue flights
United Airlines	PriceFrom $289	Free Cancellation	Rating 7.4 9,751 reviews	Search United Airlines flights
Southwest	PriceFrom $300	Free Cancellation	Rating 7.9 4,265 reviews	Search Southwest flights
Viva	PriceFrom $317	Free Cancellation	Rating 7.0 808 reviews	Search Viva flights
American Airlines	PriceFrom $319	Free Cancellation	Rating 7.1 11,631 reviews	Search American Airlines flights

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Riviera Maya from Chicago.

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?

Once you have performed a search for Chicago to Riviera Maya flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Yes momondo offers price alerts on flights to Riviera Maya from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.