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Cheap flights from Chicago Midway Airport to Riviera Maya from $101

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Riviera Maya departing on 1/26. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Chicago Midway Airport to Riviera Maya

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
6:20 am - 1:47 pm
MDW
-
CUN
6h 27m1 stop
Frontier Logo
2:57 pm - 10:19 pm
CUN
-
MDW
8h 22m1 stop
$224Frontier
Mon, Jan 26 - Mon, Feb 2
Frontier Logo
6:10 am - 3:10 pm
MDW
-
CUN
8h 00m1 stop
Frontier Logo
2:57 pm - 10:19 pm
CUN
-
MDW
8h 22m1 stop
$231Frontier
Mon, Jan 19 - Mon, Jan 26
Frontier Logo
6:00 am - 1:37 pm
MDW
-
CUN
6h 37m1 stop
Frontier Logo
11:48 am - 9:12 pm
CUN
-
MDW
10h 24m1 stop
$232Frontier
Mon, Feb 23 - Thu, Feb 26
Frontier Logo
6:20 am - 1:47 pm
MDW
-
CUN
6h 27m1 stop
Frontier Logo
2:57 pm - 10:19 pm
CUN
-
MDW
8h 22m1 stop
$233Frontier
Thu, Jan 22 - Mon, Jan 26
Frontier Logo
6:10 am - 2:04 pm
MDW
-
CUN
6h 54m1 stop
Frontier Logo
3:24 pm - 10:17 pm
CUN
-
MDW
7h 53m1 stop
$235Frontier
Thu, Jan 8 - Mon, Jan 12
Multiple Airlines Logo
6:00 am - 3:30 pm
MDW
-
CUN
8h 30m1 stop
Multiple Airlines Logo
2:57 pm - 10:19 pm
CUN
-
MDW
8h 22m1 stop
$272Multiple Airlines
Sun, Jan 25 - Thu, Jan 29
Delta Logo
6:00 am - 1:50 pm
MDW
-
CZM
7h 50m1 stop
Delta Logo
3:05 pm - 10:22 pm
CZM
-
MDW
7h 17m1 stop
$447Delta
Sun, Feb 1 - Fri, Feb 6
Aeromexico Logo
6:00 am - 1:50 pm
MDW
-
CZM
7h 50m1 stop
Aeromexico Logo
3:05 pm - 10:22 pm
CZM
-
MDW
7h 17m1 stop
$450Aeromexico
Mon, Jan 26 - Mon, Feb 2
Delta Logo
6:00 am - 1:50 pm
MDW
-
CZM
7h 50m1 stop
Delta Logo
3:05 pm - 8:52 am
CZM
-
MDW
17h 47m2 stops
$452Delta
Sun, Feb 1 - Thu, Feb 5
Aeromexico Logo
6:00 am - 1:55 pm
MDW
-
CZM
7h 55m1 stop
Aeromexico Logo
2:20 pm - 10:29 pm
CZM
-
MDW
7h 09m1 stop
$483Aeromexico
Fri, Mar 6 - Wed, Mar 11

Delta flights from Chicago Midway Airport to Riviera Maya

Our best Delta deals on Chicago Midway Airport to Riviera Maya flight tickets
Delta
Dec 15
MDW6:00 amChicago Midway
8h 33m
1 stop
CUN3:33 pmCancun
Dec 24
CUN4:30 pmCancun
6h 52m
1 stop
MDW10:22 pmChicago Midway
$327
Find similar
Delta
Dec 15
MDW6:00 amChicago Midway
5h 23m
1 stop
CUN12:23 pmCancun
Dec 17
CUN8:00 amCancun
11h 00m
2 stops
MDW6:00 pmChicago Midway
$331
Find similar
Delta
Mar 4
MDW6:00 amChicago Midway
5h 30m
1 stop
CUN12:30 pmCancun
Mar 9
CUN10:10 amCancun
12h 19m
1 stop
MDW10:29 pmChicago Midway
$333
Find similar

Frontier flights from Chicago Midway Airport to Riviera Maya

Our best Frontier deals on Chicago Midway Airport to Riviera Maya flight tickets
Frontier
Jan 26
MDW6:20 amChicago Midway
6h 27m
1 stop
CUN1:47 pmCancun
Feb 2
CUN2:57 pmCancun
8h 22m
1 stop
MDW10:19 pmChicago Midway
$224
Find similar
Frontier
Jan 19
MDW6:10 amChicago Midway
8h 00m
1 stop
CUN3:10 pmCancun
Jan 26
CUN2:57 pmCancun
8h 22m
1 stop
MDW10:19 pmChicago Midway
$231
Find similar
Frontier
Feb 23
MDW6:00 amChicago Midway
6h 37m
1 stop
CUN1:37 pmCancun
Feb 26
CUN11:48 amCancun
10h 24m
1 stop
MDW9:12 pmChicago Midway
$232
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Riviera Maya that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated December 13, 2025.
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

Mon 1/26

6:20 am-1:47 pm

1 stop6h 27m

Cancun

Mon 2/2

2:57 pm-10:19 pm

1 stop8h 22m

$224

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 1/19

6:10 am-3:10 pm

1 stop8h 00m

Cancun

Mon 1/26

2:57 pm-10:19 pm

1 stop8h 22m

$231

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 2/23

6:00 am-1:37 pm

1 stop6h 37m

Cancun

Thu 2/26

11:48 am-9:12 pm

1 stop10h 24m

$232

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 1/22

6:20 am-1:47 pm

1 stop6h 27m

Cancun

Mon 1/26

2:57 pm-10:19 pm

1 stop8h 22m

$233

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 1/8

6:10 am-2:04 pm

1 stop6h 54m

Cancun

Mon 1/12

3:24 pm-10:17 pm

1 stop7h 53m

$235

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 1/25

6:00 am-3:30 pm

1 stop8h 30m

Cancun

Thu 1/29

2:57 pm-10:19 pm

1 stop8h 22m

$272

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Sun 2/1

6:00 am-1:50 pm

1 stop7h 50m

Cozumel

Fri 2/6

3:05 pm-10:22 pm

1 stop7h 17m

$447

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Mon 1/26

6:00 am-1:50 pm

1 stop7h 50m

Cozumel

Mon 2/2

3:05 pm-10:22 pm

1 stop7h 17m

$450

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Sun 2/1

6:00 am-1:50 pm

1 stop7h 50m

Cozumel

Thu 2/5

3:05 pm-8:52 am

2 stops17h 47m

$452

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Fri 3/6

6:00 am-1:55 pm

1 stop7h 55m

Cozumel

Wed 3/11

2:20 pm-10:29 pm

1 stop7h 09m

$483

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Riviera Maya from

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

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 July is your next best option. Flight prices from Chicago Midway Airport to Riviera Maya during July average around $456.

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 $416. Flights from Chicago Midway Airport to Riviera Maya on a Friday will generally be more expensive and average around $686. 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 evening. Our users have found flights to Riviera Maya in the evening for as low as $385. At noon is when there is more demand to fly to Riviera Maya, so prices are often more expensive at around $653 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 $549 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 $372 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?

  • 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?

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
United AirlinesPriceFrom $161Free CancellationRating
7.4
9,094 reviews
Search United Airlines flights
AeromexicoPriceFrom $312Free CancellationRating
7.4
1,641 reviews
Search Aeromexico flights
SouthwestPriceFrom $345Free CancellationRating
7.9
4,251 reviews
Search Southwest flights
FrontierPriceFrom $362Free CancellationRating
5.8
3,082 reviews
Search Frontier flights
DeltaPriceFrom $380Free CancellationRating
7.9
8,007 reviews
Search Delta flights
American AirlinesPriceFrom $506Free CancellationRating
7.2
11,054 reviews
Search American Airlines flights
VolarisPriceFrom $848Free CancellationRating
6.7
1,153 reviews
Search Volaris flights
LATAM AirlinesPriceFrom $3,369Free CancellationRating
7.5
1,891 reviews
Search LATAM Airlines 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.

An easier way to manage your Riviera Maya trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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