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Cheap flights from Chicago Midway Airport to Riviera Maya from $117

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 8/9. 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

Southwest Logo
3:40 pm - 8:25 pmMDW-CUN
3h 45mnonstop
Southwest Logo
11:55 am - 2:45 pmCUN-MDW
3h 50mnonstop
$270Southwest
Find Deal
Sat, Nov 8 - Sat, Nov 15
Southwest Logo
9:15 am - 12:50 pmMDW-CUN
3h 35mnonstop
Southwest Logo
2:25 pm - 6:05 pmCUN-MDW
3h 40mnonstop
$271Southwest
Find Deal
Sat, Sep 6 - Sat, Sep 13
Aeromexico Logo
6:00 am - 12:50 pmMDW-CUN
6h 50m1 stop
Aeromexico Logo
8:00 am - 3:26 pmCUN-MDW
7h 26m1 stop
$292Aeromexico
Find Deal
Sat, Sep 6 - Sat, Sep 13
Aeromexico Logo
10:35 am - 8:20 pmMDW-CUN
9h 45m1 stop
Aeromexico Logo
8:00 am - 10:14 pmCUN-MDW
15h 14m1 stop
$305Aeromexico
Find Deal
Sat, Nov 1 - Thu, Nov 6
Delta Logo
6:00 am - 2:20 pmMDW-CUN
8h 20m1 stop
Delta Logo
8:00 am - 10:14 pmCUN-MDW
14h 14m1 stop
$324Delta
Find Deal
Tue, Sep 30 - Tue, Oct 7
Delta Logo
6:00 am - 9:20 pmMDW-CUN
14h 20m1 stop
Delta Logo
4:10 pm - 8:46 amCUN-MDW
17h 36m1 stop
$326Delta
Find Deal
Tue, Nov 4 - Tue, Nov 11
Frontier Logo
6:15 am - 12:40 pmMDW-CUN
6h 25m1 stop
Frontier Logo
1:55 pm - 11:17 pmCUN-MDW
9h 22m1 stop
$332Frontier
Find Deal
Sat, Sep 6 - Sat, Sep 13
Frontier Logo
6:15 am - 12:40 pmMDW-CUN
6h 25m1 stop
Frontier Logo
10:50 am - 12:11 amCUN-MDW
13h 21m1 stop
$333Frontier
Find Deal
Sat, Oct 4 - Sat, Oct 11
Volaris Logo
6:49 pm - 5:16 pmMDW-CZM
22h 27m2 stops
Volaris Logo
6:21 pm - 5:34 pmCZM-MDW
23h 13m2 stops
$691Volaris
Find Deal
Fri, Nov 7 - Tue, Nov 11
Volaris Logo
6:49 pm - 5:16 pmMDW-CZM
22h 27m2 stops
Volaris Logo
6:21 pm - 5:34 pmCZM-MDW
23h 13m3 stops
$731Volaris
Find Deal
Fri, Nov 7 - Tue, Nov 11

Frontier flights from Chicago Midway Airport to Riviera Maya

Our best Frontier deals on Chicago Midway Airport to Riviera Maya flight tickets
Frontier
Aug 8
MDW6:00 amChicago Midway
27h 32m
1 stop
CUN9:32 amCancun
Aug 12
CUN1:49 pmCancun
20h 51m
1 stop
MDW10:40 amChicago Midway
$321
Find similar
Frontier
Aug 8
MDW12:35 pmChicago Midway
27h 45m
1 stop
CUN4:20 pmCancun
Aug 15
CUN1:49 pmCancun
9h 28m
1 stop
MDW11:17 pmChicago Midway
$323
Find similar
Frontier
Sep 6
MDW6:15 amChicago Midway
6h 25m
1 stop
CUN12:40 pmCancun
Sep 13
CUN1:55 pmCancun
9h 22m
1 stop
MDW11:17 pmChicago Midway
$332
Find similar

Southwest flights from Chicago Midway Airport to Riviera Maya

Our best Southwest deals on Chicago Midway Airport to Riviera Maya flight tickets
Southwest
Nov 8
MDW3:40 pmChicago Midway
3h 45m
CUN8:25 pmCancun
Nov 15
CUN11:55 amCancun
3h 50m
MDW2:45 pmChicago Midway
$270
Find similar
Southwest
Sep 6
MDW9:15 amChicago Midway
3h 35m
CUN12:50 pmCancun
Sep 13
CUN2:25 pmCancun
3h 40m
MDW6:05 pmChicago Midway
$271
Find similar
Southwest
Sep 9
MDW9:55 amChicago Midway
3h 35m
CUN1:30 pmCancun
Sep 13
CUN2:25 pmCancun
3h 40m
MDW6:05 pmChicago Midway
$276
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 August 2, 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

Sat 11/8

3:40 pm-8:25 pm

Nonstop3h 45m

Cancun

Sat 11/15

11:55 am-2:45 pm

Nonstop3h 50m

$270

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 9/6

9:15 am-12:50 pm

Nonstop3h 35m

Cancun

Sat 9/13

2:25 pm-6:05 pm

Nonstop3h 40m

$271

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 9/6

6:00 am-12:50 pm

1 stop6h 50m

Cancun

Sat 9/13

8:00 am-3:26 pm

1 stop7h 26m

$292

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 11/1

10:35 am-8:20 pm

1 stop9h 45m

Cancun

Thu 11/6

8:00 am-10:14 pm

1 stop15h 14m

$305

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 9/30

6:00 am-2:20 pm

1 stop8h 20m

Cancun

Tue 10/7

8:00 am-10:14 pm

1 stop14h 14m

$324

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 11/4

6:00 am-9:20 pm

1 stop14h 20m

Cancun

Tue 11/11

4:10 pm-8:46 am

1 stop17h 36m

$326

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 9/6

6:15 am-12:40 pm

1 stop6h 25m

Cancun

Sat 9/13

1:55 pm-11:17 pm

1 stop9h 22m

$332

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 10/4

6:15 am-12:40 pm

1 stop6h 25m

Cancun

Sat 10/11

10:50 am-12:11 am

1 stop13h 21m

$333

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Fri 11/7

6:49 pm-5:16 pm

2 stops22h 27m

Cozumel

Tue 11/11

6:21 pm-5:34 pm

2 stops23h 13m

$691

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Fri 11/7

6:49 pm-5:16 pm

2 stops22h 27m

Cozumel

Tue 11/11

6:21 pm-5:34 pm

3 stops23h 13m

$731

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 $450, 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 $457.

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 $427. Flights from Chicago Midway Airport to Riviera Maya on a Friday will generally be more expensive and average around $696. 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 $713 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 $587 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 $405 on momondo.

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

There are 1 cabin classes 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

Best Price Found

$117

Fastest flight time

3h 35m

Direct flights

Every day

Airports in Riviera Maya

2 airports
The best one-way flight to Riviera Maya from Chicago Midway Airport in the past 72 hours is $117. The best round-trip flight deal from Chicago Midway Airport to Riviera Maya found on momondo in the last 72 hours is $270.
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 2 airports near Riviera Maya: Cozumel (CZM), 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
8,904 reviews
Search United Airlines flights
FrontierPriceFrom $198Free CancellationRating
5.8
3,241 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $241Free CancellationRating
6.3
8,054 reviews
Search Spirit Airlines flights
AeromexicoPriceFrom $312Free CancellationRating
7.5
1,719 reviews
Search Aeromexico flights
SouthwestPriceFrom $346Free CancellationRating
8.0
4,246 reviews
Search Southwest flights
DeltaPriceFrom $380Free CancellationRating
8.0
7,983 reviews
Search Delta flights
VolarisPriceFrom $486Free CancellationRating
6.6
1,163 reviews
Search Volaris flights
LATAM AirlinesPriceFrom $3,369Free CancellationRating
7.5
1,823 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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