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Cheap flights from Chicago Midway Airport to Riviera Maya from $111

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 3/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago Midway Airport to Riviera Maya

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago Midway Airport to Riviera Maya that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago Midway Airport to Riviera Maya.

Cheap last minute flights

Planning a quick getaway from Chicago Midway Airport to Riviera Maya? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Riviera Maya, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago Midway Airport to Riviera Maya

Find recent round-trip train or bus tickets from Chicago Midway Airport to Riviera Maya.

All round-trip flight deals to Riviera Maya

The cheapest plane tickets to Riviera Maya found on KAYAK recently.
8:01 pm - 9:01 amMDW-CUN
12h 00m1 stop
3:49 pm - 12:17 amCUN-MDW
9h 28m1 stop
$303Frontier
Find Deal
Wed, Feb 5 - Wed, Feb 12
4:30 pm - 8:25 pmMDW-CUN
3h 55mnonstop
1:10 pm - 11:00 pmCUN-MDW
9h 50m1 stop
$312Southwest
Find Deal
Mon, Mar 10 - Tue, Mar 11
4:30 pm - 9:25 pmMDW-CUN
3h 55mnonstop
1:10 pm - 7:50 pmCUN-MDW
6h 40m1 stop
$322Southwest
Find Deal
Fri, Mar 7 - Tue, Mar 11
6:40 am - 1:55 pmMDW-CUN
30h 15m1 stop
12:40 pm - 11:58 pmCUN-MDW
11h 18m1 stop
$325Frontier
Find Deal
Mon, Mar 3 - Mon, Mar 17
10:41 pm - 12:46 pmMDW-CUN
13h 05m1 stop
9:45 pm - 8:45 amCUN-MDW
12h 00m1 stop
$350Volaris
Find Deal
Mon, Feb 3 - Fri, Feb 7
12:44 pm - 9:05 pmMDW-CUN
7h 21m1 stop
1:40 pm - 10:20 pmCUN-MDW
9h 40m1 stop
$369Aeromexico
Find Deal
Mon, Feb 3 - Thu, Feb 6
6:00 am - 1:53 pmMDW-CUN
6h 53m1 stop
1:40 pm - 10:20 pmCUN-MDW
9h 40m1 stop
$375Aeromexico
Find Deal
Mon, Feb 3 - Thu, Feb 6
10:41 pm - 12:46 pmMDW-CUN
13h 05m1 stop
7:39 am - 6:40 pmCUN-MDW
12h 01m1 stop
$384Volaris
Find Deal
Sat, Feb 8 - Mon, Feb 10
9:34 am - 9:05 pmMDW-CUN
10h 31m2 stops
8:00 am - 6:11 pmCUN-MDW
11h 11m2 stops
$396Delta
Find Deal
Thu, Jan 30 - Tue, Feb 4
6:00 am - 6:31 pmMDW-CUN
11h 31m2 stops
4:25 pm - 10:20 pmCUN-MDW
6h 55m1 stop
$403Delta
Find Deal
Sun, Feb 2 - Fri, Feb 7
4:30 pm - 8:25 pmMDW-CUN
3h 55mnonstop
$111Southwest
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Mon, Mar 10
4:30 pm - 9:25 pmMDW-CUN
3h 55mnonstop
$121Southwest
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Fri, Mar 7
5:10 am - 9:56 amMDW-CUN
27h 46m1 stop
$124Frontier
Find Deal
Sat, Mar 1
5:10 am - 9:56 amMDW-CUN
27h 46m1 stop
$127Frontier
Find Deal
Sat, Feb 22
7:55 pm - 7:19 pmMDW-CUN
22h 24m1 stop
$158Volaris
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Mon, Feb 17
7:55 pm - 6:33 pmMDW-CUN
21h 38m1 stop
$166Volaris
Find Deal
Fri, Feb 7
12:44 pm - 9:05 pmMDW-CUN
7h 21m1 stop
$181Delta
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Thu, Jan 23
10:57 am - 12:58 amMDW-CUN
13h 01m2 stops
$226Aeromexico
Find Deal
Fri, Mar 7
9:54 am - 8:05 pmMDW-CUN
10h 11m1 stop
$230Delta
Find Deal
Fri, Mar 14
10:57 am - 12:58 amMDW-CUN
13h 01m2 stops
$241Aeromexico
Find Deal
Thu, Feb 20
6:00 am - 4:30 pmMDW-CUN
9h 30m1 stop
8:00 am - 4:21 pmCUN-MDW
9h 21m1 stop
$391Delta
Find Deal
Sun, Jan 12 - Wed, Jan 15
9:34 am - 9:05 pmMDW-CUN
10h 31m2 stops
6:01 am - 4:21 pmCUN-MDW
11h 20m2 stops
$396Delta
Find Deal
Sat, Jan 11 - Thu, Jan 16
6:00 am - 3:15 pmMDW-CUN
8h 15m1 stop
6:01 am - 4:21 pmCUN-MDW
11h 20m2 stops
$410Delta
Find Deal
Mon, Jan 13 - Thu, Jan 16
6:00 am - 4:30 pmMDW-CUN
9h 30m1 stop
8:00 am - 4:21 pmCUN-MDW
9h 21m1 stop
$485Aeromexico
Find Deal
Sun, Jan 12 - Tue, Jan 14
10:25 am - 3:15 pmMDW-CUN
3h 50mnonstop
3:00 pm - 5:50 pmCUN-MDW
3h 50mnonstop
$507Southwest
Find Deal
Sun, Jan 12 - Fri, Jan 17
9:05 am - 1:55 pmMDW-CUN
3h 50mnonstop
3:00 pm - 5:50 pmCUN-MDW
3h 50mnonstop
$521Southwest
Find Deal
Mon, Jan 13 - Thu, Jan 16
10:57 am - 12:53 amMDW-CUN
12h 56m2 stops
8:00 am - 4:21 pmCUN-MDW
9h 21m1 stop
$551Aeromexico
Find Deal
Mon, Jan 13 - Tue, Jan 14
7:50 pm - 9:04 amMDW-CUN
12h 14m1 stop
7:23 pm - 8:45 amCUN-MDW
14h 22m1 stop
$584Volaris
Find Deal
Tue, Jan 14 - Tue, Jan 21
7:55 pm - 12:59 pmMDW-CUN
16h 04m1 stop
7:39 am - 6:40 pmCUN-MDW
12h 01m1 stop
$648Volaris
Find Deal
Wed, Jan 15 - Sun, Jan 19
8:15 am - 1:20 pmMDW-CUN
28h 05m1 stop
10:08 am - 12:17 amCUN-MDW
15h 09m1 stop
$796Frontier
Find Deal
Wed, Jan 15 - Sun, Jan 19
9:05 am - 1:55 pmMDW-CUN
3h 50mnonstop
3:00 pm - 5:50 pmCUN-MDW
3h 50mnonstop
$387Southwest
Find Deal
Tue, Jan 28 - Thu, Jan 30
9:05 am - 1:55 pmMDW-CUN
3h 50mnonstop
3:00 pm - 5:50 pmCUN-MDW
3h 50mnonstop
$407Southwest
Find Deal
Tue, Feb 4 - Thu, Feb 6
4:30 pm - 8:25 pmMDW-CUN
3h 55mnonstop
8:20 am - 12:00 pmCUN-MDW
3h 40mnonstop
$412Southwest
Find Deal
Mon, Mar 10 - Fri, Mar 14
4:30 pm - 8:25 pmMDW-CUN
3h 55mnonstop
3:25 pm - 7:15 pmCUN-MDW
3h 50mnonstop
$427Southwest
Find Deal
Mon, Mar 10 - Tue, Mar 11
9:05 am - 1:55 pmMDW-CUN
3h 50mnonstop
3:00 pm - 5:50 pmCUN-MDW
3h 50mnonstop
$431Southwest
Find Deal
Tue, Jan 21 - Wed, Jan 29
10:25 am - 3:15 pmMDW-CUN
3h 50mnonstop
3:00 pm - 5:50 pmCUN-MDW
3h 50mnonstop
$452Southwest
Find Deal
Sun, Jan 26 - Thu, Jan 30
4:30 pm - 8:25 pmMDW-CUN
3h 55mnonstop
8:20 am - 12:00 pmCUN-MDW
3h 40mnonstop
$484Southwest
Find Deal
Sun, Mar 9 - Fri, Mar 14
9:05 am - 1:55 pmMDW-CUN
3h 50mnonstop
4:35 pm - 7:25 pmCUN-MDW
3h 50mnonstop
$490Southwest
Find Deal
Tue, Feb 11 - Fri, Feb 14
4:30 pm - 8:25 pmMDW-CUN
3h 55mnonstop
8:20 am - 12:00 pmCUN-MDW
3h 40mnonstop
$496Southwest
Find Deal
Sun, Mar 9 - Sun, Mar 16
4:30 pm - 9:25 pmMDW-CUN
3h 55mnonstop
8:20 am - 12:00 pmCUN-MDW
3h 40mnonstop
$520Southwest
Find Deal
Thu, Mar 6 - Sun, Mar 9

Volaris flights from Chicago Midway Airport to Riviera Maya

Our best Volaris deals on Chicago Midway Airport to Riviera Maya flight tickets
Volaris
Feb 3
MDW10:41 pmChicago Midway
13h 05m
1 stop
CUN12:46 pmCancun
Feb 7
CUN9:45 pmCancun
12h 00m
1 stop
MDW8:45 amChicago Midway
Volaris
Feb 8
MDW10:41 pmChicago Midway
13h 05m
1 stop
CUN12:46 pmCancun
Feb 10
CUN7:39 amCancun
12h 01m
1 stop
MDW6:40 pmChicago Midway
Volaris
Feb 6
MDW7:55 pmChicago Midway
12h 09m
1 stop
CUN9:04 amCancun
Feb 13
CUN1:43 pmCancun
8h 43m
1 stop
MDW9:26 pmChicago Midway

Aeromexico flights from Chicago Midway Airport to Riviera Maya

Our best Aeromexico deals on Chicago Midway Airport to Riviera Maya flight tickets
Aeromexico
Feb 3
MDW12:44 pmChicago Midway
7h 21m
1 stop
CUN9:05 pmCancun
Feb 6
CUN1:40 pmCancun
9h 40m
1 stop
MDW10:20 pmChicago Midway
Aeromexico
Feb 3
MDW6:00 amChicago Midway
6h 53m
1 stop
CUN1:53 pmCancun
Feb 6
CUN1:40 pmCancun
9h 40m
1 stop
MDW10:20 pmChicago Midway
Aeromexico
Jan 14
MDW6:00 amChicago Midway
16h 38m
2 stops
CUN11:38 pmCancun
Jan 23
CUN3:03 pmCancun
8h 17m
1 stop
MDW10:20 pmChicago Midway

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 February. Flight prices, which tend to average around $252, 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 May is your next best option. Flight prices from Chicago Midway Airport 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 Wednesday is the least expensive day to fly to Riviera Maya. Tickets to fly out on this day can be as low as $357. Flights from Chicago Midway Airport to Riviera Maya on a Monday will generally be more expensive and average around $550. 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. In the afternoon is when there is more demand to fly to Riviera Maya, so prices are often more expensive at around $715 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?

In general, most travelers find the cheapest time to book a flight to Riviera Maya is about 20 days prior to their departure date when tickets on average are $566. 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 $172 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.

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

$111

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 $111. The best round-trip flight deal from Chicago Midway Airport to Riviera Maya found on momondo in the last 72 hours is $303.
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)

  • 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
FrontierPriceFrom $171Free CancellationRating
6.0
3,428 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $177Free CancellationRating
6.3
8,075 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $311Free CancellationRating
7.4
8,944 reviews
Search United Airlines flights
DeltaPriceFrom $380Free CancellationRating
8.0
8,501 reviews
Search Delta flights
AeromexicoPriceFrom $382Free CancellationRating
7.5
1,847 reviews
Search Aeromexico flights
VolarisPriceFrom $425Free CancellationRating
6.7
1,248 reviews
Search Volaris flights
SouthwestPriceFrom $479Free CancellationRating
8.1
4,650 reviews
Search Southwest flights
LATAM AirlinesPriceFrom $3,369Free CancellationRating
7.5
1,836 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.


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