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Cheap flights from Chicago Midway Airport to Quintana Roo from $116

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 Quintana Roo departing on 3/15. 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 Quintana Roo

Cheap round-trip flights

Enter your travel dates to find the best prices.
Aeromexico Logo
12:46 pm - 9:11 pm
MDW
-
CUN
7h 25m1 stop
Aeromexico Logo
4:40 pm - 10:22 pm
CUN
-
MDW
6h 42m1 stop
$296Aeromexico
Wed, Feb 4 - Wed, Feb 11
Frontier Logo
9:38 am - 3:20 pm
MDW
-
CUN
28h 42m1 stop
Frontier Logo
4:30 pm - 11:45 am
CUN
-
MDW
20h 15m1 stop
$302Frontier
Sat, Jan 24 - Sat, Jan 31
Aeromexico Logo
6:45 am - 4:35 pm
MDW
-
CUN
8h 50m1 stop
Aeromexico Logo
4:40 pm - 10:07 pm
CUN
-
MDW
6h 27m1 stop
$306Aeromexico
Sun, Jan 11 - Fri, Jan 16
Volaris Logo
7:54 pm - 9:48 am
MDW
-
CUN
13h 54m1 stop
Volaris Logo
10:39 am - 6:34 pm
CUN
-
MDW
7h 55m1 stop
$307Volaris
Sun, Mar 8 - Wed, Mar 11
Multiple Airlines Logo
6:00 am - 3:35 pm
MDW
-
CUN
8h 35m1 stop
Multiple Airlines Logo
10:01 am - 9:33 pm
CUN
-
MDW
12h 32m1 stop
$308Multiple Airlines
Tue, Feb 17 - Sat, Feb 21
Multiple Airlines Logo
6:01 pm - 9:13 am
MDW
-
CUN
14h 12m1 stop
Multiple Airlines Logo
2:57 pm - 10:19 pm
CUN
-
MDW
8h 22m1 stop
$310Multiple Airlines
Sun, Jan 18 - Thu, Jan 22
Multiple Airlines Logo
6:01 pm - 9:13 am
MDW
-
CUN
14h 12m1 stop
Multiple Airlines Logo
4:30 pm - 10:19 pm
CUN
-
MDW
6h 49m1 stop
$311Multiple Airlines
Sun, Jan 18 - Fri, Jan 23
Southwest Logo
9:15 am - 1:55 pm
MDW
-
CUN
3h 40mnonstop
Southwest Logo
1:45 pm - 4:30 pm
CUN
-
MDW
3h 45mnonstop
$314Southwest
Tue, Jan 20 - Thu, Jan 22
Delta Logo
6:45 am - 1:50 pm
MDW
-
CZM
7h 05m1 stop
Delta Logo
4:15 pm - 9:08 am
CZM
-
MDW
16h 53m1 stop
$447Delta
Sun, Jan 18 - Wed, Jan 21
Delta Logo
6:14 pm - 1:50 pm
MDW
-
CZM
19h 36m2 stops
Delta Logo
3:05 pm - 10:22 pm
CZM
-
MDW
7h 17m1 stop
$452Delta
Sun, Jan 18 - Thu, Jan 22

Frontier flights from Chicago Midway Airport to Quintana Roo

Our best Frontier deals on Chicago Midway Airport to Quintana Roo flight tickets
Frontier
Jan 24
MDW9:38 amChicago Midway
28h 42m
1 stop
CUN3:20 pmCancun
Jan 31
CUN4:30 pmCancun
20h 15m
1 stop
MDW11:45 amChicago Midway
$302
Find similar
Frontier
Jan 31
MDW9:38 amChicago Midway
28h 42m
1 stop
CUN3:20 pmCancun
Feb 5
CUN2:57 pmCancun
8h 22m
1 stop
MDW10:19 pmChicago Midway
$323
Find similar
Frontier
Dec 31
MDW6:12 amChicago Midway
6h 28m
1 stop
CUN1:40 pmCancun
Jan 10
CUN3:34 pmCancun
7h 53m
1 stop
MDW10:27 pmChicago Midway
$327
Find similar

Aeromexico flights from Chicago Midway Airport to Quintana Roo

Our best Aeromexico deals on Chicago Midway Airport to Quintana Roo flight tickets
Aeromexico
Feb 4
MDW12:46 pmChicago Midway
7h 25m
1 stop
CUN9:11 pmCancun
Feb 11
CUN4:40 pmCancun
6h 42m
1 stop
MDW10:22 pmChicago Midway
$296
Find similar
Aeromexico
Jan 11
MDW6:45 amChicago Midway
8h 50m
1 stop
CUN4:35 pmCancun
Jan 16
CUN1:40 pmCancun
9h 27m
1 stop
MDW10:07 pmChicago Midway
$306
Find similar
Aeromexico
Feb 9
MDW6:00 amChicago Midway
13h 02m
2 stops
CUN8:02 pmCancun
Feb 14
CUN8:38 amCancun
14h 53m
2 stops
MDW10:31 pmChicago Midway
$334
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Quintana Roo 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 22, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Quintana Roo that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 2/4

12:46 pm-9:11 pm

1 stop7h 25m

Cancun

Wed 2/11

4:40 pm-10:22 pm

1 stop6h 42m

$296

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 1/24

9:38 am-3:20 pm

1 stop28h 42m

Cancun

Sat 1/31

4:30 pm-11:45 am

1 stop20h 15m

$302

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 1/11

6:45 am-4:35 pm

1 stop8h 50m

Cancun

Fri 1/16

4:40 pm-10:07 pm

1 stop6h 27m

$306

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 3/8

7:54 pm-9:48 am

1 stop13h 54m

Cancun

Wed 3/11

10:39 am-6:34 pm

1 stop7h 55m

$307

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 2/17

6:00 am-3:35 pm

1 stop8h 35m

Cancun

Sat 2/21

10:01 am-9:33 pm

1 stop12h 32m

$308

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 1/18

6:01 pm-9:13 am

1 stop14h 12m

Cancun

Thu 1/22

2:57 pm-10:19 pm

1 stop8h 22m

$310

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 1/18

6:01 pm-9:13 am

1 stop14h 12m

Cancun

Fri 1/23

4:30 pm-10:19 pm

1 stop6h 49m

$311

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 1/20

9:15 am-1:55 pm

Nonstop3h 40m

Cancun

Thu 1/22

1:45 pm-4:30 pm

Nonstop3h 45m

$314

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Sun 1/18

6:45 am-1:50 pm

1 stop7h 05m

Cozumel

Wed 1/21

4:15 pm-9:08 am

1 stop16h 53m

$447

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Sun 1/18

6:14 pm-1:50 pm

2 stops19h 36m

Cozumel

Thu 1/22

3:05 pm-10:22 pm

1 stop7h 17m

$452

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 Quintana Roo from

How to get the cheapest flight ticket from Chicago Midway Airport to Quintana Roo

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 Quintana Roo?

In general, September is the cheapest month to fly from Chicago Midway Airport to Quintana Roo. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $371. If you aren’t able to travel during the month of September, then book flights to Quintana Roo from Chicago Midway Airport during July instead. Flights to Quintana Roo in July, while not as cheap as those in September, still average around $456.

What is the cheapest day to depart on your flight to Quintana Roo?

On average, the least expensive day to fly to Quintana Roo from Chicago Midway Airport is on a Monday. momondo users have found tickets for Monday departures for as low as $399. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Quintana Roo is Friday, with ticket prices averaging around $669.

What is the cheapest time of day to depart on your flight to Quintana Roo?

Our data shows that the cheapest Chicago Midway Airport to Quintana Roo flights are usually those with departure times in the evening. Our users have found flights to Quintana Roo in the evening for as low as $385. In contrast, the most expensive time of day to depart to Quintana Roo is at noon when prices are around $653.

What is the cheapest Chicago Midway to Quintana Roo flight route?

Fly from Chicago Midway to Cancun for the best Chicago Midway - Quintana Roo flight prices

How far in advance should I book a flight to Quintana Roo?

You are more likely to see cheaper flights to Quintana Roo from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Quintana Roo for around $549 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Quintana Roo from Chicago Midway Airport for as low as $385 on momondo.

What cabin class options are available on Chicago Midway to Quintana Roo flights?

There is only 1 cabin class available to choose from on Chicago Midway to Quintana Roo 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 Quintana Roo flights?

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to Quintana Roo.

Cheap Chicago Midway Airport to Quintana Roo flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Quintana Roo

Best Price Found

$165

Fastest flight time

3h 30m

Direct flights

Every day

Airports in Quintana Roo

18 airports
The best one-way flight to Quintana Roo from Chicago Midway Airport in the past 72 hours is $165. The best round-trip flight deal from Chicago Midway Airport to Quintana Roo found on momondo in the last 72 hours is $398.
The fastest flight from Chicago Midway Airport to Quintana Roo takes 3h 30m
Direct flights go from Chicago Midway Airport to Quintana Roo every day.
There are 18 airports in Quintana Roo. 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 Quintana Roo?

    Prices for flights from Chicago Midway Airport to Quintana Roo are refreshed on a daily basis.

  • How many operators does momondo search for flights from Chicago Midway Airport to Quintana Roo?

  • How old do you have to be to fly from Chicago Midway Airport to Quintana Roo?

    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 Quintana Roo.

  • What documentation or ID do you need to fly to Quintana Roo?

    The necessary travel and health documents for your Quintana Roo 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 Quintana Roo?

Best airlines flying from Chicago Midway Airport to Quintana Roo

Compare and see reviews for airlines that fly from Chicago Midway Airport to Quintana Roo with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $161Free CancellationRating
7.4
9,105 reviews
Search United Airlines flights
AeromexicoPriceFrom $312Free CancellationRating
7.4
1,626 reviews
Search Aeromexico flights
SouthwestPriceFrom $336Free CancellationRating
8.0
4,253 reviews
Search Southwest flights
FrontierPriceFrom $362Free CancellationRating
5.8
3,075 reviews
Search Frontier flights
DeltaPriceFrom $380Free CancellationRating
7.9
8,014 reviews
Search Delta flights
American AirlinesPriceFrom $506Free CancellationRating
7.2
11,054 reviews
Search American Airlines flights
VolarisPriceFrom $848Free CancellationRating
6.6
1,163 reviews
Search Volaris flights
LATAM AirlinesPriceFrom $3,369Free CancellationRating
7.5
1,894 reviews
Search LATAM Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Quintana Roo?

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 Quintana Roo from Chicago.

Can I find flights from Chicago to Quintana Roo with flexible booking policies on momondo?

All flight searches from Chicago to Quintana Roo on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to Quintana Roo?

momondo helps you find the best flight between Chicago and Quintana Roo 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 Quintana Roo right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Quintana Roo 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.

An easier way to manage your Quintana Roo trip

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