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Cheap flights from Chicago Midway Airport to Quintana Roo from $115

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 5/18. 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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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.
Frontier Logo
12:04 pm - 2:07 pm
MDW
-
CUN
26h 03m
1 stop
Frontier Logo
3:22 pm - 11:09 am
CUN
-
MDW
19h 47m
1 stop
$282Frontier
Fri, May 15 - Mon, May 18
Frontier Logo
4:52 pm - 3:57 pm
MDW
-
CUN
23h 05m
1 stop
Frontier Logo
3:22 pm - 11:09 am
CUN
-
MDW
19h 47m
1 stop
$293Frontier
Fri, May 15 - Mon, May 18
Frontier Logo
6:00 am - 2:07 pm
MDW
-
CUN
8h 07m
1 stop
Frontier Logo
3:22 pm - 11:04 am
CUN
-
MDW
19h 42m
1 stop
$296Frontier
Mon, May 11 - Fri, May 15
Frontier Logo
12:04 pm - 2:07 pm
MDW
-
CUN
26h 03m
1 stop
Frontier Logo
3:22 pm - 11:09 am
CUN
-
MDW
19h 47m
1 stop
$302Frontier
Fri, May 15 - Mon, May 18
Southwest Logo
8:30 am - 12:10 pm
MDW
-
CUN
3h 40mnonstop
Southwest Logo
4:10 pm - 7:50 pm
CUN
-
MDW
3h 40mnonstop
$333Southwest
Sun, May 10 - Thu, May 14
Delta Logo
10:59 am - 8:16 pm
MDW
-
CUN
9h 17m
1 stop
Delta Logo
12:45 pm - 9:09 pm
CUN
-
MDW
8h 24m
1 stop
$340Delta
Mon, May 11 - Wed, May 20
Delta Logo
6:23 am - 8:16 pm
MDW
-
CUN
13h 53m
1 stop
Delta Logo
8:00 am - 9:09 pm
CUN
-
MDW
13h 09m
1 stop
$348Delta
Sun, May 10 - Wed, May 13
Volaris Logo
7:30 pm - 3:57 pm
MDW
-
CZM
21h 27m
3 stops
Volaris Logo
4:47 pm - 6:05 pm
CZM
-
MDW
24h 18m
3 stops
$825Volaris
Sat, Oct 10 - Sat, Oct 17
Volaris Logo
8:49 pm - 3:57 pm
MDW
-
CZM
20h 08m
2 stops
Volaris Logo
4:47 pm - 7:04 pm
CZM
-
MDW
25h 17m
2 stops
$867Volaris
Thu, Jun 4 - Thu, Jun 11
Aeromexico Logo
10:35 am - 12:11 pm
MDW
-
CZM
26h 36m
2 stops
Aeromexico Logo
3:23 pm - 4:25 pm
CZM
-
MDW
24h 02m
2 stops
$930Aeromexico
Sat, Oct 24 - Wed, Oct 28

Southwest flights from Chicago Midway Airport to Quintana Roo

Our best Southwest deals on Chicago Midway Airport to Quintana Roo flight tickets
Southwest
May 10
MDW8:30 amChicago Midway
3h 40m
CUN12:10 pmCancun
May 14
CUN4:10 pmCancun
3h 40m
MDW7:50 pmChicago Midway
$333
Southwest
May 11
MDW9:35 amChicago Midway
3h 35m
CUN1:10 pmCancun
May 16
CUN4:00 pmCancun
3h 40m
MDW7:40 pmChicago Midway
$358
Southwest
May 3
MDW11:00 amChicago Midway
3h 35m
CUN2:35 pmCancun
May 13
CUN3:15 pmCancun
3h 40m
MDW6:55 pmChicago Midway
$363

Frontier flights from Chicago Midway Airport to Quintana Roo

Our best Frontier deals on Chicago Midway Airport to Quintana Roo flight tickets
Frontier
May 15
MDW12:04 pmChicago Midway
26h 03m
1 stop
CUN2:07 pmCancun
May 18
CUN3:22 pmCancun
19h 47m
1 stop
MDW11:09 amChicago Midway
$282
Frontier
May 15
MDW4:52 pmChicago Midway
23h 05m
1 stop
CUN3:57 pmCancun
May 18
CUN3:22 pmCancun
19h 47m
1 stop
MDW11:09 amChicago Midway
$293
Frontier
May 11
MDW6:00 amChicago Midway
8h 07m
1 stop
CUN2:07 pmCancun
May 15
CUN3:22 pmCancun
19h 42m
1 stop
MDW11:04 amChicago Midway
$296

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 April 28, 2026.
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

Cheapest round-trip

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 5/15

12:04 pm-2:07 pm

1 stop26h 03m

Cancun

Mon 5/18

3:22 pm-11:09 am

1 stop19h 47m

$282

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 5/15

4:52 pm-3:57 pm

1 stop23h 05m

Cancun

Mon 5/18

3:22 pm-11:09 am

1 stop19h 47m

$293

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 5/11

6:00 am-2:07 pm

1 stop8h 07m

Cancun

Fri 5/15

3:22 pm-11:04 am

1 stop19h 42m

$296

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 5/15

12:04 pm-2:07 pm

1 stop26h 03m

Cancun

Mon 5/18

3:22 pm-11:09 am

1 stop19h 47m

$302
Quickest round-trip

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 5/10

8:30 am-12:10 pm

Nonstop3h 40m

Cancun

Thu 5/14

4:10 pm-7:50 pm

Nonstop3h 40m

$333

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 5/11

10:59 am-8:16 pm

1 stop9h 17m

Cancun

Wed 5/20

12:45 pm-9:09 pm

1 stop8h 24m

$340

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 5/10

6:23 am-8:16 pm

1 stop13h 53m

Cancun

Wed 5/13

8:00 am-9:09 pm

1 stop13h 09m

$348

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Sat 10/10

7:30 pm-3:57 pm

3 stops21h 27m

Cozumel

Sat 10/17

4:47 pm-6:05 pm

3 stops24h 18m

$825

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Thu 6/4

8:49 pm-3:57 pm

2 stops20h 08m

Cozumel

Thu 6/11

4:47 pm-7:04 pm

2 stops25h 17m

$867

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Sat 10/24

10:35 am-12:11 pm

2 stops26h 36m

Cozumel

Wed 10/28

3:23 pm-4:25 pm

2 stops24h 02m

$930

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, February 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 $198. If you aren’t able to travel during the month of February, then book flights to Quintana Roo from Chicago Midway Airport during April instead. Flights to Quintana Roo in April, while not as cheap as those in February, still average around $245.

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 Tuesday. momondo users have found tickets for Tuesday departures for as low as $383. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Quintana Roo is Saturday, with ticket prices averaging around $489.

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 afternoon. Our users have found flights to Quintana Roo in the afternoon for as low as $430. In contrast, the most expensive time of day to depart to Quintana Roo is at noon when prices are around $664.

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 from Chicago Midway Airport 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 $480 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 $403 on momondo.

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

There is only 1 cabin class available to choose from on Chicago Midway Airport 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

$150

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 $150. The best round-trip flight deal from Chicago Midway Airport to Quintana Roo found on momondo in the last 72 hours is $382.
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

Frequently asked questions about flying from Chicago Midway Airport to Quintana Roo

  • 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
FrontierPriceFrom $198Free CancellationRating
5.6
2,970 reviews
Search Frontier flights
SouthwestPriceFrom $296Free CancellationRating
8.0
4,314 reviews
Search Southwest flights
AeromexicoPriceFrom $309Free CancellationRating
7.4
1,521 reviews
Search Aeromexico flights
DeltaPriceFrom $375Free CancellationRating
7.9
8,466 reviews
Search Delta 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.

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