How many flights depart from Chicago Midway Airport to Quintana Roo on average per week?

As of August 2026, 2 flights take off from Chicago Midway Airport and land in Quintana Roo each week. The most common flight departure day for this route is Tue, with 50% of weekly flights taking off on this day.

What airlines fly to Quintana Roo?

Southwest, Frontier and Aeromexico are the top three most popular airlines that fly to Quintana Roo from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 73% of people opting to fly with this airline when traveling to Quintana Roo. Keep in mind that there are 4 different airlines that fly to Quintana Roo on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Chicago Midway to Quintana Roo?

Volaris and Southwest are the most popular carriers operating from Chicago Midway 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?

The number of operators available for flights from Chicago Midway Airport to Quintana Roo is 4 as of August 2026.

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.

$152 Cheap Flights from Chicago Midway Airport to Quintana Roo in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago Midway Airport to Quintana Roo

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:23 pm - 9:55 amMDW Chicago Midway-CUN Cancun

13h 32m1 stop Guadalajara Miguel Hidal

10:40 am - 7:04 pmCUN Cancun-MDW Chicago Midway

8h 24m1 stop Guadalajara Miguel Hidal

$341Volaris

Wed, Sep 9 - Sun, Sep 13

5:00 am - 12:10 pmMDW Chicago Midway-CUN Cancun

7h 10m1 stop Baltimore/Washington

1:05 pm - 4:40 pmCUN Cancun-MDW Chicago Midway

3h 35mnonstop

$352Southwest

Sun, Sep 20 - Thu, Sep 24

6:00 am - 5:00 pmMDW Chicago Midway-CUN Cancun

10h 00m1 stop Baltimore/Washington

6:00 pm - 8:35 pmCUN Cancun-MDW Chicago Midway

3h 35mnonstop

$352Southwest

Tue, Dec 8 - Thu, Dec 10

8:23 pm - 9:55 amMDW Chicago Midway-CUN Cancun

13h 32m1 stop Guadalajara Miguel Hidal

10:40 am - 7:04 pmCUN Cancun-MDW Chicago Midway

8h 24m1 stop Guadalajara Miguel Hidal

$357Volaris

Mon, Sep 7 - Fri, Sep 11

12:03 pm - 2:31 pmMDW Chicago Midway-CUN Cancun

26h 28m1 stop Atlanta Hartsfield-Jackson

3:41 pm - 10:58 amCUN Cancun-MDW Chicago Midway

19h 17m1 stop Atlanta Hartsfield-Jackson

$432Frontier

Wed, Oct 21 - Sat, Oct 24

6:05 am - 7:50 pmMDW Chicago Midway-CUN Cancun

13h 45m1 stop Atlanta Hartsfield-Jackson

8:05 am - 4:15 pmCUN Cancun-MDW Chicago Midway

8h 10m1 stop Atlanta Hartsfield-Jackson

$435Aeromexico

Thu, Sep 24 - Thu, Oct 1

6:05 am - 7:50 pmMDW Chicago Midway-CUN Cancun

13h 45m1 stop Atlanta Hartsfield-Jackson

8:05 am - 4:15 pmCUN Cancun-MDW Chicago Midway

8h 10m1 stop Atlanta Hartsfield-Jackson

$436Aeromexico

Thu, Sep 24 - Thu, Oct 1

12:03 pm - 1:14 pmMDW Chicago Midway-CUN Cancun

25h 11m1 stop Atlanta Hartsfield-Jackson

3:24 pm - 9:53 pmCUN Cancun-MDW Chicago Midway

7h 29m1 stop Atlanta Hartsfield-Jackson

$439Frontier

Wed, Oct 28 - Sun, Nov 1

6:05 am - 7:50 pmMDW Chicago Midway-CUN Cancun

13h 45m1 stop Atlanta Hartsfield-Jackson

2:25 pm - 10:33 pmCUN Cancun-MDW Chicago Midway

8h 08m1 stop Atlanta Hartsfield-Jackson

$458Delta

Mon, Sep 28 - Wed, Oct 7

6:00 am - 12:30 pmMDW Chicago Midway-CUN Cancun

5h 30m1 stop Atlanta Hartsfield-Jackson

1:40 pm - 10:56 pmCUN Cancun-MDW Chicago Midway

10h 16m1 stop Atlanta Hartsfield-Jackson

$466Delta

Mon, Nov 16 - Fri, Nov 20

Cheap last minute flights

Enter your travel dates to find the best prices.

8:23 pm - 9:55 amMDW Chicago Midway-CUN Cancun

13h 32m1 stop Guadalajara Miguel Hidal

11:10 am - 8:31 pmCUN Cancun-MDW Chicago Midway

9h 21m1 stop Dallas/Fort Worth

$468Volaris

Mon, Aug 17 - Fri, Aug 21

8:23 pm - 9:55 amMDW Chicago Midway-CUN Cancun

13h 32m1 stop Guadalajara Miguel Hidal

11:10 am - 8:31 pmCUN Cancun-MDW Chicago Midway

9h 21m1 stop Dallas/Fort Worth

$474Volaris

Mon, Aug 17 - Thu, Aug 20

8:23 pm - 9:55 amMDW Chicago Midway-CUN Cancun

13h 32m1 stop Guadalajara Miguel Hidal

11:10 am - 8:31 pmCUN Cancun-MDW Chicago Midway

9h 21m1 stop Dallas/Fort Worth

$481Volaris

Mon, Aug 17 - Thu, Aug 20

6:05 am - 1:53 pmMDW Chicago Midway-CUN Cancun

7h 48m1 stop Atlanta Hartsfield-Jackson

3:06 pm - 10:47 pmCUN Cancun-MDW Chicago Midway

7h 41m1 stop Atlanta Hartsfield-Jackson

$546Frontier

Sun, Aug 16 - Thu, Aug 20

6:05 am - 1:53 pmMDW Chicago Midway-CUN Cancun

7h 48m1 stop Atlanta Hartsfield-Jackson

3:06 pm - 10:47 pmCUN Cancun-MDW Chicago Midway

7h 41m1 stop Atlanta Hartsfield-Jackson

$546Frontier

Mon, Aug 17 - Thu, Aug 20

6:05 am - 1:53 pmMDW Chicago Midway-CUN Cancun

7h 48m1 stop Atlanta Hartsfield-Jackson

11:10 am - 8:31 pmCUN Cancun-MDW Chicago Midway

9h 21m1 stop Dallas/Fort Worth

$548Frontier

Sun, Aug 16 - Fri, Aug 21

8:25 am - 12:00 pmMDW Chicago Midway-CUN Cancun

3h 35mnonstop

3:10 pm - 11:20 pmCUN Cancun-MDW Chicago Midway

8h 10m1 stop Austin Bergstrom

$580Southwest

Mon, Aug 17 - Thu, Aug 20

7:25 am - 3:00 pmMDW Chicago Midway-CUN Cancun

7h 35m1 stop Houston Hobby

3:10 pm - 11:20 pmCUN Cancun-MDW Chicago Midway

8h 10m2 stops Austin Bergstrom Dallas Love Field

$584Southwest

Mon, Aug 17 - Thu, Aug 20

6:05 am - 11:25 amMDW Chicago Midway-CUN Cancun

5h 20m1 stop Atlanta Hartsfield-Jackson

8:05 am - 10:36 pmCUN Cancun-MDW Chicago Midway

14h 31m1 stop Atlanta Hartsfield-Jackson

$704Delta

Mon, Aug 17 - Sat, Aug 22

7:25 pm - 12:56 pmMDW Chicago Midway-CUN Cancun

17h 31m1 stop Minneapolis St Paul

8:05 am - 10:36 pmCUN Cancun-MDW Chicago Midway

14h 31m1 stop Atlanta Hartsfield-Jackson

$704Delta

Sat, Aug 15 - Sat, Aug 22

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Southwest flights from Chicago Midway Airport to Quintana Roo

Our best Southwest deals on Chicago Midway Airport to Quintana Roo flight tickets

Southwest

Sep 20

MDW5:00 amChicago Midway

7h 10m

1 stop

CUN12:10 pmCancun

Sep 24

CUN1:05 pmCancun

3h 35m

MDW4:40 pmChicago Midway

$352

Southwest

Dec 8

MDW6:40 amChicago Midway

7h 50m

1 stop

CUN3:30 pmCancun

Dec 15

CUN2:10 pmCancun

8h 05m

1 stop

MDW9:15 pmChicago Midway

$362

Southwest

Dec 8

MDW8:50 amChicago Midway

9h 55m

2 stops

CUN7:45 pmCancun

Dec 10

CUN12:35 pmCancun

7h 20m

1 stop

MDW6:55 pmChicago Midway

$367

Frontier flights from Chicago Midway Airport to Quintana Roo

Our best Frontier deals on Chicago Midway Airport to Quintana Roo flight tickets

Frontier

Oct 21

MDW12:03 pmChicago Midway

26h 28m

1 stop

CUN2:31 pmCancun

Oct 24

CUN3:41 pmCancun

19h 17m

1 stop

MDW10:58 amChicago Midway

$432

Frontier

Aug 22

MDW6:05 amChicago Midway

7h 49m

1 stop

CUN1:54 pmCancun

Aug 27

CUN11:10 amCancun

9h 21m

1 stop

MDW8:31 pmChicago Midway

$498

Frontier

Aug 23

MDW6:05 amChicago Midway

7h 49m

1 stop

CUN1:54 pmCancun

Aug 27

CUN11:10 amCancun

9h 21m

1 stop

MDW8:31 pmChicago Midway

$500

momondo Fare Finder

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 Chicago Midway - CUN Cancun

MDWCUN

Chicago Midway

Wed 9/9

8:23 pm-9:55 am

1 stop13h 32m

Cancun

Sun 9/13

10:40 am-7:04 pm

1 stop8h 24m

$341

Quickest round-trip

ChicagoCancún

MDW Chicago Midway - CUN Cancun

MDWCUN

Chicago Midway

Sun 9/20

5:00 am-12:10 pm

1 stop7h 10m

Cancun

Thu 9/24

1:05 pm-4:40 pm

Nonstop3h 35m

$352

ChicagoCancún

MDW Chicago Midway - CUN Cancun

MDWCUN

Chicago Midway

Tue 12/8

6:00 am-5:00 pm

1 stop10h 00m

Cancun

Thu 12/10

6:00 pm-8:35 pm

Nonstop3h 35m

$352

ChicagoCancún

MDW Chicago Midway - CUN Cancun

MDWCUN

Chicago Midway

Mon 9/7

8:23 pm-9:55 am

1 stop13h 32m

Cancun

Fri 9/11

10:40 am-7:04 pm

1 stop8h 24m

$357

ChicagoCancún

MDW Chicago Midway - CUN Cancun

MDWCUN

Chicago Midway

Wed 10/21

12:03 pm-2:31 pm

1 stop26h 28m

Cancun

Sat 10/24

3:41 pm-10:58 am

1 stop19h 17m

$432

ChicagoCancún

MDW Chicago Midway - CUN Cancun

MDWCUN

Chicago Midway

Thu 9/24

6:05 am-7:50 pm

1 stop13h 45m

Cancun

Thu 10/1

8:05 am-4:15 pm

1 stop8h 10m

$435

ChicagoCancún

MDW Chicago Midway - CUN Cancun

MDWCUN

Chicago Midway

Thu 9/24

6:05 am-7:50 pm

1 stop13h 45m

Cancun

Thu 10/1

8:05 am-4:15 pm

1 stop8h 10m

$436

ChicagoCancún

MDW Chicago Midway - CUN Cancun

MDWCUN

Chicago Midway

Wed 10/28

12:03 pm-1:14 pm

1 stop25h 11m

Cancun

Sun 11/1

3:24 pm-9:53 pm

1 stop7h 29m

$439

ChicagoCancún

MDW Chicago Midway - CUN Cancun

MDWCUN

Chicago Midway

Mon 9/28

6:05 am-7:50 pm

1 stop13h 45m

Cancun

Wed 10/7

2:25 pm-10:33 pm

1 stop8h 08m

$458

ChicagoCancún

MDW Chicago Midway - CUN Cancun

MDWCUN

Chicago Midway

Mon 11/16

6:00 am-12:30 pm

1 stop5h 30m

Cancun

Fri 11/20

1:40 pm-10:56 pm

1 stop10h 16m

$466

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

Other information

What is the cheapest month to fly to Quintana Roo?

In general, October 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 $313. If you aren’t able to travel during the month of October, then book flights to Quintana Roo from Chicago Midway Airport during February instead. Flights to Quintana Roo in February, while not as cheap as those in October, still average around $356.

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 $440. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Quintana Roo is Wednesday, with ticket prices averaging around $555.

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 morning. Our users have found flights to Quintana Roo in the morning for as low as $493. 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 $511 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 $443 on momondo.

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

There are 2 cabin classes 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.

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	$281
Fastest flight time	3h 35m
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 $281. The best round-trip flight deal from Chicago Midway Airport to Quintana Roo found on momondo in the last 72 hours is $582.

The fastest flight from Chicago Midway Airport to Quintana Roo takes 3h 35m

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?
The number of operators available for flights from Chicago Midway Airport to Quintana Roo is 4 as of August 2026.
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?
Based on momondo bookings for flights between Chicago Midway Airport and Quintana Roo, the leading plane model is Airbus A321neo, making up 15.16% of the total bookings. Other popular models include Airbus A321 (sharklets) with 14.17%, Airbus A321-100/200 with 12.85%, and Boeing 737-900 with 12.03%.

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
Aeromexico	PriceFrom $194	Free Cancellation	Rating 7.4 1,472 reviews	Search Aeromexico flights
Frontier	PriceFrom $198	Free Cancellation	Rating 5.6 2,696 reviews	Search Frontier flights
Southwest	PriceFrom $313	Free Cancellation	Rating 8.0 4,218 reviews	Search Southwest flights
Delta	PriceFrom $327	Free Cancellation	Rating 7.8 8,503 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.