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

The number of flights available between Chicago Midway Airport and Yucatan is 5 per week as of August 2026. The most frequent departure day is Mon, with 20% of weekly flights leaving on this day.

When did momondo last update prices for flights from Chicago Midway Airport to Yucatan?

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

How many operators does momondo search for flights from Chicago Midway Airport to Yucatan?

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

How old do you have to be to fly from Chicago Midway Airport to Yucatan?

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 Yucatan.

What documentation or ID do you need to fly to Yucatan?

The necessary travel and health documents for your Yucatan 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.

$97 Cheap Flights from Chicago Midway Airport to Yucatan in 2026

Find the cheapest flights from Chicago Midway Airport to Yucatan

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

$365Volaris

Sun, Oct 4 - Wed, Oct 7

9:26 pm - 10:00 amMDW Chicago Midway-CUN Cancun

12h 34m1 stop Dallas/Fort Worth

1:51 pm - 11:44 pmCUN Cancun-MDW Chicago Midway

9h 53m1 stop Atlanta Hartsfield-Jackson

$365Frontier

Sun, Sep 6 - Fri, Sep 18

6:05 am - 1:54 pmMDW Chicago Midway-CUN Cancun

7h 49m1 stop Atlanta Hartsfield-Jackson

1:51 pm - 11:44 pmCUN Cancun-MDW Chicago Midway

9h 53m1 stop Atlanta Hartsfield-Jackson

$366Frontier

Sun, Sep 6 - Fri, Sep 11

8:23 pm - 8:46 amMDW Chicago Midway-MID Mérida Rejon

13h 23m1 stop Guadalajara Miguel Hidal

9:18 am - 7:04 pmMID Mérida Rejon-MDW Chicago Midway

8h 46m1 stop Guadalajara Miguel Hidal

$372Volaris

Mon, Sep 28 - Mon, Oct 5

5:15 am - 1:30 pmMDW Chicago Midway-CUN Cancun

7h 15m1 stop Austin Bergstrom

8:20 am - 5:00 pmCUN Cancun-MDW Chicago Midway

9h 40m2 stops Houston Hobby Louisville Intl

$382Southwest

Sun, Nov 1 - Fri, Nov 6

5:15 am - 1:30 pmMDW Chicago Midway-CUN Cancun

7h 15m1 stop Austin Bergstrom

4:35 pm - 12:05 amCUN Cancun-MDW Chicago Midway

8h 30m1 stop Austin Bergstrom

$382Southwest

Sun, Nov 1 - Fri, Nov 6

6:04 am - 2:25 pmMDW Chicago Midway-CUN Cancun

8h 21m1 stop Atlanta Hartsfield-Jackson

7:01 am - 10:33 pmCUN Cancun-MDW Chicago Midway

15h 32m2 stops Mexico City Benito Juarez Atlanta Hartsfield-Jackson

$458Aeromexico

Mon, Oct 19 - Wed, Oct 28

1:00 pm - 7:50 pmMDW Chicago Midway-CUN Cancun

6h 50m1 stop Atlanta Hartsfield-Jackson

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

8h 10m1 stop Atlanta Hartsfield-Jackson

$458Aeromexico

Tue, Sep 29 - Wed, Sep 30

10:59 am - 7:55 pmMDW Chicago Midway-CUN Cancun

8h 56m1 stop Atlanta Hartsfield-Jackson

8:00 am - 10:33 pmCUN Cancun-MDW Chicago Midway

14h 33m1 stop Atlanta Hartsfield-Jackson

$458Delta

Wed, Oct 14 - Tue, Oct 20

6:04 am - 2:25 pmMDW Chicago Midway-CUN Cancun

8h 21m1 stop Atlanta Hartsfield-Jackson

8:00 am - 10:33 pmCUN Cancun-MDW Chicago Midway

14h 33m1 stop Atlanta Hartsfield-Jackson

$458Delta

Sun, Oct 18 - Tue, Oct 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

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

8h 24m1 stop Guadalajara Miguel Hidal

$492Volaris

Fri, Aug 21 - Fri, Aug 28

6:05 am - 1:54 pmMDW Chicago Midway-CUN Cancun

7h 49m1 stop Atlanta Hartsfield-Jackson

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

7h 41m1 stop Atlanta Hartsfield-Jackson

$506Frontier

Sat, Aug 22 - Sat, Aug 29

6:05 am - 1:54 pmMDW Chicago Midway-CUN Cancun

7h 49m1 stop Atlanta Hartsfield-Jackson

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

7h 41m1 stop Atlanta Hartsfield-Jackson

$524Frontier

Sat, Aug 22 - Sat, Aug 29

10:54 am - 8:05 pmMDW Chicago Midway-CUN Cancun

9h 11m1 stop Atlanta Hartsfield-Jackson

9:20 am - 10:36 pmCUN Cancun-MDW Chicago Midway

13h 16m2 stops Mexico City Benito Juarez Atlanta Hartsfield-Jackson

$537Delta

Fri, Aug 21 - Wed, Sep 2

10:54 am - 8:05 pmMDW Chicago Midway-CUN Cancun

9h 11m1 stop Atlanta Hartsfield-Jackson

2:10 pm - 10:36 pmCUN Cancun-MDW Chicago Midway

8h 26m1 stop Atlanta Hartsfield-Jackson

$537Delta

Fri, Aug 21 - Wed, Sep 2

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

3h 35mnonstop

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

3h 35mnonstop

$549Southwest

Fri, Aug 21 - Fri, Aug 28

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

3h 35mnonstop

11:35 am - 6:15 pmCUN Cancun-MDW Chicago Midway

6h 40m1 stop Houston Hobby

$582Southwest

Fri, Aug 21 - Fri, Aug 28

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

$590Volaris

Fri, Aug 21 - Mon, Aug 24

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

$607Volaris

Wed, Aug 19 - Fri, Aug 21

11:50 am - 1:54 pmMDW Chicago Midway-CUN Cancun

26h 04m1 stop Atlanta Hartsfield-Jackson

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

9h 21m1 stop Dallas/Fort Worth

$617Frontier

Fri, Aug 21 - Fri, Aug 28

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Frontier flights from Chicago Midway Airport to Yucatan

Our best Frontier deals on Chicago Midway Airport to Yucatan flight tickets

Frontier

Sep 6

MDW9:26 pmChicago Midway

12h 34m

1 stop

CUN10:00 amCancun

Sep 18

CUN1:51 pmCancun

9h 53m

1 stop

MDW11:44 pmChicago Midway

$365

Frontier

Sep 6

MDW6:05 amChicago Midway

7h 49m

1 stop

CUN1:54 pmCancun

Sep 11

CUN1:51 pmCancun

9h 53m

1 stop

MDW11:44 pmChicago Midway

$366

Frontier

Nov 9

MDW7:25 amChicago Midway

5h 49m

1 stop

CUN2:14 pmCancun

Nov 13

CUN3:24 pmCancun

7h 29m

1 stop

MDW9:53 pmChicago Midway

$376

Southwest flights from Chicago Midway Airport to Yucatan

Our best Southwest deals on Chicago Midway Airport to Yucatan flight tickets

Southwest

Nov 1

MDW5:15 amChicago Midway

7h 15m

1 stop

CUN1:30 pmCancun

Nov 6

CUN8:20 amCancun

9h 40m

2 stops

MDW5:00 pmChicago Midway

$382

Southwest

Nov 8

MDW6:30 amChicago Midway

5h 35m

1 stop

CUN1:05 pmCancun

Nov 12

CUN2:10 pmCancun

3h 40m

MDW4:50 pmChicago Midway

$392

Southwest

Nov 8

MDW6:30 amChicago Midway

5h 35m

1 stop

CUN1:05 pmCancun

Nov 13

CUN6:55 pmCancun

7h 10m

1 stop

MDW1:05 amChicago Midway

$402

momondo Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Yucatan 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

Sun 10/4

8:23 pm-9:55 am

1 stop13h 32m

Cancun

Wed 10/7

10:40 am-7:04 pm

1 stop8h 24m

$365

ChicagoCancún

MDW Chicago Midway - CUN Cancun

MDWCUN

Chicago Midway

Sun 9/6

9:26 pm-10:00 am

1 stop12h 34m

Cancun

Fri 9/18

1:51 pm-11:44 pm

1 stop9h 53m

$365

ChicagoCancún

MDW Chicago Midway - CUN Cancun

MDWCUN

Chicago Midway

Sun 9/6

6:05 am-1:54 pm

1 stop7h 49m

Cancun

Fri 9/11

1:51 pm-11:44 pm

1 stop9h 53m

$366

ChicagoMérida

MDW Chicago Midway - MID Mérida Rejon

MDWMID

Chicago Midway

Mon 9/28

8:23 pm-8:46 am

1 stop13h 23m

Mérida Rejon

Mon 10/5

9:18 am-7:04 pm

1 stop8h 46m

$372

ChicagoCancún

MDW Chicago Midway - CUN Cancun

MDWCUN

Chicago Midway

Sun 11/1

5:15 am-1:30 pm

1 stop7h 15m

Cancun

Fri 11/6

8:20 am-5:00 pm

2 stops9h 40m

$382

ChicagoCancún

MDW Chicago Midway - CUN Cancun

MDWCUN

Chicago Midway

Sun 11/1

5:15 am-1:30 pm

1 stop7h 15m

Cancun

Fri 11/6

4:35 pm-12:05 am

1 stop8h 30m

$382

ChicagoCancún

MDW Chicago Midway - CUN Cancun

MDWCUN

Chicago Midway

Mon 10/19

6:04 am-2:25 pm

1 stop8h 21m

Cancun

Wed 10/28

7:01 am-10:33 pm

2 stops15h 32m

$458

Quickest round-trip

ChicagoCancún

MDW Chicago Midway - CUN Cancun

MDWCUN

Chicago Midway

Tue 9/29

1:00 pm-7:50 pm

1 stop6h 50m

Cancun

Wed 9/30

8:05 am-4:15 pm

1 stop8h 10m

$458

ChicagoCancún

MDW Chicago Midway - CUN Cancun

MDWCUN

Chicago Midway

Wed 10/14

10:59 am-7:55 pm

1 stop8h 56m

Cancun

Tue 10/20

8:00 am-10:33 pm

1 stop14h 33m

$458

ChicagoCancún

MDW Chicago Midway - CUN Cancun

MDWCUN

Chicago Midway

Sun 10/18

6:04 am-2:25 pm

1 stop8h 21m

Cancun

Tue 10/20

8:00 am-10:33 pm

1 stop14h 33m

$458

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 Yucatan

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

Airlines

Other information

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

Volaris, Southwest, and Delta are the most popular carriers operating from Chicago Midway to Yucatan

Cheap Chicago Midway Airport to Yucatan flight deals and tips

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

Fastest flight time	3h 35m
Direct flights	Every day
Airports in Yucatan	4 airports

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

Direct flights go from Chicago Midway Airport to Yucatan every day.

There are 4 airports in Yucatan. From Chicago Midway Airport there are direct flights to Cancun (CUN).

Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Yucatan

When did momondo last update prices for flights from Chicago Midway Airport to Yucatan?
Prices for flights from Chicago Midway Airport to Yucatan are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago Midway Airport to Yucatan?
The number of operators available for flights from Chicago Midway Airport to Yucatan is 4 as of August 2026.
How old do you have to be to fly from Chicago Midway Airport to Yucatan?
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 Yucatan.
What documentation or ID do you need to fly to Yucatan?
The necessary travel and health documents for your Yucatan 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.

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Yucatan. momondo saves you time and could save you money on your trip.

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

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

How can momondo help me find flights from Chicago to Yucatan?

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

Of course. momondo tracks the price of Chicago to Yucatan flights. All you need is a valid email address and we will do the rest; it is that quick and easy.