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Cheap flights from Chicago Midway Airport to Yucatan from $119

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 Yucatan departing on 11/10. 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 Yucatan

Cheap round-trip flights

Southwest Logo
10:40 am - 3:25 pmMDW-CUN
3h 45mnonstop
Southwest Logo
1:45 pm - 4:30 pmCUN-MDW
3h 45mnonstop
$266Southwest
Find Deal
dom., nov. 16 - jue., nov. 20
Southwest Logo
3:40 pm - 8:25 pmMDW-CUN
3h 45mnonstop
Southwest Logo
11:55 am - 2:45 pmCUN-MDW
3h 50mnonstop
$271Southwest
Find Deal
sáb., dic. 6 - sáb., dic. 13
Delta Logo
6:00 am - 9:20 pmMDW-CUN
14h 20m1 stop
Delta Logo
8:00 am - 11:32 pmCUN-MDW
16h 32m1 stop
$317Delta
Find Deal
lun., nov. 10 - mar., nov. 18
Multiple Airlines Logo
3:27 pm - 9:10 amMDW-CUN
16h 43m1 stop
Multiple Airlines Logo
12:16 pm - 5:59 pmCUN-MDW
6h 43m1 stop
$324Multiple Airlines
Find Deal
vie., nov. 14 - lun., nov. 17
Multiple Airlines Logo
11:36 am - 9:10 amMDW-CUN
20h 34m1 stop
Multiple Airlines Logo
7:42 pm - 11:30 amCUN-MDW
16h 48m1 stop
$325Multiple Airlines
Find Deal
sáb., nov. 15 - mié., nov. 19
Delta Logo
10:47 am - 9:20 pmMDW-CUN
9h 33m1 stop
Delta Logo
8:00 am - 4:38 pmCUN-MDW
9h 38m1 stop
$326Delta
Find Deal
jue., nov. 13 - mar., nov. 18
Aeromexico Logo
12:43 pm - 8:15 pmMDW-CUN
7h 32m1 stop
Aeromexico Logo
3:07 pm - 11:32 pmCUN-MDW
9h 25m1 stop
$328Aeromexico
Find Deal
mar., sep. 30 - jue., dic. 11
Frontier Logo
5:28 pm - 10:26 amMDW-CUN
16h 58m1 stop
Frontier Logo
11:16 am - 11:20 pmCUN-MDW
12h 04m1 stop
$329Frontier
Find Deal
vie., oct. 24 - lun., oct. 27
Frontier Logo
12:28 pm - 2:31 pmMDW-CUN
26h 03m1 stop
Frontier Logo
4:14 pm - 9:31 amCUN-MDW
17h 17m1 stop
$335Frontier
Find Deal
vie., oct. 10 - dom., oct. 12
Aeromexico Logo
6:00 am - 1:15 amMDW-CUN
19h 15m2 stops
Aeromexico Logo
8:00 am - 10:14 pmCUN-MDW
14h 14m1 stop
$362Aeromexico
Find Deal
sáb., oct. 18 - vie., oct. 24

Southwest flights from Chicago Midway Airport to Yucatan

Our best Southwest deals on Chicago Midway Airport to Yucatan flight tickets
Southwest
Nov 16
MDW10:40 amChicago Midway
3h 45m
CUN3:25 pmCancun
Nov 20
CUN1:45 pmCancun
3h 45m
MDW4:30 pmChicago Midway
$266
Find similar
Southwest
Dec 6
MDW3:40 pmChicago Midway
3h 45m
CUN8:25 pmCancun
Dec 13
CUN11:55 amCancun
3h 50m
MDW2:45 pmChicago Midway
$271
Find similar
Southwest
Nov 1
MDW8:20 amChicago Midway
11h 30m
2 stops
CUN7:50 pmCancun
Nov 6
CUN2:15 pmCancun
3h 45m
MDW5:00 pmChicago Midway
$280
Find similar

Aeromexico flights from Chicago Midway Airport to Yucatan

Our best Aeromexico deals on Chicago Midway Airport to Yucatan flight tickets
Aeromexico
Sep 30
MDW12:43 pmChicago Midway
7h 32m
1 stop
CUN8:15 pmCancun
Dec 11
CUN3:07 pmCancun
9h 25m
1 stop
MDW11:32 pmChicago Midway
$328
Find similar
Aeromexico
Oct 18
MDW6:00 amChicago Midway
19h 15m
2 stops
CUN1:15 amCancun
Oct 24
CUN8:00 amCancun
14h 14m
1 stop
MDW10:14 pmChicago Midway
$362
Find similar
Aeromexico
Sep 23
MDW12:43 pmChicago Midway
7h 32m
1 stop
CUN8:15 pmCancun
Sep 30
CUN8:00 amCancun
9h 35m
1 stop
MDW5:35 pmChicago Midway
$451
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Yucatan 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 septiembre 18, 2025.
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

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

dom. 11/16

10:40 am-3:25 pm

Nonstop3h 45m

Cancun

jue. 11/20

1:45 pm-4:30 pm

Nonstop3h 45m

$266

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

sáb. 12/6

3:40 pm-8:25 pm

Nonstop3h 45m

Cancun

sáb. 12/13

11:55 am-2:45 pm

Nonstop3h 50m

$271

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

lun. 11/10

6:00 am-9:20 pm

1 stop14h 20m

Cancun

mar. 11/18

8:00 am-11:32 pm

1 stop16h 32m

$317

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

vie. 11/14

3:27 pm-9:10 am

1 stop16h 43m

Cancun

lun. 11/17

12:16 pm-5:59 pm

1 stop6h 43m

$324

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

sáb. 11/15

11:36 am-9:10 am

1 stop20h 34m

Cancun

mié. 11/19

7:42 pm-11:30 am

1 stop16h 48m

$325

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

jue. 11/13

10:47 am-9:20 pm

1 stop9h 33m

Cancun

mar. 11/18

8:00 am-4:38 pm

1 stop9h 38m

$326

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

mar. 9/30

12:43 pm-8:15 pm

1 stop7h 32m

Cancun

jue. 12/11

3:07 pm-11:32 pm

1 stop9h 25m

$328

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

vie. 10/24

5:28 pm-10:26 am

1 stop16h 58m

Cancun

lun. 10/27

11:16 am-11:20 pm

1 stop12h 04m

$329

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

vie. 10/10

12:28 pm-2:31 pm

1 stop26h 03m

Cancun

dom. 10/12

4:14 pm-9:31 am

1 stop17h 17m

$335

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

sáb. 10/18

6:00 am-1:15 am

2 stops19h 15m

Cancun

vie. 10/24

8:00 am-10:14 pm

1 stop14h 14m

$362

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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

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

Southwest, Frontier, 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

1 airport
The fastest flight from Chicago Midway Airport to Yucatan takes 3h 35m
Direct flights go from Chicago Midway Airport to Yucatan every day.
There is 1 airport near Yucatan: Cancun (CUN)
Search flight deals

  • 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?

  • 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.

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sáb. 10/18
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