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Cheap flights from Chicago Midway Airport to Yucatan 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 Yucatan departing on 3/9. 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

Enter your travel dates to find the best prices.
Frontier Logo
6:25 am - 3:22 pm
MDW
-
CUN
7h 57m1 stop
Frontier Logo
3:07 pm - 6:13 pm
CUN
-
MDW
4h 06mnonstop
$292Frontier
Sat, Feb 28 - Sat, Mar 7
Frontier Logo
6:25 am - 3:22 pm
MDW
-
CUN
7h 57m1 stop
Frontier Logo
3:07 pm - 6:13 pm
CUN
-
MDW
4h 06mnonstop
$293Frontier
Sat, Feb 28 - Sat, Mar 7
Aeromexico Logo
10:53 am - 9:20 pm
MDW
-
CUN
9h 27m1 stop
Aeromexico Logo
8:00 am - 3:21 pm
CUN
-
MDW
8h 21m1 stop
$298Aeromexico
Sat, Feb 7 - Sat, Feb 14
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
$308Volaris
Mon, Mar 16 - Fri, Mar 20
Volaris Logo
6:54 pm - 9:48 am
MDW
-
CUN
13h 54m1 stop
Volaris Logo
10:39 am - 6:34 pm
CUN
-
MDW
7h 55m1 stop
$317Volaris
Wed, Mar 4 - Mon, Mar 9
Multiple Airlines Logo
7:30 am - 6:00 pm
MDW
-
MID
10h 30m1 stop
Multiple Airlines Logo
7:55 pm - 1:08 pm
MID
-
MDW
17h 13m2 stops
$436Multiple Airlines
Fri, Feb 27 - Sun, Mar 1
Delta Logo
6:00 am - 7:56 pm
MDW
-
MID
13h 56m2 stops
Delta Logo
9:00 am - 10:31 pm
MID
-
MDW
13h 31m2 stops
$451Delta
Mon, Feb 9 - Wed, Feb 18
Delta Logo
6:00 am - 5:33 pm
MDW
-
MID
11h 33m2 stops
Delta Logo
9:00 am - 10:31 pm
MID
-
MDW
13h 31m2 stops
$473Delta
Tue, Feb 17 - Thu, Feb 26
Multiple Airlines Logo
3:01 pm - 5:45 pm
MDW
-
MID
26h 44m1 stop
Multiple Airlines Logo
12:05 pm - 12:05 pm
MID
-
MDW
24h 00m2 stops
$497Multiple Airlines
Mon, Jan 12 - Mon, Jan 19
Aeromexico Logo
6:30 am - 6:53 pm
MDW
-
MID
13h 23m2 stops
Aeromexico Logo
6:53 am - 10:29 pm
MID
-
MDW
14h 36m2 stops
$553Aeromexico
Sat, Apr 18 - Fri, Apr 24

Southwest flights from Chicago Midway Airport to Yucatan

Our best Southwest deals on Chicago Midway Airport to Yucatan flight tickets
Southwest
Jan 12
MDW9:15 amChicago Midway
3h 40m
CUN1:55 pmCancun
Jan 15
CUN12:55 pmCancun
9h 30m
1 stop
MDW9:25 pmChicago Midway
$329
Find similar
Southwest
Jan 19
MDW6:45 amChicago Midway
6h 00m
1 stop
CUN1:45 pmCancun
Jan 22
CUN1:45 pmCancun
3h 45m
MDW4:30 pmChicago Midway
$363
Find similar
Southwest
Jan 3
MDW3:40 pmChicago Midway
3h 45m
CUN8:25 pmCancun
Jan 10
CUN1:05 pmCancun
8h 20m
1 stop
MDW8:25 pmChicago Midway
$501
Find similar

Aeromexico flights from Chicago Midway Airport to Yucatan

Our best Aeromexico deals on Chicago Midway Airport to Yucatan flight tickets
Aeromexico
Feb 7
MDW10:53 amChicago Midway
9h 27m
1 stop
CUN9:20 pmCancun
Feb 14
CUN8:00 amCancun
8h 21m
1 stop
MDW3:21 pmChicago Midway
$298
Find similar
Aeromexico
Mar 6
MDW10:49 amChicago Midway
9h 22m
1 stop
CUN9:11 pmCancun
Mar 11
CUN8:00 amCancun
8h 55m
1 stop
MDW4:55 pmChicago Midway
$324
Find similar
Aeromexico
Jan 21
MDW12:48 pmChicago Midway
7h 23m
1 stop
CUN9:11 pmCancun
Jan 28
CUN12:15 pmCancun
11h 07m
1 stop
MDW10:22 pmChicago Midway
$328
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 December 26, 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

Sat 2/28

6:25 am-3:22 pm

1 stop7h 57m

Cancun

Sat 3/7

3:07 pm-6:13 pm

Nonstop4h 06m

$292

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 2/28

6:25 am-3:22 pm

1 stop7h 57m

Cancun

Sat 3/7

3:07 pm-6:13 pm

Nonstop4h 06m

$293

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 2/7

10:53 am-9:20 pm

1 stop9h 27m

Cancun

Sat 2/14

8:00 am-3:21 pm

1 stop8h 21m

$298

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 3/16

7:54 pm-9:48 am

1 stop13h 54m

Cancun

Fri 3/20

10:39 am-6:34 pm

1 stop7h 55m

$308

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 3/4

6:54 pm-9:48 am

1 stop13h 54m

Cancun

Mon 3/9

10:39 am-6:34 pm

1 stop7h 55m

$317

ChicagoMérida

MDW - MID

MDWMID

Chicago Midway

Fri 2/27

7:30 am-6:00 pm

1 stop10h 30m

Mérida Rejon

Sun 3/1

7:55 pm-1:08 pm

2 stops17h 13m

$436

ChicagoMérida

MDW - MID

MDWMID

Chicago Midway

Mon 2/9

6:00 am-7:56 pm

2 stops13h 56m

Mérida Rejon

Wed 2/18

9:00 am-10:31 pm

2 stops13h 31m

$451

ChicagoMérida

MDW - MID

MDWMID

Chicago Midway

Tue 2/17

6:00 am-5:33 pm

2 stops11h 33m

Mérida Rejon

Thu 2/26

9:00 am-10:31 pm

2 stops13h 31m

$473

ChicagoMérida

MDW - MID

MDWMID

Chicago Midway

Mon 1/12

3:01 pm-5:45 pm

1 stop26h 44m

Mérida Rejon

Mon 1/19

12:05 pm-12:05 pm

2 stops24h 00m

$497

ChicagoMérida

MDW - MID

MDWMID

Chicago Midway

Sat 4/18

6:30 am-6:53 pm

2 stops13h 23m

Mérida Rejon

Fri 4/24

6:53 am-10:29 pm

2 stops14h 36m

$553

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 Yucatan from

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 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 30m

Direct flights

Every day

Airports in Yucatan

4 airports
The fastest flight from Chicago Midway Airport to Yucatan takes 3h 30m
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

  • 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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