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Cheap flights from Yucatan to Chicago from $144

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Yucatan to Chicago departing on 1/22. 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 Yucatan to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
1:45 pm - 4:30 pmCUN-MDW
3h 45mnonstop
Southwest Logo
9:15 am - 1:55 pmMDW-CUN
3h 40mnonstop
$265Southwest
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Thu, Jan 22 - Mon, Jan 26
Delta Logo
8:00 am - 10:44 pmCUN-MDW
15h 44m1 stop
Delta Logo
9:34 am - 9:10 pmMDW-CUN
10h 36m2 stops
$274Delta
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Fri, Feb 13 - Tue, Feb 17
Delta Logo
8:00 am - 4:18 pmCUN-MDW
9h 18m1 stop
Delta Logo
9:34 am - 9:20 pmMDW-CUN
10h 46m2 stops
$275Delta
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Fri, Dec 5 - Tue, Dec 9
Frontier Logo
2:51 pm - 11:25 pmCUN-MDW
9h 34m1 stop
Frontier Logo
6:00 am - 1:36 pmMDW-CUN
6h 36m1 stop
$347Frontier
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Mon, Feb 2 - Thu, Feb 5
Frontier Logo
2:33 pm - 10:12 pmCUN-MDW
8h 39m1 stop
Frontier Logo
6:15 am - 1:48 pmMDW-CUN
6h 33m1 stop
$358Frontier
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Fri, Dec 12 - Mon, Dec 15
Multiple Airlines Logo
11:33 am - 10:12 pmCUN-MDW
35h 39m2 stops
Multiple Airlines Logo
2:16 pm - 11:51 amMDW-CUN
20h 35m1 stop
$425Multiple Airlines
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Tue, Dec 30 - Mon, Jan 5
Volaris Logo
9:29 am - 5:34 pmMID-MDW
8h 05m1 stop
Volaris Logo
6:54 pm - 8:45 amMDW-MID
13h 51m1 stop
$501Volaris
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Fri, Jan 23 - Mon, Feb 2
Volaris Logo
9:29 am - 5:34 pmMID-MDW
8h 05m1 stop
Volaris Logo
6:54 pm - 8:45 amMDW-MID
13h 51m1 stop
$512Volaris
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Fri, Jan 23 - Mon, Feb 2
Multiple Airlines Logo
12:05 pm - 10:39 pmMID-MDW
10h 34m1 stop
Multiple Airlines Logo
6:54 pm - 8:45 amMDW-MID
13h 51m1 stop
$639Multiple Airlines
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Fri, Dec 5 - Fri, Dec 12
Aeromexico Logo
9:46 am - 10:26 pmMID-MDW
12h 40m2 stops
Aeromexico Logo
6:00 am - 11:57 pmMDW-MID
17h 57m2 stops
$778Aeromexico
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Fri, Jan 23 - Mon, Feb 2

Southwest flights from Yucatan to Chicago Midway Airport

Our best Southwest deals on Yucatan to Chicago Midway Airport flight tickets
Southwest
Jan 22
CUN1:45 pmCancun
3h 45m
MDW4:30 pmChicago Midway
Jan 26
MDW9:15 amChicago Midway
3h 40m
CUN1:55 pmCancun
$265
Find similar
Southwest
Jan 22
CUN1:45 pmCancun
3h 45m
MDW4:30 pmChicago Midway
Jan 26
MDW6:50 amChicago Midway
7h 35m
1 stop
CUN3:25 pmCancun
$317
Find similar
Southwest
Nov 13
CUN2:15 pmCancun
3h 45m
MDW5:00 pmChicago Midway
Nov 17
MDW8:40 amChicago Midway
3h 45m
CUN1:25 pmCancun
$338
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Delta flights from Yucatan to Chicago Midway Airport

Our best Delta deals on Yucatan to Chicago Midway Airport flight tickets
Delta
Feb 13
CUN8:00 amCancun
15h 44m
1 stop
MDW10:44 pmChicago Midway
Feb 17
MDW9:34 amChicago Midway
10h 36m
2 stops
CUN9:10 pmCancun
$274
Find similar
Delta
Dec 5
CUN8:00 amCancun
9h 18m
1 stop
MDW4:18 pmChicago Midway
Dec 9
MDW9:34 amChicago Midway
10h 46m
2 stops
CUN9:20 pmCancun
$275
Find similar
Delta
Feb 13
CUN8:00 amCancun
15h 44m
1 stop
MDW10:44 pmChicago Midway
Feb 17
MDW6:00 amChicago Midway
9h 31m
1 stop
CUN4:31 pmCancun
$276
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momondo Fare Finder

 
Customize your flight search to find flights from Yucatan to Chicago Midway Airport 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 November 6, 2025.
Use the filters below to find and compare flights from Yucatan to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 1/22

1:45 pm-4:30 pm

Nonstop3h 45m

Chicago Midway

Mon 1/26

9:15 am-1:55 pm

Nonstop3h 40m

$265

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 2/13

8:00 am-10:44 pm

1 stop15h 44m

Chicago Midway

Tue 2/17

9:34 am-9:10 pm

2 stops10h 36m

$274

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 12/5

8:00 am-4:18 pm

1 stop9h 18m

Chicago Midway

Tue 12/9

9:34 am-9:20 pm

2 stops10h 46m

$275

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Mon 2/2

2:51 pm-11:25 pm

1 stop9h 34m

Chicago Midway

Thu 2/5

6:00 am-1:36 pm

1 stop6h 36m

$347

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 12/12

2:33 pm-10:12 pm

1 stop8h 39m

Chicago Midway

Mon 12/15

6:15 am-1:48 pm

1 stop6h 33m

$358

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Tue 12/30

11:33 am-10:12 pm

2 stops35h 39m

Chicago Midway

Mon 1/5

2:16 pm-11:51 am

1 stop20h 35m

$425

MéridaChicago

MID - MDW

MIDMDW

Mérida Rejon

Fri 1/23

9:29 am-5:34 pm

1 stop8h 05m

Chicago Midway

Mon 2/2

6:54 pm-8:45 am

1 stop13h 51m

$501

MéridaChicago

MID - MDW

MIDMDW

Mérida Rejon

Fri 1/23

9:29 am-5:34 pm

1 stop8h 05m

Chicago Midway

Mon 2/2

6:54 pm-8:45 am

1 stop13h 51m

$512

MéridaChicago

MID - MDW

MIDMDW

Mérida Rejon

Fri 12/5

12:05 pm-10:39 pm

1 stop10h 34m

Chicago Midway

Fri 12/12

6:54 pm-8:45 am

1 stop13h 51m

$639

MéridaChicago

MID - MDW

MIDMDW

Mérida Rejon

Fri 1/23

9:46 am-10:26 pm

2 stops12h 40m

Chicago Midway

Mon 2/2

6:00 am-11:57 pm

2 stops17h 57m

$778

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 Chicago from

How to get the cheapest flight ticket from Yucatan to Chicago Midway Airport

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 Yucatan to Chicago Midway?

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

Cheap Yucatan to Chicago Midway Airport flight deals and tips

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

Fastest flight time

3h 35m

Direct flights

Every day
The fastest flight from Yucatan to Chicago Midway Airport takes 3h 35m
Direct flights go from Yucatan to Chicago Midway Airport every day.
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  • When did momondo last update prices for flights from Yucatan to Chicago Midway Airport?

    Prices for flights from Yucatan to Chicago Midway Airport were last updated today.

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

    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 Yucatan to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

It is quick and easy to find Yucatan to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

Flights from Yucatan to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Yucatan.

I’m not ready to book a flight from Yucatan to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Yucatan to Chicago 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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