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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.
Frontier Logo
4:30 pm - 10:19 pm
CUN
-
MDW
6h 49m1 stop
Frontier Logo
6:20 am - 3:20 pm
MDW
-
CUN
8h 00m1 stop
$275Frontier
Fri, Jan 23 - Sun, Feb 1
Delta Logo
8:00 am - 5:55 pm
CUN
-
MDW
10h 55m2 stops
Delta Logo
9:32 am - 9:11 pm
MDW
-
CUN
10h 39m2 stops
$278Delta
Wed, Jan 28 - Wed, Feb 4
Delta Logo
8:00 am - 5:55 pm
CUN
-
MDW
10h 55m2 stops
Delta Logo
9:33 am - 9:11 pm
MDW
-
CUN
10h 38m2 stops
$279Delta
Thu, Jan 29 - Thu, Feb 5
Frontier Logo
3:14 pm - 10:17 pm
CUN
-
MDW
8h 03m1 stop
Frontier Logo
6:10 am - 3:10 pm
MDW
-
CUN
8h 00m1 stop
$301Frontier
Thu, Jan 8 - Sat, Jan 17
Frontier Logo
3:14 pm - 10:17 pm
CUN
-
MDW
8h 03m1 stop
Frontier Logo
4:31 pm - 12:38 pm
MDW
-
CUN
19h 07m2 stops
$308Frontier
Thu, Jan 8 - Mon, Jan 12
Frontier Logo
3:34 pm - 10:27 pm
CUN
-
MDW
7h 53m1 stop
Frontier Logo
6:10 am - 3:10 pm
MDW
-
CUN
8h 00m1 stop
$317Frontier
Sat, Jan 10 - Sun, Jan 18
Aeromexico Logo
5:46 am - 10:31 pm
MID
-
MDW
16h 45m2 stops
Aeromexico Logo
6:25 am - 8:08 am
MDW
-
MID
26h 43m2 stops
$434Aeromexico
Thu, Mar 5 - Mon, Mar 9
Volaris Logo
9:29 am - 5:34 pm
MID
-
MDW
8h 05m1 stop
Volaris Logo
6:54 pm - 8:45 am
MDW
-
MID
13h 51m1 stop
$475Volaris
Mon, Feb 9 - Mon, Feb 16
Volaris Logo
9:29 am - 5:34 pm
MID
-
MDW
8h 05m1 stop
Volaris Logo
6:54 pm - 8:45 am
MDW
-
MID
13h 51m1 stop
$519Volaris
Wed, Feb 11 - Wed, Feb 18
Aeromexico Logo
7:55 pm - 5:29 pm
MID
-
MDW
21h 34m2 stops
Aeromexico Logo
12:45 pm - 8:12 am
MDW
-
MID
19h 27m2 stops
$583Aeromexico
Mon, Feb 9 - Mon, Feb 16

Delta flights from Yucatan to Chicago Midway Airport

Our best Delta deals on Yucatan to Chicago Midway Airport flight tickets
Delta
Dec 29
CUN8:00 amCancun
10h 26m
2 stops
MDW5:26 pmChicago Midway
Jan 5
MDW6:45 amChicago Midway
6h 18m
1 stop
CUN2:03 pmCancun
$278
Find similar
Delta
Jan 29
CUN8:00 amCancun
10h 55m
2 stops
MDW5:55 pmChicago Midway
Feb 5
MDW9:33 amChicago Midway
10h 38m
2 stops
CUN9:11 pmCancun
$279
Find similar
Delta
May 6
CUN8:35 amCancun
13h 54m
2 stops
MDW10:29 pmChicago Midway
May 12
MDW6:00 amChicago Midway
6h 45m
1 stop
CUN12:45 pmCancun
$320
Find similar

Aeromexico flights from Yucatan to Chicago Midway Airport

Our best Aeromexico deals on Yucatan to Chicago Midway Airport flight tickets
Aeromexico
Jan 22
CUN12:15 pmCancun
6h 14m
1 stop
MDW5:29 pmChicago Midway
Jan 31
MDW6:25 amChicago Midway
9h 10m
1 stop
CUN4:35 pmCancun
$339
Find similar
Aeromexico
Jan 17
CUN8:00 amCancun
9h 29m
1 stop
MDW4:29 pmChicago Midway
Jan 21
MDW10:46 amChicago Midway
9h 25m
1 stop
CUN9:11 pmCancun
$342
Find similar
Aeromexico
May 5
CUN10:55 amCancun
11h 34m
1 stop
MDW10:29 pmChicago Midway
May 12
MDW10:35 amChicago Midway
12h 52m
2 stops
CUN11:27 pmCancun
$380
Find similar

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 December 28, 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

Fri 1/23

4:30 pm-10:19 pm

1 stop6h 49m

Chicago Midway

Sun 2/1

6:20 am-3:20 pm

1 stop8h 00m

$275

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 1/28

8:00 am-5:55 pm

2 stops10h 55m

Chicago Midway

Wed 2/4

9:32 am-9:11 pm

2 stops10h 39m

$278

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 1/29

8:00 am-5:55 pm

2 stops10h 55m

Chicago Midway

Thu 2/5

9:33 am-9:11 pm

2 stops10h 38m

$279

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 1/8

3:14 pm-10:17 pm

1 stop8h 03m

Chicago Midway

Sat 1/17

6:10 am-3:10 pm

1 stop8h 00m

$301

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 1/8

3:14 pm-10:17 pm

1 stop8h 03m

Chicago Midway

Mon 1/12

4:31 pm-12:38 pm

2 stops19h 07m

$308

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sat 1/10

3:34 pm-10:27 pm

1 stop7h 53m

Chicago Midway

Sun 1/18

6:10 am-3:10 pm

1 stop8h 00m

$317

MéridaChicago

MID - MDW

MIDMDW

Mérida Rejon

Thu 3/5

5:46 am-10:31 pm

2 stops16h 45m

Chicago Midway

Mon 3/9

6:25 am-8:08 am

2 stops26h 43m

$434

MéridaChicago

MID - MDW

MIDMDW

Mérida Rejon

Mon 2/9

9:29 am-5:34 pm

1 stop8h 05m

Chicago Midway

Mon 2/16

6:54 pm-8:45 am

1 stop13h 51m

$475

MéridaChicago

MID - MDW

MIDMDW

Mérida Rejon

Wed 2/11

9:29 am-5:34 pm

1 stop8h 05m

Chicago Midway

Wed 2/18

6:54 pm-8:45 am

1 stop13h 51m

$519

MéridaChicago

MID - MDW

MIDMDW

Mérida Rejon

Mon 2/9

7:55 pm-5:29 pm

2 stops21h 34m

Chicago Midway

Mon 2/16

12:45 pm-8:12 am

2 stops19h 27m

$583

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?

Delta is the most popular carrier 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 40m

Direct flights

Every day
The fastest flight from Yucatan to Chicago Midway Airport takes 3h 40m
Direct flights go from Yucatan to Chicago Midway Airport every day.
Search flight deals

  • 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
Valparaiso
Schererville
Munster
Crown Point
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.

An easier way to manage your Chicago Midway Airport trip

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