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Cheap flights from Yucatan to Chicago from $190

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 8/20. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Yucatan to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Volaris Logo
10:40 am - 7:04 pm
CUN
-
MDW
8h 24m
1 stop
Volaris Logo
8:23 pm - 9:55 am
MDW
-
CUN
13h 32m
1 stop
$356Volaris
Mon, Jul 13 - Mon, Jul 20
Southwest Logo
1:05 pm - 4:40 pm
CUN
-
MDW
3h 35mnonstop
Southwest Logo
8:25 am - 12:00 pm
MDW
-
CUN
3h 35mnonstop
$365Southwest
Thu, Aug 27 - Mon, Aug 31
Frontier Logo
3:55 pm - 10:58 am
CUN
-
MDW
19h 03m
1 stop
Frontier Logo
12:03 pm - 2:45 pm
MDW
-
CUN
26h 42m
1 stop
$383Frontier
Fri, Sep 11 - Wed, Sep 16
Frontier Logo
3:06 pm - 11:07 am
CUN
-
MDW
20h 01m
1 stop
Frontier Logo
12:11 pm - 1:46 pm
MDW
-
CUN
25h 35m
1 stop
$386Frontier
Sat, Jul 25 - Tue, Jul 28
Delta Logo
8:00 am - 4:25 pm
CUN
-
MDW
8h 25m
1 stop
Delta Logo
10:35 am - 8:15 pm
MDW
-
CUN
9h 40m
1 stop
$389Delta
Thu, Oct 22 - Mon, Oct 26
Delta Logo
8:05 am - 10:36 pm
CUN
-
MDW
14h 31m
1 stop
Delta Logo
6:05 am - 6:44 pm
MDW
-
CUN
12h 39m
2 stops
$390Delta
Mon, Aug 17 - Mon, Aug 24
Delta Logo
8:05 am - 6:33 pm
CUN
-
MDW
10h 28m
2 stops
Delta Logo
6:05 am - 11:25 am
MDW
-
CUN
5h 20m
1 stop
$391Delta
Thu, Aug 27 - Mon, Aug 31
Delta Logo
8:00 am - 10:10 pm
CUN
-
MDW
14h 10m
1 stop
Delta Logo
6:00 am - 3:10 pm
MDW
-
CUN
8h 10m
1 stop
$392Delta
Tue, Oct 27 - Tue, Nov 3
Frontier Logo
11:10 am - 8:32 pm
CUN
-
MDW
9h 22m
1 stop
Frontier Logo
6:05 am - 1:46 pm
MDW
-
CUN
7h 41m
1 stop
$394Frontier
Thu, Aug 13 - Mon, Aug 17
Multiple Airlines Logo
9:18 am - 7:04 pm
MID
-
MDW
8h 46m
1 stop
Multiple Airlines Logo
9:26 pm - 8:10 pm
MDW
-
MID
23h 44m
2 stops
$539Multiple Airlines
Sun, Aug 30 - Mon, Aug 31

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Southwest flights from Yucatan to Chicago Midway Airport

Our best Southwest deals on Yucatan to Chicago Midway Airport flight tickets
Southwest
Aug 27
CUN1:05 pmCancun
3h 35m
MDW4:40 pmChicago Midway
Aug 31
MDW8:25 amChicago Midway
3h 35m
CUN12:00 pmCancun
$365
Southwest
Aug 27
CUN1:05 pmCancun
3h 35m
MDW4:40 pmChicago Midway
Aug 31
MDW7:30 amChicago Midway
6h 40m
1 stop
CUN2:10 pmCancun
$408
Southwest
Aug 27
CUN1:05 pmCancun
3h 35m
MDW4:40 pmChicago Midway
Aug 31
MDW8:25 amChicago Midway
3h 35m
CUN12:00 pmCancun
$442

Frontier flights from Yucatan to Chicago Midway Airport

Our best Frontier deals on Yucatan to Chicago Midway Airport flight tickets
Frontier
Sep 11
CUN3:55 pmCancun
19h 03m
1 stop
MDW10:58 amChicago Midway
Sep 16
MDW12:03 pmChicago Midway
26h 42m
1 stop
CUN2:45 pmCancun
$383
Frontier
Jul 25
CUN3:06 pmCancun
20h 01m
1 stop
MDW11:07 amChicago Midway
Jul 28
MDW12:11 pmChicago Midway
25h 35m
1 stop
CUN1:46 pmCancun
$386
Frontier
Aug 13
CUN11:10 amCancun
9h 22m
1 stop
MDW8:32 pmChicago Midway
Aug 17
MDW6:05 amChicago Midway
7h 41m
1 stop
CUN1:46 pmCancun
$394

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 June 23, 2026.
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

Cheapest round-trip

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Mon 7/13

10:40 am-7:04 pm

1 stop8h 24m

Chicago Midway

Mon 7/20

8:23 pm-9:55 am

1 stop13h 32m

$356
Quickest round-trip

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 8/27

1:05 pm-4:40 pm

Nonstop3h 35m

Chicago Midway

Mon 8/31

8:25 am-12:00 pm

Nonstop3h 35m

$365

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 9/11

3:55 pm-10:58 am

1 stop19h 03m

Chicago Midway

Wed 9/16

12:03 pm-2:45 pm

1 stop26h 42m

$383

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sat 7/25

3:06 pm-11:07 am

1 stop20h 01m

Chicago Midway

Tue 7/28

12:11 pm-1:46 pm

1 stop25h 35m

$386

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 10/22

8:00 am-4:25 pm

1 stop8h 25m

Chicago Midway

Mon 10/26

10:35 am-8:15 pm

1 stop9h 40m

$389

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Mon 8/17

8:05 am-10:36 pm

1 stop14h 31m

Chicago Midway

Mon 8/24

6:05 am-6:44 pm

2 stops12h 39m

$390

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 8/27

8:05 am-6:33 pm

2 stops10h 28m

Chicago Midway

Mon 8/31

6:05 am-11:25 am

1 stop5h 20m

$391

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Tue 10/27

8:00 am-10:10 pm

1 stop14h 10m

Chicago Midway

Tue 11/3

6:00 am-3:10 pm

1 stop8h 10m

$392

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 8/13

11:10 am-8:32 pm

1 stop9h 22m

Chicago Midway

Mon 8/17

6:05 am-1:46 pm

1 stop7h 41m

$394

MéridaChicago

MID - MDW

MIDMDW

Mérida Rejon

Sun 8/30

9:18 am-7:04 pm

1 stop8h 46m

Chicago Midway

Mon 8/31

9:26 pm-8:10 pm

2 stops23h 44m

$539

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, Delta, and Volaris 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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Frequently asked questions about flying from Yucatan to Chicago Midway Airport

  • 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
Portage
Benton Harbor
Saint Joseph
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.

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