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$144+ Cheap flights from Yucatan to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
MID — CHI
Mar 8 — Mar 151
Sun 3/8
Sun 3/15
1 adult, Economy
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Cheap flight deals from Yucatan to Chicago

Cheapest flights from Yucatan to Chicago
Explore the most affordable flight options available from Yucatan to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 6, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/136:27 pm
CUN
-
ORD
Nonstop4h 10m
Frontier
Sun 2/226:10 am
ORD
-
CUN
Nonstop4h 04m
Frontier
Deal found 2/4$154
This Kiwi.com deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/711:40 am
CUN
-
ORD
Nonstop4h 09m
Frontier
Mon 2/97:11 am
ORD
-
CUN
Nonstop4h 08m
Frontier
Deal found 2/3$169
This Kiwi.com deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/196:27 pm
CUN
-
ORD
Nonstop4h 10m
Frontier
Tue 2/247:55 am
ORD
-
CUN
Nonstop4h 12m
Frontier
Deal found 2/3$170
This Frontier deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3010:40 am
CUN
-
ORD
Nonstop4h 09m
Frontier
Sun 5/106:30 am
ORD
-
CUN
Nonstop4h 03m
Frontier
Deal found 2/4$172
This Kiwi.com deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/196:27 pm
CUN
-
ORD
Nonstop4h 10m
Frontier
Sun 3/16:10 am
ORD
-
CUN
Nonstop4h 04m
Frontier
Deal found 2/3$173
This Frontier deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/196:27 pm
CUN
-
ORD
Nonstop4h 10m
Frontier
Mon 2/236:10 am
ORD
-
CUN
Nonstop4h 04m
Frontier
Deal found 2/4$176
This Frontier deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/611:40 am
CUN
-
ORD
Nonstop4h 09m
Frontier
Mon 2/97:11 am
ORD
-
CUN
Nonstop4h 08m
Frontier
Deal found 2/4$183
This Kiwi.com deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/47:19 pm
CUN
-
ORD
Nonstop4h 09m
Frontier
Wed 3/116:30 am
ORD
-
CUN
Nonstop4h 04m
Frontier
Deal found 2/3$193
This Kiwi.com deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/511:40 am
CUN
-
ORD
Nonstop4h 09m
Frontier
Sun 2/87:11 am
ORD
-
CUN
Nonstop4h 08m
Frontier
Deal found 2/3$195
This Kiwi.com deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/196:27 pm
CUN
-
ORD
Nonstop4h 10m
Frontier
Sun 2/226:10 am
ORD
-
CUN
Nonstop4h 04m
Frontier
Deal found 2/5$196
This Kiwi.com deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/56:27 pm
CUN
-
ORD
Nonstop4h 10m
Frontier
Tue 3/106:30 am
ORD
-
CUN
Nonstop4h 04m
Frontier
Deal found 2/3$197
This Priceline deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/73:07 pm
CUN
-
MDW
Nonstop4h 06m
Frontier
Wed 3/116:05 am
MDW
-
CUN
1 stop8h 54m
Frontier
Deal found 2/4$251

Find flight deals from Yucatan to Chicago

Keep the following information in mind while searching for Yucatan to Chicago flight deals. Data was last updated February 6, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$170
(Kiwi.com)

One-way from

$144
(OneTravel)

Popular in

April

Cheapest in

February

Average price

$367
Provider with most accurate pricing for Mérida Rejon-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Mérida Rejon-Chicago (CHI) flights.
Search Deals
From Yucatan to Chicago (CHI)
Search Deals
One-way flight from Yucatan to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($11 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Yucatan to Chicago 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, Cheapflights users made 2,558,603 searches. Data last updated February 6, 2026.
Use the filters below to find and compare flights from Yucatan to Chicago that are best for you.

Fly from

Yucatan

Fly to

Chicago

Route

Depart

Return

Price

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 2/19

6:27 pm-9:37 pm

Nonstop4h 10m

Chicago O'Hare Intl

Mon 2/23

6:10 am-11:14 am

Nonstop4h 04m

$194

CancúnChicago

CUN - ORD

CUNORD

Cancun

Fri 5/8

10:40 am-2:49 pm

Nonstop4h 09m

Chicago O'Hare Intl

Mon 5/11

1:59 am-10:31 am

1 stop8h 32m

$218

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 4/30

12:55 pm-5:00 pm

Nonstop4h 05m

Chicago O'Hare Intl

Sun 5/10

10:31 am-2:26 pm

Nonstop3h 55m

$221

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 4/23

12:55 pm-5:00 pm

Nonstop4h 05m

Chicago O'Hare Intl

Mon 4/27

5:48 am-12:33 pm

1 stop6h 45m

$221

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 2/19

4:45 pm-7:45 pm

Nonstop4h 00m

Chicago O'Hare Intl

Mon 2/23

8:10 pm-12:54 pm

1 stop15h 44m

$221

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 4/16

12:55 pm-5:00 pm

Nonstop4h 05m

Chicago O'Hare Intl

Tue 4/21

10:31 am-2:26 pm

Nonstop3h 55m

$221

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 5/7

12:11 pm-4:16 pm

Nonstop4h 05m

Chicago O'Hare Intl

Mon 5/11

10:45 pm-10:06 am

1 stop11h 21m

$222

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 2/19

3:18 pm-6:09 pm

Nonstop3h 51m

Chicago O'Hare Intl

Sun 3/1

5:45 am-3:59 pm

1 stop9h 14m

$222

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 2/19

3:18 pm-6:09 pm

Nonstop3h 51m

Chicago O'Hare Intl

Sun 2/22

9:15 pm-12:54 pm

1 stop14h 39m

$222

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 4/30

12:40 pm-10:28 pm

1 stop9h 48m

Chicago Midway

Tue 5/5

10:43 am-8:14 pm

1 stop9h 31m

$278

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/6

Showing 1-10 of 60 results
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Best time to book a flight from Yucatan to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Yucatan with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Yucatan to Chicago

How much does it cost to fly round-trip from Yucatan to Chicago?

Related info for your journey

Find useful and relevant information for your journey from Yucatan to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Yucatan to Chicago?

    Departing from Yucatan to Chicago will take you 4h 05m. Yucatan and Chicago are separated by a distance of 1447 mi. This flight may include one or multiple stops.

  • What are the most popular routes from Yucatan to Chicago?

    The most popular route from Yucatan to Chicago is Cancun - Chicago O'Hare Intl. You may also consider Cancun - Chicago Midway or Mérida Rejon - Chicago O'Hare Intl.

  • Can I find deals for flights from Yucatan to Chicago that include hotel bookings?

    Yes. In addition to deals on Yucatan to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Yucatan to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Yucatan to Chicago.

  • Can I find deals for business class flights from Yucatan to Chicago?

    Yes. Cheapflights offers flight deals from Yucatan to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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