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Yucatan

$92+ Cheap flights from Chicago (CHI) to Yucatan

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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MID
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Chicago to Yucatan

Keep the following information in mind while searching for Chicago to Yucatan flight deals. Data was last updated September 17, 2025.

Round-trip from

$232
(Cheapflightsfares)

One-way from

$92
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$331
From Chicago (CHI) to Yucatan
Search Deals
One-way flight from Chicago (CHI) to Yucatan
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($76 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($23 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Chicago to Yucatan

Cheapest flights from Chicago to Yucatan
Explore the most affordable flight options available from Chicago to Yucatan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/275:17 pmORD - CUN
1 stop14h 54mSpirit Airlines
Sat 10/410:20 amCUN - ORD
1 stop9h 30mSpirit Airlines
Deal found 9/17$232
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Tue 12/95:05 amORD - CUN
1 stop6h 22mMultiple Airlines
Fri 12/1211:38 amCUN - ORD
Nonstop4h 03mMultiple Airlines
Deal found 9/16$233
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Sun 10/196:30 amORD - CUN
Nonstop3h 45mMultiple Airlines
Wed 10/291:49 pmCUN - ORD
1 stop11h 14mMultiple Airlines
Deal found 9/14$234
This Expedia deal was found by Cheapflights users on 9/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/186:58 pmORD - CUN
1 stop13h 06mSpirit Airlines
Thu 10/2312:11 pmCUN - ORD
1 stop10h 15mSpirit Airlines
Deal found 9/15$235
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/15:28 pmORD - CUN
1 stop15h 36mSpirit Airlines
Sat 11/811:42 amCUN - ORD
Nonstop4h 08mSpirit Airlines
Deal found 9/14$236
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/15:28 pmORD - CUN
1 stop15h 36mSpirit Airlines
Tue 11/42:50 pmCUN - ORD
1 stop11h 13mSpirit Airlines
Deal found 9/15$238
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 11/156:00 amORD - CUN
Nonstop3h 37mSpirit Airlines
Wed 11/1911:42 amCUN - ORD
Nonstop4h 08mSpirit Airlines
Deal found 9/17$239
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 12/56:00 amORD - CUN
Nonstop3h 37mMultiple Airlines
Sat 12/1311:38 amCUN - ORD
Nonstop4h 03mMultiple Airlines
Deal found 9/16$240
This Frontier deal was found by Cheapflights users on 9/16. 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.
Tue 10/288:25 amORD - CUN
Nonstop3h 53mFrontier
Thu 11/61:28 pmCUN - ORD
Nonstop4h 08mFrontier
Deal found 9/16$241
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/46:10 amORD - CUN
Nonstop3h 37mSpirit Airlines
Mon 10/61:49 pmCUN - ORD
1 stop9h 56mSpirit Airlines
Deal found 9/16$242
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Tue 11/187:25 amORD - CUN
Nonstop3h 53mMultiple Airlines
Wed 11/2611:42 amCUN - ORD
Nonstop4h 08mMultiple Airlines
Deal found 9/17$243
This Southwest deal was found by Cheapflights users on 9/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/1610:40 amMDW - CUN
Nonstop3h 45mSouthwest
Wed 11/191:45 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 9/15$261

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago 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, Cheapflights users made 2,558,603 searches. Data last updated September 17, 2025.
Use the filters below to find and compare flights from Chicago to Yucatan that are best for you.

Fly from

Chicago

Fly to

Yucatan

Route

Depart

Return

Price

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 11/16

10:40 am-3:25 pm

Nonstop3h 45m

Cancun

Thu 11/20

1:45 pm-4:30 pm

Nonstop3h 45m

$266

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 11/15

5:05 am-2:00 pm

1 stop7h 55m

Cancun

Thu 11/20

1:45 pm-4:30 pm

Nonstop3h 45m

$285

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sat 10/4

9:00 am-7:20 pm

1 stop10h 20m

Cancun

Tue 10/7

3:38 pm-7:36 pm

Nonstop3h 58m

$307

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 10/18

6:30 am-1:40 pm

1 stop7h 10m

Cancun

Sat 11/1

11:55 am-8:20 pm

2 stops8h 25m

$310

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Fri 11/28

6:45 am-3:34 pm

1 stop7h 49m

Cancun

Tue 12/2

6:00 am-1:12 pm

1 stop8h 12m

$315

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sat 11/15

1:04 pm-9:20 pm

1 stop7h 16m

Cancun

Wed 11/19

12:25 pm-10:41 pm

1 stop11h 16m

$315

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Fri 11/28

6:45 am-9:20 pm

1 stop13h 35m

Cancun

Fri 12/5

6:00 am-1:12 pm

1 stop8h 12m

$315

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 12/9

12:55 pm-8:25 pm

1 stop6h 30m

Cancun

Sat 12/13

11:55 am-2:45 pm

Nonstop3h 50m

$315

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 11/17

8:40 am-1:25 pm

Nonstop3h 45m

Cancun

Fri 11/21

6:55 pm-12:10 am

1 stop6h 15m

$316

ChicagoMérida

ORD - MID

ORDMID

Chicago O'Hare Intl

Fri 10/24

12:25 pm-3:45 pm

1 stop28h 20m

Mérida Rejon

Sat 11/1

6:00 am-11:30 pm

1 stop16h 30m

$317

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

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

Have a flexible travel schedule? Discover the best time to fly to Yucatan from Chicago 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 Chicago to Yucatan

What is the cheapest month to book a flight from Chicago to Yucatan?

Currently, June is the cheapest month in which you can book a flight from Chicago to Yucatan (average of $499). Flying from Chicago to Yucatan in December is currently the most expensive (average of $667). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to YU?

Find hourly flight availability from Chicago to Yucatan. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 17, 2025.

When flying from Chicago to Yucatan, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Yucatan

Get insights into the airlines that provide service to Yucatan. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Yucatan. Reviews last updated September 17, 2025.
Read through reviews of airlines operating flights from Chicago to Yucatan, such as Delta, United Airlines, and American Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,961 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,961 reviews
Delta
8.0
Very good
7,961 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,926 reviews
Delta
8.0
Very good
7,961 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,961 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Viva
7.0
Good
787 reviews
Delta
8.0
Very good
7,961 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Volaris
6.6
Okay
1,154 reviews
Delta
8.0
Very good
7,961 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

Find useful and relevant information for your journey from Chicago to Yucatan. 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 Chicago to Yucatan?

    Airlines like Southwest, United Airlines, and Delta fly from Chicago to Yucatan in about 3h 45m. The time it takes to get you to your destination can typically vary by up to 6h 35m. The distance between Chicago and Yucatan is about 1434 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Chicago to Yucatan one-way?

    To fly one-way, consider booking your trip with Volaris, which is currently one of the cheapest options available, starting at $113. Southwest flights start at $119 while deals on United Airlines start at $119 one-way.

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

    When deciding which route to take from Chicago to Yucatan consider Chicago O'Hare Intl - Cancun, Chicago Midway - Cancun or Chicago O'Hare Intl - Mérida Rejon as they are the most popular.

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

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

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

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

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

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

  • What is the cheapest month to book a flight from Chicago to Yucatan?

    Currently, June is the cheapest month in which you can book a flight from Chicago to Yucatan (average of $499). Flying from Chicago to Yucatan in December is currently the most expensive (average of $667). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Chicago to Yucatan

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Chicago to Yucatan

Discover the top 5 airlines that operate flights from Chicago to Yucatan. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
VivaCheapest$234Average$345FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$285Average$320FlexibilityNo cancel feeOn-time79%
AeromexicoCheapest$473Average$531FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$490Average$596FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$540Average$706FlexibilityNo cancel feeOn-time69%

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