Yucatan

$96+ 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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MID
Mar 10 — Mar 171
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Cheap 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 February 8, 2026.

This Frontier deal was found by Cheapflights users on 2/6. 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.
Sun 2/87:11 am
ORD
-
CUN
Nonstop4h 08m
Frontier
Fri 2/136:27 pm
CUN
-
ORD
Nonstop4h 10m
Frontier
Deal found 2/6$232
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/225:15 am
ORD
-
CUN
1 stop6h 05m
Spirit Airlines
Thu 2/2611:59 am
CUN
-
ORD
Nonstop3h 54m
Spirit Airlines
Deal found 2/5$233
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.
Tue 2/2411:59 pm
ORD
-
CUN
1 stop8h 49m
Multiple Airlines
Thu 3/56:27 pm
CUN
-
ORD
Nonstop4h 10m
Multiple Airlines
Deal found 2/5$234
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/176:23 am
ORD
-
CUN
1 stop14h 03m
Multiple Airlines
Thu 2/266:27 pm
CUN
-
ORD
Nonstop4h 10m
Multiple Airlines
Deal found 2/5$236
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/166:23 am
ORD
-
CUN
1 stop14h 03m
Multiple Airlines
Wed 2/251:25 pm
CUN
-
ORD
1 stop11h 22m
Multiple Airlines
Deal found 2/4$237
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.
Sat 2/2111:59 pm
ORD
-
CUN
1 stop14h 29m
Multiple Airlines
Wed 2/251:25 pm
CUN
-
ORD
1 stop6h 46m
Multiple Airlines
Deal found 2/4$238
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.
Mon 2/97:11 am
ORD
-
CUN
Nonstop4h 08m
Frontier
Sat 2/146:27 pm
CUN
-
ORD
Nonstop4h 10m
Frontier
Deal found 2/5$239
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/186:30 am
ORD
-
CUN
Nonstop4h 03m
Frontier
Wed 4/2210:40 am
CUN
-
ORD
Nonstop4h 09m
Frontier
Deal found 2/5$240
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/226:10 am
ORD
-
CUN
Nonstop4h 04m
Frontier
Thu 2/266:27 pm
CUN
-
ORD
Nonstop4h 10m
Frontier
Deal found 2/5$241
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.
Wed 5/66:30 am
ORD
-
CUN
Nonstop4h 03m
Multiple Airlines
Wed 5/131:00 pm
CUN
-
ORD
1 stop7h 25m
Multiple Airlines
Deal found 2/4$242
This Kiwi.com deal was found by Cheapflights users on 2/6. 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 3/81:00 am
ORD
-
CUN
1 stop13h 00m
Volaris
Fri 3/1311:12 am
CUN
-
ORD
1 stop11h 36m
Volaris
Deal found 2/6$244
This Super.com deal was found by Cheapflights users on 2/8. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/79:00 am
MDW
-
CUN
Nonstop4h 02m
Frontier
Sat 3/143:07 pm
CUN
-
MDW
Nonstop4h 06m
Frontier
Deal found 2/8$245

Find flight deals from Chicago to Yucatan

Keep the following information in mind while searching for Chicago to Yucatan flight deals. Data was last updated February 8, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$232
(Kiwi.com)

One-way from

$96
(FlightHub)

Popular in

July

Cheapest in

September

Average price

$555
Provider with most accurate pricing for Chicago (CHI)-Mérida Rejon flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-Mérida Rejon flights.
From Chicago (CHI) to Yucatan
One-way flight from Chicago (CHI) to Yucatan
Highest demand for flights based on searches. 3% potential increase in price ($21 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
Average for round-trip flights in February 2026

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 February 8, 2026.
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

ChicagoMérida

ORD - MID

ORDMID

Chicago O'Hare Intl

Sat 3/7

11:59 pm-8:45 am

1 stop8h 46m

Mérida Rejon

Sat 3/14

8:17 pm-11:19 am

1 stop14h 02m

$283

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 3/9

4:05 pm-7:45 pm

Nonstop3h 40m

Cancun

Fri 3/13

8:30 am-12:10 pm

Nonstop3h 40m

$293

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 3/10

8:05 am-11:50 am

Nonstop3h 45m

Cancun

Tue 3/17

8:30 am-12:10 pm

Nonstop3h 40m

$293

ChicagoMérida

ORD - MID

ORDMID

Chicago O'Hare Intl

Sat 2/21

11:59 pm-8:45 am

1 stop8h 46m

Mérida Rejon

Thu 2/26

9:29 am-10:29 pm

1 stop13h 00m

$295

ChicagoMérida

ORD - MID

ORDMID

Chicago O'Hare Intl

Wed 4/15

2:15 am-12:40 am

1 stop23h 25m

Mérida Rejon

Sun 4/19

6:05 am-12:45 am

1 stop17h 40m

$303

ChicagoMérida

ORD - MID

ORDMID

Chicago O'Hare Intl

Tue 4/21

1:20 am-2:45 pm

1 stop14h 25m

Mérida Rejon

Mon 4/27

4:40 pm-12:45 am

1 stop7h 05m

$315

ChicagoMérida

ORD - MID

ORDMID

Chicago O'Hare Intl

Wed 3/4

1:20 am-12:55 am

1 stop23h 35m

Mérida Rejon

Thu 3/12

10:05 pm-12:45 am

1 stop25h 40m

$319

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Thu 3/5

6:30 am-9:11 pm

2 stops13h 41m

Cancun

Wed 3/11

8:40 am-12:13 am

1 stop15h 33m

$332

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sat 2/28

6:30 pm-11:50 am

2 stops16h 20m

Cancun

Wed 3/11

8:40 am-12:13 am

1 stop15h 33m

$332

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 2/28

11:06 am-9:11 pm

1 stop9h 05m

Cancun

Thu 3/5

11:00 am-5:45 pm

1 stop7h 45m

$338

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/5

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, August is the cheapest month in which you can book a flight from Chicago to Yucatan (average of $209). Flying from Chicago to Yucatan in June is currently the most expensive (average of $474). 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.

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 February 8, 2026.
Read through reviews of airlines operating flights from Chicago to Yucatan, such as United Airlines, American Airlines, and Viva. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

Food

6.6

Comfort

7.3

Crew

8.1

Entertainment

7.1

Boarding

7.7

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

Food

6.6

Comfort

7.3

Crew

8.1

Entertainment

7.1

Boarding

7.7

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

Food

6.6

Comfort

7.3

Crew

8.1

Entertainment

7.1

Boarding

7.7

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

Food

6.6

Comfort

7.3

Crew

8.1

Entertainment

7.1

Boarding

7.7

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

Food

6.6

Comfort

7.3

Crew

8.1

Entertainment

7.1

Boarding

7.7

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

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 Volaris, Southwest, and Viva fly from Chicago to Yucatan in about 3h 40m. The time it takes to get you to your destination can typically vary by up to 19h 45m. 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 most popular routes from Chicago to Yucatan?

  • 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, August is the cheapest month in which you can book a flight from Chicago to Yucatan (average of $209). Flying from Chicago to Yucatan in June is currently the most expensive (average of $474). 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

Browse thousands of different options on Cheapflights for your next trip

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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.

Top 6 airlines flying from Chicago to Yucatan

Discover the top 6 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 February 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
VolarisCheapest$156Average$336FlexibilityNo cancel feeOn-time79%
VivaCheapest$263Average$398FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$371Average$542FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$373Average$615FlexibilityNo cancel feeOn-time69%
AeromexicoCheapest$483Average$566FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$525Average$593FlexibilityNo cancel feeOn-time71%

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