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Yucatan

$94+ 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 9/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MID
ago. 4 — ago. 111
lun. 8/4
lun. 8/11
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 julio 30, 2025.

Round-trip from

$235
(Mytrip)

One-way from

$94
(eDestinos)

Popular in

December

Cheapest in

February

Average price

$690
From Chicago (CHI) to Yucatan
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One-way flight from Chicago (CHI) to Yucatan
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($91 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($32 potential savings vs. average RT price).
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Average for round-trip flights in July 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 julio 30, 2025.

This Mytrip deal was found by Cheapflights users on 7/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 9/712:25 pmORD - MID
1 stop13h 20mViva
dom. 9/147:55 pmMID - ORD
1 stop26h 55mViva
Deal found 7/28$235
This Gotogate deal was found by Cheapflights users on 7/28. 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.
sáb. 9/61:40 amORD - MID
1 stop8h 40mMultiple Airlines
dom. 9/147:55 pmMID - ORD
1 stop26h 55mMultiple Airlines
Deal found 7/28$247
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
sáb. 8/165:16 pmORD - CUN
1 stop14h 53mMultiple Airlines
jue. 8/2111:51 amCUN - ORD
Nonstop4h 01mMultiple Airlines
Deal found 7/30$257
This Booking.com deal was found by Cheapflights users on 7/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/1012:25 pmORD - CUN
1 stop7h 25mViva
mar. 10/147:10 amCUN - ORD
1 stop16h 25mViva
Deal found 7/30$258
This FlightHub deal was found by Cheapflights users on 7/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/88:50 pmORD - CUN
1 stop12h 52mSpirit Airlines
sáb. 11/151:35 pmCUN - ORD
1 stop8h 25mSpirit Airlines
Deal found 7/30$261
This Southwest deal was found by Cheapflights users on 7/30. 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.
sáb. 11/83:40 pmMDW - CUN
Nonstop3h 45mSouthwest
jue. 11/132:15 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 7/30$270
This eDestinos deal was found by Cheapflights users on 7/28. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/101:40 amORD - MID
1 stop8h 40mVolaris
jue. 9/189:09 pmMID - ORD
1 stop12h 56mVolaris
Deal found 7/28$270
This American Airlines deal was found by Cheapflights users on 7/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/278:39 amORD - CUN
Nonstop3h 40mAmerican Airlines
jue. 10/302:50 pmCUN - ORD
Nonstop4h 00mAmerican Airlines
Deal found 7/30$280
This Cheapflightsfares deal was found by Cheapflights users on 7/28. 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.
lun. 8/117:35 amORD - CUN
Nonstop3h 55mFrontier
jue. 8/1411:39 amCUN - ORD
Nonstop4h 01mFrontier
Deal found 7/28$284
This SmartFares deal was found by Cheapflights users on 7/29. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/66:00 amMDW - CUN
1 stop5h 30mAeromexico
jue. 9/1112:25 pmCUN - MDW
1 stop9h 11mAeromexico
Deal found 7/29$303
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 10/2610:35 amMDW - CUN
1 stop9h 45mDelta
sáb. 11/11:58 pmCUN - MDW
1 stop8h 16mDelta
Deal found 7/28$324
This Priceline deal was found by Cheapflights users on 7/29. 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.
sáb. 11/86:00 amMDW - CUN
1 stop14h 20mMultiple Airlines
sáb. 11/152:41 pmCUN - MDW
1 stop9h 28mMultiple Airlines
Deal found 7/29$341

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 julio 30, 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

ChicagoMérida

ORD - MID

ORDMID

Chicago O'Hare Intl

dom. 9/7

12:25 pm-12:45 am

1 stop13h 20m

Mérida Rejon

dom. 9/14

7:55 pm-11:50 pm

1 stop26h 55m

$235

ChicagoMérida

ORD - MID

ORDMID

Chicago O'Hare Intl

sáb. 9/6

1:40 am-9:20 am

1 stop8h 40m

Mérida Rejon

dom. 9/14

7:55 pm-11:50 pm

1 stop26h 55m

$247

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

sáb. 8/16

5:16 pm-8:09 am

1 stop14h 53m

Cancun

jue. 8/21

11:51 am-3:52 pm

Nonstop4h 01m

$257

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

vie. 10/10

12:25 pm-7:50 pm

1 stop7h 25m

Cancun

mar. 10/14

7:10 am-11:35 pm

1 stop16h 25m

$258

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

sáb. 8/30

8:47 pm-9:43 am

1 stop12h 56m

Cancun

mié. 9/3

9:14 am-4:10 pm

1 stop6h 56m

$261

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

lun. 10/27

9:40 am-1:15 pm

Nonstop3h 35m

Cancun

dom. 11/2

2:15 pm-5:00 pm

Nonstop3h 45m

$270

ChicagoMérida

ORD - MID

ORDMID

Chicago O'Hare Intl

mié. 9/10

1:40 am-9:20 am

1 stop8h 40m

Mérida Rejon

jue. 9/18

9:09 pm-11:05 am

1 stop12h 56m

$270

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

lun. 10/27

8:39 am-12:19 pm

Nonstop3h 40m

Cancun

jue. 10/30

2:50 pm-6:50 pm

Nonstop4h 00m

$280

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

lun. 8/11

7:35 am-11:30 am

Nonstop3h 55m

Cancun

jue. 8/14

11:39 am-3:40 pm

Nonstop4h 01m

$284

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

sáb. 9/6

6:00 am-11:30 am

1 stop5h 30m

Cancun

jue. 9/11

12:25 pm-9:36 pm

1 stop9h 11m

$303

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Showing 1-10 of 38 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 julio 30, 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 julio 30, 2025.
Read through reviews of airlines operating flights from Chicago to Yucatan, such as Southwest, Delta, and Aeromexico. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Aeromexico
7.5
Good
1,721 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,896 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

  • 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 $94. Viva flights start at $104 while deals on Spirit Airlines start at $105 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 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 julio 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
VivaCheapest$234Average$341FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$287Average$320FlexibilityNo cancel feeOn-time79%
AeromexicoCheapest$473Average$531FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$474Average$569FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$481Average$670FlexibilityNo cancel feeOn-time69%
DeltaCheapest$497Average$566FlexibilityNo cancel feeOn-timeN/A

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