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$98+ 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 6/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MID
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$238
(Cheapflightsfares)

One-way from

$98
(SmartFares)

Popular in

December

Cheapest in

February

Average price

$498
From Chicago (CHI) to Yucatan
Search Deals
One-way flight from Chicago (CHI) to Yucatan
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($112 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 June 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 June 12, 2025.

This Booking.com deal was found by Cheapflights users on 6/12. 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.
Tue 7/87:49 pmORD - CUN
1 stop12h 28mSpirit Airlines
Fri 7/1110:55 amCUN - ORD
Nonstop3h 54mSpirit Airlines
Deal found 6/12$237
This Southwest deal was found by Cheapflights users on 6/9. 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.
Thu 7/104:35 pmMDW - CUN
Nonstop3h 35mSouthwest
Tue 7/158:30 amCUN - MDW
Nonstop3h 35mSouthwest
Deal found 6/9$269
This American Airlines deal was found by Cheapflights users on 6/12. 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.
Mon 10/68:05 amORD - CUN
Nonstop3h 45mAmerican Airlines
Fri 10/1012:59 pmCUN - ORD
Nonstop4h 01mAmerican Airlines
Deal found 6/12$269
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 8/116:00 amORD - CUN
Nonstop3h 50mMultiple Airlines
Tue 8/1911:51 amCUN - ORD
Nonstop4h 01mMultiple Airlines
Deal found 6/10$270
This Priceline deal was found by Cheapflights users on 6/10. 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 8/236:10 amMDW - CUN
1 stop6h 29mFrontier
Sat 8/301:54 pmCUN - MDW
1 stop9h 17mFrontier
Deal found 6/10$292
This Trip.com deal was found by Cheapflights users on 6/10. 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 6/2412:44 pmMDW - CUN
1 stop7h 36mAeromexico
Sat 9/612:40 pmCUN - MDW
1 stop8h 32mAeromexico
Deal found 6/10$305
This Delta deal was found by Cheapflights users on 6/10. 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.
Sat 10/256:00 amORD - CUN
1 stop8h 09mDelta
Wed 10/291:24 pmCUN - ORD
1 stop10h 54mDelta
Deal found 6/10$313
This Trip.com deal was found by Cheapflights users on 6/11. 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 6/2412:44 pmMDW - CUN
1 stop7h 36mMultiple Airlines
Wed 6/253:25 pmCUN - MDW
1 stop29h 28mMultiple Airlines
Deal found 6/11$322
This Delta deal was found by Cheapflights users on 6/10. 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.
Mon 9/86:00 amMDW - CUN
1 stop8h 10mDelta
Sat 9/138:15 amCUN - MDW
1 stop7h 15mDelta
Deal found 6/10$323
This Mytrip deal was found by Cheapflights users on 6/10. 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.
Sat 10/2512:25 pmORD - MID
1 stop7h 40mMultiple Airlines
Sat 11/19:14 pmMID - ORD
1 stop13h 55mMultiple Airlines
Deal found 6/10$325
This United Airlines deal was found by Cheapflights users on 6/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1010:43 amORD - CUN
Nonstop3h 45mUnited Airlines
Sat 9/133:38 pmCUN - ORD
Nonstop3h 58mUnited Airlines
Deal found 6/11$379
This FlightHub deal was found by Cheapflights users on 6/11. 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.
Thu 9/412:25 pmORD - MID
1 stop13h 20mViva
Mon 9/89:40 pmMID - ORD
1 stop25h 10mViva
Deal found 6/11$385

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 June 12, 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

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Tue 9/9

5:05 am-11:33 am

1 stop6h 28m

Cancun

Fri 9/19

10:39 am-2:42 pm

Nonstop4h 03m

$238

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 7/10

4:35 pm-8:10 pm

Nonstop3h 35m

Cancun

Tue 7/15

8:30 am-12:05 pm

Nonstop3h 35m

$269

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sun 10/26

9:45 am-1:25 pm

Nonstop3h 40m

Cancun

Thu 10/30

2:50 pm-7:00 pm

Nonstop4h 10m

$269

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Mon 8/11

6:00 am-9:50 am

Nonstop3h 50m

Cancun

Tue 8/19

11:51 am-3:52 pm

Nonstop4h 01m

$270

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 8/23

6:10 am-12:39 pm

1 stop6h 29m

Cancun

Sat 8/30

1:54 pm-11:11 pm

1 stop9h 17m

$292

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 6/24

12:44 pm-8:20 pm

1 stop7h 36m

Cancun

Sat 9/6

12:40 pm-9:12 pm

1 stop8h 32m

$305

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sun 10/12

5:10 am-12:26 pm

1 stop7h 16m

Cancun

Sat 10/18

10:50 am-8:24 pm

1 stop9h 34m

$312

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sat 10/25

6:00 am-2:09 pm

1 stop8h 09m

Cancun

Wed 10/29

1:24 pm-12:18 am

1 stop10h 54m

$313

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 6/24

12:44 pm-8:20 pm

1 stop7h 36m

Cancun

Wed 6/25

3:25 pm-8:53 pm

1 stop29h 28m

$322

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 9/8

6:00 am-2:10 pm

1 stop8h 10m

Cancun

Sat 9/13

8:15 am-3:30 pm

1 stop7h 15m

$323

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 48 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 June 12, 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.

Rainfall in Yucatan by month

Plan your trip to Yucatan by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Yucatan ranges from 0.8 - 6.3 inches per month. September is typically the wettest month, when rainfall can reach 6.3 in. February is typically the driest time to visit Yucatan when rainfall is around 0.8 in.

Temperature in Yucatan by month

Plan your trip to Yucatan by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Yucatan, use this chart to help with planning. For those seeking warmer temperatures, May is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 73.4 F).

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 June 12, 2025.
See what other customers who have flown with Alaska Airlines, Southwest and Delta from Chicago to Yucatan have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Delta
8.0
Very good
7,950 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Aeromexico
7.5
Good
1,706 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
United Airlines
7.4
Good
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.

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 Spirit Airlines, which is currently one of the cheapest options available, starting at $98. Viva flights start at $103 while deals on Southwest start at $123 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

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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
VivaCheapest$239Average$347FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$287Average$320FlexibilityNo cancel feeOn-time79%
AeromexicoCheapest$473Average$561FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$475Average$591FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$488Average$688FlexibilityNo cancel feeOn-time69%

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