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$129+ 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 10/9. Fares are subject to change and may not be available on all flights or dates of travel.
MID — CHI
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheap flight deals from Yucatan to Chicago

Keep the following information in mind while searching for Yucatan to Chicago flight deals. Data was last updated July 31, 2025.

Round-trip from

$190
(Frontier)

One-way from

$129
(Kiwi.com)

Popular in

October

Cheapest in

February

Average price

$449
From Yucatan to Chicago (CHI)
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One-way flight from Yucatan to Chicago (CHI)
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Highest demand for flights based on searches. 3% potential increase in price ($17 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 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 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 July 31, 2025.

This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/911:31 amCUN - ORD
Nonstop3h 55mFrontier
Tue 10/146:41 amORD - CUN
Nonstop3h 45mFrontier
Deal found 7/30$204
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1310:44 amCUN - ORD
Nonstop4h 05mMultiple Airlines
Sat 9/2012:25 pmORD - CUN
1 stop9h 10mMultiple Airlines
Deal found 7/30$212
This United Airlines deal was found by Cheapflights users on 7/31. 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 10/2912:27 pmCUN - ORD
Nonstop4h 03mUnited Airlines
Mon 11/38:00 pmORD - CUN
1 stop17h 18mUnited Airlines
Deal found 7/31$229
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 8/2811:51 amCUN - ORD
Nonstop4h 01mVolaris
Sun 9/286:00 amORD - CUN
1 stop9h 53mVolaris
Deal found 7/31$244
This Cheapflightsfares deal was found by Cheapflights users on 7/31. 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.
Fri 8/229:14 amCUN - ORD
1 stop13h 08mSpirit Airlines
Mon 8/256:10 amORD - CUN
Nonstop3h 29mSpirit Airlines
Deal found 7/31$248
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/26:00 amMID - ORD
1 stop16h 50mMultiple Airlines
Fri 9/191:40 amORD - MID
1 stop8h 40mMultiple Airlines
Deal found 7/30$260
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.
Thu 10/91:20 pmCUN - ORD
Nonstop4h 00mAmerican Airlines
Tue 10/147:10 amORD - CUN
1 stop6h 35mAmerican Airlines
Deal found 7/30$270
This Delta deal was found by Cheapflights users on 7/31. 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.
Fri 10/248:00 amCUN - MDW
2 stops10h 25mDelta
Fri 10/3110:35 amMDW - CUN
1 stop9h 45mDelta
Deal found 7/31$276
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/167:55 pmMID - ORD
1 stop26h 40mViva
Tue 10/2112:25 pmORD - MID
1 stop28h 20mViva
Deal found 7/28$281
This Aeromexico deal was found by Cheapflights users on 7/31. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/93:14 pmCUN - MDW
1 stop7h 00mAeromexico
Sun 10/126:00 amMDW - CUN
2 stops11h 45mAeromexico
Deal found 7/31$287
This Southwest deal was found by Cheapflights users on 7/31. 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.
Sat 9/61:15 pmCUN - MDW
1 stop7h 30mSouthwest
Tue 9/99:55 amMDW - CUN
Nonstop3h 35mSouthwest
Deal found 7/31$289
This Frontier deal was found by Cheapflights users on 7/31. 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.
Sat 10/181:41 pmCUN - MDW
1 stop9h 28mFrontier
Sat 10/256:10 amMDW - CUN
1 stop6h 16mFrontier
Deal found 7/31$296

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 July 31, 2025.
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

Sun 9/21

11:34 am-3:43 pm

Nonstop4h 09m

Chicago O'Hare Intl

Sat 9/27

6:41 am-10:33 am

Nonstop3h 52m

$190

CancúnChicago

CUN - ORD

CUNORD

Cancun

Sat 9/13

10:44 am-2:49 pm

Nonstop4h 05m

Chicago O'Hare Intl

Wed 9/17

12:25 pm-9:35 pm

1 stop9h 10m

$222

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 10/16

3:38 pm-7:36 pm

Nonstop3h 58m

Chicago O'Hare Intl

Sun 10/19

5:01 am-1:00 pm

1 stop7h 59m

$229

CancúnChicago

CUN - ORD

CUNORD

Cancun

Fri 8/22

9:14 am-10:22 pm

1 stop13h 08m

Chicago O'Hare Intl

Mon 8/25

6:10 am-9:39 am

Nonstop3h 29m

$248

CancúnChicago

CUN - ORD

CUNORD

Cancun

Tue 10/14

7:10 am-11:35 pm

1 stop16h 25m

Chicago O'Hare Intl

Sat 10/18

12:25 pm-7:50 pm

1 stop7h 25m

$258

MéridaChicago

MID - ORD

MIDORD

Mérida Rejon

Tue 9/2

6:00 am-11:50 pm

1 stop16h 50m

Chicago O'Hare Intl

Fri 9/19

1:40 am-9:20 am

1 stop8h 40m

$260

CancúnChicago

CUN - ORD

CUNORD

Cancun

Tue 8/26

11:51 am-3:52 pm

Nonstop4h 01m

Chicago O'Hare Intl

Tue 9/2

7:25 am-9:03 pm

1 stop13h 38m

$263

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 10/9

1:20 pm-5:20 pm

Nonstop4h 00m

Chicago O'Hare Intl

Tue 10/14

7:10 am-1:45 pm

1 stop6h 35m

$270

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 10/24

8:00 am-6:25 pm

2 stops10h 25m

Chicago Midway

Fri 10/31

10:35 am-8:20 pm

1 stop9h 45m

$276

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 10/23

8:10 am-9:24 pm

2 stops13h 14m

Chicago O'Hare Intl

Sun 10/26

6:45 am-8:20 pm

1 stop13h 35m

$276

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 36 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

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

Currently, August is the cheapest month in which you can book a flight from Yucatan to Chicago (average of $245). Flying from Yucatan to Chicago in March is currently the most expensive (average of $321). 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 Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated July 31, 2025.
See what other customers who have flown with Southwest, Delta, and Aeromexico from Yucatan to Chicago have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

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
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

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
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

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
4,246 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

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
8,900 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

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
4,246 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

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 Yucatan to Chicago. 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 Yucatan to Chicago one-way?

    One-way options have recently been found by users for as low as $129 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $130 and Southwest from $149 one-way.

  • 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.

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

    Currently, August is the cheapest month in which you can book a flight from Yucatan to Chicago (average of $245). Flying from Yucatan to Chicago in March is currently the most expensive (average of $321). 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

Traveling to a place near Chicago?

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

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