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$135+ 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 1/31. Fares are subject to change and may not be available on all flights or dates of travel.
MID — CHI
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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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 November 3, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 11/3. 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.
Mon 11/2411:53 amCUN - ORD
Nonstop4h 00mSpirit Airlines
Mon 12/16:00 amORD - CUN
Nonstop3h 44mSpirit Airlines
Deal found 11/3$200
This Cheapflightsfares deal was found by Cheapflights users on 11/3. 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.
Thu 12/2511:50 amCUN - ORD
Nonstop4h 03mSpirit Airlines
Mon 1/56:05 amORD - CUN
Nonstop3h 50mSpirit Airlines
Deal found 11/3$206
This Cheapflightsfares deal was found by Cheapflights users on 11/3. 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.
Mon 11/2411:53 amCUN - ORD
Nonstop4h 00mSpirit Airlines
Tue 12/25:00 amORD - CUN
1 stop7h 35mSpirit Airlines
Deal found 11/3$213
This United Airlines deal was found by Cheapflights users on 11/3. 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.
Fri 12/51:27 pmCUN - ORD
Nonstop4h 00mUnited Airlines
Tue 12/97:35 amORD - CUN
1 stop11h 43mUnited Airlines
Deal found 11/3$218
This American Airlines deal was found by Cheapflights users on 11/3. 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 11/242:32 pmCUN - ORD
Nonstop4h 05mAmerican Airlines
Mon 12/110:00 amORD - CUN
Nonstop3h 49mAmerican Airlines
Deal found 11/3$223
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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 11/142:44 pmCUN - ORD
1 stop10h 43mSpirit Airlines
Mon 11/175:10 amORD - CUN
1 stop7h 25mSpirit Airlines
Deal found 11/2$226
This Cheapflightsfares deal was found by Cheapflights users on 11/3. 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.
Thu 11/132:44 pmCUN - ORD
1 stop10h 43mSpirit Airlines
Sun 11/165:10 amORD - CUN
1 stop7h 25mSpirit Airlines
Deal found 11/3$231
This Cheapflightsfares deal was found by Cheapflights users on 11/3. 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.
Thu 12/412:31 pmCUN - ORD
1 stop8h 38mSpirit Airlines
Mon 12/85:00 amORD - CUN
1 stop7h 13mSpirit Airlines
Deal found 11/3$232
This United Airlines deal was found by Cheapflights users on 11/3. 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.
Fri 11/143:18 pmCUN - ORD
Nonstop3h 51mUnited Airlines
Mon 11/177:10 amORD - CUN
1 stop7h 35mUnited Airlines
Deal found 11/3$234
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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 11/142:44 pmCUN - ORD
1 stop10h 43mSpirit Airlines
Sun 11/165:10 amORD - CUN
1 stop7h 25mSpirit Airlines
Deal found 11/2$235
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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 12/122:36 pmCUN - ORD
1 stop10h 33mSpirit Airlines
Sun 12/149:14 pmORD - CUN
1 stop13h 22mSpirit Airlines
Deal found 11/2$242
This Delta deal was found by Cheapflights users on 11/3. 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 11/148:00 amCUN - MDW
2 stops11h 08mDelta
Mon 11/179:34 amMDW - CUN
2 stops10h 46mDelta
Deal found 11/3$276

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 November 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$200
(Cheapflightsfares)

One-way from

$135
(Priceline)

Popular in

October

Cheapest in

February

Average price

$412
Provider with most accurate pricing for Mérida Rejon-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Mérida Rejon-Chicago (CHI) flights.
Search Deals
From Yucatan to Chicago (CHI)
Search Deals
One-way flight from Yucatan to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($36 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 November 3, 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

Fri 12/5

3:18 pm-6:09 pm

Nonstop3h 51m

Chicago O'Hare Intl

Tue 12/9

7:35 am-3:59 pm

1 stop7h 24m

$217

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 2/19

3:18 pm-6:09 pm

Nonstop3h 51m

Chicago O'Hare Intl

Mon 2/23

8:43 am-1:33 pm

Nonstop3h 50m

$218

CancúnChicago

CUN - ORD

CUNORD

Cancun

Fri 1/23

4:47 pm-7:47 pm

Nonstop4h 00m

Chicago O'Hare Intl

Mon 1/26

7:34 am-12:30 pm

Nonstop3h 56m

$218

CancúnChicago

CUN - ORD

CUNORD

Cancun

Wed 2/11

3:18 pm-6:09 pm

Nonstop3h 51m

Chicago O'Hare Intl

Sun 2/15

9:05 pm-12:54 pm

1 stop14h 49m

$218

CancúnChicago

CUN - ORD

CUNORD

Cancun

Fri 12/12

2:44 pm-10:56 pm

1 stop9h 12m

Chicago O'Hare Intl

Mon 12/15

8:07 pm-2:18 pm

1 stop17h 11m

$224

CancúnChicago

CUN - ORD

CUNORD

Cancun

Fri 2/13

2:44 pm-12:26 am

1 stop10h 42m

Chicago O'Hare Intl

Tue 2/17

7:35 am-5:50 pm

1 stop9h 15m

$224

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 12/5

8:00 am-4:18 pm

1 stop9h 18m

Chicago Midway

Tue 12/9

9:34 am-9:20 pm

2 stops10h 46m

$276

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 1/22

11:00 am-5:32 pm

1 stop7h 32m

Chicago Midway

Mon 1/26

12:48 pm-9:11 pm

1 stop7h 23m

$276

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 12/4

8:00 am-6:00 pm

2 stops11h 00m

Chicago Midway

Mon 12/8

9:34 am-9:20 pm

2 stops10h 46m

$276

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 11/14

8:00 am-6:08 pm

2 stops11h 08m

Chicago Midway

Mon 11/17

9:34 am-9:20 pm

2 stops10h 46m

$276

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 57 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

How much does it cost to fly round-trip from Yucatan to Chicago?

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.

  • How long is the flight from Yucatan to Chicago?

    Departing from Yucatan to Chicago will take you 3h 51m. Yucatan and Chicago are separated by a distance of 1447 mi. This flight may include one or multiple stops.

  • 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 $143 on Viva. Other airlines that offer cheap prices include Southwest from $144 and United Airlines from $144 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.

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
Porter
Benton Harbor

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