What is the cheapest airline that flies from Chicago to Yucatan?

United Airlines, JetBlue, and Southwest are the most popular carriers operating from Chicago to Yucatan

How many flights depart from Chicago to Yucatan on average per week?

As of September 2026, there are 25 flights per week flying from Chicago to Yucatan. The most common day of the week flights depart is Mon, with 16% of flights taking off on this day.

What airlines fly to Yucatan?

Volaris, United Airlines and Viva are the top three most popular airlines that fly to Yucatan from Chicago according to our data. Volaris is the first choice among our users, with 37% of people opting to fly with this airline when traveling to Yucatan. Keep in mind that there are 5 different airlines that fly to Yucatan on a routine basis, so you have a few additional options to choose from.

When did momondo last update prices for flights from Chicago to Yucatan?

Prices for flights from Chicago to Yucatan refresh daily.

How many operators does momondo search for flights from Chicago to Yucatan?

The number of operators available for flights from Chicago to Yucatan is 10 as of September 2026.

How old do you have to be to fly from Chicago to Yucatan?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Yucatan.

What documentation or ID do you need to fly to Yucatan?

The necessary travel and health documents for your Yucatan trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$124 Cheap Flights from Chicago to Yucatan in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Yucatan

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

1:40 am - 9:00 amORD Chicago O'Hare Intl-MID Mérida Rejon

8h 20m1 stop Mexico City Benito Juarez

10:03 am - 11:47 pmMID Mérida Rejon-ORD Chicago O'Hare Intl

12h 44m1 stop Mexico City Benito Juarez

$312Volaris

Fri, Oct 2 - Thu, Oct 22

2:41 am - 9:58 pmORD Chicago O'Hare Intl-MID Mérida Rejon

20h 17m1 stop Puebla City Huejotzingo

10:03 am - 11:47 pmMID Mérida Rejon-ORD Chicago O'Hare Intl

12h 44m1 stop Mexico City Benito Juarez

$315Multiple Airlines

Fri, Oct 9 - Tue, Oct 20

2:41 am - 9:58 pmORD Chicago O'Hare Intl-MID Mérida Rejon

20h 17m1 stop Puebla City Huejotzingo

10:03 am - 11:47 pmMID Mérida Rejon-ORD Chicago O'Hare Intl

12h 44m1 stop Mexico City Benito Juarez

$315Multiple Airlines

Fri, Oct 9 - Wed, Oct 21

12:04 am - 8:01 amORD Chicago O'Hare Intl-MID Mérida Rejon

7h 57m1 stop Mexico City Benito Juarez

9:25 pm - 11:13 amMID Mérida Rejon-ORD Chicago O'Hare Intl

13h 48m1 stop Guadalajara Miguel Hidal

$322Volaris

Wed, Feb 3 - Mon, Feb 8

4:32 pm - 1:04 amORD Chicago O'Hare Intl-MID Mérida Rejon

9h 32m1 stop Monterrey Gen Mariano Escobedo

4:19 pm - 3:02 pmMID Mérida Rejon-ORD Chicago O'Hare Intl

21h 43m1 stop Monterrey Gen Mariano Escobedo

$328Viva

Wed, Oct 7 - Tue, Oct 13

1:05 am - 3:03 pmORD Chicago O'Hare Intl-MID Mérida Rejon

14h 58m1 stop Mexico City Benito Juarez

5:13 pm - 10:50 pmMID Mérida Rejon-ORD Chicago O'Hare Intl

29h 37m1 stop Guadalajara Miguel Hidal

$337Viva

Sat, Oct 31 - Sun, Nov 8

8:45 am - 11:30 pmORD Chicago O'Hare Intl-CUN Cancun

13h 45m1 stop Toronto Pearson Intl

8:00 am - 6:30 pmCUN Cancun-ORD Chicago O'Hare Intl

11h 30m2 stops Toronto Pearson Intl Ottawa

$386Air Canada

Fri, Nov 20 - Mon, Nov 23

7:29 am - 12:52 pmORD Chicago O'Hare Intl-CUN Cancun

4h 23mnonstop

11:38 am - 2:38 pmCUN Cancun-ORD Chicago O'Hare Intl

4h 00mnonstop

$388Frontier

Wed, Feb 3 - Fri, Feb 12

7:29 am - 12:52 pmORD Chicago O'Hare Intl-CUN Cancun

4h 23mnonstop

11:38 am - 2:38 pmCUN Cancun-ORD Chicago O'Hare Intl

4h 00mnonstop

$388Frontier

Sat, Jan 23 - Thu, Jan 28

8:40 pm - 10:30 pmORD Chicago O'Hare Intl-CUN Cancun

25h 50m1 stop Toronto Pearson Intl

6:55 pm - 3:38 pmCUN Cancun-ORD Chicago O'Hare Intl

21h 43m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl

$389Air Canada

Thu, Oct 29 - Mon, Nov 2

Cheap last minute flights

Enter your travel dates to find the best prices.

8:40 pm - 8:10 pmORD Chicago O'Hare Intl-CUN Cancun

23h 30m1 stop Toronto Pearson Intl

1:20 pm - 10:15 amCUN Cancun-ORD Chicago O'Hare Intl

20h 55m1 stop Montreal Pierre Elliott Trudeau Intl

$389Air Canada

Mon, Sep 21 - Fri, Sep 25

7:35 am - 9:03 pmORD Chicago O'Hare Intl-CUN Cancun

13h 28m1 stop Mexico City Benito Juarez

10:40 am - 12:55 amCUN Cancun-ORD Chicago O'Hare Intl

14h 15m1 stop Guadalajara Miguel Hidal

$390Volaris

Mon, Sep 21 - Tue, Sep 22

7:09 am - 5:30 pmORD Chicago O'Hare Intl-CUN Cancun

10h 21m1 stop Santiago de Querétaro

6:06 pm - 5:38 amCUN Cancun-ORD Chicago O'Hare Intl

11h 32m1 stop Santiago de Querétaro

$394Volaris

Thu, Sep 24 - Sat, Sep 26

8:40 pm - 8:10 pmORD Chicago O'Hare Intl-CUN Cancun

23h 30m1 stop Toronto Pearson Intl

10:40 am - 12:55 amCUN Cancun-ORD Chicago O'Hare Intl

14h 15m1 stop Guadalajara Miguel Hidal

$395Multiple Airlines

Fri, Sep 25 - Thu, Oct 1

7:35 am - 9:03 pmORD Chicago O'Hare Intl-CUN Cancun

13h 28m1 stop Mexico City Benito Juarez

11:15 pm - 11:00 amCUN Cancun-ORD Chicago O'Hare Intl

11h 45m1 stop Mexico City Benito Juarez

$398Multiple Airlines

Thu, Sep 24 - Tue, Sep 29

9:55 am - 8:10 pmORD Chicago O'Hare Intl-CUN Cancun

10h 15m1 stop Toronto Pearson Intl

1:30 pm - 10:12 amCUN Cancun-ORD Chicago O'Hare Intl

20h 42m1 stop Montreal Pierre Elliott Trudeau Intl

$399Air Canada

Wed, Sep 23 - Wed, Oct 21

6:25 am - 12:37 pmMDW Chicago Midway-CUN Cancun

6h 12m1 stop Atlanta Hartsfield-Jackson

1:51 pm - 11:44 pmCUN Cancun-MDW Chicago Midway

9h 53m1 stop Atlanta Hartsfield-Jackson

$486Frontier

Mon, Sep 21 - Thu, Oct 1

6:25 am - 12:37 pmMDW Chicago Midway-CUN Cancun

6h 12m1 stop Atlanta Hartsfield-Jackson

1:51 pm - 11:44 pmCUN Cancun-MDW Chicago Midway

9h 53m1 stop Atlanta Hartsfield-Jackson

$486Frontier

Mon, Sep 21 - Thu, Sep 24

1:30 am - 1:15 amORD Chicago O'Hare Intl-CUN Cancun

23h 45m1 stop Mexico City Benito Juarez

6:15 am - 11:00 amCUN Cancun-ORD Chicago O'Hare Intl

28h 45m1 stop Mexico City Benito Juarez

$509Viva

Tue, Sep 22 - Sun, Sep 27

4:30 pm - 1:30 amORD Chicago O'Hare Intl-CUN Cancun

9h 00m1 stop Mexico City Benito Juarez

7:01 am - 11:59 pmCUN Cancun-ORD Chicago O'Hare Intl

16h 58m2 stops Mexico City Benito Juarez Atlanta Hartsfield-Jackson

$536Aeromexico

Sat, Sep 26 - Sat, Oct 3

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Volaris flights from Chicago to Yucatan

Our best Volaris deals on Chicago to Yucatan flight tickets

Volaris

Oct 2

ORD1:40 amChicago O'Hare Intl

8h 20m

1 stop

MID9:00 amMérida Rejon

Oct 22

MID10:03 amMérida Rejon

12h 44m

1 stop

ORD11:47 pmChicago O'Hare Intl

$312

Volaris

Oct 10

ORD1:40 amChicago O'Hare Intl

8h 20m

1 stop

MID9:00 amMérida Rejon

Oct 21

MID10:03 amMérida Rejon

12h 44m

1 stop

ORD11:47 pmChicago O'Hare Intl

$334

Volaris

Oct 10

ORD1:40 amChicago O'Hare Intl

8h 20m

1 stop

MID9:00 amMérida Rejon

Oct 19

MID10:03 amMérida Rejon

12h 44m

1 stop

ORD11:47 pmChicago O'Hare Intl

$344

Frontier flights from Chicago to Yucatan

Our best Frontier deals on Chicago to Yucatan flight tickets

Frontier

Jan 23

ORD7:29 amChicago O'Hare Intl

4h 23m

CUN12:52 pmCancun

Feb 5

CUN11:38 amCancun

4h 00m

ORD2:38 pmChicago O'Hare Intl

$388

Frontier

Nov 2

MDW6:16 amChicago Midway

6h 25m

1 stop

CUN1:41 pmCancun

Nov 6

CUN2:51 pmCancun

9h 56m

1 stop

MDW11:47 pmChicago Midway

$397

Frontier

Nov 8

MDW6:16 amChicago Midway

6h 25m

1 stop

CUN1:41 pmCancun

Nov 13

CUN2:51 pmCancun

9h 56m

1 stop

MDW11:47 pmChicago Midway

$403

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMérida

ORD Chicago O'Hare Intl - MID Mérida Rejon

ORDMID

Chicago O'Hare Intl

Fri 10/2

1:40 am-9:00 am

1 stop8h 20m

Mérida Rejon

Thu 10/22

10:03 am-11:47 pm

1 stop12h 44m

$312

ChicagoMérida

ORD Chicago O'Hare Intl - MID Mérida Rejon

ORDMID

Chicago O'Hare Intl

Fri 10/9

2:41 am-9:58 pm

1 stop20h 17m

Mérida Rejon

Tue 10/20

10:03 am-11:47 pm

1 stop12h 44m

$315

ChicagoMérida

ORD Chicago O'Hare Intl - MID Mérida Rejon

ORDMID

Chicago O'Hare Intl

Fri 10/9

2:41 am-9:58 pm

1 stop20h 17m

Mérida Rejon

Wed 10/21

10:03 am-11:47 pm

1 stop12h 44m

$315

ChicagoMérida

ORD Chicago O'Hare Intl - MID Mérida Rejon

ORDMID

Chicago O'Hare Intl

Wed 2/3

12:04 am-8:01 am

1 stop7h 57m

Mérida Rejon

Mon 2/8

9:25 pm-11:13 am

1 stop13h 48m

$322

ChicagoMérida

ORD Chicago O'Hare Intl - MID Mérida Rejon

ORDMID

Chicago O'Hare Intl

Wed 10/7

4:32 pm-1:04 am

1 stop9h 32m

Mérida Rejon

Tue 10/13

4:19 pm-3:02 pm

1 stop21h 43m

$328

ChicagoMérida

ORD Chicago O'Hare Intl - MID Mérida Rejon

ORDMID

Chicago O'Hare Intl

Sat 10/31

1:05 am-3:03 pm

1 stop14h 58m

Mérida Rejon

Sun 11/8

5:13 pm-10:50 pm

1 stop29h 37m

$337

ChicagoCancún

ORD Chicago O'Hare Intl - CUN Cancun

ORDCUN

Chicago O'Hare Intl

Fri 11/20

8:45 am-11:30 pm

1 stop13h 45m

Cancun

Mon 11/23

8:00 am-6:30 pm

2 stops11h 30m

$386

Quickest round-trip

ChicagoCancún

ORD Chicago O'Hare Intl - CUN Cancun

ORDCUN

Chicago O'Hare Intl

Wed 2/3

7:29 am-12:52 pm

Nonstop4h 23m

Cancun

Fri 2/12

11:38 am-2:38 pm

Nonstop4h 00m

$388

ChicagoCancún

ORD Chicago O'Hare Intl - CUN Cancun

ORDCUN

Chicago O'Hare Intl

Sat 1/23

7:29 am-12:52 pm

Nonstop4h 23m

Cancun

Thu 1/28

11:38 am-2:38 pm

Nonstop4h 00m

$388

ChicagoCancún

ORD Chicago O'Hare Intl - CUN Cancun

ORDCUN

Chicago O'Hare Intl

Thu 10/29

8:40 pm-10:30 pm

1 stop25h 50m

Cancun

Mon 11/2

6:55 pm-3:38 pm

2 stops21h 43m

$389

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago to Yucatan

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest month to fly to Yucatan?

The cheapest month to fly to Yucatan from Chicago is in September. Flight prices, which tend to average around $335, are often lower during this time because this is during the off-season. If you’re not able to fly to Yucatan in September, then May is your next best option. Flight prices from Chicago to Yucatan during May average around $358.

Cheap Chicago to Yucatan flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Yucatan

Best Price Found	$124
Fastest flight time	3h 35m
Direct flights	Every day
Airports in Yucatan	4 airports

The best one-way flight to Yucatan from Chicago in the past 72 hours is $124. The best round-trip flight deal from Chicago to Yucatan found on momondo in the last 72 hours is $312.

The fastest flight from Chicago to Yucatan takes 3h 35m

Direct flights go from Chicago to Yucatan every day.

There are 4 airports in Yucatan. From Chicago there are direct flights to Cancun (CUN).

Search flight deals

Frequently asked questions about flying from Chicago to Yucatan

When did momondo last update prices for flights from Chicago to Yucatan?
Prices for flights from Chicago to Yucatan refresh daily.
How many operators does momondo search for flights from Chicago to Yucatan?
The number of operators available for flights from Chicago to Yucatan is 10 as of September 2026.
How old do you have to be to fly from Chicago to Yucatan?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Yucatan.
What documentation or ID do you need to fly to Yucatan?
The necessary travel and health documents for your Yucatan trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Best airlines flying from Chicago to Yucatan

Compare and see reviews for airlines that fly from Chicago to Yucatan with momondo

Airline	Rating	Free Cancellation	Price
Volaris	PriceFrom $149	Free Cancellation	Rating 6.6 1,137 reviews	Search Volaris flights
Viva	PriceFrom $174	Free Cancellation	Rating 7.0 804 reviews	Search Viva flights
Delta	PriceFrom $371	Free Cancellation	Rating 7.8 8,592 reviews	Search Delta flights
United Airlines	PriceFrom $373	Free Cancellation	Rating 7.4 10,227 reviews	Search United Airlines flights
American Airlines	PriceFrom $631	Free Cancellation	Rating 7.0 12,074 reviews	Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Yucatan?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Yucatan for you.

Can I find flights from Chicago to Yucatan with flexible booking policies on momondo?

momondo does allow users to show only those flights to Yucatan from Chicago which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Chicago to Yucatan?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Yucatan from Chicago.

I’m not ready to book a flight from Chicago to Yucatan right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Yucatan now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Yucatan and let you know when they change.