Cheap flights from Chicago to Yucatan from $115

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Yucatan departing on 5/26. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Chicago to Yucatan

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
6:00 am - 10:03 am
ORD
-
CUN
4h 03mnonstop
Frontier Logo
10:25 am - 2:35 pm
CUN
-
ORD
4h 10mnonstop
$246Frontier
Mon, May 18 - Fri, May 22
Multiple Airlines Logo
2:53 am - 11:54 am
ORD
-
CUN
9h 01m
1 stop
Multiple Airlines Logo
11:00 am - 3:17 pm
CUN
-
ORD
4h 17mnonstop
$248Multiple Airlines
Sat, Jun 13 - Wed, Jun 17
Multiple Airlines Logo
1:59 am - 2:06 pm
ORD
-
CUN
12h 07m
1 stop
Multiple Airlines Logo
11:00 am - 3:17 pm
CUN
-
ORD
4h 17mnonstop
$249Multiple Airlines
Sun, Jun 14 - Thu, Jun 18
Multiple Airlines Logo
1:59 am - 2:06 pm
ORD
-
CUN
12h 07m
1 stop
Multiple Airlines Logo
11:00 am - 3:17 pm
CUN
-
ORD
4h 17mnonstop
$250Multiple Airlines
Mon, Jun 8 - Wed, Jun 17
Viva Logo
1:30 am - 10:54 am
ORD
-
MID
10h 24m
1 stop
Viva Logo
6:01 am - 11:45 pm
MID
-
ORD
16h 44m
1 stop
$285Viva
Wed, Sep 23 - Sun, Sep 27
Viva Logo
2:15 am - 3:50 pm
ORD
-
MID
14h 35m
1 stop
Viva Logo
1:35 pm - 11:55 pm
MID
-
ORD
9h 20m
1 stop
$304Viva
Sun, May 24 - Mon, Jun 1
Southwest Logo
11:00 am - 2:35 pm
MDW
-
CUN
3h 35mnonstop
Southwest Logo
4:10 pm - 7:50 pm
CUN
-
MDW
3h 40mnonstop
$334Southwest
Sun, May 17 - Fri, May 22
Volaris Logo
7:35 am - 3:40 pm
ORD
-
MID
9h 05m
1 stop
Volaris Logo
8:48 pm - 12:09 pm
MID
-
ORD
14h 21m
1 stop
$337Volaris
Tue, Jun 9 - Sat, Jun 13
Volaris Logo
1:40 am - 9:00 am
ORD
-
MID
8h 20m
1 stop
Volaris Logo
8:48 pm - 12:09 pm
MID
-
ORD
14h 21m
1 stop
$347Volaris
Sun, May 24 - Mon, Jun 1
Delta Logo
10:59 am - 8:16 pm
MDW
-
CUN
9h 17m
1 stop
Delta Logo
11:10 am - 9:09 pm
CUN
-
MDW
9h 59m
1 stop
$348Delta
Sun, May 17 - Wed, May 20

Volaris flights from Chicago to Yucatan

Our best Volaris deals on Chicago to Yucatan flight tickets
Volaris
Jun 14
ORD1:59 amChicago O'Hare Intl
12h 07m
1 stop
CUN2:06 pmCancun
Jun 25
CUN9:50 pmCancun
8h 02m
1 stop
ORD5:52 amChicago O'Hare Intl
$302
Volaris
Jun 7
ORD1:59 amChicago O'Hare Intl
8h 32m
1 stop
CUN10:31 amCancun
Jun 12
CUN9:50 pmCancun
8h 02m
1 stop
ORD5:52 amChicago O'Hare Intl
$305
Volaris
Jun 11
ORD2:53 amChicago O'Hare Intl
9h 01m
1 stop
CUN11:54 amCancun
Jun 16
CUN9:50 pmCancun
8h 02m
1 stop
ORD5:52 amChicago O'Hare Intl
$309

Frontier flights from Chicago to Yucatan

Our best Frontier deals on Chicago to Yucatan flight tickets
Frontier
May 18
ORD6:00 amChicago O'Hare Intl
4h 03m
CUN10:03 amCancun
May 22
CUN10:25 amCancun
4h 10m
ORD2:35 pmChicago O'Hare Intl
$246
Frontier
Jul 4
ORD6:00 amChicago O'Hare Intl
4h 01m
CUN10:01 amCancun
Jul 11
CUN11:00 amCancun
4h 09m
ORD3:09 pmChicago O'Hare Intl
$253
Frontier
Jul 7
ORD6:00 amChicago O'Hare Intl
3h 49m
CUN9:49 amCancun
Jul 12
CUN11:00 amCancun
4h 09m
ORD3:09 pmChicago O'Hare Intl
$254

momondo 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, momondo users made 832,500 searches. Data last updated May 8, 2026.
Use the filters below to find and compare flights from Chicago to Yucatan that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Mon 5/18

6:00 am-10:03 am

Nonstop4h 03m

Cancun

Fri 5/22

10:25 am-2:35 pm

Nonstop4h 10m

$246

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sat 6/13

2:53 am-11:54 am

1 stop9h 01m

Cancun

Wed 6/17

11:00 am-3:17 pm

Nonstop4h 17m

$248

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sun 6/14

1:59 am-2:06 pm

1 stop12h 07m

Cancun

Thu 6/18

11:00 am-3:17 pm

Nonstop4h 17m

$249

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Mon 6/8

1:59 am-2:06 pm

1 stop12h 07m

Cancun

Wed 6/17

11:00 am-3:17 pm

Nonstop4h 17m

$250

ChicagoMérida

ORD - MID

ORDMID

Chicago O'Hare Intl

Wed 9/23

1:30 am-10:54 am

1 stop10h 24m

Mérida Rejon

Sun 9/27

6:01 am-11:45 pm

1 stop16h 44m

$285

ChicagoMérida

ORD - MID

ORDMID

Chicago O'Hare Intl

Sun 5/24

2:15 am-3:50 pm

1 stop14h 35m

Mérida Rejon

Mon 6/1

1:35 pm-11:55 pm

1 stop9h 20m

$304
Quickest round-trip

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 5/17

11:00 am-2:35 pm

Nonstop3h 35m

Cancun

Fri 5/22

4:10 pm-7:50 pm

Nonstop3h 40m

$334

ChicagoMérida

ORD - MID

ORDMID

Chicago O'Hare Intl

Tue 6/9

7:35 am-3:40 pm

1 stop9h 05m

Mérida Rejon

Sat 6/13

8:48 pm-12:09 pm

1 stop14h 21m

$337

ChicagoMérida

ORD - MID

ORDMID

Chicago O'Hare Intl

Sun 5/24

1:40 am-9:00 am

1 stop8h 20m

Mérida Rejon

Mon 6/1

8:48 pm-12:09 pm

1 stop14h 21m

$347

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 5/17

10:59 am-8:16 pm

1 stop9h 17m

Cancun

Wed 5/20

11:10 am-9:09 pm

1 stop9h 59m

$348

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Yucatan from

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

What is the cheapest month to fly to Yucatan?

The cheapest month to fly to Yucatan from Chicago is in April. Flight prices, which tend to average around $109, are often lower during this time because this is during the off-season. If you’re not able to fly to Yucatan in April, then March is your next best option. Flight prices from Chicago to Yucatan during March average around $109.

Cheap Chicago to Yucatan flight deals and tips

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

Fastest flight time

3h 30m

Direct flights

Every day

Airports in Yucatan

4 airports
The fastest flight from Chicago to Yucatan takes 3h 30m
Direct flights go from Chicago to Yucatan every day.
There are 4 airports in Yucatan. From Chicago there are direct flights to Cancun (CUN).

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?

  • 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
VolarisPriceFrom $109Free CancellationRating
6.5
1,165 reviews
Search Volaris flights
VivaPriceFrom $199Free CancellationRating
7.0
810 reviews
Search Viva flights
United AirlinesPriceFrom $373Free CancellationRating
7.4
9,694 reviews
Search United Airlines flights
American AirlinesPriceFrom $543Free CancellationRating
7.1
11,667 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.

An easier way to manage your Yucatan trip

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1 adult
Sun 6/7
Sun 6/14

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