Cancún

$139+ Cheap flights from Chicago (CHI) to Cancún (CUN)

CHI — CUN
Sep 24 — Oct 11
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Cancún with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.
Cheapflights Tip: The best prices from Chicago to Cancun are usually found in January or February, booked 65 days in advance, depart on a Sunday or Monday and return on a Thursday

Cheap flight deals from Chicago to Cancún

Cheapest flights from Chicago to Cancún

Fri 11/1312:35 am -
1 stop20h 10m
Sun 11/1510:25 am -
1 stop13h 30m
Deal found 8/21$334
Tue 9/291:40 am -
1 stop8h 23m
Sat 10/39:50 pm -
1 stop8h 02m
Deal found 8/21$335
Thu 12/36:29 am -
1 stop13h 28m
Tue 12/159:55 pm -
1 stop7h 48m
Deal found 8/21$336
Sat 10/31:40 am -
1 stop8h 23m
Sat 10/109:50 pm -
1 stop8h 02m
Deal found 8/22$337
Mon 9/287:35 am -
1 stop13h 28m
Thu 10/19:50 pm -
1 stop8h 02m
Deal found 8/21$338
Tue 10/67:35 am -
1 stop13h 28m
Tue 10/139:50 pm -
1 stop8h 02m
Deal found 8/22$339
Sat 9/191:40 am -
1 stop8h 23m
Wed 9/2310:50 am -
1 stop12h 57m
Deal found 8/22$340
Mon 11/91:24 am -
1 stop13h 07m
Sun 11/1510:45 am -
1 stop12h 28m
Deal found 8/21$341
Sat 12/56:29 am -
1 stop13h 28m
Sat 12/1210:45 am -
1 stop12h 28m
Deal found 8/22$342
Mon 9/287:35 am -
1 stop13h 28m
Tue 9/299:50 pm -
1 stop8h 02m
Deal found 8/21$343
Sat 10/31:40 am -
1 stop8h 23m
Fri 10/99:50 pm -
1 stop8h 02m
Deal found 8/25$344
Wed 9/97:35 am -
1 stop13h 28m
Mon 9/149:50 pm -
1 stop8h 02m
Deal found 8/23$345

Find flight deals from Chicago to Cancún

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$334
(Viva)

One-way from

$139
(CheapOair)

Popular in

December

Cheapest in

January

Average price

$518

Good round-trip deal

$531 or less

Good one-way deal

$266 or less
Provider with most accurate pricing for Chicago (CHI)-Cancun flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-Cancun flights.
From Chicago (CHI) to Cancun
One-way flight from Chicago (CHI) to Cancun
Highest demand for flights based on searches. 0% potential increase in price ($1 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Average for round-trip flights in August 2026
Price to beat on a round-trip flight from Chicago (CHI) to Cancun.
Price to beat on a one-way flight from Chicago (CHI) to Cancun.

Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Chicago to Cancún that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoCancún

ORD Chicago O'Hare Intl - CUN Cancun

ORDCUN

Chicago O'Hare Intl

Tue 11/17

7:05 am-8:55 pm

2 stops12h 50m

Cancun

Wed 11/25

11:21 am-11:39 pm

1 stop13h 18m

$461

ChicagoCancún

ORD Chicago O'Hare Intl - CUN Cancun

ORDCUN

Chicago O'Hare Intl

Tue 11/3

1:30 am-1:41 pm

1 stop11h 11m

Cancun

Fri 11/13

1:37 pm-11:59 pm

2 stops11h 22m

$462

ChicagoCancún

MDW Chicago Midway - CUN Cancun

MDWCUN

Chicago Midway

Tue 10/13

6:04 am-7:55 pm

1 stop13h 51m

Cancun

Wed 10/21

9:16 am-10:33 pm

2 stops13h 17m

$466

ChicagoCancún

ORD Chicago O'Hare Intl - CUN Cancun

ORDCUN

Chicago O'Hare Intl

Sat 10/31

7:00 am-7:55 pm

2 stops12h 55m

Cancun

Fri 11/6

8:00 am-8:30 pm

2 stops13h 30m

$487

ChicagoCancún

ORD Chicago O'Hare Intl - CUN Cancun

ORDCUN

Chicago O'Hare Intl

Sun 1/3

10:30 am-3:30 pm

Nonstop4h 00m

Cancun

Fri 1/8

4:42 pm-7:46 pm

Nonstop4h 04m

$497

ChicagoCancún

MDW Chicago Midway - CUN Cancun

MDWCUN

Chicago Midway

Sat 10/17

9:29 am-7:55 pm

2 stops10h 26m

Cancun

Sat 10/24

8:00 am-6:00 pm

2 stops10h 00m

$503

ChicagoCancún

MDW Chicago Midway - CUN Cancun

MDWCUN

Chicago Midway

Mon 11/16

5:20 am-4:00 pm

1 stop9h 40m

Cancun

Mon 11/23

11:20 am-8:05 pm

2 stops9h 45m

$511
Quickest round-trip

ChicagoCancún

MDW Chicago Midway - CUN Cancun

MDWCUN

Chicago Midway

Fri 11/13

8:55 am-1:40 pm

Nonstop3h 45m

Cancun

Tue 11/17

6:00 pm-8:35 pm

Nonstop3h 35m

$514

ChicagoCancún

MDW Chicago Midway - CUN Cancun

MDWCUN

Chicago Midway

Fri 10/23

5:00 am-12:00 pm

1 stop7h 00m

Cancun

Wed 10/28

1:05 pm-9:55 pm

2 stops8h 50m

$516

ChicagoCancún

ORD Chicago O'Hare Intl - CUN Cancun

ORDCUN

Chicago O'Hare Intl

Wed 9/16

6:40 am-7:50 pm

1 stop13h 10m

Cancun

Wed 9/23

11:30 am-11:59 pm

2 stops12h 29m

$525

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/23

Showing 1-10 of 44 resultsSorted by cheapest first
1
2
3
...
5

Compare providers for flights from Chicago to Cancún

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Cancún in August.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy2 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
AranGrantPrice Accuracy3 starsTrust Score*3 stars
CheapTicketsDealPrice Accuracy1 starTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star
CheapflightsfaresPrice Accuracy2 starsTrust Score*1 star
MytripPrice Accuracy2 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Cancún flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Cancún flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Cancún flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Cancún flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Cancún flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Cancún

Have a flexible travel schedule? Discover the best time to fly to Cancún from Chicago with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

Everything you need to know about your flight from Chicago to Cancún

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

Currently, January is the cheapest month in which you can book a flight from Chicago to Cancún (average of $372). Flying from Chicago to Cancún in December is currently the most expensive (average of $547). 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 CUN?

It’s optimal to fly from Chicago to Cancún in the morning. By choosing this option you can save up to 25% on the cost of your flight, compared to a flight at noon.

Weekly flight availability from Chicago to Cancún

The most flights from CHI to CUN are scheduled on a Monday (6 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 on average).

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

Airfare is below average for this route at the moment.
Chicago to Cancún flights typically cost between $380 and $590 in November.
The cheapest round-trip price found within the last 5 days was $334 on Viva (Nov 13-Nov 15).

What’s the top layover airport for flights from Chicago to Cancún?

Mexico City (MEX) – chosen by Cheapflights users on 63% of 1-stop itineraries from Chicago to Cancún on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to Cancún?

Atlanta (ATL) is the most affordable 1-stop option, with an average round-trip price of $340.

What’s the fastest layover option from Chicago to Cancún?

Flights via Atlanta (ATL) have the shortest average one-way travel time for 1-stop routes: 7h 00m.

Which airport typically offers the quickest layover for flights from Chicago to Cancún?

Flights via Guadalajara (GDL) offer the fastest connection on this route, with an average layover time of 2h 19m.

How often are flights from Chicago to Cancún delayed?

About 21% of weekly flights between Chicago and Cancún have experienced delays in the past year, with the average delay time being 156 minutes.

What is the most punctual flight time for Chicago to Cancún flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Wednesday tends to have the lowest number of delays on this route, whereas Saturday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to Cancún flights?

Over the last year, Spirit Airlines have had the lowest number of delays on this route, with just 16% of flights being delayed.

How far ahead should I book a flight from Chicago to Cancún?

Booking 77 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Cancún. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

The best insider tips for Chicago to Cancún flights

Cheapflights partnered with top experts to bring you the best recommendations for your Chicago to Cancún trip
Our travel experts
Marisa Garcia

Marisa Garcia

Expert on Frontier

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Ramsey Qubein

Ramsey Qubein

Expert on ORD and CUN

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Reviews of airlines servicing Cancún

Peruse reviews from past customers who have flown with Southwest,United Airlines, andAmerican Airlines from Chicago to Cancún to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Related info for your journey

  • How busy are the airports in Chicago and Cancun?

    To fly to Cancun from Chicago, you can choose to board your flight at either Midway International Airport (MDW) or O’Hare International Airport (ORD). If you choose to take off to Cancun from Midway International Airport, you need not worry about encountering so many people as this airport isn’t always busy. If, however, you choose to board a flight to Cancun from Chicago at O’Hare International Airport, you can count on meeting loads of people, as this airport is one of the busiest airports in the country. At either, you can count on being assisted anytime you’re in need, as both these airports have superb airport officials. In Cancun, you’ll land at the popular Cancun International Airport (CUN). Situated nearby the heart of Cancun, this airport prides itself on processing travelers as quickly as possible. Once you land at this airport, you need not worry about being kept waiting for long as at this airport, you’ll be cleared for entry in a matter of two to three minutes.

  • Which airlines fly directly from Chicago to Cancun?

    Several airlines offer direct flights to Cancun from Chicago. Thus, if you want to fly nonstop to Cancun from Chicago, you need not worry about lacking an airline to travel with. The air travel companies that offer these nonstop flights include Spirit Airlines, American Airlines, and Southwest Airlines. Aboard a Spirit Airlines non-stop flight, you’ll reach Cancun after three hours and 30 minutes, while onboard a Southwest Airlines non-stop flight, you’ll reach Cancun after three hours and 40 minutes. If none of these two airlines have convenient flights for you, and you choose to board an American Airlines non-stop flight, you’ll land after three hours and 35 minutes.

  • What are the stopover options between Chicago to Cancun?

    The stopover options between Chicago and Cancun are quite numerous. Of these many stopover options, Charlotte, Dallas, and Atlanta are the most popular. If you board a flight with a stopover in Charlotte, you’ll land at Charlotte’s exclusive Charlotte Douglas International Airport, whereas if you choose a flight with a stopover in Atlanta, you’ll land at Hartsfield Jackson International Airport. If none of these stopover options appeal to you, and you board a flight with a stopover in Dallas, you’ll land at the Dallas-Fort Worth International Airport. At any of these airports, you’ll have a good rest, tasty meals, and a fun shopping experience, as they’ve all got comfy lounges, world-class restaurants, and well-stocked shops.

  • Do I need a passport or visa to fly from Chicago to Cancun?

    If you’d like to fly to Cancun from Chicago, there are several documents you can use to pass airport security. If you’re Mexican, you can use your national ID to pass airport security, while if you’re an American or Canadian, you only need to present your passport and correctly filled entry forms to be allowed entry into the country once you land. If you’re not from any of the mentioned countries, you must have a visa to be granted entry. Mexican authorities are renowned for being strict enforcers of the law. Thus, to avoid any issues with them, when flying to Cancun from Chicago, you should have the required documents in order.

  • What airport do you fly into for flights to Cancún from Chicago?

    Cancun (CUN) is the airport you will fly into if you book a flight from Chicago to Cancún. You should not have trouble finding flights to Cancun from Chicago; the airport handles an average of 4 inbound flights from Chicago per day. You should also have plenty of airline options to choose from since 10 airlines have flights to the Cancún airport from Chicago. It is only a 8.9 mi journey from Cancun (CUN) to Cancún’s city center.

  • How long is the flight from Chicago to Cancún?

    Departing from Chicago to Cancún will take you 4h. There are 1447 mi between Chicago and Cancún. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Chicago to Cancún round-trip?

    Our cheapest airline available from Chicago to Cancún is Volaris. Our recent data shows that you can find tickets from as low as $129 on this airline. Additional options worth looking into are Delta and Frontier, starting at $158 and $192 round-trip. These flights start at 72% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Chicago to Cancún one-way?

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $88. Users have also found prices from $98 and $102 on Volaris and JetBlue, respectively.

  • What are the most reliable airlines from Chicago to Cancún?

    Consider American Airlines (86%), Emirates (81%) or United Airlines (81%) when booking your flight. These represent the most reliable airlines when flying from Chicago to Cancún.

  • What are the cheapest flights from Chicago to Cancún?

    Looking for the cheapest flight from Chicago to Cancún? While on average our users pay $657, our data indicates the cheapest price to be $219. The most popular route (Chicago O'Hare Intl - Cancun), is priced around $314.

  • Can I find deals for flights from Chicago to Cancún that include hotel bookings?

    Yes. In addition to deals on Chicago to Cancún flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Cancún?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Cancún.

  • Can I find deals for business class flights from Chicago to Cancún?

    Yes. Cheapflights offers flight deals from Chicago to Cancún 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 Cancún?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Cancún (average of $372). Flying from Chicago to Cancún in December is currently the most expensive (average of $547). 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 are the most eco-friendly airlines from Chicago to Cancun?

    Plenty of airlines offer flights to Cancun from Chicago. Of these airlines, Air Canada, JetBlue Airlines, and Delta Airlines are the most eco-friendly. To reduce its carbon footprint, Air Canada has made many eco-friendly decisions. These decisions include investing in sustainable aviation fuel research and purchasing several energy-saving aircraft. Delta Airlines has also made several eco-friendly decisions. They include cutting down its use of single-use plastics, increasing its use of recyclable products, and reducing its emissions through carbon offsets. JetBlue Airlines, just like Air Canada and Delta Airlines, has also taken several steps to minimize its carbon footprint. Some of the steps it has taken include partnering with sustainable aviation fuel companies such as World Energy and World Fuel and reducing its operational waste.

  • How can I fly more sustainably from Chicago to Cancun?

    There are many ways you can fly sustainably to Cancun from Chicago. The said ways include flying during the day, packing light luggage, and traveling on board a direct flight. If you travel during the day, you'll achieve your goal of traveling sustainably because flights during the night often lead to the founding of clouds that hinder radiation produced by the earth from escaping. If you pack light luggage, you'll also achieve your goal of traveling sustainably because flights with light luggage usually combust less fuel than flights with heavy luggage. You'll achieve sustainable travel by traveling on board a direct flight because direct flights normally consume less fuel and emit fewer carbon gases than flights with stopovers. Everyone has the moral responsibility of protecting the environment. By practicing the tips mentioned above, it's fair to say that you'll be travelling responsibly.

See more FAQs

Traveling to a place near Cancún?

Book flights to Cancún if you plan to visit one of these locations
Puerto Aventuras
Punta Sam
Holbox

Browse thousands of different options on Cheapflights for your next trip

Top 10 airlines flying from Chicago to Cancún

AirlineCheapestAverageFlexibilityOn-time
VolarisCheapest$129Average$338FlexibilityNo cancel feeOn-time79%
DeltaCheapest$158Average$449FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$192Average$431FlexibilityNo cancel feeOn-time62%
AeromexicoCheapest$194Average$429FlexibilityNo cancel feeOn-timeN/A
VivaCheapest$253Average$433FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$262Average$484FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$292Average$521FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$304Average$493FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$322Average$522FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$360Average$492FlexibilityNo cancel feeOn-time67%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.