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Quintana Roo

$114+ Cheap flights from Chicago (CHI) to Quintana Roo

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 6/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CUN
May 25 — Jun 11
Mon 5/25
Mon 6/1
1 adult, Economy
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Cheap flight deals from Chicago to Quintana Roo

Cheapest flights from Chicago to Quintana Roo
Explore the most affordable flight options available from Chicago to Quintana Roo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 25, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/22. 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.
Mon 6/296:00 am
ORD
-
CUN
Nonstop4h 01m
Frontier
Wed 7/811:00 am
CUN
-
ORD
Nonstop4h 09m
Frontier
Deal found 4/22$239
This Kiwi.com deal was found by Cheapflights users on 4/21. 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.
Sun 5/37:35 am
ORD
-
CUN
1 stop13h 28m
Multiple Airlines
Wed 5/1310:25 am
CUN
-
ORD
Nonstop4h 10m
Multiple Airlines
Deal found 4/21$241
This Kiwi.com deal was found by Cheapflights users on 4/22. 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.
Sun 4/266:30 am
ORD
-
CUN
Nonstop4h 08m
Frontier
Fri 5/110:40 am
CUN
-
ORD
Nonstop4h 09m
Frontier
Deal found 4/22$243
This Orbitz deal was found by Cheapflights users on 4/21. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:00 am
ORD
-
CUN
Nonstop4h 03m
Frontier
Tue 5/263:22 pm
CUN
-
ORD
1 stop16h 33m
Frontier
Deal found 4/21$244
This Frontier deal was found by Cheapflights users on 4/22. 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.
Wed 4/296:30 am
ORD
-
CUN
Nonstop4h 08m
Frontier
Wed 5/610:25 am
CUN
-
ORD
Nonstop4h 10m
Frontier
Deal found 4/22$245
This Kiwi.com deal was found by Cheapflights users on 4/22. 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.
Tue 6/96:21 am
ORD
-
CUN
1 stop9h 07m
Multiple Airlines
Thu 6/1811:00 am
CUN
-
ORD
Nonstop4h 17m
Multiple Airlines
Deal found 4/22$246
This Frontier deal was found by Cheapflights users on 4/21. 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.
Sun 5/36:30 am
ORD
-
CUN
Nonstop4h 08m
Frontier
Thu 5/710:25 am
CUN
-
ORD
Nonstop4h 10m
Frontier
Deal found 4/21$247
This Frontier deal was found by Cheapflights users on 4/21. 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 5/76:00 am
ORD
-
CUN
Nonstop4h 03m
Frontier
Wed 5/1310:25 am
CUN
-
ORD
Nonstop4h 10m
Frontier
Deal found 4/21$248
This Kiwi.com deal was found by Cheapflights users on 4/22. 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.
Mon 7/66:00 am
ORD
-
CUN
Nonstop3h 54m
Frontier
Fri 7/1011:00 am
CUN
-
ORD
Nonstop4h 17m
Frontier
Deal found 4/22$249
This Kiwi.com deal was found by Cheapflights users on 4/22. 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.
Mon 5/47:35 am
ORD
-
CUN
1 stop13h 28m
Multiple Airlines
Tue 5/1210:25 am
CUN
-
ORD
Nonstop4h 10m
Multiple Airlines
Deal found 4/22$250
This Frontier deal was found by Cheapflights users on 4/21. 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.
Mon 5/46:30 am
ORD
-
CUN
Nonstop4h 08m
Frontier
Fri 5/810:25 am
CUN
-
ORD
Nonstop4h 10m
Frontier
Deal found 4/21$251
This Expedia deal was found by Cheapflights users on 4/21. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/106:00 am
MDW
-
CUN
1 stop8h 07m
Frontier
Tue 5/263:22 pm
CUN
-
MDW
1 stop19h 47m
Frontier
Deal found 4/21$282

Find flight deals from Chicago to Quintana Roo

Keep the following information in mind while searching for Chicago to Quintana Roo flight deals. Data was last updated April 25, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$239
(Kiwi.com)

One-way from

$114
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$470

Good round-trip deal

$331 or less

Good one-way deal

$145 or less
Provider with most accurate pricing for Chicago (CHI)-Cancun flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Cancun flights.
Search Deals
From Chicago (CHI) to Quintana Roo
Search Deals
One-way flight from Chicago (CHI) to Quintana Roo
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Quintana Roo.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Quintana Roo.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Quintana Roo 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 April 25, 2026.
Use the filters below to find and compare flights from Chicago to Quintana Roo that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Thu 10/8

1:30 am-11:40 pm

1 stop22h 10m

Cancun

Mon 10/12

9:40 am-11:45 pm

1 stop14h 05m

$341

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Wed 5/13

7:07 am-8:16 pm

1 stop13h 09m

Cancun

Tue 5/19

1:30 pm-10:35 pm

1 stop9h 05m

$348

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Thu 9/24

1:30 am-9:25 pm

1 stop19h 55m

Cancun

Tue 9/29

6:20 am-11:00 am

1 stop28h 40m

$360
Quickest round-trip

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Tue 8/11

9:30 am-1:10 pm

Nonstop3h 40m

Cancun

Tue 8/18

12:11 pm-4:04 pm

Nonstop3h 53m

$385

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sat 8/1

9:45 am-8:15 pm

1 stop10h 30m

Cancun

Thu 8/13

8:00 am-2:19 pm

1 stop6h 19m

$388

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Wed 6/3

7:00 am-8:16 pm

2 stops13h 16m

Cancun

Tue 6/9

9:18 am-12:07 am

1 stop14h 49m

$392

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Fri 5/8

7:07 am-8:16 pm

1 stop13h 09m

Cancun

Tue 5/12

9:14 am-10:27 pm

2 stops13h 13m

$393

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 7/23

11:05 am-8:15 pm

1 stop9h 10m

Cancun

Tue 7/28

8:00 am-10:15 pm

1 stop14h 15m

$398

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 6/24

11:05 am-8:25 pm

1 stop9h 20m

Cancun

Tue 6/30

8:00 am-10:17 pm

1 stop14h 17m

$398

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 7/3

6:05 am-2:39 pm

1 stop8h 34m

Cancun

Wed 7/8

12:30 pm-10:15 pm

1 stop9h 45m

$398

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/20

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Chicago to Quintana Roo

Have a flexible travel schedule? Discover the best time to fly to Quintana Roo from Chicago 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 Chicago to Quintana Roo

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

The best time to book flights from Chicago to Quintana Roo is 19 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, May is the cheapest month in which you can book a flight from Chicago to Quintana Roo (average of $395). Flying from Chicago to Quintana Roo in March is currently the most expensive (average of $573). 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 QR?

Find hourly flight availability from Chicago to Quintana Roo. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 25, 2026.

When flying from Chicago to Quintana Roo, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 25% versus a flight at noon.

Weekly flight availability from Chicago to Quintana Roo

Explore weekly flight availability from Chicago to Quintana Roo. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated April 25, 2026.

The most flights from CHI to MXQR are scheduled on a Monday (12 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 on average).

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

Reviews of airlines servicing Quintana Roo

Get insights into the airlines that provide service to Quintana Roo. 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 Quintana Roo. Reviews last updated April 25, 2026.
Peruse reviews from past customers who have flown with Southwest,United Airlines, andAmerican Airlines from Chicago to Quintana Roo to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,333 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,333 reviews
Southwest
8.0
Very good
4,333 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,650 reviews
Southwest
8.0
Very good
4,333 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,671 reviews
Southwest
8.0
Very good
4,333 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Spirit Airlines
6.3
Okay
8,637 reviews
Southwest
8.0
Very good
4,333 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.7
Fair
2,978 reviews
Southwest
8.0
Very good
4,333 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Quintana Roo. 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 Chicago to Quintana Roo?

    There are many flights that can get you from Chicago to Quintana Roo in 3h 40m. Fly via Viva, Delta, or United Airlines to get the fastest option. Airlines will cover a distance of 1447 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    The cheapest airlines for a one-way flight from Chicago to Quintana Roo are Spirit Airlines ($64), Frontier ($87), and Volaris ($95).

  • What are the most popular routes from Chicago to Quintana Roo?

    Most travelers choose Chicago O'Hare Intl - Cancun, Chicago Midway - Cancun or Chicago O'Hare Intl - Cozumel when deciding on the best route from Chicago to Quintana Roo.

  • What are the most reliable airlines from Chicago to Quintana Roo?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago to Quintana Roo on time: Spirit Airlines (71%), United Airlines (61%), Emirates (61%).

  • What are the cheapest flights from Chicago to Quintana Roo?

    The cheapest flight price from Chicago to Quintana Roo is $96. On average you can expect to pay $554. The most popular route, (Chicago O'Hare Intl - Cancun), can usually be booked for $303.

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

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

  • How can I find direct flights from Chicago to Quintana Roo?

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

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

    Yes. Cheapflights offers flight deals from Chicago to Quintana Roo 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 Quintana Roo?

    Currently, May is the cheapest month in which you can book a flight from Chicago to Quintana Roo (average of $395). Flying from Chicago to Quintana Roo in March is currently the most expensive (average of $573). 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

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Top 10 airlines flying from Chicago to Quintana Roo

Discover the top 10 airlines that operate flights from Chicago to Quintana Roo. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 25, 2026.
AirlineCheapestAverageFlexibilityOn-time
VolarisCheapest$112Average$315FlexibilityNo cancel feeOn-time79%
Spirit AirlinesCheapest$142Average$343FlexibilityNo cancel feeOn-time65%
AeromexicoCheapest$145Average$378FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$158Average$1,483FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$189Average$431FlexibilityNo cancel feeOn-time62%
VivaCheapest$193Average$516FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$262Average$480FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$289Average$540FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$290Average$496FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$313Average$509FlexibilityNo cancel feeOn-time71%

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