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Quintana Roo

$108+ 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 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CUN
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
1 adult, Economy
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Cheap 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 October 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$241
(Cheapflightsfares)

One-way from

$108
(Booking.com)

Popular in

March

Cheapest in

September

Average price

$396

Good round-trip deal

$281 or less

Good one-way deal

$129 or less
Provider with most accurate pricing for Chicago (CHI)-Cancun flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Cancun flights.
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From Chicago (CHI) to Quintana Roo
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One-way flight from Chicago (CHI) to Quintana Roo
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Highest demand for flights based on searches. 5% potential increase in price ($25 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Quintana Roo.
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Price to beat on a one-way flight from Chicago (CHI) to Quintana Roo.
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Find 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 October 14, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 10/12. 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 11/175:10 amORD - CUN
1 stop7h 25mSpirit Airlines
Wed 11/192:44 pmCUN - ORD
1 stop10h 43mSpirit Airlines
Deal found 10/12$241
This Kiwi.com deal was found by Cheapflights users on 10/13. 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 12/26:00 amORD - CUN
Nonstop3h 44mSpirit Airlines
Sat 12/62:36 pmCUN - ORD
1 stop10h 43mSpirit Airlines
Deal found 10/13$242
This Kiwi.com deal was found by Cheapflights users on 10/12. 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.
Sat 11/156:00 amORD - CUN
Nonstop3h 44mSpirit Airlines
Sat 11/2211:53 amCUN - ORD
Nonstop4h 00mSpirit Airlines
Deal found 10/12$243
This Kiwi.com deal was found by Cheapflights users on 10/13. 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.
Wed 11/1911:58 pmORD - CUN
1 stop14h 03mMultiple Airlines
Mon 11/2411:53 amCUN - ORD
Nonstop4h 00mMultiple Airlines
Deal found 10/13$244
This Cheapflightsfares deal was found by Cheapflights users on 10/14. 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.
Tue 10/285:05 amORD - CUN
1 stop7h 39mSpirit Airlines
Tue 11/42:44 pmCUN - ORD
1 stop10h 43mSpirit Airlines
Deal found 10/14$245
This CheapOair deal was found by Cheapflights users on 10/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/256:58 pmORD - CUN
1 stop13h 06mSpirit Airlines
Sat 11/19:09 amCUN - ORD
1 stop11h 08mSpirit Airlines
Deal found 10/14$246
This Cheapflightsfares deal was found by Cheapflights users on 10/11. 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.
Tue 11/115:10 amORD - CUN
1 stop7h 25mSpirit Airlines
Sat 11/1511:53 amCUN - ORD
Nonstop4h 00mSpirit Airlines
Deal found 10/11$247
This Cheapflightsfares deal was found by Cheapflights users on 10/12. 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.
Sat 11/156:00 amORD - CUN
Nonstop3h 44mSpirit Airlines
Wed 11/192:44 pmCUN - ORD
1 stop6h 43mSpirit Airlines
Deal found 10/12$248
This Cheapflightsfares deal was found by Cheapflights users on 10/12. 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 11/145:57 pmORD - CUN
1 stop16h 39mSpirit Airlines
Mon 11/2411:53 amCUN - ORD
Nonstop4h 00mSpirit Airlines
Deal found 10/12$249
This Priceline deal was found by Cheapflights users on 10/12. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/249:08 pmORD - CUN
1 stop12h 09mSpirit Airlines
Sat 11/110:55 amCUN - ORD
Nonstop4h 03mSpirit Airlines
Deal found 10/12$250
This Cheapflightsfares deal was found by Cheapflights users on 10/13. 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.
Tue 10/215:05 amORD - CUN
1 stop7h 39mSpirit Airlines
Sat 10/259:09 amCUN - ORD
1 stop8h 44mSpirit Airlines
Deal found 10/13$251
This Southwest deal was found by Cheapflights users on 10/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/1610:40 amMDW - CUN
Nonstop3h 45mSouthwest
Fri 11/212:15 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 10/13$252

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 October 14, 2025.
Use the filters below to find and compare flights from Chicago to Quintana Roo that are best for you.

Fly from

Chicago

Fly to

Quintana Roo

Route

Depart

Return

Price

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 11/8

3:40 pm-8:25 pm

Nonstop3h 45m

Cancun

Fri 11/14

2:15 pm-5:00 pm

Nonstop3h 45m

$257

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sat 11/8

10:35 am-8:18 pm

1 stop8h 43m

Cancun

Thu 11/13

3:18 pm-6:09 pm

Nonstop3h 51m

$271

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Tue 1/6

8:43 am-1:33 pm

Nonstop3h 50m

Cancun

Tue 1/13

4:20 pm-11:59 pm

1 stop8h 39m

$279

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sat 11/8

10:35 am-8:18 pm

1 stop8h 43m

Cancun

Fri 11/14

3:18 pm-6:09 pm

Nonstop3h 51m

$291

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sun 12/14

7:35 am-5:50 pm

1 stop9h 15m

Cancun

Wed 12/17

3:18 pm-6:09 pm

Nonstop3h 51m

$301

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 11/12

9:20 am-8:25 pm

1 stop10h 05m

Cancun

Fri 11/14

2:15 pm-5:00 pm

Nonstop3h 45m

$306

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sat 1/24

5:50 am-4:31 pm

1 stop9h 41m

Cancun

Fri 1/30

11:14 am-11:18 pm

1 stop13h 04m

$316

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sat 1/24

5:50 am-6:36 pm

2 stops11h 46m

Cancun

Thu 1/29

6:00 am-12:48 pm

1 stop7h 48m

$316

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 11/11

12:47 pm-9:20 pm

1 stop7h 33m

Cancun

Tue 11/18

8:00 am-4:38 pm

1 stop9h 38m

$326

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 1/11

10:35 am-9:10 pm

1 stop9h 35m

Cancun

Fri 1/16

3:03 pm-9:46 pm

1 stop7h 43m

$326

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/12

Showing 1-10 of 60 results
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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

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

Currently, January is the cheapest month in which you can book a flight from Chicago to Quintana Roo (average of $127). Flying from Chicago to Quintana Roo in July is currently the most expensive (average of $217). 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 October 14, 2025.

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 at noon, which can drop the price by up to 46% versus a flight in the morning.

What is the cheapest day to fly from Chicago to Quintana Roo?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Quintana Roo. Price data was last updated on October 12, 2025.

Travelers seeking maximum savings on their Chicago to Quintana Roo flight should consider departing on Wednesday at noon when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 October 14, 2025.

The most flights from CHI to MXQR are scheduled on a Saturday (9 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (7 on average).

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 October 14, 2025.
Peruse reviews from past customers who have flown with Southwest, United Airlines, and American 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
4,238 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,976 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,042 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,096 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,135 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 45m. Fly via Southwest, United Airlines, or Delta to get the fastest option. Airlines will cover a distance of 1434 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 (100%), Frontier (81%), Emirates (79%).

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

    The cheapest flight price from Chicago to Quintana Roo is $89. On average you can expect to pay $529. The most popular route, (Chicago O'Hare Intl - Cancun), can usually be booked for $229.

  • 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, January is the cheapest month in which you can book a flight from Chicago to Quintana Roo (average of $127). Flying from Chicago to Quintana Roo in July is currently the most expensive (average of $217). 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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Alternative routes for Chicago to Quintana Roo

See prices for flight routes from nearby airports that may be better suited for you.
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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 October 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$149Average$340FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$161Average$532FlexibilityNo cancel feeOn-time69%
DeltaCheapest$168Average$497FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$174Average$460FlexibilityNo cancel feeOn-time62%
VolarisCheapest$181Average$548FlexibilityNo cancel feeOn-time79%
AeromexicoCheapest$191Average$432FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$205Average$685FlexibilityNo cancel feeOn-time67%
VivaCheapest$237Average$336FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$266Average$597FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$268Average$508FlexibilityNo cancel feeOn-time71%

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