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Cheap flights from Chicago to Quintana Roo from $106

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 Quintana Roo departing on 1/22. 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 Quintana Roo

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
5:05 am - 3:22 pm
ORD
-
CUN
9h 17m1 stop
Frontier Logo
7:19 pm - 10:28 pm
CUN
-
ORD
4h 09mnonstop
$212Frontier
Sat, Feb 21 - Wed, Feb 25
Frontier Logo
7:11 am - 12:19 pm
ORD
-
CUN
4h 08mnonstop
Frontier Logo
11:40 am - 2:49 pm
CUN
-
ORD
4h 09mnonstop
$213Frontier
Sat, Jan 24 - Tue, Feb 3
Volaris Logo
6:23 am - 5:16 pm
ORD
-
CZM
10h 53m1 stop
Volaris Logo
6:21 pm - 4:36 am
CZM
-
ORD
10h 15m1 stop
$288Volaris
Sun, Feb 1 - Sun, Feb 8
Aeromexico Logo
6:00 am - 3:30 pm
MDW
-
CUN
8h 30m1 stop
Aeromexico Logo
1:40 pm - 10:22 pm
CUN
-
MDW
9h 42m1 stop
$298Aeromexico
Fri, Jan 30 - Fri, Feb 6
Volaris Logo
6:23 am - 5:16 pm
ORD
-
CZM
10h 53m1 stop
Volaris Logo
6:21 pm - 4:36 am
CZM
-
ORD
10h 15m1 stop
$299Volaris
Sat, Jan 24 - Wed, Jan 28
Viva Logo
1:20 am - 7:45 pm
ORD
-
CZM
18h 25m1 stop
Viva Logo
5:25 pm - 11:50 pm
CZM
-
ORD
6h 25m1 stop
$331Viva
Wed, Feb 11 - Sun, Feb 15
Viva Logo
1:00 am - 1:25 pm
ORD
-
CTM
12h 25m1 stop
Viva Logo
2:10 pm - 11:25 pm
CTM
-
ORD
9h 15m1 stop
$354Viva
Fri, Jan 30 - Sat, Feb 7
Delta Logo
6:45 am - 1:50 pm
MDW
-
CZM
7h 05m1 stop
Delta Logo
3:05 pm - 10:07 pm
CZM
-
MDW
7h 02m1 stop
$447Delta
Mon, Jan 12 - Wed, Jan 14
Aeromexico Logo
6:00 am - 1:50 pm
MDW
-
CZM
7h 50m1 stop
Aeromexico Logo
3:05 pm - 10:22 pm
CZM
-
MDW
7h 17m1 stop
$449Aeromexico
Thu, Jan 29 - Thu, Feb 5
Delta Logo
6:14 pm - 1:50 pm
MDW
-
CZM
19h 36m2 stops
Delta Logo
3:05 pm - 8:52 am
CZM
-
MDW
17h 47m2 stops
$452Delta
Mon, Jan 12 - Fri, Jan 23

Southwest flights from Chicago to Quintana Roo

Our best Southwest deals on Chicago to Quintana Roo flight tickets
Southwest
Jan 19
MDW5:25 amChicago Midway
6h 40m
1 stop
CUN1:05 pmCancun
Jan 22
CUN1:45 pmCancun
3h 45m
MDW4:30 pmChicago Midway
$318
Find similar
Southwest
Jan 26
MDW9:15 amChicago Midway
3h 40m
CUN1:55 pmCancun
Feb 4
CUN1:40 pmCancun
3h 45m
MDW4:25 pmChicago Midway
$344
Find similar
Southwest
Mar 6
MDW4:05 pmChicago Midway
3h 40m
CUN8:45 pmCancun
Mar 12
CUN8:30 amCancun
3h 40m
MDW12:10 pmChicago Midway
$354
Find similar

Frontier flights from Chicago to Quintana Roo

Our best Frontier deals on Chicago to Quintana Roo flight tickets
Frontier
Feb 21
ORD5:05 amChicago O'Hare Intl
9h 17m
1 stop
CUN3:22 pmCancun
Feb 25
CUN7:19 pmCancun
4h 09m
ORD10:28 pmChicago O'Hare Intl
$212
Find similar
Frontier
Jan 24
ORD7:11 amChicago O'Hare Intl
4h 08m
CUN12:19 pmCancun
Feb 3
CUN11:40 amCancun
4h 09m
ORD2:49 pmChicago O'Hare Intl
$213
Find similar
Frontier
Jan 21
ORD7:11 amChicago O'Hare Intl
4h 08m
CUN12:19 pmCancun
Jan 29
CUN11:40 amCancun
4h 09m
ORD2:49 pmChicago O'Hare Intl
$221
Find similar

momondo 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, momondo users made 832,500 searches. Data last updated December 18, 2025.
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

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sat 2/21

5:05 am-3:22 pm

1 stop9h 17m

Cancun

Wed 2/25

7:19 pm-10:28 pm

Nonstop4h 09m

$212

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sat 1/24

7:11 am-12:19 pm

Nonstop4h 08m

Cancun

Tue 2/3

11:40 am-2:49 pm

Nonstop4h 09m

$213

ChicagoCozumel

ORD - CZM

ORDCZM

Chicago O'Hare Intl

Sun 2/1

6:23 am-5:16 pm

1 stop10h 53m

Cozumel

Sun 2/8

6:21 pm-4:36 am

1 stop10h 15m

$288

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 1/30

6:00 am-3:30 pm

1 stop8h 30m

Cancun

Fri 2/6

1:40 pm-10:22 pm

1 stop9h 42m

$298

ChicagoCozumel

ORD - CZM

ORDCZM

Chicago O'Hare Intl

Sat 1/24

6:23 am-5:16 pm

1 stop10h 53m

Cozumel

Wed 1/28

6:21 pm-4:36 am

1 stop10h 15m

$299

ChicagoCozumel

ORD - CZM

ORDCZM

Chicago O'Hare Intl

Wed 2/11

1:20 am-7:45 pm

1 stop18h 25m

Cozumel

Sun 2/15

5:25 pm-11:50 pm

1 stop6h 25m

$331

ChicagoChetumal

ORD - CTM

ORDCTM

Chicago O'Hare Intl

Fri 1/30

1:00 am-1:25 pm

1 stop12h 25m

Chetumal

Sat 2/7

2:10 pm-11:25 pm

1 stop9h 15m

$354

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Mon 1/12

6:45 am-1:50 pm

1 stop7h 05m

Cozumel

Wed 1/14

3:05 pm-10:07 pm

1 stop7h 02m

$447

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Thu 1/29

6:00 am-1:50 pm

1 stop7h 50m

Cozumel

Thu 2/5

3:05 pm-10:22 pm

1 stop7h 17m

$449

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Mon 1/12

6:14 pm-1:50 pm

2 stops19h 36m

Cozumel

Fri 1/23

3:05 pm-8:52 am

2 stops17h 47m

$452

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 Quintana Roo from

How to get the cheapest flight ticket from Chicago to Quintana Roo

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 Quintana Roo?

In general, September is the cheapest month to fly from Chicago to Quintana Roo. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $368. If you aren’t able to travel during the month of September, then book flights to Quintana Roo from Chicago during July instead. Flights to Quintana Roo in July, while not as cheap as those in September, still average around $392.

What is the cheapest day to depart on your flight to Quintana Roo?

On average, the least expensive day to fly to Quintana Roo from Chicago is on a Monday. momondo users have found tickets for Monday departures for as low as $416. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Quintana Roo is Thursday, with ticket prices averaging around $520.

What is the cheapest time of day to depart on your flight to Quintana Roo?

Our data shows that the cheapest Chicago to Quintana Roo flights are usually those with departure times at noon. Our users have found flights to Quintana Roo at noon for as low as $192. In contrast, the most expensive time of day to depart to Quintana Roo is in the afternoon when prices are around $664.

What is the cheapest Chicago to Quintana Roo flight route?

Fly from Chicago O'Hare Intl to Cancun for the best Chicago - Quintana Roo flight prices

How far in advance should I book a flight to Quintana Roo?

You are more likely to see cheaper flights to Quintana Roo from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Quintana Roo for around $440 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Quintana Roo from Chicago for as low as $363 on momondo.

What cabin class options are available on Chicago to Quintana Roo flights?

There are 4 cabin classes available to choose from on Chicago to Quintana Roo flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to Quintana Roo flights?

You could potentially save up to 3% on your flight if you consider stops on a Chicago to Quintana Roo flight.

Cheap Chicago to Quintana Roo flight deals and tips

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

Best Price Found

$138

Fastest flight time

3h 30m

Direct flights

Every day

Airports in Quintana Roo

18 airports
The best one-way flight to Quintana Roo from Chicago in the past 72 hours is $138. The best round-trip flight deal from Chicago to Quintana Roo found on momondo in the last 72 hours is $314.
The fastest flight from Chicago to Quintana Roo takes 3h 30m
Direct flights go from Chicago to Quintana Roo every day.
There are 18 airports in Quintana Roo. From Chicago there are direct flights to Cancun (CUN).
Search flight deals

  • When did momondo last update prices for flights from Chicago to Quintana Roo?

    Prices for flights from Chicago to Quintana Roo refresh daily.

  • How many operators does momondo search for flights from Chicago to Quintana Roo?

  • How old do you have to be to fly from Chicago to Quintana Roo?

    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 Quintana Roo.

  • What documentation or ID do you need to fly to Quintana Roo?

    The necessary travel and health documents for your Quintana Roo 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.

  • What is the most popular plane model from Chicago to Quintana Roo?

Best airlines flying from Chicago to Quintana Roo

Compare and see reviews for airlines that fly from Chicago to Quintana Roo with momondo
Airline
Rating
Free Cancellation
Price
AeromexicoPriceFrom $145Free CancellationRating
7.4
1,629 reviews
Search Aeromexico flights
United AirlinesPriceFrom $161Free CancellationRating
7.4
9,092 reviews
Search United Airlines flights
Spirit AirlinesPriceFrom $168Free CancellationRating
6.3
8,190 reviews
Search Spirit Airlines flights
DeltaPriceFrom $168Free CancellationRating
7.9
8,005 reviews
Search Delta flights
VolarisPriceFrom $174Free CancellationRating
6.6
1,156 reviews
Search Volaris flights
FrontierPriceFrom $185Free CancellationRating
5.8
3,081 reviews
Search Frontier flights
JetBluePriceFrom $212Free CancellationRating
7.2
2,897 reviews
Search JetBlue flights
VivaPriceFrom $237Free CancellationRating
7.0
797 reviews
Search Viva flights
SouthwestPriceFrom $266Free CancellationRating
7.9
4,250 reviews
Search Southwest flights
American AirlinesPriceFrom $268Free CancellationRating
7.2
11,055 reviews
Search American Airlines flights

Why use momondo?

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

It is quick and easy to find Chicago to Quintana Roo flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Quintana Roo that suits you.

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

Flights from Chicago to Quintana Roo with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Chicago to Quintana Roo?

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 Quintana Roo from Chicago.

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

Yes. momondo can track prices for Chicago to Quintana Roo flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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Find better results for your trip to Quintana Roo

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