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Cheap flights from Chicago to Quintana Roo from $111

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 5/18. 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
6:00 am - 10:03 am
ORD
-
CUN
4h 03mnonstop
Frontier Logo
10:25 am - 2:35 pm
CUN
-
ORD
4h 10mnonstop
$244Frontier
Sat, May 16 - Wed, May 20
Frontier Logo
6:00 am - 9:49 am
ORD
-
CUN
3h 49mnonstop
Frontier Logo
11:00 am - 3:09 pm
CUN
-
ORD
4h 09mnonstop
$246Frontier
Tue, Jul 7 - Sat, Jul 11
Southwest Logo
9:35 am - 1:10 pm
MDW
-
CUN
3h 35mnonstop
Southwest Logo
4:10 pm - 7:50 pm
CUN
-
MDW
3h 40mnonstop
$333Southwest
Mon, May 18 - Fri, May 22
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
Delta Logo
10:59 am - 8:16 pm
MDW
-
CUN
9h 17m
1 stop
Delta Logo
8:00 am - 4:12 pm
CUN
-
MDW
8h 12m
1 stop
$348Delta
Sun, May 17 - Wed, May 20
Delta Logo
9:22 am - 8:16 pm
MDW
-
CUN
10h 54m
2 stops
Delta Logo
8:00 am - 9:09 pm
CUN
-
MDW
13h 09m
1 stop
$352Delta
Tue, May 19 - Thu, May 21
Volaris Logo
1:40 am - 3:57 pm
ORD
-
CZM
15h 17m
1 stop
Volaris Logo
4:47 pm - 5:52 am
CZM
-
ORD
12h 05m
1 stop
$394Volaris
Fri, Sep 25 - Sat, Oct 3
Volaris Logo
7:35 am - 3:57 pm
ORD
-
CZM
9h 22m
1 stop
Volaris Logo
4:47 pm - 5:52 am
CZM
-
ORD
12h 05m
1 stop
$396Volaris
Sun, Aug 23 - Thu, Sep 3
Aeromexico Logo
2:01 am - 4:16 pm
ORD
-
CTM
15h 15m
1 stop
Aeromexico Logo
4:54 pm - 12:00 pm
CTM
-
ORD
18h 06m
2 stops
$605Aeromexico
Mon, May 18 - Wed, May 27
Aeromexico Logo
5:30 am - 4:16 pm
ORD
-
CTM
11h 46m
2 stops
Aeromexico Logo
4:54 pm - 12:00 pm
CTM
-
ORD
18h 06m
2 stops
$610Aeromexico
Tue, May 19 - Wed, May 27

Southwest flights from Chicago to Quintana Roo

Our best Southwest deals on Chicago to Quintana Roo flight tickets
Southwest
May 18
MDW9:35 amChicago Midway
3h 35m
CUN1:10 pmCancun
May 22
CUN4:10 pmCancun
3h 40m
MDW7:50 pmChicago Midway
$333
Southwest
May 17
MDW11:00 amChicago Midway
3h 35m
CUN2:35 pmCancun
May 22
CUN4:10 pmCancun
3h 40m
MDW7:50 pmChicago Midway
$334
Southwest
May 17
MDW11:00 amChicago Midway
3h 35m
CUN2:35 pmCancun
May 23
CUN10:35 amCancun
3h 40m
MDW2:15 pmChicago Midway
$358

Volaris flights from Chicago to Quintana Roo

Our best Volaris deals on Chicago to Quintana Roo flight tickets
Volaris
May 10
ORD7:35 amChicago O'Hare Intl
13h 28m
1 stop
CUN9:03 pmCancun
May 19
CUN5:22 pmCancun
7h 23m
1 stop
ORD12:45 amChicago O'Hare Intl
$319
Volaris
May 9
ORD7:35 amChicago O'Hare Intl
13h 28m
1 stop
CUN9:03 pmCancun
May 13
CUN3:20 pmCancun
14h 32m
1 stop
ORD5:52 amChicago O'Hare Intl
$322
Volaris
May 10
ORD7:35 amChicago O'Hare Intl
13h 28m
1 stop
CUN9:03 pmCancun
May 19
CUN10:50 amCancun
12h 57m
1 stop
ORD11:47 pmChicago O'Hare Intl
$325

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 May 4, 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

Sat 5/16

6:00 am-10:03 am

Nonstop4h 03m

Cancun

Wed 5/20

10:25 am-2:35 pm

Nonstop4h 10m

$244

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Tue 7/7

6:00 am-9:49 am

Nonstop3h 49m

Cancun

Sat 7/11

11:00 am-3:09 pm

Nonstop4h 09m

$246
Quickest round-trip

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 5/18

9:35 am-1:10 pm

Nonstop3h 35m

Cancun

Fri 5/22

4:10 pm-7:50 pm

Nonstop3h 40m

$333

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

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 5/17

10:59 am-8:16 pm

1 stop9h 17m

Cancun

Wed 5/20

8:00 am-4:12 pm

1 stop8h 12m

$348

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 5/19

9:22 am-8:16 pm

2 stops10h 54m

Cancun

Thu 5/21

8:00 am-9:09 pm

1 stop13h 09m

$352

ChicagoCozumel

ORD - CZM

ORDCZM

Chicago O'Hare Intl

Fri 9/25

1:40 am-3:57 pm

1 stop15h 17m

Cozumel

Sat 10/3

4:47 pm-5:52 am

1 stop12h 05m

$394

ChicagoCozumel

ORD - CZM

ORDCZM

Chicago O'Hare Intl

Sun 8/23

7:35 am-3:57 pm

1 stop9h 22m

Cozumel

Thu 9/3

4:47 pm-5:52 am

1 stop12h 05m

$396

ChicagoChetumal

ORD - CTM

ORDCTM

Chicago O'Hare Intl

Mon 5/18

2:01 am-4:16 pm

1 stop15h 15m

Chetumal

Wed 5/27

4:54 pm-12:00 pm

2 stops18h 06m

$605

ChicagoChetumal

ORD - CTM

ORDCTM

Chicago O'Hare Intl

Tue 5/19

5:30 am-4:16 pm

2 stops11h 46m

Chetumal

Wed 5/27

4:54 pm-12:00 pm

2 stops18h 06m

$610

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, May 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 $395. If you aren’t able to travel during the month of May, then book flights to Quintana Roo from Chicago during July instead. Flights to Quintana Roo in July, while not as cheap as those in May, still average around $402.

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 $428. 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 $499.

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 in the morning. Our users have found flights to Quintana Roo in the morning for as low as $463. In contrast, the most expensive time of day to depart to Quintana Roo is in the afternoon when prices are around $557.

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 from Chicago 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 $452 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 $364 on momondo.

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

No. A direct flight is the cheapest option for a flight between Chicago to Quintana Roo.

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

$119

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 $119. The best round-trip flight deal from Chicago to Quintana Roo found on momondo in the last 72 hours is $340.
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

Frequently asked questions about flying from Chicago to Quintana Roo

  • 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
VolarisPriceFrom $112Free CancellationRating
6.6
1,166 reviews
Search Volaris flights
Spirit AirlinesPriceFrom $145Free CancellationRating
6.3
8,634 reviews
Search Spirit Airlines flights
AeromexicoPriceFrom $156Free CancellationRating
7.4
1,520 reviews
Search Aeromexico flights
DeltaPriceFrom $158Free CancellationRating
7.9
8,459 reviews
Search Delta flights
FrontierPriceFrom $190Free CancellationRating
5.6
2,966 reviews
Search Frontier flights
JetBluePriceFrom $262Free CancellationRating
7.1
2,977 reviews
Search JetBlue flights
United AirlinesPriceFrom $289Free CancellationRating
7.4
9,683 reviews
Search United Airlines flights
SouthwestPriceFrom $291Free CancellationRating
7.9
4,305 reviews
Search Southwest flights
American AirlinesPriceFrom $313Free CancellationRating
7.1
11,669 reviews
Search American Airlines flights
VivaPriceFrom $317Free CancellationRating
7.0
810 reviews
Search Viva 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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