$92 Find Cheap Flights from Chicago to Quintana Roo

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Quintana Roo departing on 6/27. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Quintana Roo

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Quintana Roo.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Quintana Roo.
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Best Quintana Roo Flight Deals from Chicago

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Cancún
Cancúnnonstop$217
Cancún
Cancúnnonstop$217

Cheap Flights from Chicago to Quintana Roo

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Quintana Roo that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Quintana Roo

Mon, Jun 23 - Sat, Jun 28
Spirit Airlines Logo
6:00 am - 9:50 amORD-CUN
3h 50mnonstop
Spirit Airlines Logo
10:55 am - 2:49 pmCUN-ORD
3h 54mnonstop
$217Spirit Airlines
Find Deal
Tue, Jul 8 - Sat, Jul 12
Spirit Airlines Logo
7:49 pm - 8:17 amORD-CUN
12h 28m1 stop
Spirit Airlines Logo
10:55 am - 2:49 pmCUN-ORD
3h 54mnonstop
$219Spirit Airlines
Find Deal
Thu, Sep 11 - Wed, Sep 17
United Airlines Logo
10:43 am - 2:28 pmORD-CUN
3h 45mnonstop
United Airlines Logo
12:20 pm - 4:18 pmCUN-ORD
3h 58mnonstop
$269United Airlines
Find Deal
Thu, Jul 10 - Tue, Jul 15
Southwest Logo
4:35 pm - 8:10 pmMDW-CUN
3h 35mnonstop
Southwest Logo
8:30 am - 12:05 pmCUN-MDW
3h 35mnonstop
$269Southwest
Find Deal
Sat, Aug 23 - Sat, Aug 30
Frontier Logo
6:10 am - 12:39 pmMDW-CUN
6h 29m1 stop
Frontier Logo
1:54 pm - 11:11 pmCUN-MDW
9h 17m1 stop
$292Frontier
Find Deal
Sat, Aug 30 - Thu, Oct 2
Frontier Logo
6:10 am - 12:39 pmMDW-CUN
6h 29m1 stop
Frontier Logo
1:41 pm - 11:25 pmCUN-MDW
9h 44m1 stop
$298Frontier
Find Deal
Wed, Aug 20 - Wed, Aug 27
American Airlines Logo
10:07 am - 1:47 pmORD-CUN
3h 40mnonstop
American Airlines Logo
4:20 pm - 11:57 pmCUN-ORD
7h 37m1 stop
$299American Airlines
Find Deal
Fri, Jul 25 - Thu, Jul 31
Southwest Logo
4:35 pm - 8:10 pmMDW-CUN
3h 35mnonstop
Southwest Logo
2:45 pm - 9:25 pmCUN-MDW
6h 40m1 stop
$349Southwest
Find Deal
Tue, Oct 28 - Tue, Nov 4
American Airlines Logo
9:45 am - 1:25 pmORD-CUN
3h 40mnonstop
American Airlines Logo
12:45 pm - 4:05 pmCUN-ORD
4h 20mnonstop
$354American Airlines
Find Deal
Fri, Aug 1 - Sat, Aug 9
United Airlines Logo
9:07 pm - 12:32 pmORD-CZM
16h 25m1 stop
United Airlines Logo
2:05 pm - 10:39 pmCZM-ORD
7h 34m1 stop
$545United Airlines
Find Deal
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KAYAK's insights & trends for Chicago to Quintana Roo flights

Get data-powered insights and trends into flights from Chicago to Quintana Roo to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago to Quintana Roo flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago to Quintana Roo.

The cheapest ticket to Quintana Roo from Chicago found in the last 72 hours was to Cancún, at $227 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Cancún (CUN), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $227.

Can I save money by flying with a layover from Chicago to Quintana Roo?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $979 on average.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Quintana Roo, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Quintana Roo is September, when tickets cost $340 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $520 and $499 respectively.

What’s the cheapest day of the week to fly from Chicago to Quintana Roo?

The average price of all round-trip flights from Chicago to Quintana Roo clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Chicago to Quintana Roo, look for departures on Mondays and avoid leaving on a Thursday, as it's usually the priciest day. When flying back from Quintana Roo, Friday is the cheapest day to fly and Thursday is the most expensive.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Quintana Roo, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to Quintana Roo, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.


Good to know

Low seasonSeptember
High seasonMarch
Cheapest flight$92
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly with an average 22% increase in price.
Flight from Chicago O'Hare Airport to Cancun

FAQs - booking Quintana Roo flights

  • How does KAYAK find such low prices on flights from Chicago to Quintana Roo?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Quintana Roo.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Quintana Roo?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to Quintana Roo is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Quintana Roo?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Chicago to Quintana Roo with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Quintana Roo?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago to Quintana Roo up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Quintana Roo?

    The cheapest time of day to fly to Quintana Roo is generally in the afternoon, when round-trip flights cost $192 on average. Morning departures are around 28% cheaper than evening flights, on average. The most expensive time of day to fly to Quintana Roo is generally in the evening, which is peak travel time and where the average cost of a ticket is $609.

Top 5 airlines serving from Chicago to Quintana Roo

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Quintana Roo. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Quintana Roo? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4287 reviews
8.2Boarding
8.0Comfort
7.6Entertainment
7.1Food
8.6Crew
Airline reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

6.0 GoodDavid, Jun 2025BWI - COS
Read more Southwest reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful

They switched out gate from terminal 1 to terminal two ten minutes before boarding. So we had to make a 20 min crazy fast walk to a different terminal. Then we boarded the plane and waited for over 40 minutes until push back. Brutal

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

Boarding was a breeze, however, two of the flights that I boarded with Spirit did not have Wi-Fi available.

Seats uncomfortable, hard to check luggage, etc. It was like the last flight out of Hanoi

Need screens for tv/movies. Seats are more cramped than any other airlines. Seats are hard. They don’t recline. And in flight time should not be used for sales pitches.

Good experience except for the drunk woman who was with a child. Sad

The ease of booking the flight was very good. Speaking with customer service was also good. However, the crew people are unfriendly and unwelcoming which I found this as unprofessional. As far as comfort it was mediocre. This was my first time flying Spirit and I chose them because of the flight times met my needs and my budget. However, I would be reluctant to fly on Spirit again. In addition, if the crew were more friendly and at least appeared somewhat happy and welcoming personally it would probably make the experience of flying with Spirit better.

Tell them to chose a better, less bumpy route :( my seat had no window all the way at the end 😔

Seats too hard, too much lumbar. Space between rows was extremely tight, so tight hard to place item under seat in front of me. No tv screens. Zero plugs for charging phones. Too many sales pitches

Prepaid for 1 bag but my prior airline did not provide it to me in time to check it with Spirit and I could not get my $75 refunded.

Plane delayed which seems to be the norm with spirt. Everything is an up charge. I had to pay an additional fee because I was late getting back to my car. Will never fly spirit again

It was horrible. We were not allowed on the flight by spirit staff at the gate during boarding because I had a guitar. The same guitar I had at check in which I paid for and they said I can take it on the plane. We missed our flight, lost our luggage, and had to pay another $900 to rebook flights. Worst travel experience ever and spirit staff are the worst staff ever.

Book with frontier airlines with the mentality that they'll cancel your flight, kick you off and lose your luggage. Anything besides that is a win. Compare prices with other airlines (to include luggage) and if frontier is still worth it, book it but know all of their policies.

You get what you pay for nothing essentially but a hard uncomfortable seat that doesn’t recline and kids screaming all around you and chaotic boarding and limited check bag weight allowance when compared to other airlines

I never got to experience the flight because they delayed my first flight and I missed this one. Then Frontier didn't want to help me rebook a flight to get me to my final destination.

The Boarding process in Denver was chaotic, and since the line was so long, we were lined up very far from the gate. If there were any announcements from the gate staff, we didn't hear them. The flight attendants were spectacular. The only negative part of the flight was sitting by a 2 1/2 year old who was unruly and unfortunately had parents that matched his behaviors. Also, the restaurants in Denver on the E concourse, they didn't have food (passengers could only order 1 item on the entire menu) or the restaurants had 12-14 people waiting for orders to be prepared and another 6 people waiting to order. If you have a layover in Denver and need to grab food, be prepared to visit the shops with pre-packaged sandwiches, or you can visit another concourse but it may take a while to transit throughout the airport.

I liked the turn-style feature at gate 209B at LAX. Very efficient process. The gate staff also made several, clearly directed announcements so I felt very informed.

Although an hour and a half early was told by staff at check in they had overbooked and could not check us in for the flight.

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

I liked the price of the flight and the chance to buy a seat with no person seated in the middle seat.. Also the flight was right on time.

Plane was down graded and I lost my uncharged exit row with more leg room. No mention or offer of refund from podium. Flight attendant was nice to explain this happens often and that I could request a refund via online form submission. I did this and have heard nothing back.

Worst airline experience. They were rude and kept changing our seats and/or giving our seats away so our family didn’t get to sit with each other. Almost everyone we dealt with at both airports with this airline was rude. The app kept giving us wrong information making things take longer. Dealing with them before TSA can take close to an hour…longer than I’ve ever had to deal with before. Never using this airline again.

Everything you need to know for your flight from Chicago to Quintana Roo

Cabin class types available on flights to Quintana Roo

Cabin classes available on flights to Quintana Roo. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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