$137 Find Cheap Flights from Chicago to Quintana Roo - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to Quintana Roo

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Sort by: Cheapest
Cancún
3h 35mNonstop
from $334per person
Cozumel
3h 56mNonstop
from $374per person
Chetumal
10h 45m2 stops
from $480per person
Booking Insights

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.

How much is a round-trip flight from Chicago to Quintana Roo?

Flight prices are below average for this route right now.

Flights to Quintana Roo from Chicago usually cost between $422 and $639 in March.
The lowest price found in the past 5 days was $334 on Volaris (Mar 3-Mar 7).

What is the cheapest Chicago to Quintana Roo flight route?

The cheapest ticket to Quintana Roo from Chicago found in the last 5 days was to Cancun, at $436 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Cancun (CUN), and the cheapest round-trip airline ticket found on this route in the last 5 days was $436.

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 morning, when round-trip flights cost $504 on average. Morning departures are around 9% 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 $554.

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

No, with an average price for the route of $569, prices are generally cheapest when you fly direct.

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

The cheapest month for flights from Chicago to Quintana Roo is January, when tickets cost $370 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $560 and $552 respectively.

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

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

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

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 3 weeks before departure.

Good to know

Low season

September

Cheapest flight

$137
Best time to beat the crowds but there is an average 7% increase in price.
Most popular time to fly with an average 10% increase in price.
Flight from Chicago O'Hare Airport to Cozumel

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.

Reviews of the top 5 airlines serving from Chicago to Quintana Roo

 
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 4190 reviews
8.1Boarding
7.5Entertainment
7.0Food
8.0Comfort
8.6Crew
Airline reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

10.0 ExcellentDenis, Aug 2026
Read more Southwest reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

On time, easy boarding. Anytime you sit in an economy seat, it’s uncomfortable. New plane and the bathrooms were in the galley at the back of the plane which seemed odd.

Terrible service - they don’t want to be there and bad food. Entertainment system in economy from the 2000s

No drink service but there was no N/A as an option to choose. Seats were extremely tight. I am under 5.5 and I bumped my knees have no idea how taller people could manage.

Flight delayed, last seat on the plane, no arrival Gate available due to the plane departing late

Kayak booked this flight with only 1h 20min layover in Chicago. This made it impossible for me and several other passengers to reach this flight. Moreover, the gate closed boarding in spite of several passengers still on their way without waiting even one more minute. However, the plane departed with 20min (!) delay, i.e., there would have been at least 15 min time to let the delayed passengers board without causing any delays. I complained and as a "thank you" the attendent booked us on the last (!) flight to Indianapolis ~7h later! Thankfully, I caught the spitefulness and the United customer line rebooked the flight to an earlier flight. Although I can't grade this particular flight since I never had a chance to take it, Kayak made the mistake of a too short layover and the crew at the gate was awful.

Flight did not have wifi service. It was experiencing technical difficulties. Definitely and old plane that needs updating.

This flight has a history of leaving late, however, I was pleasantly surprised that it was not delayed this day. The flight went smooth, except I was in a window seat and the wall and my feet were freezing. I found it difficult to sleep due to being so cold, I also was using 2 provided UAL blankets and could not get my feet warm. This was annoying, but I still made it there on time and safe.

Old 757 with poor entertainment system. United no longer partners with United for free text and email. O'Hara an absolute disaster! Limited gates clauses two hour delay. Unfortunately this appears to be the norm.

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

All planes flying to Mexico City are very old. Seats don’t even have power outlets.

DELAYED AGAIN and AGAIN and AGAIN - not only that, you delay in 20 minute increments for hours and hours instead of having an accurate delay understanding.

AA was fine....the overall experience was subpar, but not due to the airline due to broader issues

No ground air conditioner for the plane. Very hot and humid prior to take off which was an uncomfortable period of time.

Check-in process was poor, very poor, only one person to check-in all passengers, so if one passenger had a check-in issue, all other passengers were delayed. All check-ins should have two airline staff to check-in passengers.

The flight up was great no issues. The flight back home was a cluster. I was told the plane I was waiting on was giving to another flight which caused me to miss my connection flight. Granted the airline did great with getting hotel and vouchr for food.

Flight was delayed and so much of inconvenience related to the gate change.

Nothing was good about this flight. Although the flight actually departed more than 3 hours late, due to “air traffic control management” we pushed back from gate 2 hours and 20 minutes late and proceeded to sit 100 yards from gate for and then n tarmac for another 1/2 hour additional 20 minutes

One thing you can always count on is your AA flight getting delayed. This is not surprising when they operate these planes like a greyhound bus with wings.

We were delayed bc ground crew gave the flight crew the wrong paperwork. We taxiied to the runway then back to the gate to get the correct paperwork that no one bothered reviewing the first time we pushed back. Boarding was rude and stressful like it always is. Gate agents and flight attendants are all over 55 years of age, embittered by years of underpayment From AA leading to their passive agressive bitchiness for no reason.

Boarding time was easy & quick. Crew was excellent. In-flight entertainment was great/easy. Seats are too small and not enough room between rows: felt like a sardine/very cramped.

Overall a good red eye. Crew chatted very loudly the whole time making it difficult to sleep.

The fly was 2 hours delayed and the plane was old and dirty. A very umcorfotable flight, which I won't recomend to anyone

Confusion over extra fees. Held up on ramp during boarding. Thin seat cushion. Minimal leg room.

The check-in is either at a kiosk that didn’t allow me to check-in because my middle name was not on the reservation or at an agent that cost $15.

They don’t give anything for free you have to pay for everything which it’s expected but at least give out water and a snack as a courtesy for flying with them.

The app doesn’t work. I am having a lot of trouble checking in for flight tomorrow. Very disconcerting. Then they es t to charge extra for checking in at the airport;(

Overall good flight. The flight attendants were annoying and unfriendly. They would ask me to grab someone else’s trash can just waiting until the person woke up or after the flight is done. It’s not my job to pick up someone else’s trash. Especially when it’s not easily reachable.

To many extra fees, poor customer service and very uncomfortable flight. No leg room and seat wont recline.

Delayed 2 hours. Boarding line took more than 30 minutes. Flight was really hot and made sleeping on a red eye impossible. Not a pleasant experience.

The flight was 3 hrs delayed and no remorse from airline

During the flight I suddenly felt very sick, and no one from the crew even tried to help me or check on my condition. They seemed completely indifferent and showed no concern for my well-being. I was very disappointed by the lack of care and compassion. I hope the airline improves its customer service and trains its crew to respond better when passengers need assistance.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

Better than expected. Staff were friendly and nice on both flights.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

I didn’t have enough time to catch my connecting flight and had to use a different Airline. I will be requesting a refund.

I brought a ticket and car rental through Travelocity. There was no where to add a KTN. So I thought i’d add it by looking up ticket on frontier website. I tried 3 times with the frontier chat bot to add my KTN it never updated my boarding pass. So then I tried showing up early to do it in person at the airport. The first employee update my ktn in the system and gave me a new boarding pass. I was sent back by tsa to join regular line. Then I was told to add my Ktn. It would cost me $25 extra. Given the length of the cue I did pay. Congratulations! BUT I will NEVER fly frontier again. Plus the plane was very old. It had actual ashtrays and old looking tray backs. Worst travel experience ever. Im warning my friends and family not to use frontier ever.

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

More options for your flight from Chicago to Quintana Roo

Complete your trip to Quintana Roo with a hotel stay or car rental