$139 Find Cheap Flights from Chicago Midway Airport 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 Midway to Quintana Roo departing on 6/20. 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, 0 bags

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, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Quintana Roo, as well as popular online travel agencies
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Book Cheap Midway to Quintana Roo Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway 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 Midway to Quintana Roo

Wed, Aug 26 - Wed, Sep 2
Southwest Logo
7:50 am - 3:00 pm
MDW
-
CUN
7h 10m
1 stop
Southwest Logo
12:40 pm - 4:15 pm
CUN
-
MDW
3h 35mnonstop
$341Southwest
Wed, Aug 26 - Wed, Sep 2
Southwest Logo
7:50 am - 3:00 pm
MDW
-
CUN
7h 10m
1 stop
Southwest Logo
4:00 pm - 11:10 pm
CUN
-
MDW
7h 10m
1 stop
$351Southwest
Wed, Aug 26 - Wed, Sep 2
Southwest Logo
8:35 am - 12:10 pm
MDW
-
CUN
3h 35mnonstop
Southwest Logo
12:40 pm - 4:15 pm
CUN
-
MDW
3h 35mnonstop
$364Southwest
Sun, Jul 5 - Fri, Jul 10
Volaris Logo
8:23 pm - 9:55 am
MDW
-
CUN
13h 32m
1 stop
Volaris Logo
10:40 am - 7:04 pm
CUN
-
MDW
8h 24m
1 stop
$369Volaris
Mon, Jul 6 - Fri, Jul 10
Volaris Logo
8:23 pm - 9:55 am
MDW
-
CUN
13h 32m
1 stop
Volaris Logo
10:40 am - 7:04 pm
CUN
-
MDW
8h 24m
1 stop
$371Volaris
Thu, Jun 25 - Sun, Jun 28
Volaris Logo
8:49 pm - 9:55 am
MDW
-
CUN
13h 06m
1 stop
Volaris Logo
10:40 am - 7:04 pm
CUN
-
MDW
8h 24m
1 stop
$379Volaris
Mon, Jul 6 - Fri, Jul 10
Volaris Logo
8:23 pm - 9:55 am
MDW
-
CUN
13h 32m
1 stop
Volaris Logo
10:40 am - 7:04 pm
CUN
-
MDW
8h 24m
1 stop
$380Volaris
Sat, Oct 10 - Mon, Oct 26
Delta Logo
5:25 pm - 2:38 pm
MDW
-
CZM
21h 13m
2 stops
Delta Logo
4:26 pm - 10:10 pm
CZM
-
MDW
29h 44m
2 stops
$1,022Delta
Sat, Oct 10 - Sun, Oct 25
Delta Logo
5:25 pm - 2:38 pm
MDW
-
CZM
21h 13m
2 stops
Delta Logo
1:13 pm - 10:10 pm
CZM
-
MDW
32h 57m
2 stops
$1,067Delta
Sun, Sep 13 - Sat, Sep 19
Delta Logo
5:25 pm - 3:32 pm
MDW
-
CZM
22h 07m
2 stops
Delta Logo
2:28 pm - 10:25 pm
CZM
-
MDW
31h 57m
2 stops
$1,076Delta
Booking Insights

KAYAK's insights & trends for Midway to Quintana Roo flights

Get data-powered insights and trends into flights from Midway 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 Midway Airport to Quintana Roo?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago Midway Airport to Quintana Roo departing in August.

What is the cheapest Chicago Midway Airport to Quintana Roo flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Quintana Roo from Chicago Midway Airport found in the last 5 days was to Cancun, at $406 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Cancun (CUN), and the cheapest round-trip airline ticket found on this route in the last 5 days was $406.

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

The average price for all round-trip flights from Chicago Midway Airport to Quintana Roo depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Quintana Roo is generally in the evening, when round-trip flights cost $459 on average. Morning departures are around 2% more expensive than evening flights, on average. The most expensive time of day to fly to Quintana Roo is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $664.

Can I save money by flying with a layover from Chicago Midway Airport 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.

No, with an average price for the route of $543, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago Midway Airport 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 Midway Airport 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 Midway Airport to Quintana Roo is August, when tickets cost $194 (return) on average. On the other hand, the most expensive months are April and January, when the average cost of round-trip tickets is $336 and $333 respectively.

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

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

For Chicago Midway Airport to Quintana Roo, Tuesday is the cheapest day to fly on average and Wednesday is the most expensive. Flying from Quintana Roo back to Chicago Midway Airport, the best deals are generally found on Thursday, with Tuesday being the most expensive.

How far in advance should I book a flight from Chicago Midway Airport 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 Midway Airport 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 Midway Airport to Quintana Roo, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 2 weeks before departure.

Good to know

Low seasonOctober
Cheapest flight$139
Best time to beat the crowds with an average 35% drop in price.
Most popular time to fly with an average 14% increase in price.
Flight from Chicago Midway Airport to Cancun

FAQs - booking Quintana Roo flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport 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 Midway Airport to Quintana Roo.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport 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 Midway Airport 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 Midway Airport 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 Midway Airport 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 Midway Airport 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 4 airlines serving from Midway 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 Midway 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.
7.9
SouthwestOverall score based on 4238 reviews
8.6Crew
7.0Food
8.0Comfort
7.5Entertainment
8.1Boarding
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

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.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

Five hour delays every hour, I wish it were all at once

Flight delayed four separate times. I’m now one hour hours late to landing.

worst flight ever from Delta, it got delayed and kept on delaying..

Should never have had to go to Detroit from Orlando back to Tennessee!

Got rerouted from a straight flight from Orlando to Atlanta to Knoxville to a flight from Orlando to Detroit to Knoxville! Seriously!! Flight delay out of Detroit! Long day for what should have been a pretty easy travel day!

Two delays on two separate planes with parts they could not easily find and replace.

Checkin was good, fllight ws good. Onlly complaint is lack of foot on 6 hour flight from Seattle to Boston. Snacks were flimsy - chips and cookies. could have offered something more substantial for such a long flight. I know you can buy food in airport but for the price you pay for a ticket, they should step up for the passengers.

Only beverages were offered to first class and I thought the flight attendant could have also served the Delta Comfort as well instead of sitting down and staring at her phone and walking past all of us to the back of the plane to charge her phone more. There was a complete lack of turbulence and was safe enough for flights attendant to walk around in the front of the plane, collect trash and serve a few people water and turn off the seat belt light. Also didn’t enforce people putting their seats into the upright position and allowed two passengers to remain reclined during landing. They seemed out to lunch completely. Usually my experience on Delta is much better.

Long story short, it was one of the better flight experiences I've had in some time when compared with other airlines.

Flight was great! This flight from Atlanta was even better than when I paid for Comfort from SNA to Atlanta.

At my original departure Istanbul I was told my seat and flight was cancelled from the 3rd party. I had no seat to get to my other flights .. they charged me $481 USD to board the flight that I already paid for

All went very well. We used the AIFI Airport, such a lovely facility. Definitely needs better transportation options to get there.

Both ground crew and flight crew were rude, and did not provide any level of service. They made it very difficult as we were traveling with a passenger the required assistance.

From the check-in, to the flight, and arriving, everything went very smoothly. Unfortunately, when I received my baggage it was severely damaged. I have a hard shelled suitcase and it was completely smashed it. I’m not sure how this could happened but I am extremely disappointed that my belongings were damaged beyond repair and continued use.

Really nice, all good, nice crew and all on time

Unfortunately I had an awful boarding experience. Our first flight with Aeromexico was fine and landed on time however it couldn’t find a gate and we were late which made us lose our connecting flight with Aeromexico. The staff handled it horribly when we explained our situation and would not led us board when we missed the boarding time by a couple minutes. The staff were extremely rude and did not attempt to even help us. Because of this incident, my husband and I missed a full day of work which negatively impacted our salary which we need. Please compensate us for the work that we missed.

It was OK. The flight is pretty long for the airlines to only offer a simple sandwich on business class. The entertainment is similar to that on other Skyteam members. Ultimately the airline lost my bag and didn’t deliver it to me until the next day after a lengthy lost baggage report.

Good, the flight from Miami to Mexico City was better than Mexico City to Miami

Aeroméxico cancelled my ticket without advice AND It make a last minute mess in my intinerary, no solving my situation, bad advice and bad customer service

Flight was on time, good service, but there was no free WiFi, even for first class passengers

There weren't enough employees at check in took awhile to get bags checked. There wasn't a wheel chair for me, I was sent to someone who turns out to work for a different airline, if My flight hadn't been delayed I probably would have missed my flight as it was, by the time I arrived at my gate, they started boarding in about 15 minutes. I don't know who took me to my gate, definitely was not the normal people who take passengers to the gate. I'm guessing she may have been in a management position. I wish I knew her name, she went beyond to help me. With that said everyone was kind, and were doing the best they could. So, I choose to say it was an Adventure, stressful start, but good. In the end went well. The situation was not only difficult for passengers but the employee's.

The staff at the check in counter was so rude. Made you feel Incompetent

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

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

Information on your arrival and departure airports