$115 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 11/30. 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.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Quintana Roo.
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

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

Tue, Jan 20 - Thu, Jan 29
Southwest Logo
9:15 am - 1:55 pmMDW-CUN
3h 40mnonstop
Southwest Logo
1:45 pm - 4:30 pmCUN-MDW
3h 45mnonstop
$252Southwest
Find Deal
Sat, Nov 15 - Fri, Nov 21
Southwest Logo
3:40 pm - 8:25 pmMDW-CUN
3h 45mnonstop
Southwest Logo
2:15 pm - 5:00 pmCUN-MDW
3h 45mnonstop
$262Southwest
Find Deal
Sat, Nov 15 - Fri, Nov 21
Southwest Logo
5:15 am - 3:05 pmMDW-CUN
8h 50m1 stop
Southwest Logo
2:15 pm - 5:00 pmCUN-MDW
3h 45mnonstop
$271Southwest
Find Deal
Fri, Feb 20 - Thu, Feb 26
Multiple Airlines Logo
3:02 pm - 9:32 amMDW-CUN
17h 30m1 stop
Multiple Airlines Logo
11:50 am - 1:04 pmCUN-MDW
26h 14m1 stop
$288Multiple Airlines
Find Deal
Sat, Nov 15 - Fri, Nov 21
Aeromexico Logo
10:47 am - 9:20 pmMDW-CUN
9h 33m1 stop
Aeromexico Logo
4:34 pm - 11:40 pmCUN-MDW
8h 06m1 stop
$321Aeromexico
Find Deal
Sun, Nov 30 - Wed, Dec 3
Delta Logo
10:47 am - 9:20 pmMDW-CUN
9h 33m1 stop
Delta Logo
12:00 pm - 11:47 pmCUN-MDW
12h 47m1 stop
$326Delta
Find Deal
Thu, Jan 8 - Mon, Jan 12
Multiple Airlines Logo
7:00 am - 10:42 amMDW-CUN
26h 42m1 stop
Multiple Airlines Logo
2:31 pm - 11:25 pmCUN-MDW
9h 54m1 stop
$328Multiple Airlines
Find Deal
Thu, Nov 27 - Thu, Dec 4
Delta Logo
9:34 am - 9:20 pmMDW-CUN
10h 46m2 stops
Delta Logo
1:33 pm - 11:47 pmCUN-MDW
11h 14m1 stop
$331Delta
Find Deal
Thu, Dec 4 - Sun, Dec 7
Frontier Logo
7:23 pm - 1:33 pmMDW-CUN
17h 10m1 stop
Frontier Logo
2:58 pm - 10:12 pmCUN-MDW
8h 14m1 stop
$355Frontier
Find Deal
Thu, Jan 15 - Sat, Jan 24
Aeromexico Logo
6:45 am - 1:50 pmMDW-CZM
7h 05m1 stop
Aeromexico Logo
3:05 pm - 10:26 pmCZM-MDW
7h 21m1 stop
$418Aeromexico
Find Deal
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.

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 72 hours was to Cancún, at $256 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Cancún (CUN), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $256.

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 $395, 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 September, when tickets cost $371 (return) on average. On the other hand, the most expensive months are March and January, when the average cost of round-trip tickets is $695 and $694 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, Monday is the cheapest day to fly on average and Friday is the most expensive. Flying from Quintana Roo back to Chicago Midway Airport, the best deals are generally found on Monday, 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 3 weeks before departure, which saves you about 24% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$115
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 21% 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.

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

    The cheapest time of day to fly to Quintana Roo is generally at night, when round-trip flights cost $385 on average. Morning departures are around 17% 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 $653.

Reviews of the top 5 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.
8.0
SouthwestOverall score based on 4242 reviews
8.0Comfort
8.6Crew
8.1Boarding
7.5Entertainment
7.0Food
Airline reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

8.0 ExcellentGreg, Oct 2025OAK - BUR
Read more Southwest reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

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

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Non stop on long haul is the way to go. Great experience

The aircraft interior is old and tired on this aircraft. The entertainment system never worked despite the crews attempt to reset the system.

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Old plane and old configuration/seats but still comfortable for a morning flight

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

Flight was crowded and the woman sitting on my left was large & kept crouching in to my space. You need bigger seats or smaller passengers to fit into the seats you DO have! Snack were OK. Would appreciate if airlines had more savory rather than sweet snacks, thank you!

Latam may be the worst airline in the world, far worse than even the lowest of low cost airlines in the USA. I wasted hours trying to PAY THEM TO CHECK A BAG! Then they misled me at the terminal, sent me through the wrong security line, the list goes on and on... Just absolutely terrible in every way. Avoid at all costs.

Check in -- in business took over 30 mins as there was only one attendant. Boarding was also a mess. The seat was too narrow and was not working properly. Food was very bad and the entertainment very poor. Crew was very polite and helpful, in fairness.

The plane broke down at the Lima stopover and they offered to put me on a flight the be t day but I had to be back in LA that morning and so I had to buy another ticket from Avianca and United for $2k I asked LATAM for compensation and received none. Very bad experience

Poor handling of carry on luggage. We had a 8 hour stop in Santiago, are over 70 and, in spite of paying full fare they wanted to send carry on to luggage hold. No empathy. We had to show that several group 4/5 passengers were not sending their carry ons before they finally let Is keep them. Very poor .

Just to drop my already labeled bag it took 50 minutes inline. Completely disappointed with Latam operation at GRU

Really bad experience – delayed for 6 hours without any notice, no food or drinks provided, and stuck in the horrible Cartagena airport.

I’m entitled to a refund per LATAM due to the mid flight itinerary change and being stuck in São Paulo for 24 hours and needing to get a hotel. The airline was dismissive and of no help.

The flight was late. Please do not delay next time.

I couldn't travel, now I can't get a refund and to change the date I have to pay an absurd fine.

My biggest complaint is the comfort. I am not tall and there was no legroom. It was very uncomfortable. During my transfer in Sao Paola, the flight was slightly delayed so boarding was confusing because there were no instructions in English.

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

The ground staff were not as friendly and nice to the passengers as the air crew. Flight attendants, cockpit crew were great and very nice to everyone on board.

My flight was delayed, then I got transferred to a new flight that was also delayed- which wasn’t Aeromexico’s fault, it was because of weather conditions. Most of the crew was very nice and patient, except for one or two flight attendants who were rude. The entertainment wasn’t on, so all the screens were off.

My wife's entertainment system did not work. Payed for flight upgrade but did not receive advertised "free WiFi".

Annoying that we had to go to departures and get boarding passes. Should allow us to be booked all the way through, this is the only airline i have this problem with in MEX. Late boarding and take off

Lousy No wheelchair. As normal at Atlanta Cheap airline Cheap aero plane. - Neither entertainment nor food on a 5 hour saga

The airplane was an old airplane, seats were very uncomfortable and very little space, they changed my seat and that was no option to get back into my seat even when I was traveling a senior who required assistance.

This is not a low cost airline. Stop acting like o e.

Aeromexico crew made me check my hand luggage in the door of the plane. As soon as I reach Mexico City, I notice that my luggage was opened and 8 games of Nintendo Switch were stolen (700 dllrs value aprox) (the console was there) but the games were stolen. I am very dissapointed of Aeromexico and all the crew. Instead of being a good trip, It was a sad trip

Ok. But we arrived to a remote terminal which meant that a bus had to take us to the terminal building

The flight was delayed by two hours. I had paid for extended leg room. Due to the delay, the plane was different and I didn't end up having extended leg room. I finally was able to reach Volaris on Whats App and they gave me an airline credit. I wanted a refund to the credit card since I hardly ever fly Volaris. Other than that, it was a very comfortable flight.

In Mexico charges too much for my luggage and I ask for help and nothing one lady she just disappeared 😡😡😡😡😡never going to fly there

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.

Better communication about delayed flight. I am thankful for a small credit for late flight.

Liked on time, rear entry and exit from plane Dislike the use of duct tape to repair seat rests

Terrible. And they charged over $400 just for luggage. And threatened that I would loose my flight if I didn’t pay. So I didn’t have another choice but to pay.

They check you everything before entering to waiting room, if you have any liquid they take it away even if you buy it inside the airport, no recommend volaris, for mi know Alaska airline is better

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.

I got to where I needed to go quickly. There were no amenities. And the seats were painful.

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

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.