$107 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 2/23. 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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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

Sat, Feb 28 - Sat, Mar 7
Frontier Logo
6:25 am - 3:22 pm
MDW
-
CUN
7h 57m
1 stop
Frontier Logo
3:07 pm - 6:13 pm
CUN
-
MDW
4h 06mnonstop
$250Frontier
Sat, Feb 28 - Sat, Mar 7
Frontier Logo
6:25 am - 3:22 pm
MDW
-
CUN
7h 57m
1 stop
Frontier Logo
3:07 pm - 6:13 pm
CUN
-
MDW
4h 06mnonstop
$254Frontier
Sat, Apr 11 - Sat, Apr 18
Frontier Logo
8:30 am - 12:20 pm
MDW
-
CUN
3h 50mnonstop
Frontier Logo
1:25 pm - 10:19 pm
CUN
-
MDW
8h 54m
1 stop
$276Frontier
Sat, Apr 11 - Sat, Apr 18
Frontier Logo
8:30 am - 12:20 pm
MDW
-
CUN
3h 50mnonstop
Frontier Logo
1:25 pm - 10:19 pm
CUN
-
MDW
8h 54m
1 stop
$277Frontier
Mon, Feb 23 - Sat, Feb 28
Multiple Airlines Logo
6:54 pm - 9:48 am
MDW
-
CUN
13h 54m
1 stop
Multiple Airlines Logo
10:16 am - 9:39 pm
CUN
-
MDW
12h 23m
1 stop
$283Multiple Airlines
Sun, Mar 8 - Thu, Mar 12
Southwest Logo
4:35 pm - 8:15 pm
MDW
-
CUN
3h 40mnonstop
Southwest Logo
2:05 pm - 5:50 pm
CUN
-
MDW
3h 45mnonstop
$291Southwest
Mon, Feb 16 - Wed, Feb 18
Delta Logo
6:00 am - 1:55 pm
MDW
-
CZM
7h 55m
1 stop
Delta Logo
4:15 pm - 9:06 am
CZM
-
MDW
16h 51m
1 stop
$466Delta
Mon, Feb 16 - Fri, Feb 20
Delta Logo
6:20 pm - 1:55 pm
MDW
-
CZM
19h 35m
2 stops
Delta Logo
3:10 pm - 10:31 pm
CZM
-
MDW
7h 21m
1 stop
$471Delta
Mon, Mar 2 - Fri, Mar 6
Aeromexico Logo
6:00 am - 1:55 pm
MDW
-
CZM
7h 55m
1 stop
Aeromexico Logo
3:10 pm - 10:31 pm
CZM
-
MDW
7h 21m
1 stop
$478Aeromexico
Fri, Feb 20 - Tue, Feb 24
Aeromexico Logo
6:00 am - 1:55 pm
MDW
-
CZM
7h 55m
1 stop
Aeromexico Logo
3:10 pm - 10:33 pm
CZM
-
MDW
7h 23m
1 stop
$511Aeromexico
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 $291 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 $291.

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 $537, 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 January and December, when the average cost of round-trip tickets is $1,078 and $686 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 Saturday 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 2 weeks before departure, which saves you about 22% 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$107
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 7% lower on average.
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 in the evening, when round-trip flights cost $431 on average. Morning departures are around 13% 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 $693.

Top tips for finding cheap flights to Quintana Roo

  • Looking for a cheap flight? 25% of our users found tickets from Chicago Midway Airport to the following destinations at these prices or less: Cancun $263 one-way - $441 round-trip

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.
8.0
SouthwestOverall score based on 4267 reviews
7.5Entertainment
8.6Crew
8.1Boarding
8.0Comfort
7.0Food
Airline reviews

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled. No snack or drink on this flight.

10.0 ExcellentJoseph, Jan 2026
BWI - RIC
Read more Southwest reviews

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled. No snack or drink on this flight.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled.

The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

I didn't take this flight. I changed the flight. Why am I getting surveys and notifications on flights that I change. Seems like a defect with Kayak.

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

Timing, quality of service, promptness and courtesy of the staff

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

The flight was comfortable and uneventful, which is what I desire

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

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.

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

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

the guy in front of me put his seat back immediately...and then left it back including thru landing and taxiing to the runway. attendants did not check/ask him to put it up for landing.

Very well recently! Frontier is improving and less harrassing customer on luggages! Positive!

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

I am writing to express my disappointment with my recent Frontier Airlines flight. I was charged $99 at the gate because my bag was said to be too large, yet once onboard there was no available overhead bin space, and I was required to place the bag under the seat in front of me anyway. This made the charge feel unnecessary and unfair. Additionally, before the flight even took off, I was asked to move from the seat I paid for into a middle seat so another passenger and her cat could have my seat to themselves. I was not offered compensation or an explanation for being moved from a paid seat. Between the unexpected bag fee and being forced to give up my seat, this experience fell well below acceptable customer service standards. I would appreciate a review of this situation and appropriate compensation.

It was costly and difficult to check in. $85 to take a small suitcase with me, carry on or checked and $75 on the return trip, Plus $25 if I didn't check my self in check in $25, because I couldn't do it on the kiosk. Small very uncomfortable seats, waited on the runway for near an hour each way. It was my worst flight to date.

It was ok. It was expensive to check 2 bags ($75.00 per bag), and then it took a long time to wait for shuttle to take us from one terminal to the terminal where the plane was taking off at LAX. And all of this for a flight where we had to pay for any food or drink that was not water.

It didn’t happen. I booked it and then was told it wasn’t available and then forced to pay far higher prices for a worse option

A 630departure flight Delayed 6hours! They changed my gate, I moved to the new gate. Had our flight on the screen for 12noon departure. I go get above to eat, check screen again and the flight was gone, no notice no announcement, nothing!! They sent my bag on the flight I wasn’t on, got it back to me 3days later. Thank goodness they did refund my money but I will NEVER fly them again.

Due to weather, my flight was delayed, further delayed, then canceled. I eventually got through to a support person who helped me find a different route out of MSP, but to get to DIA, they didn't want to, but eventually did help with the connection ticket purchase. But even this replacement flight was delayed time and time again, and I would have missed my connecting flights and I didn't want to get stuck in a layover city, so after 12 hours at the airport with two young boys who were very tired, we just cancelled our plans and spent the week at home, instead of Nana's.

Plane and crew on board were fine. Everything else was terrible.

The third party booking with cheapflightsfares was awful. Kayak should NOT partner with them. They sold me a bundle including seat selection and carry-on, but did not book the carry-ons with Frontier, so I’m out of pocket for $414 more while I await resolution.

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

Information on your arrival and departure airports