Cheap flights from Chicago Midway Airport to Quintana Roo from $179
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Quintana Roo departing on 1/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Not ready to book? to track prices.Frontier flights from Chicago Midway Airport to Quintana Roo
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Delta flights from Chicago Midway Airport to Quintana Roo
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Fly from
Fly to
Route
Depart
Return
ChicagoCancún
MDW Chicago Midway - CUN Cancun
MDWCUN
Chicago Midway
Sun 11/1
6:16 am-1:41 pm
1 stop6h 25m
Cancun
Thu 11/5
2:51 pm-11:47 pm
1 stop9h 56m
ChicagoCancún
MDW Chicago Midway - CUN Cancun
MDWCUN
Chicago Midway
Sun 11/1
6:16 am-1:41 pm
1 stop6h 25m
Cancun
Fri 11/6
2:51 pm-11:47 pm
1 stop9h 56m
ChicagoCancún
MDW Chicago Midway - CUN Cancun
MDWCUN
Chicago Midway
Fri 11/6
6:17 pm-9:41 am
1 stop14h 24m
Cancun
Fri 11/13
2:51 pm-11:47 pm
1 stop9h 56m
ChicagoCancún
MDW Chicago Midway - CUN Cancun
MDWCUN
Chicago Midway
Mon 11/30
8:05 am-12:50 pm
Nonstop3h 45m
Cancun
Thu 12/3
6:00 pm-8:35 pm
Nonstop3h 35m
ChicagoTulum
MDW Chicago Midway - TQO Tulum Intl
MDWTQO
Chicago Midway
Tue 1/19
6:00 am-2:00 pm
1 stop7h 00m
Tulum Intl
Fri 1/22
3:25 pm-10:10 pm
1 stop7h 45m
ChicagoCancún
MDW Chicago Midway - CUN Cancun
MDWCUN
Chicago Midway
Mon 11/2
12:25 pm-7:45 pm
1 stop6h 20m
Cancun
Wed 11/11
6:00 pm-8:35 pm
Nonstop3h 35m
ChicagoCancún
MDW Chicago Midway - CUN Cancun
MDWCUN
Chicago Midway
Mon 11/30
1:05 pm-8:55 pm
1 stop6h 50m
Cancun
Thu 12/3
4:10 pm-10:54 pm
1 stop7h 44m
ChicagoCancún
MDW Chicago Midway - CUN Cancun
MDWCUN
Chicago Midway
Mon 11/2
6:04 am-8:55 pm
1 stop13h 51m
Cancun
Wed 11/11
4:06 pm-10:54 pm
1 stop7h 48m
ChicagoCancún
MDW Chicago Midway - CUN Cancun
MDWCUN
Chicago Midway
Fri 12/4
6:00 am-3:10 pm
1 stop8h 10m
Cancun
Sun 12/20
8:15 am-10:22 pm
1 stop15h 07m
ChicagoCancún
MDW Chicago Midway - CUN Cancun
MDWCUN
Chicago Midway
Sat 10/24
3:30 pm-8:45 am
1 stop17h 15m
Cancun
Fri 10/30
1:51 pm-11:47 pm
1 stop9h 56m
See travel insights to Quintana Roo from
How to get the cheapest flight ticket from Chicago Midway Airport to Quintana Roo
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to Quintana Roo?
In general, February is the cheapest month to fly from Chicago Midway Airport to Quintana Roo. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $356. If you aren’t able to travel during the month of February, then book flights to Quintana Roo from Chicago Midway Airport during January instead. Flights to Quintana Roo in January, while not as cheap as those in February, still average around $458.
What is the cheapest day to depart on your flight to Quintana Roo?
On average, the least expensive day to fly to Quintana Roo from Chicago Midway Airport is on a Monday. momondo users have found tickets for Monday departures for as low as $447. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Quintana Roo is Wednesday, with ticket prices averaging around $588.
What is the cheapest time of day to depart on your flight to Quintana Roo?
Our data shows that the cheapest Chicago Midway Airport to Quintana Roo flights are usually those with departure times in the afternoon. Our users have found flights to Quintana Roo in the afternoon for as low as $513. In contrast, the most expensive time of day to depart to Quintana Roo is at noon when prices are around $664.
What is the cheapest Chicago Midway to Quintana Roo flight route?
Fly from Chicago Midway to Cancun for the best Chicago Midway - Quintana Roo flight prices
How far in advance should I book a flight from Chicago Midway Airport to Quintana Roo?
You are more likely to see cheaper flights to Quintana Roo from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Quintana Roo for around $560 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Quintana Roo from Chicago Midway Airport for as low as $491 on momondo.
What cabin class options are available on Chicago Midway Airport to Quintana Roo flights?
There are 2 cabin classes available to choose from on Chicago Midway Airport to Quintana Roo flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
What is the cheapest airline that flies from Chicago Midway to Quintana Roo?
Delta and Southwest are the most popular carriers operating from Chicago Midway to Quintana Roo
What airlines fly to Quintana Roo?
Southwest, Frontier and Aeromexico are the top three most popular airlines that fly to Quintana Roo from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 72% of people opting to fly with this airline when traveling to Quintana Roo. Keep in mind that there are 4 different airlines that fly to Quintana Roo on a routine basis, so you have a few additional options to choose from.
How many flights depart from Chicago Midway Airport to Quintana Roo on average per day?
The number of flights available between Chicago Midway Airport and Quintana Roo is 1 per day as of October 2026. The most frequent departure time is 9:00AM, with 100% of daily flights leaving at noon.
How many flights depart from Chicago Midway Airport to Quintana Roo on average per week?
As of October 2026, 8 flights take off from Chicago Midway Airport and land in Quintana Roo each week. The most common flight departure day for this route is Sat, with 25% of weekly flights taking off on this day.
Cheap Chicago Midway Airport to Quintana Roo flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Quintana Roo
Frequently asked questions about flying from Chicago Midway Airport to Quintana Roo
When did momondo last update prices for flights from Chicago Midway Airport to Quintana Roo?
Prices for flights from Chicago Midway Airport to Quintana Roo are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago Midway Airport to Quintana Roo?
The number of operators available for flights from Chicago Midway Airport to Quintana Roo is 4 as of October 2026.
How old do you have to be to fly from Chicago Midway Airport to Quintana Roo?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to Quintana Roo.
What documentation or ID do you need to fly to Quintana Roo?
The necessary travel and health documents for your Quintana Roo trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago Midway Airport to Quintana Roo?
Based on momondo bookings for flights between Chicago Midway Airport and Quintana Roo, the leading plane model is Airbus A321neo, making up 14.97% of the total bookings. Other popular models include Airbus A321 (sharklets) with 13.69%, Airbus A321-100/200 with 12.10%, and Boeing 737-800 with 10.83%.
Best airlines flying from Chicago Midway Airport to Quintana Roo
Compare and see reviews for airlines that fly from Chicago Midway Airport to Quintana Roo with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $194 | Free Cancellation | Rating 7.5 1,437 reviews | |||
| PriceFrom $198 | Free Cancellation | Rating 5.6 2,551 reviews | |||
| PriceFrom $327 | Free Cancellation | Rating 7.8 8,655 reviews | |||
| PriceFrom $356 | Free Cancellation | Rating 7.9 4,227 reviews |
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to Quintana Roo?
To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Quintana Roo from Chicago.
Can I find flights from Chicago to Quintana Roo with flexible booking policies on momondo?
All flight searches from Chicago to Quintana Roo on momondo can be filtered to show those which offer flexible booking policies.
How can momondo help me find flights from Chicago to Quintana Roo?
momondo helps you find the best flight between Chicago and Quintana Roo by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.
I’m not ready to book a flight from Chicago to Quintana Roo right now. Can momondo alert me if prices change?
Yes momondo offers price alerts on flights to Quintana Roo from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.