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Cheap Flights from Chicago Midway to Punta Cana

Compare Chicago Midway to Punta Cana flight deals

Find the cheapest month or even day of the year to fly to Punta Cana

Book the best Punta Cana fare with no extra fees

Flight deals from Chicago Midway Airport to Punta Cana Airport

Looking for a cheap last-minute deal or the best return flight from Chicago Midway Airport to Punta Cana Airport? If you want to travel next month, return fares start from R 6,829. Find the lowest prices on one-way and return tickets right here.
Punta Cana.R 1,926 per passenger.Departing Tue, 5 May.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Tue, 5 May, arriving in Punta Cana.Price includes taxes and charges.From R 1,926, select.
Punta Cana.R 2,097 per passenger.Departing Sat, 18 Apr.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sat, 18 Apr, arriving in Punta Cana.Price includes taxes and charges.From R 2,097, select.
Punta Cana.R 2,827 per passenger.Departing Tue, 16 Jun.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Tue, 16 Jun, arriving in Punta Cana.Price includes taxes and charges.From R 2,827, select.
Punta Cana.R 3,180 per passenger.Departing Sat, 18 Jul.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sat, 18 Jul, arriving in Punta Cana.Price includes taxes and charges.From R 3,180, select.
Punta Cana.R 3,195 per passenger.Departing Mon, 10 Aug.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Mon, 10 Aug, arriving in Punta Cana.Price includes taxes and charges.From R 3,195, select.
Punta Cana.R 3,776 per passenger.Departing Sun, 5 Apr.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 5 Apr, arriving in Punta Cana.Price includes taxes and charges.From R 3,776, select.
Punta Cana.R 3,986 per passenger.Departing Sat, 9 May.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 9 May, arriving in Punta Cana.Price includes taxes and charges.From R 3,986, select.
Punta Cana.R 4,353 per passenger.Departing Wed, 2 Sep.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Wed, 2 Sep, arriving in Punta Cana.Price includes taxes and charges.From R 4,353, select.
Punta Cana.R 4,856 per passenger.Departing Mon, 30 Nov.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Mon, 30 Nov, arriving in Punta Cana.Price includes taxes and charges.From R 4,856, select.
Punta Cana.R 5,372 per passenger.Departing Fri, 24 Jul.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Fri, 24 Jul, arriving in Punta Cana.Price includes taxes and charges.From R 5,372, select.
Punta Cana.R 10,437 per passenger.Departing Tue, 16 Jun.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 16 Jun, arriving in Punta Cana.Price includes taxes and charges.From R 10,437, select.
Punta Cana.R 11,356 per passenger.Departing Sat, 19 Dec.One-way flight with WestJet.Outbound indirect flight with WestJet, departs from Chicago Midway on Sat, 19 Dec, arriving in Punta Cana.Price includes taxes and charges.From R 11,356, select.

Find the cheapest month to fly from Chicago Midway to Punta Cana

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to Punta Cana flights are currently cheapest in May.
Apr
from R 2,097
May
from R 1,926
Jun
from R 2,827
Jul
from R 3,180
Aug
from R 3,195
Sep
from R 4,353
Oct
Find prices
Nov
from R 4,856
Dec
from R 11,356
Jan
Find prices
Feb
Find prices
Mar
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Direct flights from Chicago Midway to Punta Cana

Chicago Midway to Punta Cana: Alternative routes

Compare routes from Chicago Midway to Punta Cana below. You may find an airport to fly into that's cheaper, faster, or easier than Punta Cana.

Punta Cana

1km from central Punta Cana
ClosestCheapest
from R 1,926
Search flights

La Romana

57km from central Punta Cana
Search flights

Chicago to Punta Cana: Flight information

The things to know before you go.
Cheapest flight foundR 1,926
Cheapest month to flyMay
Average flight time4 hrs, 25 mins
Most popular airlineSouthwest Airlines
Average flights per week4

Finding cheap flights from Chicago Midway to Punta Cana: Frequently asked questions

The best price we found for a return flight from Chicago Midway to Punta Cana is R 6,509. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
4 hours and 25 minutes is the average flight time from Chicago Midway to Punta Cana.
Southwest Airlines flies direct from Chicago Midway to Punta Cana.
As of April 2026, there are 4 flights per week flying from Chicago Midway to Punta Cana.
The cheapest month to fly from Chicago Midway to Punta Cana is usually April.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to Punta Cana Airport on Saturday, 25 April 2026.
Yes – the average flight time is 4 hours and 25 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Punta Cana but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Punta Cana is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, Frontier Airlines and Southwest Airlines offer the cheapest flight tickets to Punta Cana.

Travelling from Chicago Midway International Airport (MDW) to Punta Cana International Airport (PUJ): what you need to know

  • The average time for a direct flight from Chicago Midway International Airport to Punta Cana International Airport is 4 hours 30 minutes.

  • Punta Cana is one hour ahead of Chicago and observes the UTC-4 timezone.

  • Leave plenty of time to make your MDW to PUJ flight. As a general rule, arrive at least two hours before international departures and an hour ahead for domestic flights.

  • During popular months like July, it's a good idea to get to the airport earlier than usual. Plan to arrive two hours before a domestic departure and four hours ahead for an international flight whenever you're flying during peak periods in general.

  • Southwest Airlines is your gateway to exploring Punta Cana (and maybe even some other exciting corners of Dominican Republic!). Check out the direct flights from Chicago Midway International Airport to Punta Cana International Airport offered by this popular carrier.

  • The airline most travellers fly with on this route is Southwest Airlines.

  • Southwest Airlines is the most punctual carrier operating MDW to PUJ flights. A reliable 83.33% of its services on this route arrive on time.

  • We make it a breeze to book a flight with a stopover. To see all your options for tickets from Chicago Midway International Airport to Punta Cana International Airport, deselect 'Direct flights only.' Then, choose a flight with a stop long enough to tour your chosen city. Popular stopovers between MDW and PUJ include:

    • Hartsfield-Jackson Atlanta International Airport

    • Fort Lauderdale-Hollywood International Airport

    • Orlando International Airport

How to find the cheapest flights from Chicago Midway International Airport (MDW) to Punta Cana International Airport (PUJ)

  • The lowest price we've seen for a one-way Chicago Midway International Airport to Punta Cana International Airport flight is R 1,926. A round-trip fare is currently R 6,509. Depending on the availability and when you book, these fares can change.

  • Score cheap tickets from MDW to PUJ by booking at least six months ahead. According to our research, that's the sweet spot for finding a bargain.

  • The cheapest month for flights from Chicago Midway International Airport to Punta Cana International Airport is May. Use the 'Whole month' tool to see the lowest prices if you have flexible dates.

  • Snapping up cheap flights from MDW to PUJ is a piece of cake with Price Alerts. Simply create one of these automatic alerts and we'll notify you as soon as fares go down.

  • Tailor your trip with filters. Choose your preferred departure and arrival times, airlines and total journey duration. You can also sort your results by 'Cheapest,' 'Best' or 'Fastest' flights from Chicago Midway International Airport to Punta Cana International Airport.

Handy information about Chicago Midway International Airport (MDW)

  • MDW's address is 5700 South Cicero.

  • When it comes to the on-time performance of Chicago Midway International Airport, data shows 77.88% of flights arrive within the expected timeframe.

  • Chicago Midway International Airport is around 19 kilometres from central Chicago. If you're driving, catching a cab or ride-sharing from the centre, it'll take you 20 minutes or so to arrive, depending on the traffic.

  • The trip on public transport takes roughly 45 minutes.

  • Get your trip off to a hassle-free start by staying near MDW. Whether you're boarding an early flight from Chicago Midway International Airport to Punta Cana International Airport or want to avoid feeling rushed, these hotels are ideal:

Arriving at Punta Cana International Airport (PUJ)

Getting from Punta Cana International Airport (PUJ) to central Punta Cana

  • Punta Cana International Airport to the centre of Punta Cana has a drive time of around 30 minutes. It's approximately 19 kilometres away.

When to fly to Punta Cana International Airport (PUJ)

  • The quietest month for a flight from Chicago Midway International Airport to Punta Cana International Airport is May, while March is the most popular. Choose the best time to visit Punta Cana based on whether you prefer a bustling atmosphere or a more laid-back vibe.

  • The warmest month in Punta Cana is September, with the temperature ranging between 25ºC (77ºF) and 32ºC (90ºF). Lock in your flights from Chicago Midway International Airport to Punta Cana International Airport in this month if you enjoy this type of weather.

  • Look for cheap tickets from MDW to PUJ in March if you like cooler conditions. Temperatures are at their lowest then, ranging between 22ºC (72ºF) and 28ºC (82ºF) on average.

Explore more of Dominican Republic

  • Santo Domingo is just one of the many places in Dominican Republic waiting to be explored once you've seen the sights of Punta Cana. Around 161 kilometres away to the west, check out popular attractions including Alcazar de Colon, National Pantheon (Pantheon Nacional) and National Palace.

  • Santo Domingo Este is another essential stop in Dominican Republic and is around 145 kilometres west of Punta Cana. No trip is complete without a visit to Museo Las Tres Aves, billeteros Park and Abuela Mota Final Resting Place.

Plan the rest of your trip from Chicago to Punta Cana

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.