Cheap flights from Chicago Midway Airport to Punta Cana from $121
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 Punta Cana departing on 7/12. 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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Southwest flights from Chicago Midway Airport to Punta Cana
Our best Southwest deals on Chicago Midway Airport to Punta Cana flight tickets
Delta flights from Chicago Midway Airport to Punta Cana
Our best Delta deals on Chicago Midway Airport to Punta Cana flight tickets
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How to get the cheapest flight ticket from Chicago Midway Airport to Punta Cana
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 Punta Cana?
If you’re not able to fly to Punta Cana in August, then October is your next best option. Flight prices from Chicago Midway Airport to Punta Cana during October average around $471.
What is the cheapest day to depart on your flight to Punta Cana?
The cheapest day to depart from Chicago Midway Airport to Punta Cana is on a Tuesday when prices can be found for as low as $497. Be sure to avoid booking your departure on a Saturday as prices are generally higher than usual. According to our data, the average ticket price to Punta Cana on Saturday is $589.
What is the cheapest time of day to depart on your flight to Punta Cana?
In the evening is the cheapest time of day to fly from Chicago Midway Airport to Punta Cana when you can find flight prices for as low as $277. Flying to Punta Cana in the evening is an ideal time because this is during off-peak travel hours. In the morning is when there is more demand to fly to Punta Cana, so prices are often more expensive at around $556 per ticket.
What is the cheapest Chicago Midway to Punta Cana flight route?
Fly from Chicago Midway to Punta Cana for the best Chicago Midway - Punta Cana flight prices
What is the cheapest airline that flies from Chicago Midway to Punta Cana?
Southwest, Frontier, and Delta are the most popular carriers operating from Chicago Midway to Punta Cana
What airlines fly to Punta Cana?
Southwest, Frontier and Delta are the top three most popular airlines that fly to Punta Cana from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 73% of people opting to fly with this airline when traveling to Punta Cana. Keep in mind that there are 3 different airlines that fly to Punta Cana on a routine basis, so you have a few additional options to choose from.
How many flights depart from Chicago Midway Airport to Punta Cana on average per week?
As of June 2025, 5 flights take off from Chicago Midway Airport and land in Punta Cana each week. The most common flight departure day for this route is Mon, with 20% of weekly flights taking off on this day.
When to book flights from Chicago Midway Airport to Punta Cana
Cheap Chicago Midway Airport to Punta Cana (MDW to PUJ) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Punta Cana
How far is Chicago Midway to Punta Cana by plane?
The straight-line distance from Chicago Midway to Punta Cana is 1957.5 mi. A reasonable flight in good conditions will take 4h 30m.
When did momondo last update prices for flights from Chicago Midway Airport to Punta Cana Airport?
Prices for flights from Chicago Midway Airport to Punta Cana Airport are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago Midway Airport to Punta Cana Airport?
As of June 2025, there are 3 operators available to choose from for flights from Chicago Midway Airport to Punta Cana Airport.
How old do you have to be to fly from Chicago Midway Airport to Punta Cana Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Punta Cana Airport.
What documentation or ID do you need to fly to Punta Cana Airport?
The necessary travel and health documents for your Punta Cana Airport 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 Punta Cana?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago Midway Airport to Punta Cana is Boeing 737-700 Passenger/BBJ1 (winglets) (40.14% of total bookings). The next most popular plane models are Airbus A320neo (23.90%), Boeing 737 MAX 8 (14.15%), and Airbus A321-100/200 (9.05%).
What is the most popular airline from Chicago Midway Airport to Punta Cana?
momondo data reveals that the most frequently booked airline on the route from Chicago Midway Airport to Punta Cana is Southwest, representing 75% of all bookings. The subsequent popular airlines are Frontier at 17% and Delta at 7%.
Best airlines flying from Chicago Midway Airport to Punta Cana
Compare and see reviews for airlines that fly from Chicago Midway Airport to Punta Cana with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $370 | Free Cancellation | Rating 5.9 3,295 reviews | |||
| PriceFrom $435 | Free Cancellation | Rating 8.0 7,946 reviews | |||
| PriceFrom $495 | Free Cancellation | Rating 8.0 4,287 reviews |
Southwest Flights From Chicago Midway Airport to Punta Cana
Southwest operates around 5 flights from Chicago Midway Airport to Punta Cana every week. The average price of these flights found in the last 72 hours has been $742, but momondo users have found Southwest deals from Chicago Midway Airport to Punta Cana from as low as $495 round-trip. Southwest has been scored 8.0/10 in 4,287 reviews.
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Why should I use momondo to find a flight deal from Chicago to Punta Cana?
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 Punta Cana from Chicago.
Can I find flights from Chicago to Punta Cana with flexible booking policies on momondo?
All flight searches from Chicago to Punta Cana on momondo can be filtered to show those which offer flexible booking policies.
How can momondo help me find flights from Chicago to Punta Cana?
momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Punta Cana.
I’m not ready to book a flight from Chicago to Punta Cana right now. Can momondo alert me if prices change?
If you are simply researching potential flights to Punta Cana, momondo offers a useful price alert feature which will track prices for flights to Punta Cana from Chicago and alert you when they change.