Cheap Flights from Chicago Midway to Punta Cana from $616

Compare Chicago Midway to Punta Cana flight deals

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

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Flight deals from Chicago Midway to Punta Cana

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 $806. Find the lowest prices on one-way and return tickets right here.

Punta Cana.$616 per passenger.Departing Sun, 2 Aug, returning Thu, 12 Nov.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sun, 2 Aug, arriving in Punta Cana.Inbound indirect flight with Southwest Airlines, departs from Punta Cana on Thu, 12 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $616, select.

Punta Cana.$623 per passenger.Departing Mon, 9 Nov, returning Thu, 19 Nov.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 9 Nov, arriving in Punta Cana.Inbound indirect flight with Southwest Airlines, departs from Punta Cana on Thu, 19 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $623, select.

Punta Cana.$624 per passenger.Departing Tue, 27 Oct, returning Thu, 12 Nov.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 27 Oct, arriving in Punta Cana.Inbound indirect flight with Southwest Airlines, departs from Punta Cana on Thu, 12 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $624, select.

Punta Cana.$626 per passenger.Departing Tue, 29 Sep, returning Thu, 12 Nov.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 29 Sep, arriving in Punta Cana.Inbound indirect flight with Southwest Airlines, departs from Punta Cana on Thu, 12 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $626, select.

Punta Cana.$626 per passenger.Departing Fri, 31 Jul, returning Thu, 12 Nov.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Fri, 31 Jul, arriving in Punta Cana.Inbound indirect flight with Southwest Airlines, departs from Punta Cana on Thu, 12 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $626, select.

Punta Cana.$641 per passenger.Departing Tue, 1 Sep, returning Sat, 5 Sep.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Tue, 1 Sep, arriving in Punta Cana.Inbound indirect flight with Delta, departs from Punta Cana on Sat, 5 Sep, arriving in Chicago Midway.Price includes taxes and charges.From $641, select.

Punta Cana.$641 per passenger.Departing Sat, 29 Aug, returning Sat, 5 Sep.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Sat, 29 Aug, arriving in Punta Cana.Inbound indirect flight with Delta, departs from Punta Cana on Sat, 5 Sep, arriving in Chicago Midway.Price includes taxes and charges.From $641, select.

Punta Cana.$641 per passenger.Departing Wed, 28 Oct, returning Sat, 31 Oct.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Wed, 28 Oct, arriving in Punta Cana.Inbound indirect flight with Delta, departs from Punta Cana on Sat, 31 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $641, select.

Punta Cana.$806 per passenger.Departing Sat, 22 Aug, returning Fri, 28 Aug.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Sat, 22 Aug, arriving in Punta Cana.Inbound indirect flight with Delta, departs from Punta Cana on Fri, 28 Aug, arriving in Chicago Midway.Price includes taxes and charges.From $806, select.

Punta Cana.$841 per passenger.Departing Tue, 29 Sep, returning Sun, 4 Oct.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 29 Sep, arriving in Punta Cana.Inbound indirect flight with Southwest Airlines, departs from Punta Cana on Sun, 4 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $841, select.

Punta Cana.$969 per passenger.Departing Mon, 7 Dec, returning Mon, 21 Dec.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Mon, 7 Dec, arriving in Punta Cana.Inbound indirect flight with Delta, departs from Punta Cana on Mon, 21 Dec, arriving in Chicago Midway.Price includes taxes and charges.From $969, select.

Punta Cana.$1,004 per passenger.Departing Thu, 20 Aug, returning Thu, 1 Oct.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Thu, 20 Aug, arriving in Punta Cana.Inbound indirect flight with Southwest Airlines, departs from Punta Cana on Thu, 1 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $1,004, select.

Punta Cana.$1,028 per passenger.Departing Fri, 22 Jan, returning Fri, 29 Jan.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Fri, 22 Jan, arriving in Punta Cana.Inbound indirect flight with Delta, departs from Punta Cana on Fri, 29 Jan, arriving in Chicago Midway.Price includes taxes and charges.From $1,028, select.

Punta Cana.$1,056 per passenger.Departing Fri, 31 Jul, returning Mon, 3 Aug.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Fri, 31 Jul, arriving in Punta Cana.Inbound indirect flight with Southwest Airlines, departs from Punta Cana on Mon, 3 Aug, arriving in Chicago Midway.Price includes taxes and charges.From $1,056, select.

Punta Cana.$1,064 per passenger.Departing Sun, 29 Nov, returning Sun, 6 Dec.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sun, 29 Nov, arriving in Punta Cana.Inbound indirect flight with Southwest Airlines, departs from Punta Cana on Sun, 6 Dec, arriving in Chicago Midway.Price includes taxes and charges.From $1,064, select.

Punta Cana.$1,091 per passenger.Departing Sun, 21 Feb, returning Sat, 27 Feb.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sun, 21 Feb, arriving in Punta Cana.Inbound indirect flight with Southwest Airlines, departs from Punta Cana on Sat, 27 Feb, arriving in Chicago Midway.Price includes taxes and charges.From $1,091, 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 November.

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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 $616

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 found	$616
Cheapest month to fly	August
Average flight time	4 hrs, 30 mins
Most popular airline	Southwest Airlines
Average flights per week	3

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

How much are return flights from Chicago Midway to Punta Cana?

The best price we found for a return flight from Chicago Midway to Punta Cana is $616. 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.

How long does it take to fly from Chicago Midway to Punta Cana?

4 hours and 30 minutes is the average flight time from Chicago Midway to Punta Cana.

Which airlines fly direct from Chicago Midway to Punta Cana?

Southwest Airlines flies direct from Chicago Midway to Punta Cana.

How many flights are there a week from Chicago Midway to Punta Cana?

As of July 2026, there are 3 flights per week flying from Chicago Midway to Punta Cana.

When is the cheapest time to fly from Chicago Midway to Punta Cana?

The cheapest month to fly from Chicago Midway to Punta Cana is usually August.

Which upcoming date is cheapest to fly from Chicago Midway Airport to Punta Cana Airport on?

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 Sunday, 2 August 2026.

Can I get a direct flight from Chicago Midway Airport to Punta Cana Airport?

Yes – the average flight time is 4 hours and 30 minutes.

How can I find the best flight deal to Punta Cana?

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.

When is the best time to book flights to Punta Cana?

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.

Which is the cheapest airline to fly from Chicago Midway Airport to Punta Cana with?

Currently, Southwest Airlines offers the cheapest flight tickets to Punta Cana.

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

Around 4 hours 25 minutes is how long you can expect to be in the air on a direct flight from Chicago Midway Airport to Punta Cana Airport.
Punta Cana's timezone is UTC-4, making Punta Cana two hours ahead of Chicago.
Your MDW to PUJ flight won't wait if you're running late, so show up at the airport on time. Arrive up to one hour in advance for domestic flights and two hours ahead for international travel.
During popular months like July, it's a good idea to get to the airport earlier than normal. Plan to arrive two hours before domestic departures and four hours ahead of international flights when you travel during a high season in general.
Southwest Airlines is your ticket to exploring Punta Cana (and perhaps some other great corners of the Dominican Republic!). Check out the direct flights from Chicago Midway Airport to Punta Cana Airport offered by this carrier.
Most travellers choose to travel with Southwest Airlines on this route.
Among carriers operating MDW to PUJ flights, Southwest Airlines has the best track record for timely arrivals.
Think about adding a stopover when booking your ticket from Chicago Midway Airport to Punta Cana Airport. Just uncheck 'Direct flights only' to break up your journey, or visit a new city along the way. Here are some options between MDW and PUJ:
- Atlanta Hartsfield-Jackson Airport
- Orlando International Airport
- Fort Lauderdale International Airport

Handy information about Chicago Midway Airport (MDW)

You'll find MDW at 5700 South Cicero.
76% of flights that depart Chicago Midway Airport touch down at their destination on time.
Central Chicago to Chicago Midway Airport is approximately 16 kilometres. Depending on traffic, it'll take you about 25 minutes to get there if you're ride-sharing, catching a taxi or driving.
Expect a trip time of roughly 30 minutes when using public transport.
Booked an early flight from Chicago Midway Airport to Punta Cana Airport? Avoid rushing to the airport (and catch some extra z's) by choosing one of these stays near MDW:

Arriving at Punta Cana Airport (PUJ)

Reserve a hotel near PUJ if you're catching a late Chicago Midway Airport to Punta Cana Airport flight. Choose one of these options and avoid the hassle of a long transfer:
Travel at your own pace with a Punta Cana Airport rental car. Pick up a set of wheels from amerirent, Goldcar or Routes Car Rentals and experience more of Punta Cana and beyond.
Booking your ride from Punta Cana Airport about three weeks in advance gives you the best shot at securing a great deal.

When to fly to Punta Cana Airport (PUJ)

April is the busiest month for flights from Chicago Midway Airport to Punta Cana Airport. To avoid the crowds, travel to Punta Cana in September.
When booking your flight from Chicago Midway Airport to Punta Cana Airport, consider the type of weather you like. September is the warmest month in Punta Cana, with the temperature ranging from 25ºC to 32ºC.
If you'd rather travel in cooler conditions, look for a cheap ticket from MDW to PUJ in March. Average temperatures are between 22ºC and 28ºC then.

Explore more of the Dominican Republic

Punta Cana has plenty to offer, but there are so many other parts of the Dominican Republic just waiting to be discovered. About 161 kilometres west of Punta Cana, a visit to Santo Domingo will keep your itinerary packed. Start with popular sights like Catedral Primada de las Americas, Alcazar de Colon and The Cathedral of the Americas.
If you're looking to explore another great destination in the Dominican Republic, consider Santo Domingo Este, about 145 kilometres west of Punta Cana. Lago los tres ojos, National Aquarium and La Cueva del Eden are among its highlights.