$173 Find Cheap Flights from Chicago Midway Airport to Dominican Republic - Compare and Save

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 the Dominican Republic departing on 8/24. 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

Save 20% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Midway to the Dominican Republic

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Book Cheap Midway to the Dominican Republic 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 the Dominican Republic 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 the Dominican Republic

Sat, Aug 22 - Wed, Aug 26
Delta Logo
9:24 am - 11:43 am
MDW
-
PUJ
25h 19m
2 stops
Delta Logo
2:50 pm - 9:17 am
PUJ
-
MDW
19h 27m
2 stops
$385Delta
Mon, Dec 7 - Fri, Dec 18
Delta Logo
6:00 am - 2:25 pm
MDW
-
PUJ
6h 25m
1 stop
Delta Logo
5:05 pm - 10:56 pm
PUJ
-
MDW
7h 51m
1 stop
$390Delta
Mon, Aug 31 - Thu, Sep 3
Southwest Logo
5:00 am - 1:40 pm
MDW
-
PUJ
7h 40m
1 stop
Southwest Logo
1:45 pm - 10:45 pm
PUJ
-
MDW
10h 00m
1 stop
$390Southwest
Mon, Dec 7 - Wed, Dec 16
Delta Logo
6:00 am - 2:25 pm
MDW
-
PUJ
6h 25m
1 stop
Delta Logo
5:05 pm - 10:56 pm
PUJ
-
MDW
7h 51m
1 stop
$390Delta
Mon, Dec 7 - Thu, Dec 17
Delta Logo
6:00 am - 2:25 pm
MDW
-
PUJ
6h 25m
1 stop
Delta Logo
3:50 pm - 10:56 pm
PUJ
-
MDW
9h 06m
1 stop
$390Delta
Sun, Sep 13 - Thu, Sep 17
Southwest Logo
5:00 am - 1:55 pm
MDW
-
PUJ
7h 55m
1 stop
Southwest Logo
2:35 pm - 9:00 pm
PUJ
-
MDW
7h 25m
1 stop
$427Southwest
Mon, Nov 16 - Fri, Nov 20
Southwest Logo
5:15 am - 2:40 pm
MDW
-
PUJ
7h 25m
1 stop
Southwest Logo
4:50 pm - 10:55 pm
PUJ
-
MDW
8h 05m
1 stop
$460Southwest
Sat, Aug 29 - Sat, Sep 5
Frontier Logo
6:05 am - 2:27 pm
MDW
-
PUJ
7h 22m
1 stop
Frontier Logo
3:37 pm - 10:47 pm
PUJ
-
MDW
8h 10m
1 stop
$482Frontier
Mon, Aug 17 - Sat, Aug 22
Frontier Logo
6:05 am - 2:21 pm
MDW
-
PUJ
7h 16m
1 stop
Frontier Logo
3:37 pm - 10:47 pm
PUJ
-
MDW
8h 10m
1 stop
$490Frontier
Sat, Aug 22 - Sat, Aug 29
Frontier Logo
6:05 am - 2:27 pm
MDW
-
PUJ
7h 22m
1 stop
Frontier Logo
3:37 pm - 10:55 am
PUJ
-
MDW
20h 18m
1 stop
$491Frontier
Booking Insights

KAYAK's insights & trends for Midway to the Dominican Republic flights

Get data-powered insights and trends into flights from Midway to the Dominican Republic to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago Midway Airport to the Dominican Republic flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to the Dominican Republic from Chicago Midway Airport found in the last 5 days was to Punta Cana, at $690 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Punta Cana (PUJ), and the cheapest round-trip airline ticket found on this route in the last 5 days was $690.

What is the cheapest time of day to fly to the Dominican Republic?

The average price for all round-trip flights from Chicago Midway Airport to the Dominican Republic depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to the Dominican Republic is generally in the morning, when round-trip flights cost $680 on average. The most expensive time of day to fly to the Dominican Republic is generally in the morning, which is peak travel time and where the average cost of a ticket is $680.

Can I save money by flying with a layover from Chicago Midway Airport to the Dominican Republic?

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $599 on average.

What is the cheapest month to fly from Chicago Midway Airport to the Dominican Republic?

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 the Dominican Republic, 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 the Dominican Republic is April, when tickets cost $515 (return) on average. On the other hand, the most expensive months are June and March, when the average cost of round-trip tickets is $1,285 and $1,236 respectively.

Good to know

Low season

January

Cheapest flight

$173
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly with an average 43% increase in price.
Flight from Chicago Midway Airport to Punta Cana

FAQs - booking Dominican Republic flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Dominican Republic?

    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 Dominican Republic.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Dominican Republic?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport to Dominican Republic 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 Dominican Republic?

    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 Dominican Republic 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 Dominican Republic?

    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 Dominican Republic up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Midway to the Dominican Republic

 
Need help choosing which airline to fly with from Midway to the Dominican Republic? 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 4230 reviews
8.0Comfort
8.6Crew
8.1Boarding
7.5Entertainment
7.0Food
Airline reviews

Overall good, just screaming kids in the area the whole flight.

8.0 ExcellentAnonymous, Jul 2026
MDW - MHT
Read more Southwest reviews

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

During the flight I suddenly felt very sick, and no one from the crew even tried to help me or check on my condition. They seemed completely indifferent and showed no concern for my well-being. I was very disappointed by the lack of care and compassion. I hope the airline improves its customer service and trains its crew to respond better when passengers need assistance.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

Better than expected. Staff were friendly and nice on both flights.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

I didn’t have enough time to catch my connecting flight and had to use a different Airline. I will be requesting a refund.

I brought a ticket and car rental through Travelocity. There was no where to add a KTN. So I thought i’d add it by looking up ticket on frontier website. I tried 3 times with the frontier chat bot to add my KTN it never updated my boarding pass. So then I tried showing up early to do it in person at the airport. The first employee update my ktn in the system and gave me a new boarding pass. I was sent back by tsa to join regular line. Then I was told to add my Ktn. It would cost me $25 extra. Given the length of the cue I did pay. Congratulations! BUT I will NEVER fly frontier again. Plus the plane was very old. It had actual ashtrays and old looking tray backs. Worst travel experience ever. Im warning my friends and family not to use frontier ever.

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

They changed my flight and did not want to accommodate me or try to help me in any way. They do not care about their customers.

Everything you need to know for your flight from Midway to the Dominican Republic

Information on your arrival and departure airports