$129 Find Cheap Flights from Chicago Midway Airport to Dominican Republic

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 4/21. 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

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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, May 2 - Sat, May 9
Frontier Logo
6:00 am - 1:54 pm
MDW
-
PUJ
6h 54m
1 stop
Frontier Logo
3:35 pm - 11:12 am
PUJ
-
MDW
20h 37m
1 stop
$359Frontier
Tue, Apr 14 - Tue, Apr 21
Multiple Airlines Logo
7:30 am - 5:29 am
MDW
-
SDQ
20h 59m
1 stop
Multiple Airlines Logo
2:35 pm - 7:31 pm
SDQ
-
MDW
29h 56m
2 stops
$375Multiple Airlines
Sun, May 10 - Sat, May 16
Frontier Logo
6:00 am - 2:24 pm
MDW
-
PUJ
7h 24m
1 stop
Frontier Logo
3:35 pm - 11:12 am
PUJ
-
MDW
20h 37m
1 stop
$376Frontier
Mon, Apr 13 - Sat, Apr 18
Frontier Logo
6:00 am - 1:45 pm
MDW
-
PUJ
6h 45m
1 stop
Frontier Logo
11:07 am - 7:59 am
PUJ
-
MDW
21h 52m
1 stop
$377Frontier
Tue, Apr 14 - Fri, Apr 24
Multiple Airlines Logo
7:30 am - 5:29 am
MDW
-
SDQ
20h 59m
1 stop
Multiple Airlines Logo
10:19 am - 10:26 pm
SDQ
-
MDW
13h 07m
2 stops
$377Multiple Airlines
Tue, May 12 - Tue, May 19
Frontier Logo
6:00 am - 2:24 pm
MDW
-
PUJ
7h 24m
1 stop
Frontier Logo
3:35 pm - 11:09 am
PUJ
-
MDW
20h 34m
1 stop
$379Frontier
Sat, Apr 18 - Thu, Apr 23
Frontier Logo
6:00 am - 1:54 pm
MDW
-
PUJ
6h 54m
1 stop
Frontier Logo
9:13 pm - 6:37 pm
PUJ
-
MDW
46h 24m
2 stops
$380Frontier
Wed, Apr 15 - Wed, Apr 22
Delta Logo
10:41 am - 12:22 am
MDW
-
STI
12h 41m
2 stops
Delta Logo
6:00 am - 4:26 pm
STI
-
MDW
11h 26m
2 stops
$493Delta
Wed, Apr 22 - Wed, Apr 29
Delta Logo
6:00 am - 7:33 pm
MDW
-
STI
12h 33m
2 stops
Delta Logo
6:00 am - 4:26 pm
STI
-
MDW
11h 26m
2 stops
$517Delta
Mon, Apr 27 - Mon, May 4
Delta Logo
9:27 am - 12:22 am
MDW
-
STI
13h 55m
2 stops
Delta Logo
8:59 pm - 12:07 pm
STI
-
MDW
16h 08m
2 stops
$604Delta
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 72 hours was to Punta Cana, at $425 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 72 hours was $425.

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 $624 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 $624.

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 $590 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 October, when tickets cost $482 (return) on average. On the other hand, the most expensive months are March and November, when the average cost of round-trip tickets is $1,125 and $1,029 respectively.

Good to know

Low seasonAugust
Cheapest flight$129
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly and prices are also 21% lower on average.
Flight from Chicago Midway Airport to Santo Domingo

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 3 airlines serving 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 4320 reviews
7.0Food
8.1Boarding
7.5Entertainment
8.0Comfort
8.6Crew
Airline reviews

We had a 5 hour delay on the tarmac in Baltimore

2.0 MediocreDavid, Mar 2026
ALB - BWI
Read more Southwest reviews

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

My flight was canceled on Sunday. Rebooking took three hours. Had to pay for accommodations another night. New flight was delayed for 5 hours, all that was sent was a 12 dollar food voucher, which doesn’t tell you how to use it. Then when we landed we had to sit on the plane for an hour before we could get off.

Miserable. This entire round trip was miserable. I booked evening flights to and from Detroit on consecutive days that should have had me at my destination by 10:30. Instead I arrived after 3am on my flight to Detroit and after midnight on my return. Multiple unforced errors like awaiting bags to get put on the plane for almost an hour in Detroit and a 20 minute delay to pull up to the gate in Atlanta has me rethinking my assumption that delta is the best and most reliable airline

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

First class is comfortable. Enjoyed a movie and was able to relax compared to coach.

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

The WiFi was not working. That made for a long flight.

With Aeromexico it ended up good but with Delta it was bad because we did everything through Delta... Showed up at the Delta terminal... It was the wrong place! Nothing ever told us to go to the Aeromexico terminal. It said "in partnership with Aeromexico" but I was never instructed to check in with them or go to their terminal. We had to haul @$$ running through the airport and almost didn't make it thanks to this poor communication. 👎🏽

Absolutely no communication on why there's a delay and multiple flight time reschedules. I would have canceled the flight and drove back home if I known it was going to be rescheduled 3 or 4 times.

Another late night flight and MORE men belligerently drinking and yelling. I had to move from first to economy because they were so obnoxious and disruptive. Crazy to go from a cozy chair to cardboard when you were supposed to be in first. Delta allows was too much drinking which leads to belligerent behavior.

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

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 !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

Frontier.. nickel and dime add-ons. Flight late, on time, late again, last minute gate change, arrival gate required a shuttle to the terminal. They sure keep you guessing.. if you like a little chaos and airport anxiety, this is the airline for you!

This is my second time flying with Frontier. My current experience was very favorable. The staff from the gate to the plane was friendly, warm and professional. The food options lacked in my opinion. This area needs some attention in my opinion.

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

Information on your arrival and departure airports