$133 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 12/31. 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

Wed, Dec 24 - Wed, Dec 31
Multiple Airlines Logo
6:12 am - 4:50 pmMDW-PUJ
32h 38m2 stops
Multiple Airlines Logo
4:19 pm - 10:12 pmPUJ-MDW
7h 53m1 stop
$306Multiple Airlines
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Sat, Dec 6 - Sat, Dec 13
Multiple Airlines Logo
2:59 pm - 6:38 pmMDW-PUJ
25h 39m1 stop
Multiple Airlines Logo
9:38 am - 10:30 pmPUJ-MDW
14h 52m1 stop
$314Multiple Airlines
Find Deal
Thu, Dec 4 - Thu, Dec 11
Multiple Airlines Logo
2:16 pm - 7:54 pmMDW-PUJ
27h 38m1 stop
Multiple Airlines Logo
9:38 am - 9:53 pmPUJ-MDW
14h 15m1 stop
$317Multiple Airlines
Find Deal
Sat, Dec 6 - Sat, Dec 13
Multiple Airlines Logo
2:59 pm - 6:38 pmMDW-PUJ
25h 39m1 stop
Multiple Airlines Logo
9:38 am - 10:30 pmPUJ-MDW
14h 52m1 stop
$319Multiple Airlines
Find Deal
Mon, Jan 5 - Sat, Jan 10
Multiple Airlines Logo
6:15 am - 9:29 pmMDW-PUJ
13h 14m1 stop
Multiple Airlines Logo
1:49 pm - 9:13 amPUJ-MDW
21h 24m1 stop
$322Multiple Airlines
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Tue, Dec 9 - Wed, Dec 10
Delta Logo
6:00 am - 3:39 pmMDW-PUJ
7h 39m1 stop
Delta Logo
5:04 pm - 11:47 pmPUJ-MDW
8h 43m1 stop
$338Delta
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Fri, Dec 5 - Wed, Dec 10
Delta Logo
7:02 pm - 2:20 pmMDW-PUJ
17h 18m1 stop
Delta Logo
2:57 pm - 9:54 amPUJ-MDW
20h 57m2 stops
$342Delta
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Sat, Jan 24 - Sat, Jan 31
Southwest Logo
8:15 am - 2:35 pmMDW-PUJ
4h 20mnonstop
Southwest Logo
3:00 pm - 5:55 pmPUJ-MDW
4h 55mnonstop
$353Southwest
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Sat, Nov 15 - Sat, Nov 22
Southwest Logo
7:40 am - 4:05 pmMDW-PUJ
6h 25m1 stop
Southwest Logo
3:20 pm - 6:20 pmPUJ-MDW
5h 00mnonstop
$355Southwest
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Wed, Dec 24 - Wed, Dec 31
Frontier Logo
6:12 am - 10:27 amMDW-PUJ
26h 15m1 stop
Frontier Logo
4:19 pm - 10:12 pmPUJ-MDW
7h 53m1 stop
$369Frontier
Find Deal
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 $617 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 $617.

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.

No, with an average price for the route of $403, prices are generally cheapest when you fly direct.

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 November and December, when the average cost of round-trip tickets is $1,029 and $912 respectively.

Good to know

Low seasonAugust
Cheapest flight$133
Best time to beat the crowds but there is an average 20% increase in price.
Most popular time to fly and prices are also 21% lower on average.
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.

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

    The cheapest time of day to fly to the Dominican Republic is generally at night, when round-trip flights cost $281 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 $686.

  • How many flights are there between Chicago Midway Airport and Dominican Republic per day?

    There is a maximum of 1 nonstop flight a day that takes off from Chicago Midway Airport and lands in the Dominican Republic, with an average flight time of 4h 20m. The most common departure time is 8:00 am and most flights take off in the morning. Each week, there are 1 flights.

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 4242 reviews
7.0Food
8.0Comfort
7.5Entertainment
8.6Crew
8.1Boarding
Airline reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

8.0 ExcellentGreg, Oct 2025OAK - BUR
Read more Southwest reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

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

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Non stop on long haul is the way to go. Great experience

The aircraft interior is old and tired on this aircraft. The entertainment system never worked despite the crews attempt to reset the system.

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Old plane and old configuration/seats but still comfortable for a morning flight

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

Flight was crowded and the woman sitting on my left was large & kept crouching in to my space. You need bigger seats or smaller passengers to fit into the seats you DO have! Snack were OK. Would appreciate if airlines had more savory rather than sweet snacks, thank you!

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

Boarding was on time and plane departed as scheduled. There are obviously no amenities (food, drink, entertainment) on Frontier, but there also didn't seem to be any issues with luggage space either.

Inbound plane was on time and flight departed on time with no issues while boarding.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

i was unable to check in the flight. refund requested

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

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.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Everyone seemed to be in zone 1 for boarding. Maybe break it up a little. Otherwise, smooth flight.

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

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