$171 Find Cheap Flights from Chicago Midway Airport to Dominican Republic - Compare and Save

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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 5 days
Booking Insights

Price, demand and travel trends for Chicago Midway Airport to the Dominican Republic flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

What are the cheapest fares from Chicago Midway Airport to the Dominican Republic right now?

The cheapest fares from Chicago Midway Airport to the Dominican Republic on KAYAK in the last week were to Punta Cana (PUJ) from $400 round-trip, and to Santo Domingo Las Americas (SDQ) from $447 round-trip.

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

August is the cheapest time of year to fly, with average fares of $478. Prices are highest in November, when average flight costs increase to around $773.

When is the best time to book flights from Chicago Midway Airport to the Dominican Republic?

Book your flights 25 weeks before your trip. KAYAK data collected over the past 12 months shows that booking in this window can save you around 45% compared to booking last-minute (within 2 weeks of departure).

Which airport in the Dominican Republic is the cheapest to fly to from Chicago Midway Airport?

Based on KAYAK data from the past 12 months, the cheapest airports to fly into the Dominican Republic are:

• Punta Cana (PUJ) (avg. price $619)
• Santo Domingo Las Americas (SDQ) (avg. price $624)

What’s the cheapest day to fly from Chicago Midway Airport to the Dominican Republic?

Tuesday tends to be the cheapest day to fly from Chicago Midway Airport to the Dominican Republic, while Friday is the most expensive. Fares run about 33% higher that day, based on the past 12 months of KAYAK data.

What's the cheapest time of day to fly from Chicago Midway Airport to the Dominican Republic?

Data from the past 12 months shows it's cheapest to fly to the Dominican Republic during the evening with average prices of $472. The afternoon is the most expensive time to fly, with average prices of $1,250.

Key details for Chicago Midway Airport to the Dominican Republic flights

Low season

November

Cheapest flight

$171
Beat the crowds with an average 73% drop in travelers.
The most popular month to fly with an average 98% increase in travelers.
One-way flight from Chicago Midway Airport to Santo Domingo

Your Chicago Midway Airport to the Dominican Republic flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Is now a good time to book a flight from Chicago Midway Airport to the Dominican Republic?

    Yes. Fares from Chicago Midway Airport to the Dominican Republic are low right now. As a rule of thumb, a round-trip under $493 (cheaper than most fares this year) is a good deal, so if you spot one at or below that, it's a good time to book.

  • How much should I budget for a flight from Chicago Midway Airport to the Dominican Republic?

    Over the past 12 months, round-trip fares from Chicago Midway Airport to the Dominican Republic have ranged from $493 to $858.

  • What airlines fly nonstop from Chicago Midway Airport to the Dominican Republic?

    Based on the flight schedule for the next 3 months, just one airline regularly flies nonstop from Chicago Midway Airport to the Dominican Republic: Southwest.

  • Where in the Dominican Republic can I fly nonstop from Chicago Midway Airport?

    Based on the flight schedule for the next 3 months, you can only fly nonstop from Chicago Midway Airport to Punta Cana.

  • Is it cheaper to fly with a layover from Chicago Midway Airport to the Dominican Republic?

    Yes. Nonstop flights from Chicago Midway Airport to the Dominican Republic average $690 over the past 12 months. Flights with a layover can cost less, cheapest when connecting through Atlanta Hartsfield-Jackson (ATL) (avg. price $638) or Baltimore/Washington (BWI) (avg. price $682).

  • How long is a flight from Chicago Midway Airport to the Dominican Republic?

    Flights from Chicago Midway Airport to the Dominican Republic take 4h 35m on average.

  • How often are flights from Chicago Midway Airport to the Dominican Republic delayed and what's the average delay?

    39% of flights on this route are delayed by at least 15 minutes. The average delay is 1h 30m.

  • Which cabin classes are available on flights from Chicago Midway Airport to the Dominican Republic?

    On flights from Chicago Midway Airport to the Dominican Republic you can only book Economy Class.

  • What are some popular landmarks in the Dominican Republic?

    KAYAK travelers' favorite landmarks in the Dominican Republic include:

    • Playa Dorada
    • Catedral Primada de América
    • Playa Juanillo
    • Centro Olimpico Juan Pablo Duarte

  • What are the earliest and latest flights from Chicago Midway Airport to the Dominican Republic?

    The earliest nonstop flight from Chicago Midway Airport to the Dominican Republic departs at 8:40 am and the latest departs at 8:40 am. Nonstop flights take about 4h 35m.

Your guide to booking Chicago Midway Airport to the Dominican Republic flights

Get tips on when to book, when to fly and what to know before your trip.
  • If you can plan ahead, the sweet spot for booking your flight is 25 weeks before your trip. KAYAK data shows fares in this window are around 45% lower than last-minute bookings (made within 2 weeks of departure). Not ready to commit? Set a Price Alert and we'll let you know when prices change.
  • If your travel dates are flexible, book your trip for August when flights are typically cheapest and avoid November when prices are at their highest.
  • Flying on Tuesday is usually the cheapest. Flights on Friday cost about 33% more on average, so being flexible with your travel dates could help you save.
  • If you're looking to save, Punta Cana (PUJ) is the cheapest airport to fly into from Chicago Midway Airport. If you have onward travel, don't forget to factor in the cost of your journey by train, bus or domestic flight.
  • Start your trip in Punta Cana, which is the most popular destination in the Dominican Republic. From there, it's easy to continue on to other popular destinations such as Puerto Plata, Santo Domingo and La Romana.
  • If you want the shortest trip, choose the Chicago Midway Airport to the Dominican Republic nonstop route. If you'd rather save money, the route via Atlanta Hartsfield-Jackson (ATL) is usually the cheapest.

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.
7.9
SouthwestOverall score based on 4218 reviews
7.0Food
8.1Boarding
8.6Crew
7.4Entertainment
8.0Comfort
Airline reviews

Multiple delays due to weather in Chicago, but the crew did their best to get flights rescheduled and on to their destination. I felt like the crews handled a frustrating situation very well, kudos to them! I was very glad to not have a cancelled flight.

8.0 ExcellentEmmalee, Oct 2026
Read more Southwest reviews

Multiple delays due to weather in Chicago, but the crew did their best to get flights rescheduled and on to their destination. I felt like the crews handled a frustrating situation very well, kudos to them! I was very glad to not have a cancelled flight.

Southwest’s point to point system caused a 2 hour delay due to the crew being late from their inbound flight. Also, the WiFi and entertainment didn’t work on the plane.

A) Checked my luggage at the gate but never got to pre board B) if we are helping with checking our carryon and waiting 40 minutes for it we should have some privileges c) luggage took 40-45 minutes to come.. d) I asked for another snack and was told the plane is full.. seriously a small snack

I like the staff members they were super nice and helpful very sweet people :)

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

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.

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

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.

More options for your flight from Midway to the Dominican Republic

Complete your trip to the Dominican Republic with a hotel stay or car rental