$114 Find Cheap Flights from Chicago to the 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 Chicago to the Dominican Republic departing on 11/29. 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.
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Best Dominican Republic Flight Deals from Chicago

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

Cheap Flights from Chicago to the Dominican Republic

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago 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 Chicago to the Dominican Republic

Tue, Nov 18 - Sun, Nov 23
Arajet Logo
4:35 am - 11:20 amORD-PUJ
4h 45mnonstop
Arajet Logo
6:00 pm - 9:10 pmPUJ-ORD
5h 10mnonstop
$249Arajet
Find Deal
Tue, Dec 2 - Sun, Dec 7
Arajet Logo
4:35 am - 11:20 amORD-PUJ
4h 45mnonstop
Arajet Logo
6:00 pm - 9:10 pmPUJ-ORD
5h 10mnonstop
$253Arajet
Find Deal
Tue, Aug 12 - Sun, Aug 17
Frontier Logo
6:45 am - 12:25 pmORD-PUJ
4h 40mnonstop
Frontier Logo
5:45 pm - 9:53 pmPUJ-ORD
5h 08mnonstop
$290Frontier
Find Deal
Sun, Aug 10 - Sun, Aug 17
Frontier Logo
6:45 am - 12:25 pmORD-PUJ
4h 40mnonstop
Frontier Logo
5:45 pm - 9:53 pmPUJ-ORD
5h 08mnonstop
$294Frontier
Find Deal
Mon, Aug 11 - Fri, Aug 15
American Airlines Logo
8:34 pm - 2:15 pmORD-PUJ
16h 41m1 stop
American Airlines Logo
3:30 pm - 7:30 pmPUJ-ORD
5h 00mnonstop
$333American Airlines
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Mon, Aug 11 - Wed, Aug 20
Southwest Logo
5:05 am - 1:55 pmMDW-PUJ
7h 50m1 stop
Southwest Logo
2:50 pm - 9:40 pmPUJ-MDW
7h 50m1 stop
$343Southwest
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Mon, Aug 11 - Thu, Aug 21
Delta Logo
6:04 am - 2:34 pmMDW-PUJ
7h 30m1 stop
Delta Logo
1:05 pm - 9:44 pmPUJ-MDW
9h 39m1 stop
$353Delta
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Sun, Aug 10 - Fri, Aug 22
Delta Logo
9:25 am - 11:40 amMDW-PUJ
25h 15m2 stops
Delta Logo
1:50 pm - 9:36 amPUJ-MDW
20h 46m2 stops
$357Delta
Find Deal
Tue, Sep 16 - Sat, Sep 20
Southwest Logo
6:25 am - 2:05 pmMDW-PUJ
6h 40m1 stop
Southwest Logo
1:30 pm - 8:45 pmPUJ-MDW
8h 15m1 stop
$368Southwest
Find Deal
Wed, Aug 20 - Thu, Aug 28
American Airlines Logo
6:55 am - 8:48 pmORD-STI
12h 53m2 stops
American Airlines Logo
7:00 am - 7:44 pmSTI-ORD
13h 44m1 stop
$381American Airlines
Find Deal
Booking Insights

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

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

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

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago to the Dominican Republic.

The cheapest ticket to the Dominican Republic from Chicago found in the last 72 hours was to Punta Cana, at $244 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Punta Cana (PUJ), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $244.

Can I save money by flying with a layover from Chicago 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 $777, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago 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 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 to the Dominican Republic is July, when tickets cost $482 (return) on average. On the other hand, the most expensive months are March and September, when the average cost of round-trip tickets is $658 and $590 respectively.

What’s the cheapest day of the week to fly from Chicago to Dominican Republic?

The average price of all round-trip flights from Chicago to the Dominican Republic clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Dominican Republic on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Thursday is the most expensive day to fly from Chicago to Dominican Republic. For your return ticket, we recommend flying on a Saturday and avoiding Wednesdays for the best deals.

How far in advance should I book a flight from Chicago to the Dominican Republic?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to the Dominican Republic, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to the Dominican Republic, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.


Good to know

Low seasonSeptember
High seasonMarch
Cheapest flight$114
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly with an average 9% increase in price.
Flight from Chicago O'Hare Airport to Punta Cana

FAQs - booking Dominican Republic flights

  • Does the Midway Chicago International Airport have pet relief areas?

    The Midway Chicago Airport has an outdoor facility fenced in area with benches and bags provided for pet owners. There is also an indoor facility with pet parent sitting area. The facilities are wheelchair accessible and pet owners are provided with bags for disposing off pet waste.

  • What are the kid’s friendly features offered by the Midway Chicago Airport?

    The airport offers safe and convenient travel for kids. It also offers child friendly restaurants which are easy to find through the midway. The restaurants provide high chairs and kid’s menus.

  • Does the Midway Chicago Airport offer facilities for business travelers?

    The airport has power stations available for the business travelers. There are also a number of amenities which can help in relaxing and traveling comfortably. It also offers rooms for business meetings and conventions just an easy drive from the midway.

  • What are the car rental services at Santo Domingo Airport (SDQ)?

    If you are a driver with 25 years and above you can enjoy car rental services such as zero credit card fees and flexibility on most bookings with free cancellation. Some of the companies that offer rental services at this airport include Alamo, Economy AVIS, Budget, National and Sixt. Head to the airport’s North terminal at the centralized exit to the location of the car rental desks.

  • How does KAYAK find such low prices on flights from Chicago to the 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 to the Dominican Republic.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to the 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 to the 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 to the 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 to the 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 to the 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 in the afternoon, when round-trip flights cost $321 on average. Morning departures are around 34% more expensive than evening flights, 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 $544.

Top tips for finding cheap flights to the Dominican Republic

  • If you are traveling to the Dominican Republic from Chicago Midway International Airport (MDW) there are several ways you can use to get to the airport. You can either use public transportation by taking a train from the orange line station to the airport. You can also take the airport shuttles and regional buses that service the midway to the airport. There are also a number of taxis and ride share companies that can also take you to the airport. If you have a personal car you can also conveniently access the airport.
  • If you are a private car owner, there are several parking options available at the Chicago Midway International Airport. Such options include daily, hourly and long term economy parking. Parking facilities include friendly customer care service, secured indoor parking garages and 24/7 video CCTV camera surveillance.
  • If you need to relax and travel comfortably there are spacious rooms and lounges at the Midway Chicago Airport. They offer services and amenities such as beverages, freshly made food and also yoga room where one can meditate .There are also various hotels that offer accommodations for passengers that require an extended stay or rest between flights at the airport.
  • Wheelchair and disability features are available at The Midway Chicago International Airport. They offer features such as the accessibility guide which will point you in all the directions and help you with your navigation through the airport. If you need assistance through the midway the airline offers wheelchair assistance to passengers with mobility impairment. All the elevators have braille and raised numerals for the passengers with eye defections.
  • If you are a nursing mother The Midway Chicago International Airport offers a number of facilities. Such facilities include MAMAVA pods that offer a tranquil space for the breastfeeding mothers who would like to do so in a private setting. The Midway Chicago Airport also offers mother’s rooms with comfortable seating and baby changing stations .The rooms also offer electric breast pumps.

Reviews of the top 5 airlines serving from Chicago to the Dominican Republic

 
Need help choosing which airline to fly with from Chicago 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 4241 reviews
8.6Crew
8.0Comfort
7.6Entertainment
7.0Food
8.1Boarding
Airline reviews

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

4.0 OkayBobby, Jul 2025BNA - MDW
Read more Southwest reviews

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

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

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Sat on tarmac for 2 hours and then missed my connecting flight

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

Food was surprisingly good but the WiFi was not great

this crew didn't care much. bumping carts into seats more times than i care to remember

Very late arrival at PWM. Late jet getting to ATL. Equipment problem with aircraft - could not get enough water onto plane., Another delay getting FAA approval for flight with bottled H2O. Not the crew’s problem.

Everything was fine except the entertainment was not working for half of the flight.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

My flight was canceled I was promised a reginf still not received.

Late, terrible communication, horrible planning of passenger seating until the literal last minute. One of the worst flying experiences of my life. Y'all suck

Both legs of the flight were changed. The day of the flight and length of the trip.

First of all, we never got on the connecting flight to Denver. They delayed our flight for two hours. If we would have gotten on that flight, we would have been stuck in Denver for 13 hours. So we re- routed our flight for a straight through flight to Oklahoma two days later. THEN, they delayed that flight for two hours. After that we were able to finally get on our flight and come home. Frontier Airlines - one of the worst airlines I have ever been on.

Terrible communication with weather delay, lost baggage, near impossible to reach customer service

My tickets got canceled on me by your site and I didn't have a flight. Then you kept sending me emails on the status of q flight I didn't have tickets for.

The delay was ridiculous because nary a word escaped from the gate attendant regarding our flight status. It was a complete joke.

I missed a flight because of a delay. I had to buy a new ticket through Southwest.

The crew was mostly okay. The flight attendant who answered our questions was curt and unhelpful unfortunately. He seemed upset and I understand having off days.

Flight was delayed one hour. Notification to the crowd waiting near the gate was terrible…announcements were unclear and very hard to hear and therefore understand. Frontier does NOT send texts to notify, only email. The reader board over the gate itself was NEVER updated to indicate the gate had been changed. It’s like a bunch of children are running things.

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

Cabin class types available on flights to the Dominican Republic

Cabin classes available on flights to the Dominican Republic. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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