$93 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 11/15. 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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Cheap Flights from Chicago to the Dominican Republic

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

Book Cheap Chicago 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 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

Sat, Oct 4 - Sat, Oct 11
Spirit Airlines Logo
5:05 am - 2:42 pmORD-SDQ
8h 37m1 stop
Spirit Airlines Logo
3:59 pm - 11:45 pmSDQ-ORD
8h 46m1 stop
$252Spirit Airlines
Find Deal
Wed, Sep 24 - Sat, Sep 27
Spirit Airlines Logo
5:05 am - 4:00 pmORD-SDQ
9h 55m1 stop
Spirit Airlines Logo
3:47 pm - 10:48 pmSDQ-ORD
8h 01m1 stop
$266Spirit Airlines
Find Deal
Sun, Nov 30 - Sun, Dec 7
Frontier Logo
7:00 am - 1:33 pmORD-PUJ
4h 33mnonstop
Frontier Logo
6:49 pm - 9:59 pmPUJ-ORD
5h 10mnonstop
$317Frontier
Find Deal
Wed, Nov 26 - Fri, Dec 5
Frontier Logo
6:45 am - 1:19 pmORD-PUJ
4h 34mnonstop
Frontier Logo
6:49 pm - 9:59 pmPUJ-ORD
5h 10mnonstop
$321Frontier
Find Deal
Mon, Oct 27 - Thu, Oct 30
United Airlines Logo
9:30 am - 3:02 pmORD-PUJ
4h 32mnonstop
United Airlines Logo
1:55 pm - 6:08 pmPUJ-ORD
5h 13mnonstop
$340United Airlines
Find Deal
Mon, Oct 27 - Fri, Oct 31
United Airlines Logo
8:50 am - 4:25 pmORD-PUJ
6h 35m1 stop
United Airlines Logo
1:55 pm - 6:08 pmPUJ-ORD
5h 13mnonstop
$345United Airlines
Find Deal
Tue, Oct 7 - Fri, Oct 10
American Airlines Logo
4:28 pm - 10:50 amORD-PUJ
17h 22m1 stop
American Airlines Logo
3:21 pm - 7:36 pmPUJ-ORD
5h 15mnonstop
$347American Airlines
Find Deal
Sun, Nov 16 - Thu, Nov 20
American Airlines Logo
9:50 am - 4:27 pmORD-PUJ
4h 37mnonstop
American Airlines Logo
2:26 pm - 5:49 pmPUJ-ORD
5h 23mnonstop
$349American Airlines
Find Deal
Mon, Nov 10 - Fri, Nov 14
Delta Logo
6:00 am - 3:38 pmMDW-PUJ
7h 38m1 stop
Delta Logo
5:03 pm - 11:32 pmPUJ-MDW
8h 29m1 stop
$363Delta
Find Deal
Mon, Dec 29 - Thu, Jan 8
Delta Logo
5:59 pm - 2:26 pmMDW-PUJ
18h 27m1 stop
Delta Logo
5:11 pm - 8:54 amPUJ-MDW
17h 43m1 stop
$365Delta
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?

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

The cheapest ticket to the Dominican Republic from Chicago found in the last 72 hours was to Punta Cana, at $252 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 $252.

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 $457, 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 $474 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $657 and $649 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 Monday, 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 Sunday 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, which saves you about 6% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$93
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 11% 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 32% 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 $536.

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 4248 reviews
8.1Boarding
8.6Crew
7.5Entertainment
7.0Food
8.0Comfort
Airline reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

The food was terrible especially for a 15 hour international flight. The crew was unpleasant as well.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Quick check in. Everything went smooth. I don't know what can be done about airline food.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Nothing special. The crew never went out of their way for anything.

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

We had a layover from YVR to Denver. We bought 4 bottles of Absolut Vodka at the YVR Duty Free for $116.20, after going through security and American Customs Pre Clearance at YVR, Vancouver. When we landed in Denver, United put us behind the American Customs as well as TSA again for some reason. We were forced to go through American Customs and TSA again. TSA confiscated our rightfully owned Duty Free Absolut Vodka bottles. Because United incorrectly forced our flight behind American border and TSA again, we missed the connecting flight. After United put us on a later flight, we eventually arrived in Chicago very late, with hardly any sleep. I am looking for compensation from United for our incorrectly confiscated Absolut Vodka bottles worth $116.20, as well as compensation for incorrectly putting us behind American Customs and TSA again, causing us to miss our connecting flight, making us arrive extremely late in Chicago.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

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!

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

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.

Seats were new and comfortable. Staff was fine. Missed my connection due to weather -which wasn’t their fault- but got no help at all. Gate staff sent me to customer service, which was and stayed unstaffed. Sign with QR code directed me to call or chat. Chat was useless. Call was returned after an hour. No itinerary offered by Frontier could get me home in less than 30 hours. Rebooked with another airline and got a partial refund that came to about 10 percent of what I paid to get home.

Finally a Frontier on time and efficient. I've had problems before with your airline, but this time everything went fine.

The experience was good. No frills but I got there safe and sound and on time.

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

sluggish boarding and arrival procedures, fake nice flight attendants, and lots of delays.

Disaster. They lied every step of the way. We ended up being delayed due to crew and then allegedly abandoned the flight because of a curfew at LGA. No rebooking to LGA at any reasonable time. No hotel. No meal vouchers. Had to sleep in the airport and fly to Newark instead. Will never fly Frontier again.

What I expected, nickeled and dined and a frontier flight attendant loudly complained about her job and lack of communication as she headed to the gate on her cell phone. Not professional.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

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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