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Find cheap flights from Chicago to the Dominican Republic from $81

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 4/29. 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.
1 adult
0 bags
So 5/26
So 6/2

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Best Dominican Republic Flight Deals

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

Good to know

Low season

September

High season

March

Cheapest flight

$81
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 4% 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 to the Dominican Republic from Chicago 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 to the Dominican Republic with an airline and back to Chicago 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 to the Dominican Republic from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to the Dominican Republic

  • Morning departure is around 11% more expensive than an evening flight, on average*.
  • 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.
See more tips
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

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
DeltaOverall score based on 10966 reviews
8.0entertainment
7.9comfort
8.6crew
8.2boarding
7.4food
Airline reviews

Delta is one of the best airlines I have flown

10.0 ExcellentKellie, Apr 2024ANC - SEA
Read more about Delta reviews

Delta is one of the best airlines I have flown

Made the Atlanta to Pittsburgh trip many times, with Delta no issues

I always fly with Delta. My friends tell me their horror stories of flying with other airlines. I just smile and say, “You should fly Delta”

I'm a larger, athletic guy (6'2", 260lbs powerlifter) and I found the seats incredibly uncomfortable with minimal leg room, especially in a window seat. Now, I full understand that being smaller may change my view but even if I was 80lbs less, my legs would be the same size and I was sandwiched between my seat and the seat in front of me.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

This flight was ridiculous. I had to have a connecting flight from New York to orlando Florida??? The flight left late and because it was a short flight there was no first class amenities. I had one alcohol drink. The flight crew was fine, but it sure did not feel like first class. Delta to me dropped the ball by giving me a connecting flight. By the time we got to Raleigh we would have missed the next flight. Lucky for me the flight never came so now I was stuck waiting for a later flight that came in late also.

Our flight was delayed in Atlanta. The staff could have gave us an explanation for the delay and how long it would be.

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive. I also upgraded to comfort + , I didn’t feel it was worth it. There was no benefit

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive.

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

Nothing beats ANA customer service on my opinion. Maybe because of their Japanese culture (and food). Arigatō

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

Flight delayed for 2 hours due to a part. The plane sat waiting for boarding for a long time and during final preflight inspection the issue was found. Why not do the preflight inspection sooner if you know the plane is being used?

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

Aircraft has better leg room than any of United's larger planes. We had requested mobility assistance for this and related flights. United's response to all was superb.

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

my seat got changed twice after checking on then boarding it had been given to a family so by the time they found a seat for me no overhead storage left. i ended up losing my Sony Headphones case because i could even access underthe seat in front of my when deplaning.

It was spectacular. I had basic Economy and was given so much space and their seats lean back so far. Staff was superb, food was superb, everything was superb, Finnair is Fantastic.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

We were delayed bc ground crew gave the flight crew the wrong paperwork. We taxiied to the runway then back to the gate to get the correct paperwork that no one bothered reviewing the first time we pushed back. Boarding was rude and stressful like it always is. Gate agents and flight attendants are all over 55 years of age, embittered by years of underpayment From AA leading to their passive agressive bitchiness for no reason.

Boarding time was easy & quick. Crew was excellent. In-flight entertainment was great/easy. Seats are too small and not enough room between rows: felt like a sardine/very cramped.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Not much seat room, but that was unexpected. But the seat headrest was very uncomfortable.

First the good, everyone was friendly and efficient. Flight was smooth and plane was very clean and new. Now the bad, seats have almost no padding on your behind. I was in exit row so I had tons of leg room for a 6' 2" bean pole with long legs. Everything was extra - water, soda, snacks everything besides oxygen. Ya get what you pay for, and my flight was cheap as you could ever want it, so no worries.

First the good, everyone was friendly and efficient. Flight was smooth and plane was very clean and new. Now the bad, seats have almost no padding on your behind. I was in exit row so I had tons of leg room for a 6' 2" bean pole with long legs. Everything was extra - water, soda, snacks everything besides oxygen. Ya get what you pay for, and my flight was cheap as you could ever want it, so no worries. They dont really bother you about carry-on size, I brought a descent sized backpack and they didnt even check.

Spirit canceled the flight in March and never notified me!

Seats suck, not enough room, overcrowded planes, hectic situation all together.

Pretty good. Would’ve been excellent if we would have left on time and the crew wasn’t late.

I do not like the customer service, I had an emergency and needed to cancel a pet reservation right after I had booked it and they would not do anything but issue a credit. I haven't flown in years as I have 7 kids and don't have spare time. I want my $125 back on my card please

Spirit airline tries to screw you at every opportunity. Spirit wanted 65$ for an extra pound in the suitcase Made me open the suitcase at the counter to remove 1 pound. Staff very cold and rude Will never fly spirit again and will recommend same to family and friends

Delayed..4 times...completely disorganized boarding. After 5 hours they scrambled to move ppl off plane bc they overbooked. Then they didn't have a cabin crew. WiFi on plane didn't work. Zero amenities. Once we boarded we sat on tarmac for an hour. Explore all alternate options including purchasing a pair of hiking boots and walking to your destination instead of flying spirit.

what I like about Spirit is that the pilot and crew are good communicators. The plane itself - well, its a budget airline and you get what is expected, But I generally just feel safer, somehow, when I know more about what is going on - and Spirit has always done a good job of telling me what is going on: why the delay, why the turbulence, why this and that... and that means a lot to me.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight was OK. Seats were good no cell phone charges on the plane no TVs or entertainment.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

Flight cancelled and was told by a rude gate agent that they don’t accommodate on other airlines. Had to wait 5 hours for a connecting flight that had a 7 hour layover. Would not allow bags to be checked early so we couldn’t go through security .Had to rent a car for the afternoon to store bags and get a meal. Also incurred a hotel fee. No apology or reason given for the cancellation- just rudeness.

They cancelled the flight then did nothing to help us rebook. It was awful - I won’t fly with them again

The process of buying the ticket and navigating all the hidden charges that Frontier throws at you was a terrible experience. The actual airport experience and flying was fine.

The truck that was refueling the plane drove away with the hose still connected to the plane and ripped part of the plane off with it

Not have to pay for every single item to take a flight. Seating and delays sucked.

Flight was cancelled and I had to spend the night in the airport lugging my suitcase around

If you don’t check in 24 hours in advance, they will charge you $110 to check your bag instead of the $30. I did not get an email with this information and did not check in. In addition, my flight home was cancelled at layover and I had to spend the night in the airport, and then have another layover at another airport before making it home. Will not fly frontier again.

Book cheap flights from Chicago to the Dominican Republic

Recent round-trip flight deals

5/12So
1 stopFrontier
28h 11mMDW-PUJ
5/15Mi
1 stopFrontier
15h 09mPUJ-MDW
$209
5/7Di
2 stopsFrontier
16h 29mMDW-PUJ
5/14Di
1 stopFrontier
8h 58mPUJ-MDW
$210
5/8Mi
1 stopSpirit Airlines
14h 01mORD-STI
5/21Di
1 stopSpirit Airlines
15h 41mSTI-ORD
$210
5/18Sa
1 stopSpirit Airlines
6h 19mORD-STI
5/24Fr
1 stopSpirit Airlines
15h 41mSTI-ORD
$217
5/18Sa
1 stopAmerican Airlines
16h 40mORD-STI
5/25Sa
1 stopAmerican Airlines
9h 03mSTI-ORD
$343
5/18Sa
1 stopAmerican Airlines
16h 40mORD-STI
5/25Sa
2 stopsAmerican Airlines
16h 36mSTI-ORD
$348
5/18Sa
2 stopsDelta
16h 47mORD-STI
5/25Sa
2 stopsDelta
23h 12mSTI-ORD
$386
5/10Fr
1 stopDelta
8h 59mORD-STI
5/14Di
1 stopDelta
16h 43mSTI-ORD
$395
5/18Sa
1 stopJetBlue
10h 37mORD-SDQ
5/25Sa
1 stopJetBlue
14h 46mSDQ-ORD
$478
5/14Di
1 stopJetBlue
13h 59mORD-SDQ
5/20Mo
1 stopJetBlue
14h 46mSDQ-ORD
$483

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Recent one-way flight deals

4/29Mo
nonstopFrontier
4h 41mORD-PUJ
$81
5/21Di
1 stopSpirit Airlines
7h 35mORD-SDQ
$91
5/28Di
nonstopUnited Airlines
4h 36mORD-PUJ
$152
5/10Fr
1 stopAmerican Airlines
17h 00mORD-PUJ
$171
5/29Mi
2 stopsAmerican Airlines
18h 55mORD-PUJ
$193
5/14Di
2 stopsDelta
14h 23mMDW-SDQ
$221
6/25Di
nonstopUnited Airlines
4h 36mORD-PUJ
$238
7/15Mo
2 stopsDelta
16h 49mORD-PUJ
$256
5/2Do
2 stopsAir Canada
17h 33mORD-PUJ
$335
5/2Do
2 stopsAir Canada
19h 23mORD-PUJ
$341

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Last minute flights from Chicago to the Dominican Republic

Last minute flight, train and bus deals

4/29Mo
multi-stopFrontier
14h 18mORD-PUJ
5/9Do
nonstopFrontier
5h 29mPUJ-ORD
$243
4/29Mo
multi-stopFrontier
14h 18mORD-PUJ
5/3Fr
nonstopFrontier
5h 28mPUJ-ORD
$244
4/27Sa
multi-stopSpirit Airlines
7h 25mORD-PUJ
5/8Mi
multi-stopSpirit Airlines
8h 32mPUJ-ORD
$321
5/1Mi
multi-stopSpirit Airlines
6h 28mORD-SDQ
5/4Sa
multi-stopSpirit Airlines
9h 31mSDQ-ORD
$365
4/28So
nonstopAmerican Airlines
4h 30mORD-PUJ
5/4Sa
nonstopAmerican Airlines
5h 10mPUJ-ORD
$382
4/28So
multi-stopAmerican Airlines
6h 15mORD-PUJ
5/4Sa
nonstopAmerican Airlines
5h 10mPUJ-ORD
$385
4/30Di
multi-stopDelta
7h 40mMDW-PUJ
5/1Mi
multi-stopDelta
8h 13mPUJ-MDW
$435
4/27Sa
multi-stopDelta
16h 53mMDW-PUJ
5/1Mi
multi-stopDelta
10h 11mPUJ-MDW
$440
4/30Di
nonstopUnited Airlines
4h 36mORD-PUJ
5/1Mi
multi-stopUnited Airlines
7h 55mPUJ-ORD
$471
4/27Sa
nonstopUnited Airlines
4h 36mORD-PUJ
4/30Di
multi-stopUnited Airlines
7h 55mPUJ-ORD
$841

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Flights to the Dominican Republic

Return flight deals:

Dominican Republic - Chicago

Cabin classes:

$603
$872
$178