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$100 Find cheap flights from the Dominican Republic to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 5/2. 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
週六 5/25
週六 6/1

Search hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 44,979,812 times on KAYAK, and here is why:

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Flights to Chicago - Travel Insights & Trends

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

What is the cheapest day to fly to Chicago?

The average price of all flights to Chicago clicked on KAYAK for each day over the last 12 months.
Based on KAYAK data, the cheapest day to fly to Chicago is Friday where tickets can be as cheap as $432. On the other hand, the most expensive day to fly is Monday, where prices are $587 on average.

What is the cheapest month to fly to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights to Chicago, 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 to Chicago is January, where tickets cost $304 on average for one-way flights. On the other hand, the most expensive months are November and July, where the average cost of tickets from the Dominican Republic is $615 and $531 respectively. For return trips, the best month to travel is January with an average price of $304.

What is the cheapest time of day to fly to Chicago?

The average price for all flights to Chicago depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.
The cheapest time of day to fly to Chicago is generally in the morning, when flights cost $296 on average. The most expensive time of day to fly to Chicago is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $508.

What is a good deal for flights to Chicago?

If you’re looking for cheap airfare to Chicago, 25% of our users found tickets to Chicago for the following prices or less: From Punta Cana $236 one-way - $250 round-trip.

How far in advance should I book a flight to Chicago?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price, you should book around 0 weeks before departure. For the absolute cheapest price, our data suggests you should book 35 days before departure.

Which is the cheapest airport to fly into in Chicago?

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Chicago is Chicago Midway Airport, with an average flight price of $121.

Which airlines fly to Chicago?

Airlines flying the most to Chicago from Dominican Republic are American Airlines, Frontier and United Airlines. See the amount of flights per week for popular airlines flying to Chicago.

Which airline offers the most flights to Chicago?

Of the 14 airlines that fly to Chicago, United Airlines offers the most flights, with around 4,938 per week, followed by American Airlines with 3,701 flights per week.

How many airports are there in Chicago?

There are 3 airports in Chicago: Chicago O'Hare Airport (ORD), Chicago Midway Airport (MDW) and Chicago Greater Rockford Airport (RFD). The busiest airport is Chicago O'Hare Airport (ORD), with 86% of all flights arriving there.

How long is the flight to Chicago?

The duration of your flight to Chicago depends on your departure and arrival airports. Obviously any flights that include a layover will also be longer. The most popular routes to Chicago on KAYAK are from Punta Cana, which takes 4h 59m, Santo Domingo, which takes 9h 16m, and Santiago de los Caballeros, which takes 9h 42m.

How many direct flights to Chicago are there each day?

There are around 1,657 direct flights from within Dominican Republic to Chicago every day. Most flights depart in the morning, with 6:00 am the most common departure time and 51% of flights departing in the morning.

How many direct flights to Chicago are there each week?

Each week there are around 11,596 direct flights from within Dominican Republic to Chicago. The most common day for departures is Friday, with 15% of flights taking off on this day.

How many long-haul flights are there to Chicago each week?

There are not any long-haul (6-12 hour flight duration) or short-haul (up to 3 hour flight duration) flights to Chicago. Instead, there are 26 medium-haul flights (3-6 hour flight duration), with the most arriving from Punta Cana.

How many cities have direct flights to Chicago?

From the Dominican Republic, there are direct flights to Chicago from 1 city. This city is Punta Cana and there are 26 direct flights each week.

Good to know

Low season

February

High season

August

Cheapest flight

$100
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from Punta Cana to Chicago O'Hare Airport

FAQs - booking Chicago flights

  • Which Chicago airport is closest to central Chicago?

    9 miles away from Chicago’s city center, Chicago Midway Airport is the closest of the 3 major airports in the city. There are 16 miles separating Chicago city center to Chicago O'Hare Airport, and 79 miles to Chicago Greater Rockford.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $301. The cheapest price found on KAYAK in the last 2 weeks cost $112 and departed from Punta Cana Airport.

  • How does KAYAK find such low prices on flights to Chicago?

    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 to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to 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 to Chicago?

    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 Chicago 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 to Chicago?

    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 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 Chicago

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Prefer to fly non-stop to Chicago?

Find which airlines fly direct to Chicago, which days they fly and book direct flights.

Nonstop departures

Dominican Republic to Chicago

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

See more direct flights

Nonstop returns

Chicago to Dominican Republic

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

See more direct flights
See more direct flights

Top 5 airlines serving from the Dominican Republic to Chicago

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from the Dominican Republic to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with to Chicago? 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 10975 reviews
8.0entertainment
8.6crew
7.9comfort
7.4food
8.2boarding
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.

Flight was delayed an no one make an announcement about it., they only have Coca Cola and nothing else., the food that was served was cold… very bad experience and service

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

One problem, but a serious one - the plane is built with electric windows that tint dark to reduce light. Sitting next to the window is VERY UNCOMFORTABLE as it emits so much HEAT in the face when tinted.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

Wifi wasn't working on one of the UA flights after boarding.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Crew was not very helpful. They forgot to serve me coffee and had to wait for a long time.It looked as if they were not very happy with what they were doing.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Unfortunately this is not a happy ending comment. Positive: flown United before no issue Negative: it only takes one bad experience to not plan future travel with United Cancún departure was delayed by 1h20 minutes, connection in Chicago was 1h30 minutes. Flight departure time 6:08 Miraculously 7 of us ran 4 kilometres through Chicago to arrive at 6:00 to be told very rudely by the 2 unprofessional United attendants you missed your flight and that we should of arrived early. Did I mention that reason I was flying? I received a call that my brother was dying and to get home. They provided no assistance would not answer any of our questions, ignorantly walked away. Deplorable

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

If United expects people to use their own devices for entertainment they should put charging outlets in each seating area. I arrived with 14%battery power. That is not good when you arrive anywhere and need to communicate for transportation.

The plane was old and in new of a cleaning up and renovating on the interior. Seats and carpets were very worn and dirty looking. Cushioning on the seats was broken down and not as comfortable as newer jet seats. Food was a little below average but okay. Staff were friendly and hard working but did not pick up debris or food they spilled when collecting from the customers. But they were very helpful and professional.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

lounge was the highlight - seats weren't that comfortable - it was a full flight but no complaints

The seat are terrible. Don’t even think of sleeping on a Spirit flight. The kids that run the plane aka flight attendants are pretty rude and straight forward. They get the job done but without class.

I had a death in my family and booked my flight on Spirit. My flight was cancelled the morning of my flight, no explanation, no help to rebook, nobody to talk to. The next available flight was 2days later !!!! Terrible airline, will NEVER fly with them again!

They took a horrible route with a lot of turbulence and I eneded up getting sick. Even if the flight takes longer. Don't put people life at risk just to get to the airport on time.

Every thing was fine ,low price,easy on time ,clean, good staff, really no issues

Had to board plan 2x due to lack of security check after 1st boarding

Miserable. The crew was rude, the flight was delayed 5 hours for mechanical reasons and then “weather” even though other planes were leaving.

They kept Changing the flight times. It was delayed several times and at one point it was supposed to depart at 3.40am! At which point we ended up staying overnight and booked long a separate United flight for early morning departure. The spirit flight then got moved up and left at 1.30 in the morning when it was supposed to leave at 9.40pm the night before.

Flight was delayed...not horribly late. Just before push back engine shut down for a quick replacement item that took about five minutes. After that, everything was smooth and the pilot was able to make up time in the air so that our arrival time was not too far off the original anticipated arrival time.

Only inflight purchases for food and water. Nothing comes with ticket price. Have to purchase bags, food...

The flight was delayed almost two hours on the front end, and an hour on the backend once we landed and waited for a gate to open up. We were told to remain in our seats during that whole delay and I had to go to the bathroom badly. I was unable to hold it and was forced to urinate in my pants while in my seat. I then had to sit in it until we finally deboarded and I was able to change my clothes.

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 the Dominican Republic to Chicago

Recent round-trip flight deals

 
These are the cheapest round-trip flights to Chicago found on KAYAK in the last 72 hours.
5/15週三
nonstopFrontier
5h 29mPUJ-ORD
5/17週五
1 stopFrontier
13h 55mORD-PUJ
$200
5/15週三
nonstopFrontier
5h 29mPUJ-ORD
5/21週二
1 stopFrontier
28h 13mORD-PUJ
$203
5/14週二
nonstopFrontier
5h 29mPUJ-ORD
5/17週五
1 stopFrontier
13h 55mORD-PUJ
$212
5/7週二
1 stopSpirit Airlines
13h 40mSDQ-ORD
5/14週二
1 stopSpirit Airlines
6h 36mORD-SDQ
$216
5/16週四
1 stopSpirit Airlines
14h 30mSDQ-ORD
5/21週二
1 stopSpirit Airlines
7h 35mORD-SDQ
$230
9/19週四
1 stopAmerican Airlines
17h 11mPUJ-ORD
9/24週二
1 stopAmerican Airlines
7h 02mORD-PUJ
$316
5/6週一
2 stopsDelta
17h 50mSDQ-ORD
5/15週三
1 stopDelta
15h 20mORD-SDQ
$370
5/6週一
1 stopDelta
18h 05mSDQ-MDW
5/15週三
1 stopDelta
6h 05mMDW-SDQ
$370
7/4週四
1 stopAmerican Airlines
19h 15mPUJ-ORD
7/15週一
1 stopAmerican Airlines
15h 43mORD-PUJ
$411
10/10週四
1 stopUnited Airlines
8h 02mSTI-ORD
10/15週二
1 stopUnited Airlines
9h 01mORD-STI
$674

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Recent one-way flight deals

 
Only flying one-way? Below are some of the best deals for one-way flights to Chicago found on KAYAK in the last 72 hours.
5/2週四
nonstopFrontier
5h 29mPUJ-ORD
$100
5/7週二
1 stopSpirit Airlines
14h 41mSDQ-ORD
$107
5/4週六
nonstopFrontier
5h 21mPUJ-ORD
$107
5/17週五
1 stopSpirit Airlines
14h 36mSTI-ORD
$127
7/4週四
nonstopAmerican Airlines
5h 05mPUJ-ORD
$160
7/4週四
1 stopAmerican Airlines
19h 15mPUJ-ORD
$170
5/5週日
nonstopUnited Airlines
4h 59mPUJ-ORD
$201
5/18週六
2 stopsDelta
19h 36mSDQ-MDW
$202
5/25週六
1 stopDelta
16h 42mSTI-ORD
$212
8/14週三
nonstopUnited Airlines
4h 59mPUJ-ORD
$287

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Last minute flights to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights to Chicago that are departing in the next 10 days.
4/28週日
multi-stopFrontier
25h 31mPUJ-MDW
5/5週日
multi-stopFrontier
16h 57mMDW-PUJ
$325
4/28週日
multi-stopFrontier
25h 31mPUJ-MDW
5/5週日
multi-stopFrontier
20h 04mMDW-PUJ
$331
4/30週二
multi-stopSpirit Airlines
30h 26mSDQ-ORD
5/22週三
multi-stopSpirit Airlines
7h 35mORD-SDQ
$364
4/30週二
multi-stopSpirit Airlines
18h 59mSDQ-ORD
5/22週三
multi-stopSpirit Airlines
7h 35mORD-SDQ
$369
4/30週二
multi-stopSpirit Airlines
30h 26mSDQ-ORD
5/22週三
multi-stopSpirit Airlines
18h 16mORD-SDQ
$387
4/30週二
multi-stopSpirit Airlines
28h 32mSDQ-ORD
5/22週三
multi-stopSpirit Airlines
17h 56mORD-SDQ
$422
4/26週五
multi-stopDelta
8h 13mPUJ-MDW
4/29週一
multi-stopDelta
6h 36mMDW-PUJ
$480
4/28週日
multi-stopFrontier
50h 19mPUJ-MDW
5/5週日
multi-stopFrontier
34h 18mMDW-PUJ
$482
4/29週一
multi-stopJetBlue
15h 01mSDQ-ORD
5/22週三
multi-stopJetBlue
8h 31mORD-SDQ
$975
4/30週二
multi-stopAeromexico
26h 35mSDQ-ORD
5/21週二
multi-stopAeromexico
28h 35mORD-SDQ
$1,508

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Flights to Chicago

Return flight deals:

Chicago - Dominican Republic

Cabin classes:

$1,188
$112

Popular routes

The most searched flights to Chicago by KAYAK users.