$111 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 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.
1 adult
1 adult, Economy

KAYAK searches 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
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Flight Deals

Cheap Flights from the Dominican Republic to Chicago

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

Tue, Nov 25 - Sun, Nov 30
Arajet Logo
7:30 pm - 10:40 pmPUJ-ORD
5h 10mnonstop
Arajet Logo
3:30 am - 10:15 amORD-PUJ
4h 45mnonstop
$219Arajet
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Sat, Feb 28 - Sat, Mar 7
Arajet Logo
5:47 am - 8:57 amPUJ-ORD
5h 10mnonstop
Arajet Logo
10:27 am - 5:12 pmORD-PUJ
4h 45mnonstop
$240Arajet
Find Deal
Thu, Oct 9 - Mon, Oct 20
American Airlines Logo
3:21 pm - 7:36 pmPUJ-ORD
5h 15mnonstop
American Airlines Logo
8:35 am - 2:05 pmORD-PUJ
4h 30mnonstop
$371American Airlines
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Thu, Feb 26 - Tue, Mar 3
United Airlines Logo
2:55 pm - 6:08 pmPUJ-ORD
5h 13mnonstop
United Airlines Logo
8:45 am - 5:25 pmORD-PUJ
6h 40m1 stop
$374United Airlines
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Thu, Oct 9 - Mon, Oct 20
American Airlines Logo
3:21 pm - 7:36 pmPUJ-ORD
5h 15mnonstop
American Airlines Logo
5:22 am - 3:45 pmORD-PUJ
9h 23m1 stop
$376American Airlines
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Fri, Nov 14 - Sun, Nov 30
United Airlines Logo
12:56 pm - 7:41 amPUJ-ORD
20h 45m1 stop
United Airlines Logo
7:52 am - 2:22 pmORD-PUJ
4h 30mnonstop
$377United Airlines
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Wed, Oct 1 - Mon, Oct 6
Delta Logo
8:40 pm - 9:56 amSTI-ORD
14h 16m1 stop
Delta Logo
7:00 am - 7:06 pmORD-STI
11h 06m1 stop
$386Delta
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Fri, Oct 3 - Tue, Oct 7
Delta Logo
7:40 pm - 9:56 amSDQ-ORD
15h 16m1 stop
Delta Logo
7:10 am - 6:24 pmORD-SDQ
10h 14m2 stops
$388Delta
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Thu, Oct 30 - Mon, Nov 3
Frontier Logo
3:19 pm - 10:03 pmSDQ-MDW
7h 44m1 stop
Frontier Logo
6:20 am - 5:21 pmMDW-SDQ
9h 01m2 stops
$439Frontier
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Sun, Oct 12 - Sun, Oct 19
Frontier Logo
3:14 pm - 11:46 pmSDQ-MDW
9h 32m1 stop
Frontier Logo
6:20 am - 2:01 pmMDW-SDQ
6h 41m1 stop
$454Frontier
Find Deal

Everything you should know

Top airlines
American Airlines
Most flights • 7 per week
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
May
Cheapest • 26% price drop
December
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$219
Typical prices: $306-442
Arajet
Tue 11/25Sun 11/30
PUJ - ORD • Non-stop
Cheapest one-way
$111
Typical prices: $192-372
Arajet
Sat 11/15
PUJ - ORD • Non-stop
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We hope you love your trip to Chicago!
Booking Insights

KAYAK's insights & trends for flights to Chicago

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 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 May, where tickets cost $302 on average for return flights. On the other hand, the most expensive months are June and January, where the average cost of tickets from the Dominican Republic is $685 and $481 respectively. For one-way flights, the best month to travel is May with an average price of $302.

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 $320 round-trip.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights to Chicago, 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, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 12 weeks 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 Greater Rockford Airport (RFD), with an average flight price of $204.

Good to know

Low seasonMarch
Cheapest flight$111
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly and prices are also 17% 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 $346. The cheapest price found on KAYAK in the last 2 weeks cost $216 and departed from Punta Cana Airport.

  • What is the cheapest day to fly to Chicago?

    Based on KAYAK data, the cheapest day to fly to Chicago is Sunday where round-trip tickets can be as cheap as $365. On the other hand, the most expensive day to fly is Wednesday, where round-trip prices are $515 on average.

  • 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.

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

    The cheapest time of day to fly to Chicago is generally at night, when round-trip flights cost $306 on average. The most expensive time of day to fly to Chicago is generally in the evening, which is peak travel time and where the average cost of a ticket is $413.

Top tips for finding cheap flights to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $306 or less one-way and $320 or less round-trip.
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Reviews of the top 4 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.
7.9
DeltaOverall score based on 7954 reviews
8.2Boarding
8.5Crew
7.9Entertainment
7.3Food
7.9Comfort
Airline reviews

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

10.0 ExcellentAnonymous, Sep 2025CLT - BOS
Read more Delta reviews

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

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.

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.

The airport crew helped a lot, what I didn’t like? We were not informed that we needed to pick our luggage’s, if the crew at the luggage center didn’t tell me I would have been home without my belongings, I was heading out to my next connecting flight while looking for what gate to go to, I asked one of the crews for help, he told me and he also told me to not forget to grab my luggage’s which was chocking, because on my way out the country that wasn’t required, I just hope none of your customers lost their luggage’s because of this.

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

The flight crew was friendly. I tried to adjust my seat online ahead of time but no option existed without additional fees. My friend asked at the gate about a seat change and was able to make it happen. That was great! The flight crew moved a very tall gentleman and his companion which allowed us to have more space which was nice. Overall, good experience. Appreciated the blanket and pillow.

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

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Inoperable monitor left no entert for 9 hours. Crew was not helpful Food was awful.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

All flight attendants could benefit by taking an international flight on Qantas Airline. Qantas attendants are much more hospitable in every way. Much superior than and attendants on any US airline.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The flight was on time and crew were nice, seats were tight and there was entertainment available

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

Worst flight ever. I was suppose to have a 3 1/2 hour layover in Chicago but got to the gate 4 minutes before boarding.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

They should have MSNBC available on board. A 4- hour flight should provide more than a cookie.

Was not able to watch most shows on the entertainment site. They would not load

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

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.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Everything you need to know for your flight to Chicago

Cabin class types available on flights to Chicago

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

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