$188 Find Cheap Flights from Dominican Republic to Chicago O'Hare Airport - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from the Dominican Republic to O'Hare Intl

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from the Dominican Republic to O'Hare Intl

Sat, Nov 21 - Sat, Nov 28
Arajet Logo
7:00 am - 10:10 amPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 10mnonstop
Arajet Logo
11:10 am - 5:55 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 45mnonstop
$321Arajet
Sat, Nov 21 - Sat, Nov 28
Arajet Logo
7:00 am - 10:10 amPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 10mnonstop
Arajet Logo
11:10 am - 5:55 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 45mnonstop
$328Arajet
Sat, Dec 26 - Sat, Jan 2
Arajet Logo
7:00 am - 10:10 amPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 10mnonstop
Arajet Logo
11:10 am - 5:55 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 45mnonstop
$331Arajet
Fri, Nov 20 - Sat, Nov 28
Multiple Airlines Logo
1:40 am - 10:10 amSDQ  Santo Domingo Las Americas-ORD Chicago O'Hare Intl
10h 30m1 stop Punta Cana
Multiple Airlines Logo
11:10 am - 9:40 pmORD  Chicago O'Hare Intl-SDQ Santo Domingo Las Americas
8h 30m1 stop Punta Cana
$356Multiple Airlines
Thu, Oct 29 - Sun, Nov 1
United Airlines Logo
1:55 pm - 6:10 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 15mnonstop
United Airlines Logo
8:50 am - 5:28 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
6h 38m1 stop Washington, D.C. Dulles Intl
$360United Airlines
Thu, Nov 5 - Mon, Nov 9
United Airlines Logo
2:55 pm - 6:10 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 15mnonstop
United Airlines Logo
5:59 am - 5:28 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
9h 29m1 stop Washington, D.C. Reagan-National
$360United Airlines
Fri, Dec 25 - Fri, Jan 1
American Airlines Logo
5:34 pm - 9:08 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 34mnonstop
American Airlines Logo
9:52 am - 4:29 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 37mnonstop
$373American Airlines
Sat, Nov 21 - Sat, Nov 28
American Airlines Logo
4:08 pm - 7:47 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 39mnonstop
American Airlines Logo
6:00 am - 3:48 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
7h 48m1 stop Miami
$377American Airlines
Tue, Nov 17 - Tue, Nov 24
JetBlue Logo
2:32 pm - 11:36 pmSDQ  Santo Domingo Las Americas-ORD Chicago O'Hare Intl
11h 04m1 stop Fort Lauderdale
JetBlue Logo
2:59 pm - 12:59 amORD  Chicago O'Hare Intl-SDQ Santo Domingo Las Americas
8h 00m1 stop Fort Lauderdale
$544JetBlue
Mon, Nov 9 - Mon, Nov 16
JetBlue Logo
2:32 pm - 11:36 pmSDQ  Santo Domingo Las Americas-ORD Chicago O'Hare Intl
11h 04m1 stop Fort Lauderdale
JetBlue Logo
7:00 am - 4:18 pmORD  Chicago O'Hare Intl-SDQ Santo Domingo Las Americas
7h 18m1 stop Fort Lauderdale
$544JetBlue
Booking Insights

KAYAK's insights & trends for flights to O'Hare Intl

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

What is the cheapest flight to Chicago O'Hare Airport?

In the last 5 days, the cheapest flight deal to Chicago O'Hare Airport was found on the route from Punta Cana, at $321 return. The most popular connection is from Santo Domingo to Chicago O'Hare Airport and KAYAK users have found round-trip deals for as low as $356 in the last 5 days.

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 $386. On the other hand, the most expensive day to fly is Friday, where round-trip prices are $589 on average.

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The cheapest month for flights to Chicago O'Hare Intl Airport is February, where tickets cost $384 on average for return flights. On the other hand, the most expensive months are March and August, where the average cost of tickets from the Dominican Republic is $688 and $681 respectively. For one-way flights, the best month to travel is December with an average price of $239.

What is the cheapest time of day to fly to Chicago O'Hare Intl Airport?

The cheapest time of day to fly to Chicago O'Hare Intl Airport is generally at night, when round-trip flights cost $236 on average. The most expensive time of day to fly to Chicago O'Hare Intl Airport is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $502.

What is a good deal for flights to Chicago O'Hare Intl Airport?

If you’re looking for cheap airfare to Chicago O'Hare Intl Airport, 25% of our users found tickets to Chicago O'Hare Intl Airport for the following prices or less: From Punta Cana $303 round-trip.

Good to know

Low season

March

Cheapest flight

$188
Best time to beat the crowds but there is an average 6% increase in price.
Most popular time to fly with an average 4% increase in price.
Flight from Punta Cana to Chicago O'Hare Airport

FAQs - booking Chicago O'Hare Airport flights

  • What is the cheapest flight to Chicago O'Hare Airport?

    In the last 5 days, the cheapest flight deal to Chicago O'Hare Airport was found on the route from Punta Cana, at $321 return. The most popular connection is from Santo Domingo to Chicago O'Hare Airport and KAYAK users have found round-trip deals for as low as $356 in the last 5 days.

  • How far is Chicago O'Hare Intl Airport from central Chicago?

    The city center of Chicago is 16 miles from Chicago O'Hare Intl Airport.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $398. The cheapest price found on KAYAK in the last 2 weeks cost $167 and departed from Punta Cana Airport.

  • How does KAYAK find such low prices on flights to Chicago O'Hare Airport?

    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 O'Hare Airport.

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

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

    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 O'Hare Airport 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 O'Hare Airport?

    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 O'Hare Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Chicago O'Hare Airport

  • Looking for cheap airfare to Chicago O'Hare Airport? 25% of our users found round-trip tickets to Chicago O'Hare Airport for the following prices or less: From Punta Cana $299

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

Reviews of the top 3 airlines serving from the Dominican Republic to O'Hare Intl

 
Need help choosing which airline to fly with to O'Hare Intl? 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.
7.1
JetBlueOverall score based on 3046 reviews
7.9Crew
7.3Boarding
7.2Entertainment
7.4Comfort
6.6Food
Airline reviews

There was more leg room in what was most likely a basic assigned seat (row 25) then on other airlines I've flown lately.

8.0 ExcellentJoyce, Oct 2026
Read more JetBlue reviews

There was more leg room in what was most likely a basic assigned seat (row 25) then on other airlines I've flown lately.

Jet Blue cancelled my flight after I had boarded. They attempted to rebook me for a new flight two days later. I was able to rebook with a different airline, but not until the next morning. As such, I was forced to get an expensive hotel and missed important work meetings Monday morning. I am very disappointed with the customer service and will be pursuing full reimbursement for my hotel cost.

Boarding was great, communication from the crew was excellent. My only complaint is the seating seems to have gotten smaller, and felt a bit tight. I can’t imagine doing a long haul flight in those seats.

Probably won't be traveling with JetBlue again. The planes for both flights were so old; I was honestly nervous it was going to hold up. The screens had so much static. I couldn't change the volume and my movie changed to Portuguese five minutes in and refused to switch back to English. Onboarding process on the way back was utter chaos.

Every time I leave from sti Dominican Republic, there is always a delay with a flight , causing a rush to make it to the next flight considering you have to go threw immigration

Jet blue is always good - the one weird thing was that they started boarding about 20-30 minutes before the official boarding time on the app. Just something to be aware of!

The seats have so much room. They give great free snacks. Staff was so nice.

I paid for the service of having the right to choose my seat and it was not like that, they put me where they wanted and I explained to one of the staff that they were before boarding and they were very rude. I am traveling with the family and they put us in separate seats.

I volunteered to let them put my carry on suitcase in the baggage storage area. But when we landed I was told it was being unloaded IN A DIFFERENT TERMINAL! I had to walk (painful for me) a long way to retrieve my bag and my ride had to move from the waiting area they were in to a totally different one. Not happy.

Good, just some of the staffs have such a bad attitude.

I was truly shocked at how poor this flight went. The crew was not friendly during the checking process. The asked for people to gate check and were rude about it. They didn't handle my luggage with care. When I got to my seat I noticed a large section of the ceiling vent area was, no joke, TAPED TOGETHER WITH CLEAR PACKING TAPE! To add insult to injury, the back rest button was disabled on my seat and all the seats I could see. The wifi, never connected for me, despite troubleshooting it for a while. I did everything from restarting my wifi/phone to forgetting the network and restarting the app. But that didn't stop the mandatory 2 ads from playing every single time. Even the bags took over 45 mins to arrive at the carousel. Everything about this flight was a flop and I am beginning to notice that some of these events are becoming a trend. Perhaps it's time I switch loyalty programs.

Horrible airline, will never buy another ticket with the airline or Kayak. They close the gate 2 hours early in Kenya, I had to buy a new ticket and get a hotel room

It would be helpful to be able to download an eticket from either American airlines or Cathay Pacific; not just Cathay Pacific.

Another American Airlines flight, another significant delay. At least this one wasn't canceled like many others have been. This time we sat on the runway at LaGuardia for 2.5 hours. By my count that is 7 American flights the last three months that have been delayed 2 hours or more or canceled entirely.

There was no clear update on the flight until last minute and made it an hour delay. No clear flight aircraft or incoming flight which we will be boarding. We would plan accordingly for our connecting flight. This is one one the worst service, I also had to buy an another ticket with different ai carrier. American airline was not letting me plan my trip, made us just waiting. Not a good service at all.

The plane was delayed after we boarded - although they sent an email to my work email (which I did not get until later) there was no announcement from the PA about the delay in flight. Fortunately, they made up the time in the air and we landed around the original time.

My luggage was lost at some point during my layover between Chicago and LHR. I landed Tuesday morning, and did not get it until Thursday night. Ironically, the people at the ticket desk had added a “priority” sticker to my tracking tag.

My experience was fine, with one surprising exception. After leveling off at cruising altitude, the main cabin flight attendant made an announcement that he had a cold, so he would not be coming through the aisle to provide cabin service. He claimed this was in consideration of his health and safety and ours. However, if passengers wanted a beverage, he invited them to come to the back of he plane, where he would provide service. I understand that a flight attendant's primary responsibility is to ensure passenger safety, but a secondary role is to provide service. If this flight attendant was too sick to perform his duties - and if he truly cared about passenger health and safety , as he claimed - he should have stayed home and called in sick, rather than exposing the cabin to his germs.

The flight was delayed multiple times. Breakfast was not served and only an apology given and statement that we could find better pastries in Paris. Seats were extremely narrow and uncomfortable.

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

I got to the airport and the airline told me i did not have a flight. I never got a confirmation email yet I did get charged. Please refund my money asap

Was charged for ticket, unable to check in online, made the line to speak to someone at the counter but was told I did not show up in the system as having a ticket to fly - even though I have the email with confirmation and credit card was charged. I could not purchase another ticket at the counter, only online which was not working. Ended up buying a flight on another airline at the airport. Called customer service to claim the cost of the original ticket, was told I showed up in their system as having a ticket but did not check-in or show up to board the flight. Currently pending review for refund via their customer service team, they were very nice and helpful over the phone despite the many glitches.

Do not book with this airline. Flights delayed over 3 hours and no explanation. They keep changing your itinerary every hour.

Awful. Not water, or chargers or space under the seats, the plane was very old and poor maintenance, seats really dirty, sticky, seats pockets with wires pinching your knees. Connection with no announcements, plane departed 1.30 hour earlier for an extra stop to refueling in Trinidad & Tobago. Even that we had a 3 hrs delay, seated in the plane in the runway.

Staff were unfriendly and rude. Was stuck on runway for 2 hours after arrival in Boston.

Horrible service. No communication from the crew as to why a 6 hour delay then cancellation

We waited in an overcrowded bus for over a half hour. It was uncomfortable. It would have been better to have waited in the terminal in a line

The food for sale on board has opportunity for improvement.

The Arajet person who greeted us initially was unhelpful & rude about the mandatory migration form which has to be completed digitally but the systems don’t work properly. The boarding gate was changed twice and initial boarding was delayed. Once on board we we had to wait an hour and a half before take off. It was hot and there was very little room for tall-ish people to fit their knees in. The crew were pleasant but working in a poor situation. The plane was delayed because we were waiting for people from a delayed interconnecting flight. Arajet must have known that before we were asked to board. Better information, decisions & communication were needed.

My seat was broken and the crew had to find me somewhere else to sit. The crew was extremely courteous about this

Traveling to a place near O'Hare Intl?

Book flights to O'Hare Intl if you plan to visit one of these locations
Merrillville
Gurnee
South Haven
Oak Brook
Tinley Park
Hammond
Saint Joseph
Des Plaines
Elk Grove Village
Hoffman Estates
Oakbrook Terrace
Portage
South Holland
Willowbrook
Lansing
Lisle
Alsip
Delavan
Valparaiso
Northbrook

More options for your flight to O'Hare Intl