$187 Find Cheap Flights from Dominican Republic to Chicago O'Hare Airport - Compare and Save

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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

Thu, Sep 24 - Mon, Sep 28
Arajet Logo
7:30 pm - 11:40 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 10mnonstop
Arajet Logo
5:30 am - 11:15 amORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 45mnonstop
$322Arajet
Thu, Jan 14 - Fri, Jan 29
Arajet Logo
7:30 pm - 10:40 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 10mnonstop
Arajet Logo
5:45 am - 12:30 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 45mnonstop
$357Arajet
Thu, Jan 14 - Sun, Jan 31
Arajet Logo
7:30 pm - 10:40 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 10mnonstop
Arajet Logo
3:20 am - 10:05 amORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 45mnonstop
$357Arajet
Thu, Oct 22 - Mon, Oct 26
Multiple Airlines Logo
1:45 pm - 11:40 pmSDQ  Santo Domingo Las Americas-ORD Chicago O'Hare Intl
10h 55m1 stop Punta Cana
Multiple Airlines Logo
4:30 am - 4:55 pmORD  Chicago O'Hare Intl-SDQ Santo Domingo Las Americas
11h 25m1 stop Punta Cana
$370Multiple Airlines
Thu, Sep 17 - Fri, Sep 25
Multiple Airlines Logo
7:30 pm - 11:40 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 10mnonstop
Multiple Airlines Logo
3:40 pm - 4:05 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
23h 25m1 stop Montreal Pierre Elliott Trudeau Intl
$371Multiple Airlines
Thu, Oct 1 - Mon, Oct 5
Multiple Airlines Logo
3:30 pm - 11:40 pmSDQ  Santo Domingo Las Americas-ORD Chicago O'Hare Intl
9h 10m1 stop Punta Cana
Multiple Airlines Logo
5:30 am - 4:55 pmORD  Chicago O'Hare Intl-SDQ Santo Domingo Las Americas
10h 25m1 stop Punta Cana
$377Multiple Airlines
Thu, Dec 24 - Sat, Jan 2
American Airlines Logo
5:34 pm - 9:08 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 34mnonstop
American Airlines Logo
9:30 am - 4:10 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 40mnonstop
$431American Airlines
Thu, Dec 24 - Fri, Jan 1
American Airlines Logo
5:34 pm - 9:08 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 34mnonstop
American Airlines Logo
8:10 am - 2:48 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 38mnonstop
$431American Airlines
Thu, Nov 5 - Wed, Nov 11
JetBlue Logo
3:57 pm - 11:57 pmSDQ  Santo Domingo Las Americas-ORD Chicago O'Hare Intl
10h 00m1 stop Atlanta Hartsfield-Jackson
JetBlue Logo
5:30 am - 2:40 pmORD  Chicago O'Hare Intl-SDQ Santo Domingo Las Americas
7h 10m1 stop Atlanta Hartsfield-Jackson
$514JetBlue
Wed, Oct 14 - Tue, Oct 20
JetBlue Logo
2:57 pm - 11:57 pmSDQ  Santo Domingo Las Americas-ORD Chicago O'Hare Intl
10h 00m1 stop Atlanta Hartsfield-Jackson
JetBlue Logo
6:00 pm - 12:37 pmORD  Chicago O'Hare Intl-SDQ Santo Domingo Las Americas
17h 37m1 stop New York John F Kennedy Intl
$514JetBlue
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 Santo Domingo, at $322 return. The most popular connection is from Punta Cana to Chicago O'Hare Airport and KAYAK users have found round-trip deals for as low as $322 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 Wednesday where round-trip tickets can be as cheap as $359. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $506 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 June, where the average cost of tickets from the Dominican Republic is $688 and $664 respectively. For one-way flights, the best month to travel is December with an average price of $231.

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 morning, which is peak travel time and where the average cost of a ticket is $445.

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 $490 round-trip.

Good to know

Low season

March

Cheapest flight

$187
Best time to beat the crowds but there is an average 10% increase in price.
Most popular time to fly with an average 8% increase in price.
Flight from Santo Domingo to Chicago

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 Santo Domingo, at $322 return. The most popular connection is from Punta Cana to Chicago O'Hare Airport and KAYAK users have found round-trip deals for as low as $322 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 $491. The cheapest price found on KAYAK in the last 2 weeks cost $198 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 $380
  • 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
American AirlinesOverall score based on 11963 reviews
7.5Boarding
7.9Crew
6.4Food
7.2Comfort
6.8Entertainment
Airline reviews

We landed slightly early but then sat in holding area waiting for our gate to clear out for about an hour, so technically we arrived one hour late at the gate at ORD. The airport may be partially responsible here, but regardless of who is responsible, it was a bad experience to be so close yet unable to get off the plane.

6.0 GoodAnonymous, Aug 2026
Read more American Airlines reviews

We landed slightly early but then sat in holding area waiting for our gate to clear out for about an hour, so technically we arrived one hour late at the gate at ORD. The airport may be partially responsible here, but regardless of who is responsible, it was a bad experience to be so close yet unable to get off the plane.

Delays and cancellations. Mechanics weren’t on site. Replacement plane took hours to arrive although it should have arrived within 90 minutes. Flight back was cancelled. Ended up driving over 12 hours and wasting 3 days between everything.

Little bit of trouble getting my KTN and pre-check status onto the ticket, but otherwise the counter staff were friendly and truly concerned to get it right.

The flight could have actually taken place. Canceled flight and no option to rebook that day.

Missed connection from delays and times changing multiple times and then involuntarily booked on another airline next day

The flight was delayed in 30 minute increments for a total of 4 hours and 30 minute delay. All other flights to Chicago left on time except for this one flight. If there is an issue with the inbound flight, just let customers know so they can find another flight right away, Once we got on the plane there was another 30 minute delay taking off at 10:30 at night which is very unusual that a flight wouldn't be ready to take off

My seat had a worn out cushion, which made it a bit uncomfortable. Other than that, the flight was excellent.

Take this flight regularly. Every single week same thing. Departure delayed. Make up some time in the air. Land at ORD and then wait for gate in "L" concourse Terminal 3 for 30-40 min-which yields a very delayed final arrival. Plus I get to taxi around and see every runway and drive over the bridge (IFKYK) over the expressway 2-4 times in most cases. Change the sched of incoming plane/work with FAA to improve traffic flow at ORD/change the timing of these flights. Whatever it takes. But do better.

- flight was delayed several hours due to weather (understandable) - flight delayed further and we were told by attendants "we are not sure where the pilots are but they are on their way" as we have to find different pilots for the flight - announcements over the PA were somewhat unprofessional by the attendants, seems they need more training and were not reading off the script. They showed their young age and immaturity in their communications with the passengers. They were not clear and lacked professional communication language. - going from a hub to hub we were also parked at the tarmac at ohare for an additional hour and kept being told "few more minutes". Please just let the passengers know the real wait time instead of hiding the truth. We understand there is traffic and weather delays, but we just want transparency. There are several logistics of our lives that revolve around what the attendants and pilots are sharing with us but they are not being transparant.

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

My screen didn’t work, my seat didn’t recline, the flight attendant was rude and completely dismissive, the airplane was freezing, the seats are way old, slanted and uncomfortable. I payed for a full ticket and got a horrific experience, with a flight attendant who dismissed me even though I was calm respectful and polite.

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 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
Gurnee
Merrillville
South Haven
Oak Brook
Saint Joseph
Tinley Park
Hammond
Elk Grove Village
Des Plaines
Hoffman Estates
South Holland
Portage
Oakbrook Terrace
Willowbrook
Lansing
Delavan
Alsip
Northbrook
Lisle
Valparaiso

Everything you need to know for your flight to O'Hare Intl

Information on the airport you'll fly into in Chicago