$208 Find Cheap Flights from Dominican Republic to Chicago O'Hare Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to O'Hare Intl departing on 10/14. 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, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago O'Hare Intl Airport

 
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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Cheap Flights from the Dominican Republic to O'Hare Intl

 
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 O'Hare Intl 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 O'Hare Intl

Sat, Sep 12 - Sat, Sep 19
Arajet Logo
7:02 am - 11:12 am
PUJ
-
ORD
5h 10mnonstop
Arajet Logo
12:12 pm - 5:57 pm
ORD
-
PUJ
4h 45mnonstop
$280Arajet
Sat, Sep 12 - Sat, Sep 19
Arajet Logo
7:02 am - 11:12 am
PUJ
-
ORD
5h 10mnonstop
Arajet Logo
12:12 pm - 5:57 pm
ORD
-
PUJ
4h 45mnonstop
$289Arajet
Sun, Aug 30 - Fri, Sep 4
Multiple Airlines Logo
3:30 pm - 10:26 pm
SDQ
-
ORD
7h 56m
1 stop
Multiple Airlines Logo
12:29 am - 7:18 pm
ORD
-
SDQ
17h 49m
1 stop
$354Multiple Airlines
Mon, Aug 31 - Fri, Sep 4
Multiple Airlines Logo
12:41 pm - 10:26 pm
SDQ
-
ORD
10h 45m
1 stop
Multiple Airlines Logo
12:29 am - 7:18 pm
ORD
-
SDQ
17h 49m
1 stop
$369Multiple Airlines
Thu, Aug 20 - Tue, Aug 25
Delta Logo
2:53 pm - 7:56 am
SDQ
-
ORD
18h 03m
2 stops
Delta Logo
1:00 pm - 12:54 am
ORD
-
SDQ
10h 54m
1 stop
$403Delta
Sat, Aug 29 - Tue, Sep 8
JetBlue Logo
5:01 am - 1:39 pm
SDQ
-
ORD
9h 38m
1 stop
JetBlue Logo
7:00 am - 3:21 pm
ORD
-
SDQ
7h 21m
1 stop
$405JetBlue
Mon, Aug 31 - Wed, Sep 9
Delta Logo
2:53 pm - 11:57 pm
SDQ
-
ORD
10h 04m
1 stop
Delta Logo
7:05 am - 6:07 pm
ORD
-
SDQ
10h 02m
2 stops
$406Delta
Thu, Aug 27 - Tue, Sep 1
JetBlue Logo
5:01 am - 1:39 pm
SDQ
-
ORD
9h 38m
1 stop
JetBlue Logo
2:35 pm - 11:59 pm
ORD
-
SDQ
8h 24m
1 stop
$414JetBlue
Tue, Oct 6 - Wed, Oct 14
American Airlines Logo
1:40 pm - 9:22 pm
STI
-
ORD
8h 42m
1 stop
American Airlines Logo
1:51 pm - 12:10 pm
ORD
-
STI
21h 19m
1 stop
$491American Airlines
Sat, Oct 3 - Wed, Oct 14
American Airlines Logo
3:15 pm - 7:58 am
STI
-
ORD
17h 43m
2 stops
American Airlines Logo
1:51 pm - 12:10 pm
ORD
-
STI
21h 19m
1 stop
$495American Airlines
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?

These are the best round-trip prices found by users searching on KAYAK in the last 5 days.

In the last 5 days, the cheapest flight deal to Chicago O'Hare Airport was found on the route from Santo Domingo, at $280 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 $280 in the last 5 days.

What is the cheapest day to fly to Chicago?

The average price of all round-trip flights to Chicago O'Hare Intl Airport 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 round-trip tickets can be as cheap as $331. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $476 on average.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights to Chicago O'Hare Intl Airport, 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 O'Hare Intl Airport is August, where tickets cost $139 on average for return flights. On the other hand, the most expensive months are June and September, where the average cost of tickets from the Dominican Republic is $460 and $327 respectively. For one-way flights, the best month to travel is December with an average price of $101.

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

The average price for all round-trip flights to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport is generally at night, when round-trip flights cost $297 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 $433.

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 $213 round-trip.

Good to know

Low seasonMarch
Cheapest flight$208
Best time to beat the crowds but there is an average 14% increase in price.
Most popular time to fly with an average 13% increase in price.
Flight from Santo Domingo 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 Santo Domingo, at $280 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 $280 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 $263. The cheapest price found on KAYAK in the last 2 weeks cost $157 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 $221
  • 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 airlines flying from the Dominican Republic to O'Hare Intl

 
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 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 11722 reviews
7.2Comfort
7.9Crew
6.4Food
7.5Boarding
6.8Entertainment
Airline reviews

We had a mechanical delay which made us 90 minutes late (9:30 PM) then land and put into the penalty box because a plane was in our gate? What the hell! We should get priority.Damn American.

6.0 GoodHardin, Jun 2026
ICT - ORD
Read more American Airlines reviews

We had a mechanical delay which made us 90 minutes late (9:30 PM) then land and put into the penalty box because a plane was in our gate? What the hell! We should get priority.Damn American.

The seats were extremely cramped, with very little legroom or personal space. There was no room left in the overhead bins for a backpack, and the space under the seat in front was so limited that I could barely fit my bag underneath. Overall, the seating arrangement felt very uncomfortable and overcrowded.

weather delay of almost 2 hours then we landed and our gate wasn't available so we waited another 30 min

Delayed flight more than I hour. When boarding we spent some additional time on the plane before takeoff ....

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

The flight from LA to Chicago was smooth and service was very good overall.

The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

They lost my baggage and I am still struggling to the information and update

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.

Really bad. Uncommunicated stop in Trinidad & Tobago for refueling. Extra stop added 3 hours of discomfort without allowing off the seat. Not even water, or chargers or boarding groups.

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.

I paid extra for a comfortable seat in the second flight, but the plane didn't have those seats, the first one did

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
South Haven
Merrillville
Oak Brook
Saint Joseph
Tinley Park
Hammond
Elk Grove Village
Des Plaines
Hoffman Estates
Portage
South Holland
Willowbrook
Delavan
Lansing
Northbrook
Lisle
Elmhurst
Alsip
Pleasant Prairie

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

Information on the airport you'll fly into in Chicago