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$202+ Cheap flights from the Dominican Republic to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/28. Fares are subject to change and may not be available on all flights or dates of travel.
PUJ — CHI
Jul 19 — Jul 261
Sun 7/19
Sun 7/26
1 adult, Economy
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Cheap flight deals from Dominican Republic to Chicago

Cheapest flights from Dominican Republic to Chicago
Explore the most affordable flight options available from Dominican Republic to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 19, 2026.

This Booking.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:02 am
PUJ
-
ORD
Nonstop5h 10m
Arajet
Sat 9/1912:12 pm
ORD
-
PUJ
Nonstop4h 45m
Arajet
Deal found 6/16$280
This Booking.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:02 am
PUJ
-
ORD
Nonstop5h 10m
Arajet
Sat 10/2412:12 pm
ORD
-
PUJ
Nonstop4h 45m
Arajet
Deal found 6/16$290
This Booking.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/75:47 am
PUJ
-
ORD
Nonstop5h 10m
Arajet
Sat 11/1410:27 am
ORD
-
PUJ
Nonstop4h 45m
Arajet
Deal found 6/16$291
This Booking.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/267:02 am
PUJ
-
ORD
Nonstop5h 10m
Arajet
Sat 10/312:12 pm
ORD
-
PUJ
Nonstop4h 45m
Arajet
Deal found 6/16$325
This Arajet deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:30 pm
PUJ
-
ORD
Nonstop5h 10m
Arajet
Sun 11/13:20 am
ORD
-
PUJ
Nonstop4h 45m
Arajet
Deal found 6/18$330
This Booking.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/197:02 am
PUJ
-
ORD
Nonstop5h 10m
Arajet
Sat 9/2612:12 pm
ORD
-
PUJ
Nonstop4h 45m
Arajet
Deal found 6/16$333
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/46:00 pm
PUJ
-
ORD
Nonstop5h 10m
Arajet
Mon 10/195:30 am
ORD
-
PUJ
Nonstop4h 45m
Arajet
Deal found 6/16$335
This eDestinos deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:02 am
PUJ
-
ORD
Nonstop5h 10m
Arajet
Sat 9/1212:12 pm
ORD
-
PUJ
Nonstop4h 45m
Arajet
Deal found 6/14$337
This Booking.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/315:47 am
PUJ
-
ORD
Nonstop5h 10m
Arajet
Sat 11/710:27 am
ORD
-
PUJ
Nonstop4h 45m
Arajet
Deal found 6/16$338
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/46:00 pm
PUJ
-
ORD
Nonstop5h 10m
Arajet
Fri 10/236:45 am
ORD
-
PUJ
Nonstop4h 45m
Arajet
Deal found 6/16$345
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/303:30 pm
SDQ
-
ORD
1 stop7h 56m
Multiple Airlines
Fri 9/412:29 am
ORD
-
SDQ
1 stop17h 49m
Multiple Airlines
Deal found 6/16$354
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/306:00 pm
PUJ
-
ORD
Nonstop5h 10m
Arajet
Sat 9/1912:12 pm
ORD
-
PUJ
Nonstop4h 45m
Arajet
Deal found 6/15$354

Find flight deals from Dominican Republic to Chicago

Keep the following information in mind while searching for Dominican Republic to Chicago flight deals. Data was last updated June 19, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$280
(Booking.com)

One-way from

$202
(SmartFares)

Popular in

June

Cheapest in

December

Average price

$1,503

Good round-trip deal

$213 or less

Good one-way deal

$227 or less
Provider with most accurate pricing for Punta Cana-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Punta Cana-Chicago (CHI) flights.
Search Deals
From Dominican Republic to Chicago (CHI)
Search Deals
One-way flight from Dominican Republic to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 40% potential increase in price ($374 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 18% potential price decrease ($87 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
Search Deals
Price to beat on a round-trip flight from Dominican Republic to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Dominican Republic to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Dominican Republic to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 19, 2026.
Use the filters below to find and compare flights from the Dominican Republic to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 10/29

7:30 pm-11:40 pm

Nonstop5h 10m

Chicago O'Hare Intl

Sun 11/1

3:20 am-10:05 am

Nonstop4h 45m

$330

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Fri 8/28

5:01 am-1:39 pm

1 stop9h 38m

Chicago O'Hare Intl

Tue 9/15

6:00 am-2:49 pm

1 stop7h 49m

$392

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Thu 8/27

2:53 pm-7:56 am

2 stops18h 03m

Chicago O'Hare Intl

Tue 9/1

6:00 am-6:06 pm

1 stop11h 06m

$403

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Sat 10/10

2:56 pm-11:50 pm

1 stop9h 54m

Chicago O'Hare Intl

Thu 10/15

5:30 am-1:41 pm

1 stop7h 11m

$403

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Thu 11/5

2:28 pm-11:44 pm

1 stop11h 16m

Chicago O'Hare Intl

Mon 11/9

2:35 pm-12:59 am

1 stop8h 24m

$410

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Wed 10/28

4:28 pm-11:44 pm

1 stop8h 16m

Chicago O'Hare Intl

Sat 10/31

7:00 am-3:16 pm

1 stop7h 16m

$410

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Sun 9/6

1:55 pm-10:10 pm

1 stop9h 15m

Chicago O'Hare Intl

Sat 9/12

12:12 pm-9:40 pm

1 stop8h 28m

$417

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Thu 8/20

5:01 am-1:39 pm

1 stop9h 38m

Chicago O'Hare Intl

Tue 8/25

7:00 am-3:21 pm

1 stop7h 21m

$422

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 7/18

7:02 am-11:12 am

Nonstop5h 10m

Chicago O'Hare Intl

Sat 7/25

12:12 pm-5:57 pm

Nonstop4h 45m

$429

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Mon 8/17

2:53 pm-7:56 am

2 stops18h 03m

Chicago O'Hare Intl

Mon 8/24

5:30 am-6:06 pm

2 stops11h 36m

$445

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/15

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Dominican Republic to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Dominican Republic with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from the Dominican Republic to Chicago

What is the cheapest month to book a flight from Dominican Republic to Chicago?

Currently, August is the cheapest month in which you can book a flight from Dominican Republic to Chicago (average of $139). Flying from Dominican Republic to Chicago in October is currently the most expensive (average of $235). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from DO to CHI?

Find hourly flight availability from Dominican Republic to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 19, 2026.

It’s optimal to fly from Dominican Republic to Chicago in the evening. By choosing this option you can save up to 51% on the cost of your flight, compared to a flight at noon.

Weekly flight availability from Dominican Republic to Chicago

Explore weekly flight availability from Dominican Republic to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 19, 2026.

The most flights from DO0 to CHI are scheduled on a Thursday (4 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 on average).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated June 19, 2026.
Peruse reviews from past customers who have flown with American Airlines from the Dominican Republic to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.1
Good
11,703 reviews

Entertainment

6.8

Crew

7.9

Overall

7.1

Boarding

7.5

Food

6.4

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.
American Airlines
7.1
Good
11,703 reviews
American Airlines
7.1
Good
11,703 reviews

Entertainment

6.8

Crew

7.9

Overall

7.1

Boarding

7.5

Food

6.4

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.

Related info for your journey

Find useful and relevant information for your journey from Dominican Republic to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Dominican Republic to Chicago?

    A quick flight from Dominican Republic to Chicago can take about 5h 10m. Arajet provides one of the quickest options available for as low as $330. The distance between Dominican Republic and Chicago is about 1982 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Dominican Republic to Chicago one-way?

    The cheapest airlines for a one-way flight from Dominican Republic to Chicago are Arajet ($121), Frontier ($134), and JetBlue ($151).

  • What are the most popular routes from Dominican Republic to Chicago?

    Most travelers choose Punta Cana - Chicago O'Hare Intl, Santo Domingo Las Americas - Chicago O'Hare Intl or Santo Domingo Las Americas - Chicago Midway when deciding on the best route from Dominican Republic to Chicago.

  • What are the most reliable airlines from Dominican Republic to Chicago?

    Consider Qatar Airways (83%), United Airlines (75%) or American Airlines (72%) when booking your flight. These represent the most reliable airlines when flying from Dominican Republic to Chicago.

  • What are the cheapest flights from Dominican Republic to Chicago?

    While on average a flight from Dominican Republic to Chicago is generally $263, our data shows the cheapest flight currently is $157. When looking at the most popular route, (Punta Cana - Chicago O'Hare Intl), you can expect to pay $280 for that flight.

  • Can I find deals for flights from Dominican Republic to Chicago that include hotel bookings?

    Yes. In addition to deals on Dominican Republic to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Dominican Republic to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Dominican Republic to Chicago.

  • Can I find deals for business class flights from Dominican Republic to Chicago?

    Yes. Cheapflights offers flight deals from Dominican Republic to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Dominican Republic to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Dominican Republic to Chicago (average of $139). Flying from Dominican Republic to Chicago in October is currently the most expensive (average of $235). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Lansing
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Hammond
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Top 2 airlines flying from Dominican Republic to Chicago

Discover the top 2 airlines that operate flights from Dominican Republic to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 19, 2026.
AirlineCheapestAverageFlexibilityOn-time
ArajetCheapest$195Average$404FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$283Average$509FlexibilityNo cancel feeOn-time71%

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