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$154+ 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 3/23. Fares are subject to change and may not be available on all flights or dates of travel.
PUJ — CHI
1월 15 — 1월 221
목 1/15
목 1/22
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 12월 16, 2025.

This Mytrip deal was found by Cheapflights users on 12/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
토 12/277:17 amPUJ - ORD
Nonstop5h 10mArajet
월 1/55:45 amORD - PUJ
Nonstop4h 45mArajet
Deal found 12/14$233
This Expedia deal was found by Cheapflights users on 12/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
토 12/277:17 amPUJ - ORD
Nonstop5h 10mArajet
토 1/310:27 amORD - PUJ
Nonstop4h 45mArajet
Deal found 12/16$236
This Expedia deal was found by Cheapflights users on 12/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
화 12/3011:37 amPUJ - ORD
1 stop12h 47mFrontier
화 1/67:10 amORD - PUJ
Nonstop4h 37mFrontier
Deal found 12/16$268
This Expedia deal was found by Cheapflights users on 12/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
토 12/277:17 amPUJ - ORD
Nonstop5h 10mMultiple Airlines
토 1/36:10 amORD - PUJ
1 stop6h 59mMultiple Airlines
Deal found 12/15$285
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
토 12/277:17 amPUJ - ORD
Nonstop5h 10mMultiple Airlines
월 1/512:09 pmORD - PUJ
1 stop24h 00mMultiple Airlines
Deal found 12/14$294
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
수 12/246:08 pmPUJ - ORD
1 stop22h 54mMultiple Airlines
수 12/315:45 amORD - PUJ
Nonstop4h 45mMultiple Airlines
Deal found 12/16$296
This Orbitz deal was found by Cheapflights users on 12/15. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
수 12/311:28 pmPUJ - ORD
1 stop8h 38mMultiple Airlines
수 1/75:45 amORD - PUJ
Nonstop4h 45mMultiple Airlines
Deal found 12/15$302
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
화 12/306:08 pmPUJ - ORD
2 stops30h 16mMultiple Airlines
화 1/67:10 amORD - PUJ
Nonstop4h 37mMultiple Airlines
Deal found 12/16$303
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
화 12/2310:41 amSDQ - ORD
1 stop14h 44mMultiple Airlines
수 1/75:29 pmORD - SDQ
2 stops19h 43mMultiple Airlines
Deal found 12/14$330
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
목 12/253:08 pmPUJ - MDW
1 stop8h 50mMultiple Airlines
목 1/13:10 pmMDW - PUJ
1 stop27h 15mMultiple Airlines
Deal found 12/16$345
This Expedia deal was found by Cheapflights users on 12/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
수 12/3112:25 pmSDQ - ORD
1 stop9h 41mFrontier
월 1/59:47 amORD - SDQ
1 stop24h 53mFrontier
Deal found 12/15$349
This eDestinos deal was found by Cheapflights users on 12/14. 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.
화 12/2310:41 amSDQ - ORD
2 stops33h 52mFrontier
수 1/75:29 pmORD - SDQ
2 stops19h 43mFrontier
Deal found 12/14$350

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 12월 16, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$212
(Booking.com)

One-way from

$154
(Trip.com)

Popular in

June

Cheapest in

February

Average price

$397

Good round-trip deal

$195 or less

Good one-way deal

$203 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. 16% potential increase in price ($81 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($31 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 12월 16, 2025.
Use the filters below to find and compare flights from the Dominican Republic to Chicago that are best for you.

Fly from

Dominican Republic

Fly to

Chicago

Route

Depart

Return

Price

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

목 1/22

3:32 pm-9:03 pm

1 stop7h 31m

Chicago O'Hare Intl

목 2/5

5:15 am-2:27 pm

1 stop7h 12m

$291

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

토 2/7

3:32 pm-11:46 pm

1 stop10h 14m

Chicago O'Hare Intl

수 2/11

5:15 am-2:27 pm

1 stop7h 12m

$310

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

금 1/30

3:32 pm-11:46 pm

1 stop10h 14m

Chicago O'Hare Intl

금 2/6

8:43 pm-2:27 pm

1 stop15h 44m

$319

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

수 1/21

3:32 pm-11:46 pm

1 stop10h 14m

Chicago O'Hare Intl

월 1/26

5:15 am-2:27 pm

1 stop7h 12m

$320

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

금 1/30

3:32 pm-7:44 pm

1 stop30h 12m

Chicago O'Hare Intl

토 2/14

12:06 pm-2:20 pm

1 stop24h 14m

$336

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

목 2/26

12:31 pm-10:51 am

2 stops48h 20m

Chicago O'Hare Intl

월 3/2

5:05 am-11:56 am

2 stops28h 51m

$339

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

토 1/17

2:37 pm-12:08 pm

2 stops23h 31m

Chicago O'Hare Intl

화 2/17

6:02 pm-11:26 am

2 stops39h 24m

$346

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

금 1/30

9:34 pm-4:40 pm

2 stops21h 06m

Chicago O'Hare Intl

금 2/6

8:43 pm-2:27 pm

1 stop15h 44m

$349

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

수 12/31

12:25 pm-8:06 pm

1 stop9h 41m

Chicago O'Hare Intl

월 1/5

9:47 am-12:40 pm

1 stop24h 53m

$349

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

수 2/18

3:32 pm-8:54 pm

1 stop7h 22m

Chicago O'Hare Intl

토 2/28

7:59 pm-2:20 pm

1 stop16h 21m

$350

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 60 results
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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 June is currently the most expensive (average of $341). 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 12월 16, 2025.

It’s optimal to fly from Dominican Republic to Chicago in the morning. By choosing this option you can save up to 15% on the cost of your flight, compared to a flight in the afternoon.

What is the cheapest day to fly from Dominican Republic to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Dominican Republic to Chicago. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Dominican Republic to Chicago flight should consider departing on Thursday evenings when fares are most often at their lowest. Monday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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 12월 16, 2025.

The most flights from DO0 to CHI are scheduled on a Tuesday (5 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (1 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 12월 16, 2025.
Peruse reviews from past customers who have flown with Delta, American Airlines, and Frontier 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.
Delta
7.9
Good
8,009 reviews

Boarding

8.1

Comfort

7.9

Crew

8.5

Food

7.3

Overall

7.9

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,009 reviews
Delta
7.9
Good
8,009 reviews

Boarding

8.1

Comfort

7.9

Crew

8.5

Food

7.3

Overall

7.9

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,047 reviews
Delta
7.9
Good
8,009 reviews

Boarding

8.1

Comfort

7.9

Crew

8.5

Food

7.3

Overall

7.9

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Frontier
5.8
Fair
3,082 reviews
Delta
7.9
Good
8,009 reviews

Boarding

8.1

Comfort

7.9

Crew

8.5

Food

7.3

Overall

7.9

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 7h 31m. Spirit Airlines provides one of the quickest options available for as low as $291. The distance between Dominican Republic and Chicago is about 1947 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 Frontier ($117), Arajet ($133), and United Airlines ($145).

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

    Most travelers choose Punta Cana - Chicago O'Hare Intl, Punta Cana - Chicago Midway or Santo Domingo Las Americas - Chicago O'Hare Intl 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 (91%), American Airlines (85%) or Frontier (76%) 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 $288, our data shows the cheapest flight currently is $127. When looking at the most popular route, (Punta Cana - Chicago O'Hare Intl), you can expect to pay $212 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 June is currently the most expensive (average of $341). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Dominican Republic to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Punta Cana to O'Hare Intl flights
Punta Cana to Midway flights
Luis Munoz Marin Intl to O'Hare Intl flights
Luis Munoz Marin Intl to Midway flights
Santo Domingo to O'Hare Intl flights
Nassau to O'Hare Intl flights
Luis Munoz Marin Intl to St. Louis flights
Oranjestad to O'Hare Intl flights
Christiansted to O'Hare Intl flights
Simpson Bay to O'Hare Intl flights
Saint Thomas Island to O'Hare Intl flights
Willemstad to O'Hare Intl flights
Kingston to O'Hare Intl flights
Santo Domingo to Midway flights
Montego Bay to O'Hare Intl flights
Nassau to Midway flights
Port of Spain to O'Hare Intl flights
George Town to O'Hare Intl flights
Santiago de los Caballeros to O'Hare Intl flights
Montego Bay to Midway flights
Port of Spain to St. Louis flights
Aguadilla to O'Hare Intl flights
Nassau to St. Louis flights
Saint Thomas Island to St. Louis flights
Oranjestad to St. Louis flights
Road Town to O'Hare Intl flights
Simpson Bay to Midway flights
Port Au Prince to O'Hare Intl flights
Roseau to O'Hare Intl flights
Culebra to O'Hare Intl flights
Bridgetown to O'Hare Intl flights
St. John's to O'Hare Intl flights
Vieques to O'Hare Intl flights
St. George's to St. Louis flights
Port Au Prince to Midway flights
Aguadilla to Midway flights

Top 5 airlines flying from Dominican Republic to Chicago

Discover the top 5 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 12월 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$189Average$371FlexibilityNo cancel feeOn-time65%
FrontierCheapest$216Average$439FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$315Average$423FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$354Average$516FlexibilityNo cancel feeOn-time71%
DeltaCheapest$449Average$714FlexibilityNo cancel feeOn-timeN/A

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