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Dominican Republic

$114+ Cheap flights from Chicago (CHI) to the Dominican Republic

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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PUJ
Jan 16 — Jan 231
Fri 1/16
Fri 1/23
1 adult, Economy
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Cheap flight deals from Chicago to Dominican Republic

Cheapest flights from Chicago to Dominican Republic
Explore the most affordable flight options available from Chicago to Dominican Republic. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 17, 2025.

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.
Tue 12/237:10 amORD - PUJ
Nonstop4h 37mFrontier
Tue 12/306:49 pmPUJ - ORD
Nonstop5h 10mFrontier
Deal found 12/16$290
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.
Tue 12/237:10 amORD - PUJ
Nonstop4h 37mFrontier
Thu 12/256:49 pmPUJ - ORD
Nonstop5h 10mFrontier
Deal found 12/16$297
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.
Wed 12/315:45 amORD - PUJ
Nonstop4h 45mMultiple Airlines
Wed 1/76:08 pmPUJ - ORD
1 stop19h 14mMultiple Airlines
Deal found 12/16$302
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.
Mon 12/227:10 amORD - PUJ
Nonstop4h 37mMultiple Airlines
Sat 12/277:17 amPUJ - ORD
Nonstop5h 10mMultiple Airlines
Deal found 12/15$303
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.
Mon 12/227:10 amORD - PUJ
Nonstop4h 37mFrontier
Wed 12/311:28 pmPUJ - ORD
1 stop8h 38mFrontier
Deal found 12/16$309
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.
Tue 12/237:10 amORD - PUJ
Nonstop4h 37mFrontier
Wed 12/316:49 pmPUJ - ORD
Nonstop5h 10mFrontier
Deal found 12/16$310
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.
Tue 12/237:10 amORD - PUJ
Nonstop4h 37mMultiple Airlines
Sun 12/286:00 pmPUJ - ORD
Nonstop5h 10mMultiple Airlines
Deal found 12/16$311
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/217:10 amORD - PUJ
Nonstop4h 37mMultiple Airlines
Sun 12/286:00 pmPUJ - ORD
Nonstop5h 10mMultiple Airlines
Deal found 12/15$317
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2312:50 pmORD - PUJ
1 stop26h 30mMultiple Airlines
Tue 12/306:49 pmPUJ - ORD
Nonstop5h 10mMultiple Airlines
Deal found 12/16$318
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.
Tue 12/167:10 amORD - PUJ
Nonstop4h 37mMultiple Airlines
Tue 12/237:30 pmPUJ - ORD
Nonstop5h 10mMultiple Airlines
Deal found 12/15$319
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/176:00 amMDW - PUJ
1 stop7h 39mDelta
Wed 12/243:38 pmPUJ - MDW
1 stop8h 44mDelta
Deal found 12/15$366
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/186:00 amMDW - PUJ
1 stop6h 25mDelta
Thu 12/252:06 pmPUJ - MDW
1 stop10h 16mDelta
Deal found 12/15$396

Find flight deals from Chicago to Dominican Republic

Keep the following information in mind while searching for Chicago to Dominican Republic flight deals. Data was last updated December 17, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$248
(Booking.com)

One-way from

$114
(Expedia)

Popular in

March

Cheapest in

August

Average price

$612

Good round-trip deal

$379 or less

Good one-way deal

$187 or less
Provider with most accurate pricing for Chicago (CHI)-Punta Cana flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Punta Cana flights.
Search Deals
From Chicago (CHI) to Dominican Republic
Search Deals
One-way flight from Chicago (CHI) to Dominican Republic
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($19 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 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 Chicago (CHI) to Dominican Republic.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Dominican Republic.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Dominican Republic 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 December 17, 2025.
Use the filters below to find and compare flights from Chicago to the Dominican Republic that are best for you.

Fly from

Chicago

Fly to

Dominican Republic

Route

Depart

Return

Price

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Wed 2/11

5:15 am-3:33 pm

1 stop8h 18m

Santiago de los Caballeros

Wed 2/25

4:40 pm-11:47 pm

1 stop9h 07m

$261

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Wed 2/4

7:20 am-3:33 pm

1 stop6h 13m

Santiago de los Caballeros

Sat 2/7

4:40 pm-11:46 pm

1 stop9h 06m

$262

ChicagoSanto Domingo

ORD - SDQ

ORDSDQ

Chicago O'Hare Intl

Tue 2/17

9:18 am-4:29 pm

1 stop29h 11m

Santo Domingo Las Americas

Mon 2/23

3:32 pm-9:13 pm

1 stop7h 41m

$287

ChicagoSanto Domingo

ORD - SDQ

ORDSDQ

Chicago O'Hare Intl

Sat 1/17

3:49 pm-9:54 am

1 stop16h 05m

Santo Domingo Las Americas

Tue 1/20

12:52 pm-8:18 am

1 stop21h 26m

$287

ChicagoSanto Domingo

ORD - SDQ

ORDSDQ

Chicago O'Hare Intl

Tue 1/6

3:26 pm-2:54 am

1 stop9h 28m

Santo Domingo Las Americas

Sat 1/17

3:32 pm-11:46 pm

1 stop10h 14m

$290

ChicagoSanto Domingo

ORD - SDQ

ORDSDQ

Chicago O'Hare Intl

Sat 1/31

6:57 pm-7:18 pm

2 stops22h 21m

Santo Domingo Las Americas

Sat 2/7

3:32 pm-9:03 pm

1 stop7h 31m

$325

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Thu 1/29

5:15 am-3:33 pm

1 stop8h 18m

Santiago de los Caballeros

Mon 2/2

11:47 am-10:46 pm

2 stops12h 59m

$330

ChicagoSanto Domingo

ORD - SDQ

ORDSDQ

Chicago O'Hare Intl

Mon 1/12

5:15 am-2:27 pm

1 stop7h 12m

Santo Domingo Las Americas

Fri 1/23

3:32 pm-11:46 pm

1 stop10h 14m

$334

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Fri 1/30

4:38 pm-3:33 pm

2 stops20h 55m

Santiago de los Caballeros

Mon 2/2

4:40 pm-11:22 am

1 stop20h 42m

$342

ChicagoSanto Domingo

ORD - SDQ

ORDSDQ

Chicago O'Hare Intl

Fri 1/9

5:15 am-2:27 pm

1 stop7h 12m

Santo Domingo Las Americas

Sat 1/17

3:32 pm-9:03 pm

1 stop7h 31m

$343

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 60 results
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Best time to book a flight from Chicago to Dominican Republic

Have a flexible travel schedule? Discover the best time to fly to Dominican Republic from Chicago 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 Chicago to the Dominican Republic

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

Currently, November is the cheapest month in which you can book a flight from Chicago to Dominican Republic (average of $206). Flying from Chicago to Dominican Republic in October is currently the most expensive (average of $289). 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 CHI to DO?

Find hourly flight availability from Chicago to Dominican Republic. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 17, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 25% on flights from Chicago to Dominican Republic by exploring options for tickets in the afternoon.

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

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

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

How often are flights from Chicago to the Dominican Republic delayed?

About 15% of weekly flights between Chicago and Dominican Republic have experienced delays in the past year, with the average delay time being 133 minutes.

What is the most punctual flight time for Chicago to the Dominican Republic flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Thursday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to the Dominican Republic flights?

Over the last year, TUI fly have had the lowest number of delays on this route, with just 11% of flights being delayed.

Reviews of airlines servicing Dominican Republic

Get insights into the airlines that provide service to Dominican Republic. 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 Dominican Republic. Reviews last updated December 17, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines, and American Airlines from Chicago to the Dominican Republic 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
8,005 reviews

Food

7.3

Boarding

8.1

Entertainment

7.9

Crew

8.5

Overall

7.9

Comfort

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
8,005 reviews
Delta
7.9
Good
8,005 reviews

Food

7.3

Boarding

8.1

Entertainment

7.9

Crew

8.5

Overall

7.9

Comfort

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.
United Airlines
7.4
Good
9,091 reviews
Delta
7.9
Good
8,005 reviews

Food

7.3

Boarding

8.1

Entertainment

7.9

Crew

8.5

Overall

7.9

Comfort

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
11,054 reviews
Delta
7.9
Good
8,005 reviews

Food

7.3

Boarding

8.1

Entertainment

7.9

Crew

8.5

Overall

7.9

Comfort

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
3,081 reviews
Delta
7.9
Good
8,005 reviews

Food

7.3

Boarding

8.1

Entertainment

7.9

Crew

8.5

Overall

7.9

Comfort

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 Chicago to Dominican Republic. 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 Chicago to Dominican Republic?

    There are many flights that can get you from Chicago to Dominican Republic in 4h 32m. Fly via Spirit Airlines, United Airlines, or Copa Airlines to get the fastest option. Airlines will cover a distance of 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 Chicago to Dominican Republic one-way?

    The cheapest airlines for a one-way flight from Chicago to Dominican Republic are Arajet ($96), Frontier ($101), and Southwest ($126).

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

    While some choose either Chicago Midway - Punta Cana or Chicago O'Hare Intl - Santo Domingo Las Americas, Chicago O'Hare Intl - Punta Cana is the most popular route from Chicago to Dominican Republic.

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

    Before booking your flight to Dominican Republic from Chicago, check out the most reliable airlines to get you to your destination on time: American Airlines (83%), United Airlines (78%), Arajet( 78%).

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

    The cheapest flight price from Chicago to Dominican Republic is $113. On average you can expect to pay $756. The most popular route, (Chicago O'Hare Intl - Punta Cana), can usually be booked for $175.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Dominican Republic 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 Chicago to Dominican Republic?

    Currently, November is the cheapest month in which you can book a flight from Chicago to Dominican Republic (average of $206). Flying from Chicago to Dominican Republic in October is currently the most expensive (average of $289). 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

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Alternative routes for Chicago to Dominican Republic

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Luis Munoz Marin Intl flights
O'Hare Intl to Punta Cana flights
Midway to Luis Munoz Marin Intl flights
Midway to Punta Cana flights
O'Hare Intl to Oranjestad flights
O'Hare Intl to Saint Thomas Island flights
O'Hare Intl to Nassau flights
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O'Hare Intl to Providenciales flights
O'Hare Intl to George Town flights
St. Louis to Luis Munoz Marin Intl flights
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St. Louis to Punta Cana flights
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Midway to Montego Bay flights
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O'Hare Intl to Castries flights
O'Hare Intl to Santo Domingo flights
Midway to Nassau flights
Midway to Saint Thomas Island flights
O'Hare Intl to Bridgetown flights
O'Hare Intl to Christiansted flights
Midway to Providenciales flights
St. Louis to Oranjestad flights
O'Hare Intl to Ponce flights
O'Hare Intl to Kingston flights
Midway to Simpson Bay flights
St. Louis to Simpson Bay flights
Midway to Santo Domingo flights
O'Hare Intl to St. John's flights
St. Louis to Montego Bay flights
Midway to George Town flights
O'Hare Intl to Road Town flights
St. Louis to Castries flights
O'Hare Intl to Puerto Plata flights
O'Hare Intl to Port of Spain flights
O'Hare Intl to Santiago de los Caballeros flights
St. Louis to Nassau flights
Peoria to Luis Munoz Marin Intl flights
O'Hare Intl to Aguadilla flights
O'Hare Intl to Basseterre flights
St. Louis to Willemstad flights
St. Louis to Georgetown flights
Moline to Luis Munoz Marin Intl flights
O'Hare Intl to Freeport flights
St. Louis to Christiansted flights
O'Hare Intl to Kralendijk flights
Midway to Castries flights
O'Hare Intl to St. George's flights

Top 9 airlines flying from Chicago to Dominican Republic

Discover the top 9 airlines that operate flights from Chicago to Dominican Republic. 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 December 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$188Average$431FlexibilityNo cancel feeOn-time70%
Spirit AirlinesCheapest$208Average$377FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$215Average$605FlexibilityNo cancel feeOn-time69%
FrontierCheapest$224Average$435FlexibilityNo cancel feeOn-time62%
ArajetCheapest$236Average$335FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$255Average$474FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$274Average$573FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$277Average$693FlexibilityNo cancel feeOn-time63%
Air CanadaCheapest$335Average$624FlexibilityNo cancel feeOn-time67%

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