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Dominican Republic

$86+ 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 12/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PUJ
nov. 29 — dic. 61
sáb. 11/29
sáb. 12/6
1 adult, Economy
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Cheap 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 octubre 30, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$289
(Cheapflightsfares)

One-way from

$86
(Priceline)

Popular in

December

Cheapest in

August

Average price

$508

Good round-trip deal

$383 or less

Good one-way deal

$191 or less
Provider with most accurate pricing for Chicago (CHI)-Punta Cana flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Punta Cana flights.
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From Chicago (CHI) to Dominican Republic
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One-way flight from Chicago (CHI) to Dominican Republic
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Highest demand for flights based on searches. 6% potential increase in price ($38 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Dominican Republic.
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Price to beat on a one-way flight from Chicago (CHI) to Dominican Republic.
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Find 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 octubre 30, 2025.

This CheapOair deal was found by Cheapflights users on 10/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/35:45 amORD - PUJ
Nonstop4h 45mArajet
dom. 12/76:00 pmPUJ - ORD
Nonstop5h 10mArajet
Deal found 10/28$301
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
sáb. 12/610:27 amORD - PUJ
Nonstop4h 45mMultiple Airlines
jue. 12/116:08 pmPUJ - ORD
1 stop8h 01mMultiple Airlines
Deal found 10/28$302
This United Airlines deal was found by Cheapflights users on 10/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/58:45 amORD - PUJ
1 stop6h 40mUnited Airlines
mié. 12/1012:56 pmPUJ - ORD
1 stop12h 47mUnited Airlines
Deal found 10/28$303
This CheapOair deal was found by Cheapflights users on 10/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/275:00 amORD - SDQ
1 stop8h 30mSpirit Airlines
jue. 12/44:21 pmSDQ - ORD
1 stop9h 48mSpirit Airlines
Deal found 10/28$303
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
sáb. 11/2910:27 amORD - PUJ
Nonstop4h 45mMultiple Airlines
sáb. 12/66:08 pmPUJ - ORD
1 stop8h 01mMultiple Airlines
Deal found 10/28$304
This Cheapflightsfares deal was found by Cheapflights users on 10/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/165:10 amORD - PUJ
1 stop8h 10mSpirit Airlines
jue. 11/203:11 pmPUJ - ORD
1 stop9h 55mSpirit Airlines
Deal found 10/30$305
This United Airlines deal was found by Cheapflights users on 10/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/289:30 amORD - PUJ
Nonstop4h 32mUnited Airlines
vie. 12/52:55 pmPUJ - ORD
Nonstop5h 13mUnited Airlines
Deal found 10/27$306
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
mié. 12/246:12 amMDW - PUJ
2 stops32h 38mMultiple Airlines
mié. 12/314:19 pmPUJ - MDW
1 stop7h 53mMultiple Airlines
Deal found 10/28$306
This Expedia deal was found by Cheapflights users on 10/30. 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.
lun. 11/175:10 amORD - PUJ
1 stop8h 10mSpirit Airlines
vie. 11/215:45 pmPUJ - ORD
1 stop17h 32mSpirit Airlines
Deal found 10/30$307
This United Airlines deal was found by Cheapflights users on 10/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/118:45 amORD - PUJ
1 stop6h 40mUnited Airlines
lun. 12/152:55 pmPUJ - ORD
Nonstop5h 13mUnited Airlines
Deal found 10/28$308
This Priceline deal was found by Cheapflights users on 10/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/246:45 amORD - PUJ
Nonstop4h 34mMultiple Airlines
jue. 11/273:11 pmPUJ - ORD
1 stop9h 55mMultiple Airlines
Deal found 10/29$309
This United Airlines deal was found by Cheapflights users on 10/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/158:45 amORD - PUJ
1 stop6h 40mUnited Airlines
vie. 12/194:25 pmPUJ - ORD
Nonstop5h 13mUnited Airlines
Deal found 10/29$311

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 octubre 30, 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

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

sáb. 12/6

8:45 am-5:25 pm

1 stop6h 40m

Punta Cana

sáb. 12/13

2:55 pm-6:08 pm

Nonstop5h 13m

$318

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

dom. 12/14

8:50 am-5:25 pm

1 stop6h 35m

Punta Cana

mié. 12/17

5:20 pm-11:43 pm

1 stop8h 23m

$321

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

lun. 12/15

6:00 am-5:25 pm

1 stop9h 25m

Punta Cana

lun. 12/22

3:28 pm-12:14 am

1 stop10h 46m

$321

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

mié. 12/10

6:00 am-5:25 pm

1 stop9h 25m

Punta Cana

mié. 12/17

5:20 pm-11:43 pm

1 stop8h 23m

$321

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

vie. 11/28

8:50 am-5:25 pm

1 stop6h 35m

Punta Cana

mié. 12/3

5:20 pm-11:43 pm

1 stop8h 23m

$321

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

sáb. 12/6

1:16 pm-1:32 pm

2 stops22h 16m

Punta Cana

sáb. 12/13

5:19 pm-10:43 pm

1 stop7h 24m

$330

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

mar. 2/17

8:50 am-5:25 pm

1 stop6h 35m

Punta Cana

jue. 2/26

2:55 pm-6:08 pm

Nonstop5h 13m

$332

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

vie. 12/5

6:30 pm-1:12 pm

1 stop16h 42m

Punta Cana

jue. 12/11

2:38 pm-9:56 pm

1 stop9h 18m

$338

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

vie. 12/5

7:02 pm-2:20 pm

1 stop17h 18m

Punta Cana

mié. 12/10

5:04 pm-11:47 pm

1 stop8h 43m

$338

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

mar. 12/9

6:00 am-2:25 pm

1 stop6h 25m

Punta Cana

mar. 12/16

5:04 pm-11:47 pm

1 stop8h 43m

$338

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

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, March is the cheapest month in which you can book a flight from Chicago to Dominican Republic (average of $194). Flying from Chicago to Dominican Republic in October is currently the most expensive (average of $292). 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 octubre 30, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 26% 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.

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 octubre 30, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United 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.
Southwest
8.0
Very good
4,243 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
7,998 reviews
Southwest
8.0
Very good
4,243 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,998 reviews
Southwest
8.0
Very good
4,243 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,035 reviews
Southwest
8.0
Very good
4,243 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,122 reviews
Southwest
8.0
Very good
4,243 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 20m. Fly via United Airlines, Delta, or Southwest to get the fastest option. Airlines will cover a distance of 1967 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 ($117), United Airlines ($127), and Delta ($157).

  • 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 (84%), United Airlines (64%), Frontier( 33%).

  • 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 $806. The most popular route, (Chicago O'Hare Intl - Punta Cana), can usually be booked for $219.

  • 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, March is the cheapest month in which you can book a flight from Chicago to Dominican Republic (average of $194). Flying from Chicago to Dominican Republic in October is currently the most expensive (average of $292). 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 Punta Cana flights
Midway to Luis Munoz Marin Intl flights
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O'Hare Intl to Oranjestad flights
O'Hare Intl to Saint Thomas Island flights
O'Hare Intl to Nassau flights
O'Hare Intl to Providenciales flights
St. Louis to Luis Munoz Marin Intl flights
O'Hare Intl to George Town flights
O'Hare Intl to Simpson Bay flights
Midway to Montego Bay flights
Midway to Oranjestad flights
O'Hare Intl to St. George's flights
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Midway to Nassau flights
Midway to Saint Thomas Island flights
O'Hare Intl to Castries flights
St. Louis to Punta Cana flights
O'Hare Intl to Bridgetown flights
O'Hare Intl to Santo Domingo flights
St. Louis to Saint Thomas Island flights
St. Louis to Montego Bay flights
Midway to Providenciales flights
Midway to Simpson Bay flights
O'Hare Intl to St. John's flights
Midway to George Town flights
O'Hare Intl to Christiansted flights
O'Hare Intl to Puerto Plata flights
St. Louis to Oranjestad flights
O'Hare Intl to Road Town flights
O'Hare Intl to Ponce flights
St. Louis to Simpson Bay flights
O'Hare Intl to Kingston flights
St. Louis to Nassau flights
St. Louis to Georgetown flights
St. Louis to Bridgetown flights
O'Hare Intl to Port of Spain flights
Moline to Luis Munoz Marin Intl flights
O'Hare Intl to Kralendijk flights
O'Hare Intl to The Valley flights
Peoria to Luis Munoz Marin Intl flights
St. Louis to Willemstad flights
Midway to Santo Domingo flights
O'Hare Intl to Aguadilla flights
St. Louis to Castries flights
Midway to Castries flights
St. Louis to Santo Domingo 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 octubre 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$188Average$431FlexibilityNo cancel feeOn-time70%
FrontierCheapest$223Average$436FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$226Average$623FlexibilityNo cancel feeOn-time69%
ArajetCheapest$233Average$331FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$274Average$581FlexibilityNo cancel feeOn-time71%
Spirit AirlinesCheapest$277Average$409FlexibilityNo cancel feeOn-time65%
DeltaCheapest$356Average$612FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$367Average$476FlexibilityNo cancel feeOn-time62%
Air CanadaCheapest$388Average$664FlexibilityNo cancel feeOn-time67%

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