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Dominican Republic

$102+ 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 8/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PUJ
jul. 23 — jul. 301
mié. 7/23
mié. 7/30
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 julio 18, 2025.

Round-trip from

$262
(JetBlue Airways)

One-way from

$124
(JetBlue Airways)

Popular in

March

Cheapest in

July

Average price

$482

Good round-trip deal

$260 or less

Good one-way deal

$146 or less
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. 2% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in July 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 julio 18, 2025.

This JetBlue Airways deal was found by Cheapflights users on 7/17. 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 JetBlue Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/161:35 pmORD - SDQ
1 stop10h 20mJetBlue
lun. 10/205:35 amSDQ - ORD
1 stop16h 15mJetBlue
Deal found 7/17$262
This FlightHub deal was found by Cheapflights users on 7/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/125:05 amORD - SDQ
1 stop9h 42mSpirit Airlines
mar. 8/195:05 pmSDQ - ORD
1 stop7h 54mSpirit Airlines
Deal found 7/17$266
This Cheapflightsfares deal was found by Cheapflights users on 7/17. 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.
mar. 8/198:12 pmORD - STI
1 stop12h 03mSpirit Airlines
mar. 8/2610:20 amSTI - ORD
1 stop9h 47mSpirit Airlines
Deal found 7/17$303
This Cheapflightsfares deal was found by Cheapflights users on 7/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/235:05 amORD - PUJ
1 stop8h 55mSpirit Airlines
mié. 8/274:05 pmPUJ - ORD
1 stop8h 54mSpirit Airlines
Deal found 7/15$316
This Kiwi.com deal was found by Cheapflights users on 7/15. 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.
dom. 11/97:39 pmORD - PUJ
1 stop16h 06mMultiple Airlines
sáb. 11/155:47 amPUJ - ORD
Nonstop5h 10mMultiple Airlines
Deal found 7/15$318
This Kiwi.com deal was found by Cheapflights users on 7/15. 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.
mar. 8/56:45 amORD - PUJ
Nonstop4h 40mFrontier
mié. 8/135:08 pmPUJ - ORD
Nonstop5h 08mFrontier
Deal found 7/15$327
This American Airlines deal was found by Cheapflights users on 7/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/118:35 amORD - PUJ
Nonstop4h 40mAmerican Airlines
mié. 8/203:30 pmPUJ - ORD
Nonstop5h 00mAmerican Airlines
Deal found 7/17$328
This Southwest deal was found by Cheapflights users on 7/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/115:05 amMDW - PUJ
1 stop7h 50mSouthwest
mié. 8/202:50 pmPUJ - MDW
1 stop7h 50mSouthwest
Deal found 7/15$343
This Delta deal was found by Cheapflights users on 7/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/116:04 amMDW - PUJ
1 stop7h 30mDelta
jue. 8/211:05 pmPUJ - MDW
1 stop9h 39mDelta
Deal found 7/16$353
This United Airlines deal was found by Cheapflights users on 7/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/97:52 amORD - PUJ
Nonstop4h 30mUnited Airlines
jue. 11/132:55 pmPUJ - ORD
Nonstop5h 13mUnited Airlines
Deal found 7/15$356
This Orbitz deal was found by Cheapflights users on 7/16. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 7/305:40 pmORD - SDQ
1 stop15h 10mMultiple Airlines
mar. 8/51:48 amSDQ - ORD
1 stop9h 37mMultiple Airlines
Deal found 7/16$364
This Frontier deal was found by Cheapflights users on 7/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/99:12 pmMDW - PUJ
1 stop10h 42mFrontier
sáb. 8/1610:06 amPUJ - MDW
1 stop11h 16mFrontier
Deal found 7/17$376

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 julio 18, 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

ChicagoSanto Domingo

ORD - SDQ

ORDSDQ

Chicago O'Hare Intl

mar. 8/12

5:05 am-3:47 pm

1 stop9h 42m

Santo Domingo Las Americas

mar. 8/19

5:05 pm-11:59 pm

1 stop7h 54m

$266

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

mar. 8/19

8:12 pm-9:15 am

1 stop12h 03m

Santiago de los Caballeros

mar. 8/26

10:20 am-7:07 pm

1 stop9h 47m

$303

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

mar. 9/16

5:05 am-2:14 pm

1 stop8h 09m

Punta Cana

sáb. 9/20

3:19 pm-10:48 pm

1 stop8h 29m

$323

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

lun. 8/11

8:35 am-2:15 pm

Nonstop4h 40m

Punta Cana

mié. 8/20

3:30 pm-7:30 pm

Nonstop5h 00m

$328

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

mar. 8/12

6:45 am-12:25 pm

Nonstop4h 40m

Punta Cana

mar. 8/19

12:40 pm-10:22 pm

1 stop10h 42m

$330

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

mar. 8/5

6:45 am-12:25 pm

Nonstop4h 40m

Punta Cana

lun. 8/11

5:08 pm-9:16 pm

Nonstop5h 08m

$340

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

lun. 8/11

5:05 am-1:55 pm

1 stop7h 50m

Punta Cana

mié. 8/20

2:50 pm-9:40 pm

1 stop7h 50m

$343

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

lun. 8/11

6:04 am-2:34 pm

1 stop7h 30m

Punta Cana

jue. 8/21

2:40 pm-9:44 pm

1 stop8h 04m

$353

ChicagoSanto Domingo

ORD - SDQ

ORDSDQ

Chicago O'Hare Intl

mié. 7/30

5:40 pm-9:50 am

1 stop15h 10m

Santo Domingo Las Americas

mar. 8/5

1:48 am-10:25 am

1 stop9h 37m

$364

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

dom. 11/9

6:00 am-2:23 pm

1 stop6h 23m

Punta Cana

jue. 11/13

3:50 pm-11:53 pm

1 stop10h 03m

$371

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/17

Showing 1-10 of 52 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, January is the cheapest month in which you can book a flight from Chicago to Dominican Republic (average of $443). Flying from Chicago to Dominican Republic in March is currently the most expensive (average of $594). 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 julio 18, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 35% on flights from Chicago to Dominican Republic by exploring options for tickets at noon.

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 Wednesday evenings when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Dominican Republic

Explore weekly flight availability from Chicago to Dominican Republic. 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 julio 18, 2025.

The most flights from CHI to DO0 are scheduled on a Monday (4 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 on average).

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 julio 18, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and KLM 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
4,238 reviews

Crew

8.6

Entertainment

7.6

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Entertainment

7.6

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,958 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Entertainment

7.6

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
KLM
7.8
Good
1,374 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Entertainment

7.6

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Copa Airlines
7.5
Good
1,483 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Entertainment

7.6

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Aeromexico
7.5
Good
1,715 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Entertainment

7.6

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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.

  • 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 JetBlue ($124), Spirit Airlines ($125), and Frontier ($138).

  • 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: United Airlines (85%), American Airlines (77%), Frontier( 69%).

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

    The cheapest flight price from Chicago to Dominican Republic is $149. On average you can expect to pay $374. The most popular route, (Chicago O'Hare Intl - Punta Cana), can usually be booked for $281.

  • 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, January is the cheapest month in which you can book a flight from Chicago to Dominican Republic (average of $443). Flying from Chicago to Dominican Republic in March is currently the most expensive (average of $594). 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
O'Hare Intl to Montego Bay flights
Midway to Luis Munoz Marin Intl flights
O'Hare Intl to Oranjestad flights
O'Hare Intl to Saint Thomas Island flights
Midway to Punta Cana flights
Midway to Montego Bay flights
O'Hare Intl to Nassau flights
O'Hare Intl to Providenciales flights
O'Hare Intl to Willemstad flights
St. Louis to Luis Munoz Marin Intl flights
O'Hare Intl to Santo Domingo flights
St. Louis to Punta Cana flights
O'Hare Intl to George Town flights
O'Hare Intl to Castries flights
O'Hare Intl to Simpson Bay flights
Midway to Saint Thomas Island flights
Midway to Oranjestad flights
O'Hare Intl to Bridgetown flights
O'Hare Intl to Puerto Plata flights
St. Louis to Nassau flights
Midway to Nassau flights
St. Louis to Saint Thomas Island flights
O'Hare Intl to Kingston flights
St. Louis to Montego Bay flights
Midway to Providenciales flights
Midway to Santo Domingo flights
O'Hare Intl to Christiansted flights
O'Hare Intl to Santiago de los Caballeros flights
Midway to George Town flights
St. Louis to Oranjestad flights
St. Louis to Willemstad flights
St. Louis to Simpson Bay flights
O'Hare Intl to St. George's flights
O'Hare Intl to St. John's flights
Midway to Simpson Bay flights
Moline to Punta Cana flights
O'Hare Intl to Port of Spain flights
Moline to Luis Munoz Marin Intl flights
O'Hare Intl to Georgetown flights
Midway to Castries flights
O'Hare Intl to Road Town flights
O'Hare Intl to Freeport flights
Peoria to Luis Munoz Marin Intl flights
O'Hare Intl to Havana flights
O'Hare Intl to Basseterre flights
St. Louis to Santo Domingo flights
O'Hare Intl to Kralendijk flights
O'Hare Intl to Aguadilla flights

Top 10 airlines flying from Chicago to Dominican Republic

Discover the top 10 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 julio 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$193Average$536FlexibilityNo cancel feeOn-time70%
FrontierCheapest$223Average$435FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$226Average$636FlexibilityNo cancel feeOn-time69%
ArajetCheapest$234Average$313FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$270Average$383FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$274Average$631FlexibilityNo cancel feeOn-time71%
DeltaCheapest$334Average$581FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$335Average$861FlexibilityNo cancel feeOn-time67%
JetBlueCheapest$343Average$498FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$495Average$741FlexibilityNo cancel feeOn-time63%

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