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Dominican Republic

$93+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PUJ
oct. 11 — oct. 181
sáb. 10/11
sáb. 10/18
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 septiembre 11, 2025.

Round-trip from

$252
(Priceline)

One-way from

$93
(Expedia)

Popular in

March

Cheapest in

July

Average price

$550

Good round-trip deal

$377 or less

Good one-way deal

$126 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. 3% potential increase in price ($17 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in September 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 septiembre 11, 2025.

This Priceline deal was found by Cheapflights users on 9/10. 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.
sáb. 10/45:05 amORD - SDQ
1 stop8h 37mSpirit Airlines
sáb. 10/113:59 pmSDQ - ORD
1 stop8h 46mSpirit Airlines
Deal found 9/10$252
This Cheapflightsfares deal was found by Cheapflights users on 9/9. 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. 10/55:05 amORD - SDQ
1 stop8h 43mSpirit Airlines
sáb. 10/113:59 pmSDQ - ORD
1 stop8h 46mSpirit Airlines
Deal found 9/9$276
This Priceline deal was found by Cheapflights users on 9/9. 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.
jue. 10/25:05 amORD - SDQ
1 stop9h 55mSpirit Airlines
sáb. 10/113:59 pmSDQ - ORD
1 stop8h 46mSpirit Airlines
Deal found 9/9$279
This CheapOair deal was found by Cheapflights users on 9/9. 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. 9/245:05 amORD - SDQ
1 stop9h 55mSpirit Airlines
vie. 10/245:12 pmSDQ - ORD
1 stop7h 33mSpirit Airlines
Deal found 9/9$280
This Cheapflightsfares deal was found by Cheapflights users on 9/8. 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.
mié. 11/58:41 amORD - SDQ
1 stop7h 09mSpirit Airlines
sáb. 11/86:55 pmSDQ - ORD
1 stop16h 28mSpirit Airlines
Deal found 9/8$282
This Cheapflightsfares deal was found by Cheapflights users on 9/9. 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. 10/185:05 amORD - SDQ
1 stop8h 49mSpirit Airlines
sáb. 10/253:59 pmSDQ - ORD
1 stop8h 46mSpirit Airlines
Deal found 9/9$283
This Cheapflightsfares deal was found by Cheapflights users on 9/9. 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. 11/118:41 amORD - SDQ
1 stop7h 09mSpirit Airlines
mar. 11/186:55 pmSDQ - ORD
1 stop16h 28mSpirit Airlines
Deal found 9/9$285
This Cheapflightsfares deal was found by Cheapflights users on 9/9. 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.
mié. 11/55:05 amORD - SDQ
1 stop10h 45mSpirit Airlines
mié. 11/126:55 pmSDQ - ORD
1 stop16h 28mSpirit Airlines
Deal found 9/9$295
This Mytrip deal was found by Cheapflights users on 9/10. 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.
lun. 11/105:59 pmORD - PUJ
2 stops16h 55mMultiple Airlines
mar. 11/257:30 pmPUJ - ORD
Nonstop5h 10mMultiple Airlines
Deal found 9/10$312
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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.
lun. 10/272:14 pmORD - PUJ
2 stops20h 28mSpirit Airlines
dom. 11/24:57 pmPUJ - ORD
1 stop10h 06mSpirit Airlines
Deal found 9/10$313
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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.
vie. 10/35:17 pmORD - PUJ
1 stop17h 24mSpirit Airlines
vie. 10/103:57 pmPUJ - ORD
1 stop8h 48mSpirit Airlines
Deal found 9/10$314
This Kiwi.com deal was found by Cheapflights users on 9/10. 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. 9/305:05 amORD - PUJ
1 stop8h 09mMultiple Airlines
dom. 10/511:56 amPUJ - ORD
1 stop26h 45mMultiple Airlines
Deal found 9/10$315

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 septiembre 11, 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

sáb. 10/18

5:05 am-2:54 pm

1 stop8h 49m

Santo Domingo Las Americas

sáb. 10/25

3:59 pm-11:45 pm

1 stop8h 46m

$283

ChicagoSanto Domingo

ORD - SDQ

ORDSDQ

Chicago O'Hare Intl

mié. 11/5

8:41 am-5:50 pm

1 stop7h 09m

Santo Domingo Las Americas

sáb. 11/8

6:55 pm-9:23 am

1 stop16h 28m

$290

ChicagoSanto Domingo

ORD - SDQ

ORDSDQ

Chicago O'Hare Intl

sáb. 10/4

6:44 pm-2:48 pm

1 stop19h 04m

Santo Domingo Las Americas

vie. 10/10

5:12 pm-6:38 pm

1 stop26h 26m

$300

ChicagoSanto Domingo

ORD - SDQ

ORDSDQ

Chicago O'Hare Intl

sáb. 10/4

6:30 am-7:03 pm

2 stops11h 33m

Santo Domingo Las Americas

sáb. 10/11

3:59 pm-11:45 pm

1 stop8h 46m

$302

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

jue. 10/16

4:59 pm-10:38 am

1 stop16h 39m

Santiago de los Caballeros

lun. 10/20

11:43 am-6:38 pm

1 stop7h 55m

$319

ChicagoSanto Domingo

ORD - SDQ

ORDSDQ

Chicago O'Hare Intl

mié. 9/24

5:05 am-4:00 pm

1 stop9h 55m

Santo Domingo Las Americas

sáb. 9/27

3:47 pm-10:48 pm

1 stop8h 01m

$325

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

lun. 11/17

5:59 pm-12:16 pm

1 stop16h 17m

Punta Cana

mié. 11/26

6:49 pm-10:01 pm

Nonstop5h 12m

$327

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

dom. 11/2

7:43 pm-11:38 am

1 stop13h 55m

Santiago de los Caballeros

mié. 11/5

6:18 pm-9:23 am

1 stop17h 05m

$331

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

dom. 10/26

7:52 am-1:22 pm

Nonstop4h 30m

Punta Cana

vie. 10/31

1:55 pm-6:08 pm

Nonstop5h 13m

$340

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

lun. 10/27

9:30 am-3:02 pm

Nonstop4h 32m

Punta Cana

jue. 10/30

1:55 pm-6:08 pm

Nonstop5h 13m

$340

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

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, 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 June is currently the most expensive (average of $591). 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 septiembre 11, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 34% 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.

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 septiembre 11, 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
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

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
8.0
Very good
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

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
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

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
10,000 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

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
3,177 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

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 30m. 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 ($98), Frontier ($126), and Spirit Airlines ($131).

  • 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 (82%), American Airlines (77%), Frontier( 55%).

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

    The cheapest flight price from Chicago to Dominican Republic is $96. On average you can expect to pay $695. The most popular route, (Chicago O'Hare Intl - Punta Cana), can usually be booked for $203.

  • 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 June is currently the most expensive (average of $591). 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

Browse thousands of different options on Cheapflights for your next trip

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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
O'Hare Intl to Montego Bay flights
O'Hare Intl to Oranjestad flights
O'Hare Intl to Saint Thomas Island flights
Midway to Punta Cana flights
O'Hare Intl to Nassau flights
O'Hare Intl to George Town flights
O'Hare Intl to Providenciales flights
Midway to Montego Bay flights
O'Hare Intl to Simpson Bay flights
St. Louis to Luis Munoz Marin Intl flights
O'Hare Intl to Willemstad flights
Midway to Oranjestad flights
Midway to Saint Thomas Island flights
St. Louis to Saint Thomas Island flights
O'Hare Intl to Santo Domingo flights
St. Louis to Punta Cana flights
O'Hare Intl to Castries flights
St. Louis to Montego Bay flights
Midway to Nassau flights
O'Hare Intl to Christiansted flights
St. Louis to Oranjestad flights
Midway to Providenciales flights
O'Hare Intl to Bridgetown flights
Midway to Simpson Bay flights
O'Hare Intl to Puerto Plata flights
Midway to Santo Domingo flights
O'Hare Intl to St. John's flights
Midway to George Town flights
St. Louis to Georgetown flights
St. Louis to Simpson Bay flights
O'Hare Intl to Road Town flights
St. Louis to Nassau flights
O'Hare Intl to Kingston flights
St. Louis to Willemstad flights
Moline to Luis Munoz Marin Intl flights
O'Hare Intl to Aguadilla flights
O'Hare Intl to Freeport flights
St. Louis to George Town flights
O'Hare Intl to Port of Spain flights
O'Hare Intl to Kralendijk flights
O'Hare Intl to Castries flights
Midway to Castries flights
O'Hare Intl to Basseterre flights
Peoria to Luis Munoz Marin Intl flights
O'Hare Intl to Georgetown flights
O'Hare Intl to Kingstown flights
O'Hare Intl to Santiago de los Caballeros 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 septiembre 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$193Average$458FlexibilityNo cancel feeOn-time70%
FrontierCheapest$224Average$434FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$226Average$670FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$231Average$353FlexibilityNo cancel feeOn-time65%
ArajetCheapest$235Average$320FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$274Average$587FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$335Average$861FlexibilityNo cancel feeOn-time67%
DeltaCheapest$345Average$600FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$391Average$498FlexibilityNo cancel feeOn-time62%

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