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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 3/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PUJ
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

This Orbitz deal was found by Cheapflights users on 1/28. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/35:15 am
ORD
-
SDQ
1 stop7h 05m
Spirit Airlines
Sat 3/73:32 pm
SDQ
-
ORD
1 stop7h 41m
Spirit Airlines
Deal found 1/28$242
This FlightHub deal was found by Cheapflights users on 1/26. 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.
Sat 2/288:16 pm
ORD
-
SDQ
1 stop16h 04m
Spirit Airlines
Sat 3/73:32 pm
SDQ
-
ORD
1 stop7h 41m
Spirit Airlines
Deal found 1/26$258
This FlightHub deal was found by Cheapflights users on 1/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/45:15 am
ORD
-
STI
1 stop8h 18m
Spirit Airlines
Sat 2/74:40 pm
STI
-
ORD
1 stop9h 07m
Spirit Airlines
Deal found 1/28$263
This CheapOair deal was found by Cheapflights users on 1/28. 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.
Wed 2/185:15 am
ORD
-
SDQ
1 stop7h 05m
Spirit Airlines
Wed 2/253:32 pm
SDQ
-
ORD
1 stop7h 41m
Spirit Airlines
Deal found 1/28$265
This Orbitz deal was found by Cheapflights users on 1/28. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/45:15 am
ORD
-
SDQ
1 stop7h 05m
Spirit Airlines
Mon 3/92:32 pm
SDQ
-
ORD
1 stop10h 15m
Spirit Airlines
Deal found 1/28$266
This Expedia deal was found by Cheapflights users on 1/27. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/288:16 pm
ORD
-
SDQ
1 stop16h 04m
Spirit Airlines
Wed 3/43:32 pm
SDQ
-
ORD
1 stop7h 41m
Spirit Airlines
Deal found 1/27$268
This Expedia deal was found by Cheapflights users on 1/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/255:15 am
ORD
-
SDQ
1 stop7h 05m
Spirit Airlines
Wed 3/43:32 pm
SDQ
-
ORD
1 stop10h 15m
Spirit Airlines
Deal found 1/28$269
This Expedia deal was found by Cheapflights users on 1/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/45:45 am
ORD
-
PUJ
Nonstop4h 45m
Multiple Airlines
Wed 2/115:47 pm
PUJ
-
ORD
1 stop8h 00m
Multiple Airlines
Deal found 1/28$280
This Travelocity deal was found by Cheapflights users on 1/28. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/77:00 am
ORD
-
PUJ
1 stop7h 36m
Multiple Airlines
Sun 3/156:00 pm
PUJ
-
ORD
Nonstop5h 10m
Multiple Airlines
Deal found 1/28$281
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/97:00 am
ORD
-
PUJ
1 stop7h 36m
Multiple Airlines
Sun 3/155:39 pm
PUJ
-
ORD
Nonstop5h 25m
Multiple Airlines
Deal found 1/27$282
This Cheapflightsfares deal was found by Cheapflights users on 1/26. 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.
Tue 2/35:15 am
ORD
-
PUJ
1 stop9h 21m
Spirit Airlines
Tue 2/105:47 pm
PUJ
-
ORD
1 stop8h 00m
Spirit Airlines
Deal found 1/26$283
This Expedia deal was found by Cheapflights users on 1/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/115:15 am
ORD
-
PUJ
1 stop9h 21m
Spirit Airlines
Sat 2/145:47 pm
PUJ
-
ORD
1 stop8h 00m
Spirit Airlines
Deal found 1/28$284

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$242
(Orbitz)

One-way from

$114
(Super.com)

Popular in

March

Cheapest in

August

Average price

$461

Good round-trip deal

$354 or less

Good one-way deal

$163 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 ($17 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 January 2026
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 January 29, 2026.
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

Tue 3/3

5:15 am-2:20 pm

1 stop7h 05m

Santo Domingo Las Americas

Sat 3/7

3:32 pm-9:13 pm

1 stop7h 41m

$242

ChicagoSanto Domingo

ORD - SDQ

ORDSDQ

Chicago O'Hare Intl

Sat 2/28

8:16 pm-2:20 pm

1 stop16h 04m

Santo Domingo Las Americas

Sat 3/7

3:32 pm-9:13 pm

1 stop7h 41m

$258

ChicagoSanto Domingo

ORD - SDQ

ORDSDQ

Chicago O'Hare Intl

Wed 2/18

5:15 am-2:20 pm

1 stop7h 05m

Santo Domingo Las Americas

Wed 2/25

3:32 pm-9:13 pm

1 stop7h 41m

$265

ChicagoSanto Domingo

ORD - SDQ

ORDSDQ

Chicago O'Hare Intl

Wed 3/4

5:15 am-2:20 pm

1 stop7h 05m

Santo Domingo Las Americas

Mon 3/9

2:32 pm-11:47 pm

1 stop10h 15m

$266

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Wed 2/11

7:20 am-3:33 pm

1 stop6h 13m

Santiago de los Caballeros

Wed 2/25

4:40 pm-11:47 pm

1 stop9h 07m

$289

ChicagoSanto Domingo

ORD - SDQ

ORDSDQ

Chicago O'Hare Intl

Fri 2/27

5:15 am-2:20 pm

1 stop7h 05m

Santo Domingo Las Americas

Thu 3/5

12:31 pm-9:06 am

1 stop22h 35m

$300

ChicagoSanto Domingo

ORD - SDQ

ORDSDQ

Chicago O'Hare Intl

Sat 3/14

6:01 pm-5:31 am

1 stop10h 30m

Santo Domingo Las Americas

Wed 3/18

2:59 am-11:21 am

1 stop9h 22m

$304

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Sat 4/18

7:05 am-2:35 pm

1 stop6h 30m

Santiago de los Caballeros

Sat 4/25

3:40 pm-11:41 pm

1 stop9h 01m

$310

ChicagoSanto Domingo

ORD - SDQ

ORDSDQ

Chicago O'Hare Intl

Wed 3/25

7:17 am-1:38 am

1 stop17h 21m

Santo Domingo Las Americas

Tue 3/31

2:59 am-11:21 am

1 stop9h 22m

$314

ChicagoSanto Domingo

ORD - SDQ

ORDSDQ

Chicago O'Hare Intl

Wed 4/22

1:27 pm-2:32 pm

1 stop24h 05m

Santo Domingo Las Americas

Mon 4/27

3:37 pm-9:17 pm

1 stop30h 40m

$315

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

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, December is the cheapest month in which you can book a flight from Chicago to Dominican Republic (average of $195). 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 January 29, 2026.

When flying from Chicago to Dominican Republic, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 January 29, 2026.

The most flights from CHI to DO0 are scheduled on a Monday (3 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).

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

About 16% 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 at night 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 January 29, 2026.
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
8,125 reviews

Boarding

8.1

Entertainment

7.8

Comfort

7.9

Food

7.2

Crew

8.5

Overall

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
8,125 reviews
Delta
7.9
Good
8,125 reviews

Boarding

8.1

Entertainment

7.8

Comfort

7.9

Food

7.2

Crew

8.5

Overall

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
9,215 reviews
Delta
7.9
Good
8,125 reviews

Boarding

8.1

Entertainment

7.8

Comfort

7.9

Food

7.2

Crew

8.5

Overall

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
11,206 reviews
Delta
7.9
Good
8,125 reviews

Boarding

8.1

Entertainment

7.8

Comfort

7.9

Food

7.2

Crew

8.5

Overall

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
5.7
Fair
3,056 reviews
Delta
7.9
Good
8,125 reviews

Boarding

8.1

Entertainment

7.8

Comfort

7.9

Food

7.2

Crew

8.5

Overall

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 42m. Fly via Spirit Airlines, Delta, or United 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 ($100), 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 (81%), United Airlines (72%), Arajet( 72%).

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

    The cheapest flight price from Chicago to Dominican Republic is $100. On average you can expect to pay $689. The most popular route, (Chicago O'Hare Intl - Punta Cana), can usually be booked for $208.

  • 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, December is the cheapest month in which you can book a flight from Chicago to Dominican Republic (average of $195). 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
Midway to Luis Munoz Marin Intl flights
O'Hare Intl to Punta Cana flights
O'Hare Intl to Oranjestad flights
O'Hare Intl to Nassau flights
O'Hare Intl to Saint Thomas Island flights
O'Hare Intl to Montego Bay flights
O'Hare Intl to Providenciales flights
Midway to Punta Cana flights
St. Louis to Luis Munoz Marin Intl flights
O'Hare Intl to George Town flights
O'Hare Intl to Simpson Bay flights
St. Louis to Punta Cana flights
Midway to Nassau flights
Midway to Oranjestad flights
O'Hare Intl to Castries flights
Midway to Montego Bay flights
Midway to Saint Thomas Island flights
O'Hare Intl to Santo Domingo flights
O'Hare Intl to Willemstad flights
O'Hare Intl to Christiansted flights
Midway to Providenciales flights
O'Hare Intl to Bridgetown flights
O'Hare Intl to St. John's flights
St. Louis to Oranjestad flights
St. Louis to Nassau flights
St. Louis to Saint Thomas Island flights
O'Hare Intl to Aguadilla flights
Midway to Santo Domingo flights
Midway to George Town flights
Midway to Simpson Bay flights
O'Hare Intl to Road Town flights
St. Louis to Kingston flights
O'Hare Intl to Kingston flights
St. Louis to Montego Bay flights
O'Hare Intl to Puerto Plata flights
O'Hare Intl to Georgetown flights
St. Louis to Castries flights
O'Hare Intl to Santiago de los Caballeros flights
St. Louis to Simpson Bay flights
O'Hare Intl to St. George's flights
St. Louis to Providenciales flights
St. Louis to George Town flights
O'Hare Intl to Marsh Harbour flights
Peoria to Luis Munoz Marin Intl flights
O'Hare Intl to Freeport flights
Moline to Punta Cana flights
Moline to Luis Munoz Marin Intl flights
O'Hare Intl to The Valley flights
O'Hare Intl to Port of Spain 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$180Average$373FlexibilityNo cancel feeOn-time65%
ArajetCheapest$185Average$320FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$188Average$431FlexibilityNo cancel feeOn-time70%
Air CanadaCheapest$193Average$614FlexibilityNo cancel feeOn-time67%
Hahn AirCheapest$213Average$343FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$215Average$601FlexibilityNo cancel feeOn-time69%
FrontierCheapest$222Average$429FlexibilityNo cancel feeOn-time62%
DeltaCheapest$242Average$536FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$255Average$491FlexibilityNo cancel feeOn-time62%

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