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$111+ Cheap flights from the Dominican Republic to Chicago (CHI)

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.
PUJ — CHI
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Dominican Republic to Chicago

Keep the following information in mind while searching for Dominican Republic to Chicago flight deals. Data was last updated September 11, 2025.

Round-trip from

$264
(Priceline)

One-way from

$111
(Priceline)

Popular in

June

Cheapest in

May

Average price

$356

Good round-trip deal

$306 or less

Good one-way deal

$285 or less
From Dominican Republic to Chicago (CHI)
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One-way flight from Dominican Republic to Chicago (CHI)
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Highest demand for flights based on searches. 16% potential increase in price ($79 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($26 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 Dominican Republic to Chicago (CHI).
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Price to beat on a one-way flight from Dominican Republic to Chicago (CHI).
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Find flight deals from Dominican Republic to Chicago

Cheapest flights from Dominican Republic to Chicago
Explore the most affordable flight options available from Dominican Republic to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Priceline deal was found by Cheapflights users on 9/11. 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.
Sat 10/113:59 pmSDQ - ORD
1 stop8h 46mSpirit Airlines
Thu 10/235:05 amORD - SDQ
1 stop8h 43mSpirit Airlines
Deal found 9/11$264
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 12/167:30 pmPUJ - ORD
Nonstop5h 10mArajet
Sun 1/113:30 amORD - PUJ
Nonstop4h 45mArajet
Deal found 9/11$264
This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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.
Sat 10/43:47 pmSDQ - ORD
1 stop8h 01mSpirit Airlines
Sat 10/115:05 amORD - SDQ
1 stop8h 49mSpirit Airlines
Deal found 9/11$273
This Spirit deal was found by Cheapflights users on 9/11. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/113:59 pmSDQ - ORD
1 stop8h 46mSpirit Airlines
Sat 10/255:05 amORD - SDQ
1 stop8h 49mSpirit Airlines
Deal found 9/11$276
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/225:47 amPUJ - ORD
Nonstop5h 10mMultiple Airlines
Fri 11/287:00 amORD - PUJ
Nonstop4h 33mMultiple Airlines
Deal found 9/10$278
This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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.
Thu 10/233:57 pmPUJ - ORD
1 stop8h 48mSpirit Airlines
Sun 10/265:05 amORD - PUJ
1 stop8h 55mSpirit Airlines
Deal found 9/11$284
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.
Wed 11/121:21 pmPUJ - ORD
1 stop12h 21mSpirit Airlines
Mon 11/175:59 pmORD - PUJ
1 stop16h 17mSpirit Airlines
Deal found 9/10$286
This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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.
Thu 10/303:54 pmSDQ - ORD
1 stop10h 09mSpirit Airlines
Wed 11/55:05 amORD - SDQ
1 stop10h 45mSpirit Airlines
Deal found 9/11$290
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/266:49 pmPUJ - ORD
Nonstop5h 12mMultiple Airlines
Tue 12/24:35 amORD - PUJ
Nonstop4h 45mMultiple Airlines
Deal found 9/10$291
This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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.
Sat 10/253:59 pmSDQ - ORD
1 stop8h 46mSpirit Airlines
Fri 10/315:05 amORD - SDQ
1 stop10h 02mSpirit Airlines
Deal found 9/11$292
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.
Thu 10/303:54 pmSDQ - ORD
1 stop10h 09mSpirit Airlines
Mon 11/35:05 amORD - SDQ
1 stop10h 02mSpirit Airlines
Deal found 9/10$298
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.
Fri 10/105:12 pmSDQ - ORD
1 stop7h 33mSpirit Airlines
Mon 10/135:05 amORD - SDQ
1 stop10h 02mSpirit Airlines
Deal found 9/10$299

Cheapflights Fare Finder

 
Customize your flight search to find flights from Dominican Republic to Chicago 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 September 11, 2025.
Use the filters below to find and compare flights from the Dominican Republic to Chicago that are best for you.

Fly from

Dominican Republic

Fly to

Chicago

Route

Depart

Return

Price

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 2/14

5:47 am-8:57 am

Nonstop5h 10m

Chicago O'Hare Intl

Sat 2/21

10:27 am-5:12 pm

Nonstop4h 45m

$264

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Sat 10/11

3:59 pm-11:45 pm

1 stop8h 46m

Chicago O'Hare Intl

Sat 10/25

5:05 am-2:54 pm

1 stop8h 49m

$276

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 10/23

3:57 pm-11:45 pm

1 stop8h 48m

Chicago O'Hare Intl

Sun 10/26

5:05 am-3:00 pm

1 stop8h 55m

$284

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 11/12

1:21 pm-11:42 pm

1 stop12h 21m

Chicago O'Hare Intl

Mon 11/17

5:59 pm-12:16 pm

1 stop16h 17m

$286

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Fri 12/19

3:35 pm-2:55 pm

1 stop25h 20m

Chicago O'Hare Intl

Sun 12/28

3:30 am-10:15 am

Nonstop4h 45m

$299

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Fri 10/10

5:12 pm-11:45 pm

1 stop7h 33m

Chicago O'Hare Intl

Mon 10/13

5:05 am-4:07 pm

1 stop10h 02m

$299

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Fri 10/3

5:05 pm-10:52 am

1 stop18h 47m

Chicago O'Hare Intl

Sat 10/11

7:43 pm-2:48 pm

1 stop18h 05m

$303

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Mon 10/27

5:12 pm-1:03 am

1 stop8h 51m

Chicago O'Hare Intl

Mon 11/3

5:05 am-5:07 pm

1 stop10h 02m

$306

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Thu 11/13

6:55 pm-9:23 am

1 stop16h 28m

Chicago O'Hare Intl

Wed 11/19

5:05 am-5:50 pm

1 stop10h 45m

$312

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Sun 10/5

3:54 pm-10:31 am

2 stops19h 37m

Chicago O'Hare Intl

Sat 10/11

7:43 pm-2:48 pm

1 stop18h 05m

$349

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

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

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

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

Currently, August is the cheapest month in which you can book a flight from Dominican Republic to Chicago (average of $245). Flying from Dominican Republic to Chicago in March is currently the most expensive (average of $321). 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 DO to CHI?

Find hourly flight availability from Dominican Republic to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

It’s optimal to fly from Dominican Republic to Chicago in the evening. By choosing this option you can save up to 26% on the cost of your flight, compared to a flight in the afternoon.

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

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

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

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated September 11, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines, and American Airlines from the Dominican Republic to Chicago 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
8.0
Very good
7,960 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Delta
8.0
Very good
7,960 reviews
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
United Airlines
7.4
Good
8,937 reviews
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Frontier
5.8
Fair
3,177 reviews
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others

Related info for your journey

Find useful and relevant information for your journey from Dominican Republic to Chicago. 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 Dominican Republic to Chicago?

    A quick flight from Dominican Republic to Chicago can take about 5h 10m. Arajet provides one of the quickest options available for as low as $264. The distance between Dominican Republic and Chicago is about 1982 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    Most travelers choose Santo Domingo Las Americas - Chicago O'Hare Intl, Punta Cana - Chicago O'Hare Intl or Santo Domingo Las Americas - Chicago Midway when deciding on the best route from Dominican Republic to Chicago.

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

    Consider American Airlines (83%), United Airlines (76%) or Frontier (66%) when booking your flight. These represent the most reliable airlines when flying from Dominican Republic to Chicago.

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

    While on average a flight from Dominican Republic to Chicago is generally $330, our data shows the cheapest flight currently is $181. When looking at the most popular route, (Santo Domingo Las Americas - Chicago O'Hare Intl), you can expect to pay $281 for that flight.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Dominican Republic to Chicago (average of $245). Flying from Dominican Republic to Chicago in March is currently the most expensive (average of $321). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Dominican Republic to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Luis Munoz Marin Intl to O'Hare Intl flights
Luis Munoz Marin Intl to Midway flights
Santo Domingo to O'Hare Intl flights
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Santo Domingo to Midway flights
Luis Munoz Marin Intl to St. Louis flights
Kingston to O'Hare Intl flights
Nassau to O'Hare Intl flights
Montego Bay to O'Hare Intl flights
Oranjestad to O'Hare Intl flights
Saint Thomas Island to O'Hare Intl flights
Santiago de los Caballeros to O'Hare Intl flights
Bridgetown to O'Hare Intl flights
Willemstad to O'Hare Intl flights
Simpson Bay to O'Hare Intl flights
Port of Spain to O'Hare Intl flights
Montego Bay to Midway flights
Punta Cana to Midway flights
Nassau to Midway flights
Port of Spain to St. Louis flights
Aguadilla to O'Hare Intl flights
Christiansted to O'Hare Intl flights
George Town to O'Hare Intl flights
Simpson Bay to Midway flights
Aguadilla to Midway flights
Nassau to St. Louis flights
Roseau to O'Hare Intl flights
St. John's to O'Hare Intl flights
Port Au Prince to O'Hare Intl flights
Road Town to O'Hare Intl flights
Culebra to O'Hare Intl flights
Port Au Prince to Midway flights
Vieques to O'Hare Intl flights
Oranjestad to St. Louis flights
St. George's to St. Louis flights
Saint Thomas Island to St. Louis flights

Top 5 airlines flying from Dominican Republic to Chicago

Discover the top 5 airlines that operate flights from Dominican Republic to Chicago. 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$189Average$330FlexibilityNo cancel feeOn-time65%
FrontierCheapest$224Average$439FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$269Average$433FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$354Average$530FlexibilityNo cancel feeOn-time71%
DeltaCheapest$400Average$507FlexibilityNo cancel feeOn-timeN/A

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