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$102+ 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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
PUJ — CHI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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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 October 30, 2025.

This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/76:50 pmPUJ - ORD
Nonstop5h 10mFrontier
Sun 12/147:10 amORD - PUJ
Nonstop4h 37mFrontier
Deal found 10/30$182
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/56:50 pmPUJ - ORD
Nonstop5h 10mFrontier
Fri 12/127:10 amORD - PUJ
Nonstop4h 37mFrontier
Deal found 10/30$183
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.
Sat 12/66:50 pmPUJ - ORD
Nonstop5h 10mFrontier
Sat 12/137:10 amORD - PUJ
Nonstop4h 37mFrontier
Deal found 10/29$197
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.
Tue 12/96:50 pmPUJ - ORD
Nonstop5h 10mFrontier
Tue 12/167:10 amORD - PUJ
Nonstop4h 37mFrontier
Deal found 10/29$214
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.
Wed 12/106:50 pmPUJ - ORD
Nonstop5h 10mFrontier
Wed 12/177:10 amORD - PUJ
Nonstop4h 37mFrontier
Deal found 10/29$221
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/257:30 pmPUJ - ORD
Nonstop5h 10mMultiple Airlines
Tue 12/27:00 amORD - PUJ
Nonstop4h 37mMultiple Airlines
Deal found 10/29$226
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.
Thu 12/46:50 pmPUJ - ORD
Nonstop5h 10mFrontier
Thu 12/117:10 amORD - PUJ
Nonstop4h 37mFrontier
Deal found 10/29$228
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/216:49 pmPUJ - ORD
Nonstop5h 12mFrontier
Fri 11/286:45 amORD - PUJ
Nonstop4h 34mFrontier
Deal found 10/29$240
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.
Wed 12/246:49 pmPUJ - ORD
Nonstop5h 10mFrontier
Wed 12/317:10 amORD - PUJ
Nonstop4h 37mFrontier
Deal found 10/29$244
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/225:47 amPUJ - ORD
Nonstop5h 10mArajet
Sat 11/2910:27 amORD - PUJ
Nonstop4h 45mArajet
Deal found 10/29$245
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/65:47 amPUJ - ORD
Nonstop5h 10mArajet
Sat 12/1310:27 amORD - PUJ
Nonstop4h 45mArajet
Deal found 10/29$247
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/44:21 pmSDQ - ORD
1 stop9h 48mSpirit Airlines
Sun 12/75:00 amORD - SDQ
1 stop8h 23mSpirit Airlines
Deal found 10/29$290

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 October 30, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$182
(Priceline)

One-way from

$102
(Trip.com)

Popular in

June

Cheapest in

May

Average price

$511

Good round-trip deal

$195 or less

Good one-way deal

$206 or less
Provider with most accurate pricing for Punta Cana-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Punta Cana-Chicago (CHI) flights.
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From Dominican Republic to Chicago (CHI)
Search Deals
One-way flight from Dominican Republic to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($60 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Dominican Republic to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Dominican Republic to Chicago (CHI).
Search Deals

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 October 30, 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 2/7

5:47 am-8:57 am

Nonstop5h 10m

Chicago O'Hare Intl

Sat 2/14

10:27 am-5:12 pm

Nonstop4h 45m

$243

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 4/25

5:47 am-9:57 am

Nonstop5h 10m

Chicago O'Hare Intl

Sat 5/2

11:27 am-5:12 pm

Nonstop4h 45m

$243

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Fri 12/5

2:55 pm-6:08 pm

Nonstop5h 13m

Chicago O'Hare Intl

Tue 12/9

9:30 am-4:02 pm

Nonstop4h 32m

$267

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 12/4

12:56 pm-11:43 pm

1 stop12h 47m

Chicago O'Hare Intl

Thu 12/11

9:05 pm-5:25 pm

1 stop18h 20m

$274

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 12/6

5:20 pm-9:36 am

1 stop18h 16m

Chicago O'Hare Intl

Tue 12/9

9:05 pm-5:25 pm

1 stop18h 20m

$302

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Thu 12/4

4:21 pm-11:13 am

1 stop20h 52m

Chicago O'Hare Intl

Thu 12/11

5:00 am-3:23 pm

1 stop8h 23m

$307

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Wed 11/26

4:35 pm-4:25 pm

1 stop25h 50m

Chicago O'Hare Intl

Sat 12/6

3:26 pm-3:23 pm

1 stop21h 57m

$325

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Tue 11/25

12:56 pm-7:45 am

1 stop20h 49m

Chicago O'Hare Intl

Tue 12/2

4:00 pm-5:25 pm

1 stop23h 25m

$325

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 1/14

5:20 pm-9:43 am

1 stop18h 23m

Chicago O'Hare Intl

Wed 1/21

8:45 am-5:25 pm

1 stop6h 40m

$348

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 1/29

12:56 pm-6:37 pm

1 stop7h 41m

Chicago O'Hare Intl

Thu 2/5

2:00 pm-5:25 pm

1 stop25h 25m

$348

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

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, December is the cheapest month in which you can book a flight from Dominican Republic to Chicago (average of $126). Flying from Dominican Republic to Chicago in June is currently the most expensive (average of $341). 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 October 30, 2025.

It’s optimal to fly from Dominican Republic to Chicago at noon. By choosing this option you can save up to 16% 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 Thursday evenings when fares are most often at their lowest. Monday afternoons 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 October 30, 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
7.9
Good
7,993 reviews

Crew

8.5

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

7.9

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
Delta
7.9
Good
7,993 reviews
Delta
7.9
Good
7,993 reviews

Crew

8.5

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

7.9

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
United Airlines
7.4
Good
8,998 reviews
Delta
7.9
Good
7,993 reviews

Crew

8.5

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

7.9

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
American Airlines
7.2
Good
11,030 reviews
Delta
7.9
Good
7,993 reviews

Crew

8.5

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

7.9

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
Frontier
5.8
Fair
3,123 reviews
Delta
7.9
Good
7,993 reviews

Crew

8.5

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

7.9

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!

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 $243. 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 cheapest airlines to fly from Dominican Republic to Chicago one-way?

    The cheapest airlines for a one-way flight from Dominican Republic to Chicago are Arajet ($134), Frontier ($145), and United Airlines ($148).

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

    Most travelers choose Punta Cana - Chicago O'Hare Intl, Punta Cana - Chicago Midway or Santo Domingo Las Americas - Chicago O'Hare Intl 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 (82%), Frontier (67%) or United Airlines (58%) 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 $288, our data shows the cheapest flight currently is $112. When looking at the most popular route, (Punta Cana - Chicago O'Hare Intl), you can expect to pay $226 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, December is the cheapest month in which you can book a flight from Dominican Republic to Chicago (average of $126). Flying from Dominican Republic to Chicago in June is currently the most expensive (average of $341). 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
Porter
Benton Harbor

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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.
Punta Cana to O'Hare Intl flights
Punta Cana to Midway flights
Luis Munoz Marin Intl to O'Hare Intl flights
Luis Munoz Marin Intl to Midway flights
Santo Domingo to O'Hare Intl flights
Luis Munoz Marin Intl to St. Louis flights
Oranjestad to O'Hare Intl flights
Nassau to O'Hare Intl flights
Santo Domingo to Midway flights
Montego Bay to O'Hare Intl flights
Willemstad to O'Hare Intl flights
Saint Thomas Island to O'Hare Intl flights
Nassau to Midway flights
Kingston to O'Hare Intl flights
Simpson Bay to O'Hare Intl flights
Santiago de los Caballeros to O'Hare Intl flights
George Town to O'Hare Intl flights
Port of Spain to O'Hare Intl flights
Christiansted to O'Hare Intl flights
Bridgetown to O'Hare Intl flights
Simpson Bay to Midway flights
Montego Bay to Midway flights
Roseau to O'Hare Intl flights
Aguadilla to O'Hare Intl flights
St. George's to St. Louis flights
Oranjestad to St. Louis flights
Vieques to O'Hare Intl flights
Nassau to St. Louis flights
Port of Spain to St. Louis flights
Saint Thomas Island to St. Louis flights
Port Au Prince to O'Hare Intl flights
Road Town to O'Hare Intl flights
Culebra to O'Hare Intl flights
St. John's to O'Hare Intl flights
Port Au Prince to Midway flights
Aguadilla to Midway 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$181Average$412FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$189Average$341FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$269Average$423FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$354Average$530FlexibilityNo cancel feeOn-time71%
DeltaCheapest$449Average$651FlexibilityNo cancel feeOn-timeN/A

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