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$127+ 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 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
PUJ — CHI
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap 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 January 29, 2026.

This Spirit 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/55:47 pm
PUJ
-
ORD
1 stop8h 00m
Spirit Airlines
Sun 2/87:20 am
ORD
-
PUJ
1 stop7h 16m
Spirit Airlines
Deal found 1/28$225
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/114:40 pm
STI
-
ORD
1 stop9h 07m
Spirit Airlines
Wed 3/45:15 am
ORD
-
STI
1 stop8h 20m
Spirit Airlines
Deal found 1/27$237
This Flightnetwork 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/75:47 pm
PUJ
-
ORD
1 stop8h 00m
Spirit Airlines
Sun 2/87:20 am
ORD
-
PUJ
1 stop7h 16m
Spirit Airlines
Deal found 1/28$239
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.
Wed 3/45:47 pm
PUJ
-
ORD
1 stop8h 00m
Multiple Airlines
Wed 3/117:20 am
ORD
-
PUJ
Nonstop4h 43m
Multiple Airlines
Deal found 1/27$243
This Flightnetwork 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/45:47 pm
PUJ
-
ORD
1 stop8h 00m
Spirit Airlines
Sun 2/85:15 am
ORD
-
PUJ
1 stop9h 21m
Spirit Airlines
Deal found 1/28$249
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/243:32 pm
SDQ
-
ORD
1 stop10h 15m
Spirit Airlines
Tue 3/35:15 am
ORD
-
SDQ
1 stop7h 05m
Spirit Airlines
Deal found 1/27$254
This Flightnetwork 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/35:47 pm
PUJ
-
ORD
1 stop8h 00m
Spirit Airlines
Sun 2/87:20 am
ORD
-
PUJ
1 stop7h 16m
Spirit Airlines
Deal found 1/28$261
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/72:46 am
STI
-
ORD
1 stop9h 35m
Spirit Airlines
Mon 4/134:35 pm
ORD
-
STI
1 stop8h 14m
Spirit Airlines
Deal found 1/27$268
This Spirit 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/65:47 pm
PUJ
-
ORD
1 stop8h 00m
Spirit Airlines
Sun 2/87:20 am
ORD
-
PUJ
1 stop7h 16m
Spirit Airlines
Deal found 1/28$271
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.
Tue 2/103:32 pm
SDQ
-
ORD
1 stop7h 31m
Spirit Airlines
Mon 2/235:15 am
ORD
-
SDQ
1 stop7h 05m
Spirit Airlines
Deal found 1/28$281
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/253:32 pm
SDQ
-
ORD
1 stop7h 41m
Spirit Airlines
Wed 3/45:15 am
ORD
-
SDQ
1 stop7h 05m
Spirit Airlines
Deal found 1/27$283
This Flightnetwork 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/185:47 pm
PUJ
-
ORD
1 stop8h 00m
Spirit Airlines
Sun 2/227:00 am
ORD
-
PUJ
1 stop7h 36m
Spirit Airlines
Deal found 1/27$286

Find 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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$237
(Priceline)

One-way from

$127
(Super.com)

Popular in

June

Cheapest in

February

Average price

$459

Good round-trip deal

$160 or less

Good one-way deal

$187 or less
Provider with most accurate pricing for Punta Cana-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Punta Cana-Chicago (CHI) flights.
Search Deals
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. 16% potential increase in price ($83 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($31 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 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 January 29, 2026.
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

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Tue 2/24

3:32 pm-11:47 pm

1 stop10h 15m

Chicago O'Hare Intl

Tue 3/3

5:15 am-2:20 pm

1 stop7h 05m

$254

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Tue 2/10

3:32 pm-9:03 pm

1 stop7h 31m

Chicago O'Hare Intl

Mon 2/23

5:15 am-2:20 pm

1 stop7h 05m

$281

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Thu 2/26

3:32 pm-9:13 pm

1 stop7h 41m

Chicago O'Hare Intl

Mon 3/2

8:16 pm-2:20 pm

1 stop16h 04m

$283

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 2/21

5:47 am-8:57 am

Nonstop5h 10m

Chicago O'Hare Intl

Sun 2/22

7:00 am-4:36 pm

1 stop7h 36m

$289

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Sun 3/15

2:59 am-6:21 pm

1 stop16h 22m

Chicago O'Hare Intl

Tue 3/24

5:05 am-1:25 pm

1 stop7h 20m

$289

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Wed 2/18

3:32 pm-11:47 pm

1 stop10h 15m

Chicago O'Hare Intl

Sat 2/28

8:16 pm-2:20 pm

1 stop16h 04m

$290

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Fri 2/13

5:47 pm-11:47 pm

1 stop8h 00m

Chicago O'Hare Intl

Tue 2/17

7:00 am-4:36 pm

1 stop7h 36m

$297

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 2/25

5:47 pm-11:47 pm

1 stop8h 00m

Chicago O'Hare Intl

Sun 3/1

5:15 am-4:36 pm

1 stop9h 21m

$299

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Fri 2/13

4:40 pm-11:47 pm

1 stop9h 07m

Chicago O'Hare Intl

Wed 3/4

5:15 am-3:35 pm

1 stop8h 20m

$302

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 2/19

5:47 pm-11:47 pm

1 stop8h 00m

Chicago O'Hare Intl

Sun 2/22

5:15 am-4:36 pm

1 stop9h 21m

$307

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

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 $139). Flying from Dominican Republic to Chicago in June is currently the most expensive (average of $334). 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 January 29, 2026.

It’s optimal to fly from Dominican Republic to Chicago in the evening. By choosing this option you can save up to 40% on the cost of your flight, compared to a flight in the afternoon.

Weekly flight availability from Dominican Republic to Chicago

Explore weekly flight availability from Dominican Republic to Chicago. 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 DO0 to CHI 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 (1 on average).

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 January 29, 2026.
Peruse reviews from past customers who have flown with American Airlines and Frontier 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.
American Airlines
7.2
Good
11,206 reviews

Comfort

7.2

Entertainment

6.9

Food

6.4

Boarding

7.5

Crew

8.0

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.
American Airlines
7.2
Good
11,206 reviews
American Airlines
7.2
Good
11,206 reviews

Comfort

7.2

Entertainment

6.9

Food

6.4

Boarding

7.5

Crew

8.0

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.
Frontier
5.7
Fair
3,056 reviews
American Airlines
7.2
Good
11,206 reviews

Comfort

7.2

Entertainment

6.9

Food

6.4

Boarding

7.5

Crew

8.0

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.

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 8h 20m. Spirit Airlines provides one of the quickest options available for as low as $472. The distance between Dominican Republic and Chicago is about 1967 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 Frontier ($108), Arajet ($127), and Spirit Airlines ($132).

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

    Most travelers choose Punta Cana - Chicago O'Hare Intl, Santo Domingo Las Americas - 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 Qatar Airways (88%), American Airlines (80%) or Frontier (60%) 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 $376, our data shows the cheapest flight currently is $116. When looking at the most popular route, (Punta Cana - Chicago O'Hare Intl), you can expect to pay $243 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 $139). Flying from Dominican Republic to Chicago in June is currently the most expensive (average of $334). 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
Lansing
Merrillville
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.
Luis Munoz Marin Intl to O'Hare Intl flights
Luis Munoz Marin Intl to Midway flights
Luis Munoz Marin Intl to St. Louis flights
Punta Cana to O'Hare Intl flights
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Santo Domingo to O'Hare Intl flights
Saint Thomas Island to O'Hare Intl flights
Kingston to O'Hare Intl flights
George Town to O'Hare Intl flights
Montego Bay to O'Hare Intl flights
Oranjestad to O'Hare Intl flights
Simpson Bay to O'Hare Intl flights
Santo Domingo to Midway flights
Punta Cana to Midway flights
Willemstad to O'Hare Intl flights
Nassau to Midway flights
St. John's to O'Hare Intl flights
Aguadilla to O'Hare Intl flights
Santiago de los Caballeros to O'Hare Intl flights
Christiansted to O'Hare Intl flights
Bridgetown to O'Hare Intl flights
Simpson Bay to Midway flights
Port of Spain to O'Hare Intl flights
Oranjestad to St. Louis flights
Nassau to St. Louis flights
Port of Spain to St. Louis flights
Montego Bay to Midway flights
Vieques to O'Hare Intl flights
St. George's 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
Roseau to O'Hare Intl flights
Culebra to O'Hare Intl flights
Port Au Prince to Midway flights
Aguadilla to Midway flights

Top 4 airlines flying from Dominican Republic to Chicago

Discover the top 4 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$181Average$443FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$189Average$341FlexibilityNo cancel feeOn-time65%
DeltaCheapest$191Average$714FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$354Average$538FlexibilityNo cancel feeOn-time71%

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