HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$144+ 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 7/9. Fares are subject to change and may not be available on all flights or dates of travel.
PUJ — CHI
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Dominican Republic to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 May 1, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$234
(Cheapflightsfares)

One-way from

$144
(Cheapflightsfares)

Popular in

June

Cheapest in

May

Average price

$313

Good round-trip deal

$269 or less

Good one-way deal

$251 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. 11% potential increase in price ($55 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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

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 May 1, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Tue 5/65:54 pmPUJ - ORD
Nonstop5h 06mFrontier
Sun 5/116:10 amORD - PUJ
Nonstop4h 41mFrontier
Deal found 4/29$234
This Booking.com deal was found by Cheapflights users on 5/1. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/85:54 pmPUJ - ORD
Nonstop5h 06mMultiple Airlines
Tue 5/135:05 amORD - PUJ
1 stop8h 12mMultiple Airlines
Deal found 5/1$293
This United Airlines deal was found by Cheapflights users on 4/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/161:50 pmPUJ - ORD
Nonstop5h 05mUnited Airlines
Wed 8/69:23 amORD - PUJ
Nonstop4h 42mUnited Airlines
Deal found 4/30$313
This eDestinos deal was found by Cheapflights users on 5/1. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/812:42 pmPUJ - ORD
1 stop11h 47mSpirit Airlines
Tue 5/135:05 amORD - PUJ
1 stop8h 12mSpirit Airlines
Deal found 5/1$316
This American Airlines deal was found by Cheapflights users on 4/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/611:46 amPUJ - ORD
1 stop9h 38mAmerican Airlines
Sun 5/116:00 amORD - PUJ
1 stop8h 49mAmerican Airlines
Deal found 4/29$325
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/82:47 pmPUJ - MDW
1 stop7h 41mDelta
Sun 5/116:00 amMDW - PUJ
1 stop7h 45mDelta
Deal found 4/29$341
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/92:52 pmPUJ - ORD
1 stop10h 17mDelta
Wed 8/67:00 amORD - PUJ
1 stop6h 51mDelta
Deal found 4/30$341
This Mytrip deal was found by Cheapflights users on 4/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/203:35 pmSDQ - ORD
2 stops32h 04mMultiple Airlines
Sat 5/245:05 amORD - SDQ
1 stop8h 30mMultiple Airlines
Deal found 4/30$374
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/17:30 amSDQ - ORD
1 stop7h 45mSpirit Airlines
Tue 10/146:34 pmORD - SDQ
1 stop6h 07mSpirit Airlines
Deal found 4/30$387
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1912:34 pmPUJ - MDW
1 stop8h 43mMultiple Airlines
Sun 6/229:12 pmMDW - PUJ
2 stops15h 58mMultiple Airlines
Deal found 4/30$430
This Copa Airlines deal was found by Cheapflights users on 4/30. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/811:54 amSDQ - ORD
1 stop13h 26mCopa Airlines
Thu 7/173:07 pmORD - SDQ
1 stop10h 38mCopa Airlines
Deal found 4/30$433
This Copa Airlines deal was found by Cheapflights users on 4/30. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/165:16 amPUJ - ORD
1 stop20h 04mCopa Airlines
Wed 8/67:54 amORD - PUJ
1 stop8h 43mCopa Airlines
Deal found 4/30$433

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 May 1, 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

Wed 7/16

5:08 pm-9:16 pm

Nonstop5h 08m

Chicago O'Hare Intl

Wed 8/13

6:45 am-12:25 pm

Nonstop4h 40m

$234

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 7/16

5:08 pm-9:16 pm

Nonstop5h 08m

Chicago O'Hare Intl

Wed 8/6

8:00 am-3:08 pm

1 stop6h 08m

$303

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 5/28

3:22 pm-11:04 pm

1 stop8h 42m

Chicago O'Hare Intl

Wed 6/25

5:05 am-2:10 pm

1 stop8h 05m

$309

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 7/16

1:50 pm-5:55 pm

Nonstop5h 05m

Chicago O'Hare Intl

Wed 8/6

9:23 am-3:05 pm

Nonstop4h 42m

$313

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 7/9

2:52 pm-12:09 am

1 stop10h 17m

Chicago O'Hare Intl

Wed 8/6

7:00 am-2:51 pm

1 stop6h 51m

$341

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Tue 5/13

2:12 pm-12:11 am

1 stop10h 59m

Chicago O'Hare Intl

Mon 5/19

7:16 pm-1:35 pm

1 stop17h 19m

$353

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Tue 5/20

3:35 pm-10:39 pm

2 stops32h 04m

Chicago O'Hare Intl

Sat 5/24

5:05 am-2:35 pm

1 stop8h 30m

$374

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Wed 10/1

7:30 am-2:15 pm

1 stop7h 45m

Chicago O'Hare Intl

Tue 10/14

6:34 pm-1:41 am

1 stop6h 07m

$387

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 6/19

12:34 pm-8:17 pm

1 stop8h 43m

Chicago Midway

Sun 6/22

9:12 pm-2:10 pm

2 stops15h 58m

$430

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Tue 7/8

11:54 am-12:20 am

1 stop13h 26m

Chicago O'Hare Intl

Thu 7/17

3:07 pm-2:45 am

1 stop10h 38m

$433

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 58 results
1
2
3
...
6

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 May 1, 2025.

It’s optimal to fly from Dominican Republic to Chicago in the morning. By choosing this option you can save up to 23% 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 afternoons 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.

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 May 1, 2025.

The most flights from DO0 to CHI are scheduled on a Monday (3 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 May 1, 2025.
See what other customers who have flown with Delta, Southwest and Copa Airlines from Dominican Republic to Chicago have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,934 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Southwest
8.0
Very good
4,294 reviews
Delta
8.0
Very good
7,934 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Copa Airlines
7.5
Good
1,414 reviews
Delta
8.0
Very good
7,934 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Aeromexico
7.5
Good
1,698 reviews
Delta
8.0
Very good
7,934 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
LATAM Airlines
7.5
Good
1,767 reviews
Delta
8.0
Very good
7,934 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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.

  • 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 ($144), Spirit Airlines ($148), and United Airlines ($149).

  • 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 Frontier (69%), American Airlines (58%) or United Airlines (51%) 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 $406, our data shows the cheapest flight currently is $131. When looking at the most popular route, (Santo Domingo Las Americas - Chicago O'Hare Intl), you can expect to pay $335 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 the Dominican Republic?

Book flights to the Dominican Republic if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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
Punta Cana to O'Hare Intl flights
Luis Munoz Marin Intl to St. Louis flights
Santo Domingo to Midway flights
Bridgetown to O'Hare Intl flights
Nassau to O'Hare Intl flights
Kingston to O'Hare Intl flights
Punta Cana to Midway flights
Port of Spain to O'Hare Intl flights
Montego Bay to O'Hare Intl flights
Saint Thomas Island to O'Hare Intl flights
George Town to O'Hare Intl flights
Oranjestad to O'Hare Intl flights
Nassau to Midway flights
Montego Bay to Midway flights
Santiago de los Caballeros to O'Hare Intl flights
Willemstad to O'Hare Intl flights
Simpson Bay to O'Hare Intl flights
St. George's to St. Louis flights
Nassau to St. Louis flights
Aguadilla to O'Hare Intl flights
Saint Thomas Island to St. Louis flights
Oranjestad to St. Louis flights
Port of Spain to St. Louis flights
Simpson Bay to Midway flights
Culebra to O'Hare Intl flights
Christiansted to O'Hare Intl flights
St. John's to O'Hare Intl flights
Aguadilla to Midway flights
Port Au Prince to O'Hare Intl flights
Road Town to O'Hare Intl flights
Roseau to O'Hare Intl flights
Vieques to O'Hare Intl flights
Port Au Prince 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$224Average$379FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$312Average$426FlexibilityNo cancel feeOn-time69%
DeltaCheapest$324Average$507FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$405Average$613FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.