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$146+ 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 5/20. Fares are subject to change and may not be available on all flights or dates of travel.
PUJ — CHI
Apr 29 — May 61
Tue 4/29
Tue 5/6
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 April 24, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$226
(CheapOair)

One-way from

$146
(Frontier)

Popular in

June

Cheapest in

May

Average price

$357

Good round-trip deal

$269 or less

Good one-way deal

$268 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)
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One-way flight from Dominican Republic to Chicago (CHI)
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Highest demand for flights based on searches. 12% potential increase in price ($57 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 24, 2025.

This CheapOair deal was found by Cheapflights users on 4/23. 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.
Thu 5/85:54 pmPUJ - ORD
Nonstop5h 06mFrontier
Sun 5/116:10 amORD - PUJ
Nonstop4h 41mFrontier
Deal found 4/23$226
This Booking.com deal was found by Cheapflights users on 4/22. 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
Sun 5/115:05 amORD - PUJ
1 stop8h 12mMultiple Airlines
Deal found 4/22$270
This American Airlines deal was found by Cheapflights users on 4/23. 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.
Wed 7/94:55 pmPUJ - ORD
1 stop8h 02mAmerican Airlines
Wed 8/67:00 amORD - PUJ
1 stop6h 45mAmerican Airlines
Deal found 4/23$296
This United Airlines deal was found by Cheapflights users on 4/22. 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.
Thu 5/11:50 pmPUJ - ORD
Nonstop5h 05mUnited Airlines
Mon 5/59:23 amORD - PUJ
Nonstop4h 42mUnited Airlines
Deal found 4/22$310
This eDestinos deal was found by Cheapflights users on 4/23. 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 5/83:22 pmPUJ - ORD
1 stop9h 43mSpirit Airlines
Sun 5/115:05 amORD - PUJ
1 stop8h 12mSpirit Airlines
Deal found 4/23$313
This Delta deal was found by Cheapflights users on 4/23. 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 4/23$341
This eDestinos deal was found by Cheapflights users on 4/23. 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.
Wed 5/214:05 pmSDQ - ORD
1 stop7h 59mSpirit Airlines
Wed 9/38:00 amORD - SDQ
1 stop16h 41mSpirit Airlines
Deal found 4/23$347
This Mytrip deal was found by Cheapflights users on 4/23. 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.
Wed 5/2110:19 amSDQ - ORD
2 stops10h 48mMultiple Airlines
Wed 9/33:11 pmORD - SDQ
1 stop29h 34mMultiple Airlines
Deal found 4/23$412
This Delta deal was found by Cheapflights users on 4/22. 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.
Sat 5/31:24 pmSTI - ORD
1 stop9h 01mDelta
Wed 5/71:30 pmORD - STI
1 stop9h 44mDelta
Deal found 4/22$420
This Delta deal was found by Cheapflights users on 4/23. 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 5/212:41 pmSDQ - ORD
1 stop10h 17mDelta
Wed 5/281:30 pmORD - SDQ
1 stop9h 49mDelta
Deal found 4/23$426
This Delta deal was found by Cheapflights users on 4/23. 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 5/217:00 amSDQ - MDW
2 stops15h 27mDelta
Wed 9/36:00 amMDW - SDQ
1 stop6h 24mDelta
Deal found 4/23$426
This Copa Airlines deal was found by Cheapflights users on 4/23. 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.
Thu 5/82:05 pmSDQ - ORD
1 stop11h 29mCopa Airlines
Mon 5/127:54 amORD - SDQ
1 stop13h 14mCopa Airlines
Deal found 4/23$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 April 24, 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 5/14

5:54 pm-10:00 pm

Nonstop5h 06m

Chicago O'Hare Intl

Wed 5/21

7:25 am-1:15 pm

Nonstop4h 50m

$226

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 5/8

5:54 pm-10:00 pm

Nonstop5h 06m

Chicago O'Hare Intl

Sun 5/11

5:05 am-2:17 pm

1 stop8h 12m

$291

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 7/9

4:55 pm-11:57 pm

1 stop8h 02m

Chicago O'Hare Intl

Wed 8/6

7:00 am-2:45 pm

1 stop6h 45m

$296

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 5/8

3:22 pm-12:05 am

1 stop9h 43m

Chicago O'Hare Intl

Sun 5/11

5:05 am-2:17 pm

1 stop8h 12m

$313

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 5/8

2:47 pm-9:28 pm

1 stop7h 41m

Chicago Midway

Sun 5/11

6:00 am-2:45 pm

1 stop7h 45m

$341

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Wed 5/21

4:05 pm-11:04 pm

1 stop7h 59m

Chicago O'Hare Intl

Wed 9/3

8:00 am-1:41 am

1 stop16h 41m

$347

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 7/16

1:50 pm-5:55 pm

Nonstop5h 05m

Chicago O'Hare Intl

Wed 7/30

9:23 am-3:05 pm

Nonstop4h 42m

$369

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Wed 5/21

10:19 am-8:07 pm

2 stops10h 48m

Chicago O'Hare Intl

Wed 9/3

3:11 pm-9:45 pm

1 stop29h 34m

$412

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Sat 5/3

1:24 pm-9:25 pm

1 stop9h 01m

Chicago O'Hare Intl

Wed 5/7

1:30 pm-12:14 am

1 stop9h 44m

$420

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Wed 5/21

2:41 pm-11:58 pm

1 stop10h 17m

Chicago O'Hare Intl

Wed 5/28

1:30 pm-12:19 am

1 stop9h 49m

$426

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

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 April 24, 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 April 24, 2025.

The most flights from DO0 to CHI are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 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 April 24, 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
7,920 reviews

Food

7.3

Crew

8.5

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Overall

8.0

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
7,920 reviews
Delta
8.0
Very good
7,920 reviews

Food

7.3

Crew

8.5

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Overall

8.0

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
4,287 reviews
Delta
8.0
Very good
7,920 reviews

Food

7.3

Crew

8.5

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Overall

8.0

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
7.6
Good
1,411 reviews
Delta
8.0
Very good
7,920 reviews

Food

7.3

Crew

8.5

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Overall

8.0

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
1,700 reviews
Delta
8.0
Very good
7,920 reviews

Food

7.3

Crew

8.5

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Overall

8.0

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
Avelo Airlines
7.5
Good
Delta
8.0
Very good
7,920 reviews

Food

7.3

Crew

8.5

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Overall

8.0

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 ($146), United Airlines ($148), and American Airlines ($150).

  • 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 $385, 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 $391 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

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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
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Montego Bay to Midway flights
Port of Spain to O'Hare Intl flights
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St. George's to St. Louis flights
Nassau to St. Louis flights
Saint Thomas Island to O'Hare Intl flights
Willemstad to O'Hare Intl flights
Oranjestad to O'Hare Intl flights
Aguadilla to O'Hare Intl flights
Christiansted to O'Hare Intl flights
Oranjestad to St. Louis flights
Aguadilla to Midway flights
Road Town to O'Hare Intl flights
Culebra to O'Hare Intl flights
Nassau to Midway flights
Port Au Prince to O'Hare Intl flights
Roseau to O'Hare Intl flights
St. John's to O'Hare Intl flights
Simpson Bay to Midway flights
Vieques to O'Hare Intl flights
Port Au Prince to Midway flights
Port of Spain to St. Louis flights
Saint Thomas Island to St. Louis 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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$190Average$339FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$312Average$423FlexibilityNo cancel feeOn-time69%
DeltaCheapest$324Average$507FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$405Average$614FlexibilityNo cancel feeOn-time71%

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