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$129+ 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 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
PUJ — CHI
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
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 July 29, 2025.

Round-trip from

$275
(Cheapflightsfares)

One-way from

$129
(Cheapflightsfares)

Popular in

June

Cheapest in

May

Average price

$476

Good round-trip deal

$418 or less

Good one-way deal

$164 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 ($78 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 July 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 July 29, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 7/27. 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.
Thu 8/145:45 pmPUJ - ORD
Nonstop5h 08mFrontier
Mon 8/186:45 amORD - PUJ
Nonstop4h 40mFrontier
Deal found 7/27$275
This CheapOair deal was found by Cheapflights users on 7/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/274:05 pmPUJ - ORD
1 stop8h 54mSpirit Airlines
Wed 9/35:05 amORD - PUJ
1 stop8h 55mSpirit Airlines
Deal found 7/28$276
This eDestinos deal was found by Cheapflights users on 7/27. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/265:05 pmSDQ - ORD
1 stop7h 54mSpirit Airlines
Mon 9/15:05 amORD - SDQ
1 stop9h 55mSpirit Airlines
Deal found 7/27$302
This Mytrip deal was found by Cheapflights users on 7/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/210:20 amSTI - ORD
1 stop14h 39mSpirit Airlines
Mon 9/156:44 pmORD - STI
1 stop15h 21mSpirit Airlines
Deal found 7/28$314
This Orbitz deal was found by Cheapflights users on 7/27. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/144:05 pmPUJ - ORD
1 stop8h 54mMultiple Airlines
Mon 8/186:45 amORD - PUJ
Nonstop4h 40mMultiple Airlines
Deal found 7/27$328
This Expedia deal was found by Cheapflights users on 7/27. 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.
Tue 8/51:48 amSDQ - ORD
1 stop15h 16mMultiple Airlines
Tue 8/195:05 amORD - SDQ
1 stop9h 55mMultiple Airlines
Deal found 7/27$347
This Delta deal was found by Cheapflights users on 7/29. 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.
Fri 9/52:40 pmPUJ - MDW
1 stop7h 46mDelta
Sun 9/146:00 amMDW - PUJ
1 stop7h 32mDelta
Deal found 7/29$350
This Expedia deal was found by Cheapflights users on 7/27. 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.
Sat 12/205:47 amPUJ - ORD
Nonstop5h 10mArajet
Sat 1/310:27 amORD - PUJ
Nonstop4h 45mArajet
Deal found 7/27$351
This United Airlines deal was found by Cheapflights users on 7/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1412:10 pmPUJ - ORD
1 stop20h 46mUnited Airlines
Mon 8/189:31 pmORD - PUJ
1 stop14h 09mUnited Airlines
Deal found 7/27$352
This Delta deal was found by Cheapflights users on 7/29. 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.
Fri 9/52:40 pmPUJ - ORD
1 stop8h 57mDelta
Sun 9/147:20 amORD - PUJ
1 stop6h 12mDelta
Deal found 7/29$360
This SmartFares deal was found by Cheapflights users on 7/29. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/205:47 amPUJ - ORD
Nonstop5h 10mWorldTicket
Sat 1/310:27 amORD - PUJ
Nonstop4h 45mWorldTicket
Deal found 7/29$362
This American Airlines deal was found by Cheapflights users on 7/29. 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.
Thu 10/93:21 pmPUJ - ORD
Nonstop5h 15mAmerican Airlines
Wed 10/155:20 amORD - PUJ
1 stop9h 09mAmerican Airlines
Deal found 7/29$367

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 July 29, 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

Thu 8/14

5:45 pm-9:53 pm

Nonstop5h 08m

Chicago O'Hare Intl

Mon 8/18

6:45 am-12:25 pm

Nonstop4h 40m

$275

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 8/27

4:05 pm-11:59 pm

1 stop8h 54m

Chicago O'Hare Intl

Wed 9/3

5:05 am-3:00 pm

1 stop8h 55m

$276

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Tue 8/26

5:05 pm-11:59 pm

1 stop7h 54m

Chicago O'Hare Intl

Mon 9/1

5:05 am-4:00 pm

1 stop9h 55m

$302

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Tue 9/2

10:20 am-11:59 pm

1 stop14h 39m

Chicago O'Hare Intl

Mon 9/15

6:44 pm-11:05 am

1 stop15h 21m

$314

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 8/14

4:05 pm-11:59 pm

1 stop8h 54m

Chicago O'Hare Intl

Mon 8/18

6:45 am-12:25 pm

Nonstop4h 40m

$328

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Tue 8/5

1:48 am-4:04 pm

1 stop15h 16m

Chicago O'Hare Intl

Tue 8/19

5:05 am-4:00 pm

1 stop9h 55m

$347

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 9/5

2:40 pm-9:26 pm

1 stop7h 46m

Chicago Midway

Sun 9/14

6:00 am-2:32 pm

1 stop7h 32m

$350

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 12/20

5:47 am-8:57 am

Nonstop5h 10m

Chicago O'Hare Intl

Sat 1/3

10:27 am-5:12 pm

Nonstop4h 45m

$351

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 8/14

12:10 pm-7:56 am

1 stop20h 46m

Chicago O'Hare Intl

Mon 8/18

9:31 pm-12:40 pm

1 stop14h 09m

$352

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Fri 9/5

2:40 pm-10:37 pm

1 stop8h 57m

Chicago O'Hare Intl

Sun 9/14

7:20 am-2:32 pm

1 stop6h 12m

$360

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Showing 1-10 of 49 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 July 29, 2025.

It’s optimal to fly from Dominican Republic to Chicago in the morning. By choosing this option you can save up to 20% 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 Saturday at noon when fares are most often at their lowest. Tuesday at noon 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 July 29, 2025.

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 (3 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 July 29, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and LATAM 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.
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,977 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
LATAM Airlines
7.5
Good
1,821 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Copa Airlines
7.5
Good
1,493 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,899 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 ($129), Arajet ($132), and Spirit Airlines ($138).

  • 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 (85%), United Airlines (82%) or Frontier (75%) 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 $373, our data shows the cheapest flight currently is $164. When looking at the most popular route, (Santo Domingo Las Americas - Chicago O'Hare Intl), you can expect to pay $305 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
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
Punta Cana to O'Hare Intl flights
Santo Domingo to O'Hare Intl flights
Luis Munoz Marin Intl to St. Louis flights
Christiansted to O'Hare Intl flights
Nassau to O'Hare Intl flights
Montego Bay to O'Hare Intl flights
Santo Domingo to Midway flights
Punta Cana to Midway flights
Aguadilla to O'Hare Intl flights
Port of Spain to O'Hare Intl flights
Nassau to Midway flights
George Town to O'Hare Intl flights
Simpson Bay to O'Hare Intl flights
Oranjestad to O'Hare Intl flights
Willemstad to O'Hare Intl flights
Nassau to St. Louis flights
Santiago de los Caballeros to O'Hare Intl flights
Montego Bay to Midway flights
Bridgetown to O'Hare Intl flights
Saint Thomas Island to O'Hare Intl flights
Simpson Bay to Midway flights
Roseau to O'Hare Intl flights
Oranjestad to St. Louis flights
St. John's to O'Hare Intl flights
St. George's to St. Louis flights
Vieques to O'Hare Intl flights
Saint Thomas Island to St. Louis flights
Port of Spain to St. Louis flights
Port Au Prince to O'Hare Intl flights
Kingston to O'Hare Intl flights
Road Town 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 July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$224Average$421FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$312Average$578FlexibilityNo cancel feeOn-time69%
DeltaCheapest$324Average$507FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$385Average$560FlexibilityNo cancel feeOn-time71%

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