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Dominican Republic

$108+ Cheap flights from Chicago (CHI) to the Dominican Republic

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 1/31. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PUJ
ene. 26 — feb. 21
dom. 1/26
dom. 2/2
1 adult, Economy
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Cheap flight deals from Chicago to Dominican Republic

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Dominican Republic (DO0). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated enero 21, 2025.

Round-trip from

$294
(Booking.com)

One-way from

$108
(Frontier)

Good round-trip deal

$415 or less

Good one-way deal

$185 or less
From Chicago (CHI) to Dominican Republic
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One-way flight from Chicago (CHI) to Dominican Republic
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Price to beat on a round-trip flight from Chicago (CHI) to Dominican Republic.
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Price to beat on a one-way flight from Chicago (CHI) to Dominican Republic.
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Find flight deals from Chicago to Dominican Republic

Cheapest flights from Chicago to Dominican Republic
Explore the most affordable flight options available from Chicago to Dominican Republic. Find the lowest fares from popular airlines and budget airlines, with prices last updated on enero 21, 2025.

This Booking.com deal was found by Cheapflights users on 1/20. 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.
mar. 4/12:36 pmMDW - PUJ
1 stop18h 42mFrontier
lun. 4/72:49 pmPUJ - MDW
1 stop10h 01mFrontier
Deal found 1/20$294
This Kiwi.com deal was found by Cheapflights users on 1/20. 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.
vie. 2/78:12 pmORD - PUJ
1 stop12h 58mMultiple Airlines
jue. 2/202:29 pmPUJ - ORD
1 stop10h 51mMultiple Airlines
Deal found 1/20$295
This CheapOair deal was found by Cheapflights users on 1/21. 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.
lun. 2/247:10 amORD - PUJ
1 stop6h 33mSpirit Airlines
jue. 2/274:48 pmPUJ - ORD
1 stop19h 52mSpirit Airlines
Deal found 1/21$306
This FlightHub deal was found by Cheapflights users on 1/20. 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.
vie. 2/215:46 pmORD - PUJ
1 stop14h 54mFrontier
vie. 2/283:10 pmPUJ - ORD
1 stop18h 08mFrontier
Deal found 1/20$321
This American Airlines deal was found by Cheapflights users on 1/21. 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.
lun. 2/248:05 amORD - PUJ
Nonstop4h 35mAmerican Airlines
jue. 2/2712:55 pmPUJ - ORD
1 stop12h 58mAmerican Airlines
Deal found 1/21$350
This Delta deal was found by Cheapflights users on 1/21. 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.
mar. 2/256:00 amMDW - PUJ
1 stop7h 25mDelta
vie. 2/282:00 pmPUJ - MDW
1 stop10h 20mDelta
Deal found 1/21$355
This Delta deal was found by Cheapflights users on 1/20. 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.
sáb. 2/225:45 amORD - PUJ
1 stop8h 57mDelta
mar. 3/44:50 pmPUJ - ORD
1 stop8h 59mDelta
Deal found 1/20$365
This Kissandfly.com deal was found by Cheapflights users on 1/20. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 1/276:00 amMDW - PUJ
1 stop7h 25mKLM
mié. 2/54:50 pmPUJ - MDW
1 stop7h 30mKLM
Deal found 1/20$378
This United Airlines deal was found by Cheapflights users on 1/19. 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.
mar. 2/410:43 amORD - PUJ
Nonstop4h 28mUnited Airlines
vie. 2/72:50 pmPUJ - ORD
Nonstop5h 10mUnited Airlines
Deal found 1/19$380
This Kiwi.com deal was found by Cheapflights users on 1/20. 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.
dom. 2/23:56 pmORD - STI
2 stops23h 33mMultiple Airlines
vie. 2/1410:59 amSTI - ORD
1 stop13h 04mMultiple Airlines
Deal found 1/20$386
This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
vie. 1/246:06 pmORD - SDQ
2 stops41h 20mMultiple Airlines
lun. 1/2712:51 pmSDQ - ORD
1 stop9h 22mMultiple Airlines
Deal found 1/19$388
This Gotogate deal was found by Cheapflights users on 1/19. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 2/267:18 pmORD - SDQ
1 stop17h 22mFrontier
lun. 3/32:36 pmSDQ - ORD
2 stops27h 55mFrontier
Deal found 1/19$391

Find flights from Chicago to Dominican Republic within your budget

Customize your flight search to find flights from Chicago to Dominican Republic 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 enero 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

mar. 4/1

2:36 pm-10:18 am

1 stop18h 42m

Punta Cana

lun. 4/7

2:49 pm-11:50 pm

1 stop10h 01m

$294

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

vie. 2/7

8:12 pm-11:10 am

1 stop12h 58m

Punta Cana

jue. 2/20

2:29 pm-11:20 pm

1 stop10h 51m

$295

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

lun. 2/24

7:10 am-3:43 pm

1 stop6h 33m

Punta Cana

vie. 2/28

4:48 pm-11:58 pm

1 stop9h 10m

$306

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

vie. 2/21

5:46 pm-10:40 am

1 stop14h 54m

Punta Cana

vie. 2/28

3:10 pm-7:18 am

1 stop18h 08m

$321

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

lun. 2/24

8:05 am-2:40 pm

Nonstop4h 35m

Punta Cana

jue. 2/27

12:55 pm-11:53 pm

1 stop12h 58m

$350

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

mar. 2/25

6:00 am-3:25 pm

1 stop7h 25m

Punta Cana

jue. 2/27

4:50 pm-10:20 pm

1 stop7h 30m

$355

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

sáb. 2/22

5:45 am-4:42 pm

1 stop8h 57m

Punta Cana

mar. 3/4

4:50 pm-11:49 pm

1 stop8h 59m

$365

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

mar. 2/4

10:43 am-5:11 pm

Nonstop4h 28m

Punta Cana

vie. 2/7

2:50 pm-6:00 pm

Nonstop5h 10m

$380

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

dom. 2/2

3:56 pm-5:29 pm

2 stops23h 33m

Santiago de los Caballeros

vie. 2/14

10:59 am-10:03 pm

1 stop13h 04m

$386

ChicagoSanto Domingo

ORD - SDQ

ORDSDQ

Chicago O'Hare Intl

vie. 1/31

6:06 pm-12:55 pm

1 stop16h 49m

Santo Domingo Las Americas

jue. 2/20

4:31 pm-10:03 pm

1 stop7h 32m

$388

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 60 results
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Best time to book a flight from Chicago to Dominican Republic

Have a flexible travel schedule? Discover the best time to fly to Dominican Republic from Chicago 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.

Travel insights for flights from Chicago to Dominican Republic

Get recent, data-driven insights about flights from Chicago to Dominican Republic including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Chicago to Dominican Republic?

Currently, January is the cheapest month in which you can book a flight from Chicago to Dominican Republic (average of $443). Flying from Chicago to Dominican Republic in March is currently the most expensive (average of $630). 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 CHI to DO?

Find hourly flight availability from Chicago to Dominican Republic. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated enero 21, 2025.

When flying from Chicago to Dominican Republic, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Chicago to Dominican Republic

Explore weekly flight availability from Chicago to Dominican Republic. 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 enero 21, 2025.

The most flights from CHI to DO0 are scheduled on a Saturday (5 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 Dominican Republic by month

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

In terms of precipitation, rainfall in Dominican Republic ranges from 2.1 - 6.0 inches per month. October is typically the wettest month, when rainfall can reach 6.0 in. February is typically the driest time to visit Dominican Republic when rainfall is around 2.1 in.

Temperature in Dominican Republic by month

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

If weather is an important factor for your trip to Dominican Republic, 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 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Dominican Republic

Get insights into the airlines that provide service to Dominican Republic. 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 Dominican Republic. Reviews last updated enero 21, 2025.
Peruse reviews from past customers who have flown with Frontier, Delta and United Airlines from Chicago to Dominican Republic to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,662 reviews

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

KLM
7.8
Good
1,341 reviews
Southwest
8.1
Very good
4,662 reviews

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Copa Airlines
7.7
Good
1,662 reviews
Southwest
8.1
Very good
4,662 reviews

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Aeromexico
7.5
Good
1,849 reviews
Southwest
8.1
Very good
4,662 reviews

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Dominican Republic. 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 Chicago to Dominican Republic one-way?

    The cheapest airlines for a one-way flight from Chicago to Dominican Republic are Frontier ($108), Spirit Airlines ($118), and United Airlines ($161).

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

    While some choose either Chicago Midway - Punta Cana or Chicago O'Hare Intl - Santo Domingo Las Americas, Chicago O'Hare Intl - Punta Cana is the most popular route from Chicago to Dominican Republic.

  • What are the most reliable airlines from Chicago to Dominican Republic?

    Before booking your flight to Dominican Republic from Chicago, check out the most reliable airlines to get you to your destination on time: American Airlines (90%), Frontier (75%), United Airlines( 47%).

  • What are the cheapest flights from Chicago to Dominican Republic?

    The cheapest flight price from Chicago to Dominican Republic is $106. On average you can expect to pay $656. The most popular route, (Chicago O'Hare Intl - Punta Cana), can usually be booked for $259.

  • Can I find deals for flights from Chicago to Dominican Republic that include hotel bookings?

    Yes. In addition to deals on Chicago to Dominican Republic flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Dominican Republic?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Dominican Republic.

  • Can I find deals for business class flights from Chicago to Dominican Republic?

    Yes. Cheapflights offers flight deals from Chicago to Dominican Republic 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 Chicago to Dominican Republic?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Dominican Republic (average of $443). Flying from Chicago to Dominican Republic in March is currently the most expensive (average of $630). 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

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Alternative routes for Chicago to Dominican Republic

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Luis Munoz Marin Intl flights
O'Hare Intl to Punta Cana flights
O'Hare Intl to Montego Bay flights
Midway to Luis Munoz Marin Intl flights
O'Hare Intl to Nassau flights
O'Hare Intl to Oranjestad flights
Midway to Punta Cana flights
O'Hare Intl to Saint Thomas Island flights
Midway to Montego Bay flights
O'Hare Intl to George Town flights
O'Hare Intl to Castries flights
O'Hare Intl to Simpson Bay flights
St. Louis to Luis Munoz Marin Intl flights
Midway to Saint Thomas Island flights
O'Hare Intl to Providenciales flights
Midway to Nassau flights
Midway to Oranjestad flights
O'Hare Intl to Santo Domingo flights
O'Hare Intl to Willemstad flights
O'Hare Intl to Christiansted flights
St. Louis to Punta Cana flights
O'Hare Intl to Bridgetown flights
Midway to Providenciales flights
O'Hare Intl to Castries flights
Midway to Simpson Bay flights
Midway to Santo Domingo flights
St. Louis to Montego Bay flights
O'Hare Intl to St. John's flights
St. Louis to Nassau flights
Midway to George Town flights
St. Louis to Saint Thomas Island flights
O'Hare Intl to Puerto Plata flights
St. Louis to Oranjestad flights
O'Hare Intl to Santiago de los Caballeros flights
St. Louis to Castries flights
O'Hare Intl to Kingston flights
St. Louis to George Town flights
O'Hare Intl to Basseterre flights
St. Louis to Providenciales flights
O'Hare Intl to Road Town flights
O'Hare Intl to Georgetown flights
O'Hare Intl to Freeport flights
Midway to Castries flights
St. Louis to Christiansted flights
O'Hare Intl to St. George's flights
O'Hare Intl to Marsh Harbour flights
St. Louis to Simpson Bay flights
O'Hare Intl to Port of Spain flights
O'Hare Intl to Gregory Town flights

Top 10 airlines flying from Chicago to Dominican Republic

Discover the top 10 airlines that operate flights from Chicago to Dominican Republic. 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 enero 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$203Average$505FlexibilityNo cancel feeOn-time62%
Copa AirlinesCheapest$226Average$518FlexibilityNo cancel feeOn-time70%
Spirit AirlinesCheapest$233Average$370FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$318Average$603FlexibilityNo cancel feeOn-time69%
DeltaCheapest$331Average$659FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$335Average$700FlexibilityNo cancel feeOn-time67%
JetBlueCheapest$343Average$573FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$353Average$636FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$671Average$878FlexibilityNo cancel feeOn-time63%
AviancaCheapest$1,422Average$1,422FlexibilityNo cancel feeOn-time71%
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