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Dominican Republic

$104+ 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 5/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PUJ
may. 6 — may. 131
mar. 5/6
mar. 5/13
1 adult, Economy
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Cheap flight deals from Chicago to Dominican Republic

Keep the following information in mind while searching for Chicago to Dominican Republic flight deals. Data was last updated mayo 1, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$283
(CheapOair)

One-way from

$104
(Frontier)

Popular in

March

Cheapest in

May

Average price

$479

Good round-trip deal

$424 or less

Good one-way deal

$166 or less
Provider with most accurate pricing for Chicago (CHI)-Punta Cana flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Punta Cana flights.
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From Chicago (CHI) to Dominican Republic
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One-way flight from Chicago (CHI) to Dominican Republic
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Highest demand for flights based on searches. 2% potential increase in price ($16 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in May 2025
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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 mayo 1, 2025.

This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 5/46:10 amORD - PUJ
Nonstop4h 41mMultiple Airlines
vie. 5/912:42 pmPUJ - ORD
1 stop11h 47mMultiple Airlines
Deal found 4/30$285
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/306:45 amORD - PUJ
Nonstop4h 41mFrontier
mar. 6/35:54 pmPUJ - ORD
Nonstop5h 11mFrontier
Deal found 4/29$289
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 5/115:00 amORD - PUJ
1 stop9h 49mAmerican Airlines
jue. 5/153:16 pmPUJ - ORD
Nonstop5h 20mAmerican Airlines
Deal found 4/30$295
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.
mar. 5/205:05 amORD - PUJ
1 stop8h 12mSpirit Airlines
sáb. 5/2412:42 pmPUJ - ORD
1 stop8h 21mSpirit Airlines
Deal found 4/30$298
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 6/245:01 amORD - SDQ
1 stop18h 18mFrontier
mié. 6/256:41 pmSDQ - ORD
2 stops29h 47mFrontier
Deal found 4/29$329
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.
lun. 8/116:00 amMDW - PUJ
1 stop6h 17mDelta
vie. 8/151:10 pmPUJ - MDW
1 stop9h 37mDelta
Deal found 4/30$335
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 6/25:05 amORD - SDQ
1 stop9h 40mSpirit Airlines
lun. 6/94:50 pmSDQ - ORD
1 stop17h 00mSpirit Airlines
Deal found 4/29$341
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.
sáb. 5/35:20 amORD - PUJ
1 stop9h 12mDelta
jue. 5/82:47 pmPUJ - ORD
1 stop7h 33mDelta
Deal found 4/29$345
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/98:24 pmORD - SDQ
1 stop14h 24mMultiple Airlines
sáb. 5/243:50 pmSDQ - ORD
1 stop9h 15mMultiple Airlines
Deal found 4/29$390
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.
dom. 8/106:00 amORD - STI
1 stop13h 48mAmerican Airlines
sáb. 8/161:31 pmSTI - ORD
1 stop11h 26mAmerican Airlines
Deal found 4/29$393
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.
lun. 6/99:12 pmMDW - PUJ
2 stops14h 43mMultiple Airlines
jue. 6/1210:06 amPUJ - MDW
1 stop11h 11mMultiple Airlines
Deal found 4/30$394
This Copa Airlines deal was found by Cheapflights users on 4/28. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 6/27:54 amORD - SDQ
1 stop17h 51mCopa Airlines
jue. 6/55:21 amSDQ - ORD
1 stop20h 13mCopa Airlines
Deal found 4/28$395

Cheapflights Fare Finder

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 mayo 1, 2025.
Use the filters below to find and compare flights from Chicago to the Dominican Republic that are best for you.

Fly from

Chicago

Fly to

Dominican Republic

Route

Depart

Return

Price

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

dom. 5/4

6:10 am-11:51 am

Nonstop4h 41m

Punta Cana

vie. 5/9

12:42 pm-11:29 pm

1 stop11h 47m

$285

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

vie. 5/30

6:45 am-12:26 pm

Nonstop4h 41m

Punta Cana

mar. 6/3

5:54 pm-10:05 pm

Nonstop5h 11m

$289

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

dom. 5/11

5:00 am-3:49 pm

1 stop9h 49m

Punta Cana

jue. 5/15

3:16 pm-7:36 pm

Nonstop5h 20m

$295

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

mar. 5/20

5:05 am-2:17 pm

1 stop8h 12m

Punta Cana

sáb. 5/24

12:42 pm-8:03 pm

1 stop8h 21m

$298

ChicagoSanto Domingo

ORD - SDQ

ORDSDQ

Chicago O'Hare Intl

mar. 6/24

5:01 am-12:19 am

1 stop18h 18m

Santo Domingo Las Americas

mié. 6/25

6:41 pm-11:28 pm

2 stops29h 47m

$329

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

lun. 8/11

6:00 am-1:17 pm

1 stop6h 17m

Punta Cana

vie. 8/15

1:10 pm-9:47 pm

1 stop9h 37m

$335

ChicagoSanto Domingo

ORD - SDQ

ORDSDQ

Chicago O'Hare Intl

lun. 6/2

5:05 am-3:45 pm

1 stop9h 40m

Santo Domingo Las Americas

lun. 6/9

4:50 pm-8:50 am

1 stop17h 00m

$341

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

sáb. 5/3

5:20 am-3:32 pm

1 stop9h 12m

Punta Cana

jue. 5/8

2:47 pm-9:20 pm

1 stop7h 33m

$345

ChicagoSanto Domingo

ORD - SDQ

ORDSDQ

Chicago O'Hare Intl

vie. 5/9

8:24 pm-11:48 am

1 stop14h 24m

Santo Domingo Las Americas

sáb. 5/24

3:50 pm-12:05 am

1 stop9h 15m

$390

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

dom. 8/10

6:00 am-8:48 pm

1 stop13h 48m

Santiago de los Caballeros

sáb. 8/16

1:31 pm-11:57 pm

1 stop11h 26m

$393

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 58 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.

Cheapflights Insights

Everything you need to know about your flight from Chicago to the Dominican Republic

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 June is currently the most expensive (average of $598). 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 mayo 1, 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.

What is the cheapest day to fly from Chicago to Dominican Republic?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Dominican Republic. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Dominican Republic flight should consider departing on Tuesday mornings when fares are most often at their lowest. Saturday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 mayo 1, 2025.

The most flights from CHI to DO0 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 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 mayo 1, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and Copa 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
8.0
Very good
4,294 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Copa Airlines
7.5
Good
1,414 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Aeromexico
7.5
Good
1,698 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,696 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 ($104), Southwest ($116), and United Airlines ($116).

  • 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: Frontier (84%), American Airlines (79%), United Airlines( 77%).

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

    The cheapest flight price from Chicago to Dominican Republic is $101. On average you can expect to pay $695. The most popular route, (Chicago O'Hare Intl - Punta Cana), can usually be booked for $223.

  • 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 June is currently the most expensive (average of $598). 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
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Midway to Montego Bay flights
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St. Louis to Nassau flights
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Midway to Nassau flights
O'Hare Intl to Santiago de los Caballeros flights
Midway to Providenciales flights
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Midway to Santo Domingo flights
St. Louis to Castries flights
Midway to George Town flights
O'Hare Intl to Road Town flights
O'Hare Intl to St. John's flights
Midway to Santiago de los Caballeros flights
St. Louis to Providenciales flights
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O'Hare Intl to Ponce flights
St. Louis to Simpson Bay flights
Midway to Kingston flights
O'Hare Intl to Castries flights
St. Louis to Willemstad flights
O'Hare Intl to The Valley flights
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St. Louis to George Town flights
O'Hare Intl to Havana flights
O'Hare Intl to Port of Spain flights
St. Louis to Christiansted 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 mayo 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$193Average$542FlexibilityNo cancel feeOn-time70%
FrontierCheapest$222Average$506FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$226Average$640FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$249Average$362FlexibilityNo cancel feeOn-time65%
DeltaCheapest$334Average$628FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$335Average$861FlexibilityNo cancel feeOn-time67%
JetBlueCheapest$343Average$529FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$345Average$644FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$671Average$868FlexibilityNo cancel feeOn-time63%
AviancaCheapest$1,422Average$1,422FlexibilityNo cancel feeOn-time71%

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