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Dominican Republic

$131+ 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 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PUJ
Feb 28 — Mar 71
Fri 2/28
Fri 3/7
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 February 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$303
(Frontier)

One-way from

$131
(Kiwi.com)

Popular in

March

Cheapest in

April

Average price

$506

Good round-trip deal

$472 or less

Good one-way deal

$197 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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High demand for flights, 1% potential price rise
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Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 23, 2025.

This Frontier deal was found by Cheapflights users on 2/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/239:12 pmMDW - PUJ
1 stop10h 39mFrontier
Thu 5/293:05 pmPUJ - MDW
1 stop9h 50mFrontier
Deal found 2/21$303
This Kiwi.com deal was found by Cheapflights users on 2/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/66:10 amORD - PUJ
Nonstop4h 50mFrontier
Tue 3/115:54 pmPUJ - ORD
Nonstop5h 20mFrontier
Deal found 2/21$304
This CheapOair deal was found by Cheapflights users on 2/21. 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.
Mon 4/285:10 amORD - PUJ
1 stop8h 32mMultiple Airlines
Fri 5/23:07 pmPUJ - ORD
1 stop9h 04mMultiple Airlines
Deal found 2/21$306
This FlightHub deal was found by Cheapflights users on 2/22. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/65:10 amORD - PUJ
1 stop8h 32mSpirit Airlines
Wed 5/144:03 pmPUJ - ORD
1 stop29h 37mSpirit Airlines
Deal found 2/22$307
This American Airlines deal was found by Cheapflights users on 2/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/65:00 amORD - PUJ
1 stop8h 40mAmerican Airlines
Tue 5/133:16 pmPUJ - ORD
Nonstop5h 20mAmerican Airlines
Deal found 2/22$335
This Kiwi.com deal was found by Cheapflights users on 2/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/78:39 amORD - STI
1 stop7h 47mMultiple Airlines
Mon 4/146:46 pmSTI - ORD
2 stops13h 17mMultiple Airlines
Deal found 2/21$340
This Delta deal was found by Cheapflights users on 2/21. 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.
Tue 4/156:04 amMDW - PUJ
1 stop7h 26mDelta
Tue 4/223:55 pmPUJ - MDW
1 stop7h 31mDelta
Deal found 2/21$345
This Delta deal was found by Cheapflights users on 2/20. 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.
Thu 4/106:15 amORD - PUJ
1 stop8h 51mDelta
Tue 4/151:45 pmPUJ - ORD
1 stop10h 11mDelta
Deal found 2/20$355
This Kiwi.com deal was found by Cheapflights users on 2/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/46:44 pmMDW - PUJ
1 stop19h 53mMultiple Airlines
Wed 4/912:39 pmPUJ - MDW
1 stop7h 56mMultiple Airlines
Deal found 2/21$383
This Booking.com deal was found by Cheapflights users on 2/20. 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.
Tue 6/179:01 amORD - SDQ
1 stop27h 49mFrontier
Sun 6/2212:00 pmSDQ - ORD
1 stop29h 53mFrontier
Deal found 2/20$383
This Kiwi.com deal was found by Cheapflights users on 2/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/55:10 amORD - SDQ
1 stop9h 34mMultiple Airlines
Sun 3/91:28 pmSDQ - ORD
1 stop31h 23mMultiple Airlines
Deal found 2/22$384
This FlightHub deal was found by Cheapflights users on 2/22. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/315:10 amORD - SDQ
1 stop9h 39mSpirit Airlines
Sat 4/53:44 pmSDQ - ORD
2 stops18h 00mSpirit Airlines
Deal found 2/22$386

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 February 23, 2025.

Fly from

Chicago

Fly to

Dominican Republic

Route

Depart

Return

Price

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Fri 5/23

9:12 pm-8:51 am

1 stop10h 39m

Punta Cana

Thu 5/29

3:05 pm-11:55 pm

1 stop9h 50m

$303

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Thu 3/6

6:10 am-1:00 pm

Nonstop4h 50m

Punta Cana

Tue 3/11

5:54 pm-10:14 pm

Nonstop5h 20m

$304

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 4/28

5:10 am-2:42 pm

1 stop8h 32m

Punta Cana

Fri 5/2

3:07 pm-11:11 pm

1 stop9h 04m

$306

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 5/6

5:10 am-2:42 pm

1 stop8h 32m

Punta Cana

Wed 5/14

4:03 pm-8:40 pm

1 stop29h 37m

$307

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 5/6

5:00 am-2:40 pm

1 stop8h 40m

Punta Cana

Tue 5/13

3:16 pm-7:36 pm

Nonstop5h 20m

$335

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Mon 4/7

8:39 am-5:26 pm

1 stop7h 47m

Santiago de los Caballeros

Mon 4/14

6:46 pm-7:03 am

2 stops13h 17m

$340

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 4/15

6:04 am-2:30 pm

1 stop7h 26m

Punta Cana

Tue 4/22

3:55 pm-10:26 pm

1 stop7h 31m

$345

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Thu 4/10

6:15 am-4:06 pm

1 stop8h 51m

Punta Cana

Tue 4/15

1:45 pm-10:56 pm

1 stop10h 11m

$355

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Fri 4/4

6:44 pm-3:37 pm

1 stop19h 53m

Punta Cana

Wed 4/9

12:39 pm-7:35 pm

1 stop7h 56m

$383

ChicagoSanto Domingo

ORD - SDQ

ORDSDQ

Chicago O'Hare Intl

Wed 3/5

5:10 am-4:44 pm

1 stop9h 34m

Santo Domingo Las Americas

Sun 3/9

1:28 pm-7:51 pm

1 stop31h 23m

$384

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

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 $623). 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 February 23, 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 February 23, 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 February 23, 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
8.1
Very good
4,396 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.6

Comfort

8.1

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,396 reviews
Southwest
8.1
Very good
4,396 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.6

Comfort

8.1

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,203 reviews
Southwest
8.1
Very good
4,396 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.6

Comfort

8.1

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Copa Airlines
7.6
Good
1,500 reviews
Southwest
8.1
Very good
4,396 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.6

Comfort

8.1

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Aeromexico
7.5
Good
1,767 reviews
Southwest
8.1
Very good
4,396 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.6

Comfort

8.1

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,754 reviews
Southwest
8.1
Very good
4,396 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.6

Comfort

8.1

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 ($132), Spirit Airlines ($133), and United Airlines ($156).

  • 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 (87%), Frontier (82%), United Airlines( 58%).

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

    The cheapest flight price from Chicago to Dominican Republic is $96. On average you can expect to pay $888. The most popular route, (Chicago O'Hare Intl - Punta Cana), can usually be booked for $245.

  • 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 $623). 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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O'Hare Intl to Nassau flights
Midway to Punta Cana flights
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O'Hare Intl to Providenciales flights
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Midway to Saint Thomas Island flights
O'Hare Intl to Christiansted flights
O'Hare Intl to Castries flights
Midway to Oranjestad flights
Midway to Nassau flights
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Midway to George Town flights
O'Hare Intl to Puerto Plata flights
St. Louis to Simpson Bay flights
O'Hare Intl to Bridgetown flights
St. Louis to Montego Bay flights
St. Louis to George Town flights
Midway to Santo Domingo flights
O'Hare Intl to Kingston flights
O'Hare Intl to Basseterre flights
Midway to Simpson Bay flights
Midway to Providenciales flights
St. Louis to Oranjestad flights
St. Louis to Nassau flights
St. Louis to Providenciales flights
St. Louis to Christiansted flights
O'Hare Intl to Santiago de los Caballeros flights
O'Hare Intl to St. John's flights
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St. Louis to Castries flights
St. Louis to Willemstad flights
O'Hare Intl to Marsh Harbour flights
O'Hare Intl to St. George's flights
O'Hare Intl to Georgetown flights
O'Hare Intl to Castries flights
Evansville to Luis Munoz Marin Intl flights
O'Hare Intl to Gregory Town flights
St. Louis to Marsh Harbour 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 February 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$204Average$508FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$226Average$600FlexibilityNo cancel feeOn-time69%
Copa AirlinesCheapest$226Average$524FlexibilityNo cancel feeOn-time70%
Spirit AirlinesCheapest$233Average$349FlexibilityNo cancel feeOn-time65%
DeltaCheapest$334Average$650FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$335Average$861FlexibilityNo cancel feeOn-time67%
JetBlueCheapest$343Average$557FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$377Average$644FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$671Average$876FlexibilityNo cancel feeOn-time63%
AviancaCheapest$1,422Average$1,422FlexibilityNo cancel feeOn-time71%
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