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$154+ 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 4/21. Fares are subject to change and may not be available on all flights or dates of travel.
PUJ — CHI
feb. 25 — mar. 41
mar. 2/25
mar. 3/4
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 febrero 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$210
(Kiwi.com)

One-way from

$154
(Mytrip)

Popular in

June

Cheapest in

May

Average price

$459

Good round-trip deal

$315 or less

Good one-way deal

$281 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. 5% potential increase in price ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($15 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 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 febrero 20, 2025.

This Kiwi.com deal was found by Cheapflights users on 2/19. 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.
mar. 4/225:50 pmPUJ - ORD
Nonstop5h 18mFrontier
lun. 4/286:20 amORD - PUJ
Nonstop4h 36mFrontier
Deal found 2/19$210
This Priceline deal was found by Cheapflights users on 2/19. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/225:50 pmPUJ - ORD
Nonstop5h 18mMultiple Airlines
lun. 4/285:10 amORD - PUJ
1 stop8h 32mMultiple Airlines
Deal found 2/19$266
This OneTravel deal was found by Cheapflights users on 2/18. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/11:14 pmPUJ - ORD
1 stop25h 34mSpirit Airlines
mar. 4/89:08 pmORD - PUJ
1 stop13h 36mSpirit Airlines
Deal found 2/18$298
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/13:07 pmPUJ - MDW
1 stop9h 32mFrontier
lun. 5/56:15 amMDW - PUJ
2 stops10h 23mFrontier
Deal found 2/20$299
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/88:00 amSDQ - MDW
2 stops16h 39mFrontier
lun. 5/126:15 amMDW - SDQ
2 stops16h 40mFrontier
Deal found 2/20$352
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 4/61:44 pmSDQ - ORD
1 stop20h 22mMultiple Airlines
dom. 4/137:49 pmORD - SDQ
1 stop19h 00mMultiple Airlines
Deal found 2/20$358
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/88:00 amSDQ - ORD
2 stops16h 11mFrontier
lun. 5/126:40 amORD - SDQ
2 stops16h 15mFrontier
Deal found 2/20$377
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 4/114:44 pmSDQ - ORD
1 stop17h 40mSpirit Airlines
lun. 4/145:10 amORD - SDQ
1 stop9h 39mSpirit Airlines
Deal found 2/20$430
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.
jue. 3/137:16 amSDQ - ORD
2 stops14h 28mDelta
lun. 3/177:35 amORD - SDQ
1 stop9h 41mDelta
Deal found 2/20$450
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.
vie. 5/22:43 pmSDQ - MDW
1 stop8h 43mDelta
mar. 5/66:04 amMDW - SDQ
2 stops11h 15mDelta
Deal found 2/20$450
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 3/52:30 amSDQ - ORD
1 stop10h 29mJetBlue
mié. 3/1211:44 amORD - SDQ
1 stop14h 08mJetBlue
Deal found 2/20$454
This Copa Airlines deal was found by Cheapflights users on 2/18. 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.
vie. 10/31:56 pmPUJ - ORD
1 stop11h 26mCopa Airlines
mié. 10/83:07 pmORD - PUJ
1 stop19h 34mCopa Airlines
Deal found 2/18$460

Find flights from Dominican Republic to Chicago within your budget

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 febrero 20, 2025.

Fly from

Dominican Republic

Fly to

Chicago

Route

Depart

Return

Price

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

mar. 4/22

5:50 pm-10:08 pm

Nonstop5h 18m

Chicago O'Hare Intl

lun. 4/28

6:20 am-11:56 am

Nonstop4h 36m

$210

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

mar. 4/22

5:50 pm-10:08 pm

Nonstop5h 18m

Chicago O'Hare Intl

lun. 4/28

5:10 am-2:42 pm

1 stop8h 32m

$266

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

mar. 4/1

1:14 pm-1:48 pm

1 stop25h 34m

Chicago O'Hare Intl

mar. 4/8

9:08 pm-11:44 am

1 stop13h 36m

$298

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

jue. 5/1

3:07 pm-11:39 pm

1 stop9h 32m

Chicago Midway

lun. 5/5

6:15 am-5:38 pm

2 stops10h 23m

$299

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

jue. 5/8

8:00 am-11:39 pm

2 stops16h 39m

Chicago Midway

lun. 5/12

6:15 am-11:55 pm

2 stops16h 40m

$352

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

dom. 4/6

1:44 pm-9:06 am

1 stop20h 22m

Chicago O'Hare Intl

dom. 4/13

7:49 pm-3:49 pm

1 stop19h 00m

$358

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

jue. 5/8

8:00 am-11:11 pm

2 stops16h 11m

Chicago O'Hare Intl

lun. 5/12

6:40 am-11:55 pm

2 stops16h 15m

$377

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

vie. 4/11

4:44 pm-9:24 am

1 stop17h 40m

Chicago O'Hare Intl

lun. 4/14

5:10 am-3:49 pm

1 stop9h 39m

$430

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

jue. 3/13

7:16 am-8:44 pm

2 stops14h 28m

Chicago O'Hare Intl

lun. 3/17

7:35 am-6:16 pm

1 stop9h 41m

$450

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

vie. 5/2

2:43 pm-10:26 pm

1 stop8h 43m

Chicago Midway

mar. 5/6

6:04 am-6:19 pm

2 stops11h 15m

$450

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 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.

Travel insights for flights from Dominican Republic to Chicago

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

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 febrero 20, 2025.

It’s optimal to fly from Dominican Republic to Chicago in the morning. By choosing this option you can save up to 27% 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 Wednesday mornings when fares are most often at their lowest. Monday mornings 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 febrero 20, 2025.

The most flights from DO0 to CHI are scheduled on a Monday (3 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 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 febrero 20, 2025.
See what other customers who have flown with Southwest, Delta and Air Transat 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.
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

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
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

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
8,219 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

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.

Air Transat
7.8
Good
380 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

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
1,510 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

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.

LATAM Airlines
7.5
Good
1,795 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

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 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 ($154), Spirit Airlines ($166), and American Airlines ($188).

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

    Most travelers choose Punta Cana - Chicago O'Hare Intl, Santo Domingo Las Americas - 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 (76%), Frontier (76%) or United Airlines (66%) 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 $673, our data shows the cheapest flight currently is $117. When looking at the most popular route, (Punta Cana - Chicago O'Hare Intl), you can expect to pay $265 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
New Buffalo
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.
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Aguadilla to Midway flights

Top 5 airlines flying from Dominican Republic to Chicago

Discover the top 5 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 febrero 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$190Average$373FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$312Average$430FlexibilityNo cancel feeOn-time69%
DeltaCheapest$313Average$507FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$347Average$596FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$400Average$568FlexibilityNo cancel feeOn-time70%
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