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Cheap flights from Chicago to the Dominican Republic from $116

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to the Dominican Republic departing on 1/7. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago to the Dominican Republic

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
7:10 am - 1:47 pmORD-PUJ
4h 37mnonstop
Multiple Airlines Logo
6:08 pm - 12:30 amPUJ-ORD
8h 22m1 stop
$249Multiple Airlines
Find Deal
Tue, Dec 16 - Tue, Dec 23
Spirit Airlines Logo
8:43 pm - 3:35 pmORD-SDQ
16h 52m1 stop
Spirit Airlines Logo
4:37 pm - 12:18 amSDQ-ORD
9h 41m1 stop
$250Spirit Airlines
Find Deal
Thu, Feb 5 - Wed, Feb 18
Arajet Logo
11:27 am - 5:12 pmORD-PUJ
4h 45mnonstop
Arajet Logo
5:47 am - 9:57 amPUJ-ORD
5h 10mnonstop
$251Arajet
Find Deal
Sat, May 2 - Sat, May 9
Frontier Logo
7:10 am - 1:47 pmORD-PUJ
4h 37mnonstop
Frontier Logo
6:49 pm - 9:59 pmPUJ-ORD
5h 10mnonstop
$252Frontier
Find Deal
Mon, Dec 15 - Mon, Dec 22
Arajet Logo
11:27 am - 5:12 pmORD-PUJ
4h 45mnonstop
Arajet Logo
5:47 am - 9:57 amPUJ-ORD
5h 10mnonstop
$254Arajet
Find Deal
Sat, Apr 11 - Sat, Apr 18
Frontier Logo
6:00 am - 2:56 pmMDW-PUJ
6h 56m1 stop
Frontier Logo
4:11 pm - 11:25 pmPUJ-MDW
9h 14m1 stop
$328Frontier
Find Deal
Sat, Feb 14 - Sat, Feb 21
Delta Logo
5:30 am - 3:53 pmORD-POP
8h 23m1 stop
Delta Logo
5:08 pm - 11:59 pmPOP-ORD
8h 51m1 stop
$388Delta
Find Deal
Thu, Jan 8 - Mon, Jan 12
Delta Logo
6:00 am - 2:21 pmMDW-SDQ
6h 21m1 stop
Delta Logo
3:46 pm - 10:22 pmSDQ-MDW
8h 36m1 stop
$390Delta
Find Deal
Thu, Feb 5 - Fri, Feb 6
American Airlines Logo
8:50 pm - 2:32 pmORD-POP
15h 42m2 stops
American Airlines Logo
4:36 pm - 11:06 pmPOP-ORD
8h 30m1 stop
$392American Airlines
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Sat, Feb 7 - Sat, Feb 14
American Airlines Logo
6:05 am - 2:32 pmORD-POP
6h 27m1 stop
American Airlines Logo
4:42 pm - 11:06 amPOP-ORD
20h 24m1 stop
$397American Airlines
Find Deal
Thu, Jan 8 - Mon, Jan 12

Arajet flights from Chicago to Dominican Republic

Our best Arajet deals on Chicago to Dominican Republic flight tickets
Arajet
May 2
ORD11:27 amChicago O'Hare Intl
4h 45m
PUJ5:12 pmPunta Cana
May 9
PUJ5:47 amPunta Cana
5h 10m
ORD9:57 amChicago O'Hare Intl
$251
Find similar
Arajet
Apr 11
ORD11:27 amChicago O'Hare Intl
4h 45m
PUJ5:12 pmPunta Cana
Apr 18
PUJ5:47 amPunta Cana
5h 10m
ORD9:57 amChicago O'Hare Intl
$254
Find similar
Arajet
Mar 7
ORD10:27 amChicago O'Hare Intl
4h 45m
PUJ5:12 pmPunta Cana
Mar 10
PUJ7:30 pmPunta Cana
5h 10m
ORD11:40 pmChicago O'Hare Intl
$255
Find similar

Frontier flights from Chicago to Dominican Republic

Our best Frontier deals on Chicago to Dominican Republic flight tickets
Frontier
Dec 15
ORD7:10 amChicago O'Hare Intl
4h 37m
PUJ1:47 pmPunta Cana
Dec 22
PUJ6:49 pmPunta Cana
5h 10m
ORD9:59 pmChicago O'Hare Intl
$252
Find similar
Frontier
Dec 6
ORD7:10 amChicago O'Hare Intl
4h 37m
PUJ1:47 pmPunta Cana
Dec 12
PUJ6:50 pmPunta Cana
5h 10m
ORD10:00 pmChicago O'Hare Intl
$266
Find similar
Frontier
Dec 14
ORD7:10 amChicago O'Hare Intl
4h 37m
PUJ1:47 pmPunta Cana
Dec 21
PUJ6:49 pmPunta Cana
5h 10m
ORD9:59 pmChicago O'Hare Intl
$269
Find similar

momondo 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, momondo users made 832,500 searches. Data last updated December 3, 2025.
Use the filters below to find and compare flights from Chicago to the Dominican Republic that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 12/16

7:10 am-1:47 pm

Nonstop4h 37m

Punta Cana

Tue 12/23

6:08 pm-12:30 am

1 stop8h 22m

$249

ChicagoSanto Domingo

ORD - SDQ

ORDSDQ

Chicago O'Hare Intl

Thu 2/5

8:43 pm-3:35 pm

1 stop16h 52m

Santo Domingo Las Americas

Wed 2/18

4:37 pm-12:18 am

1 stop9h 41m

$250

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 5/2

11:27 am-5:12 pm

Nonstop4h 45m

Punta Cana

Sat 5/9

5:47 am-9:57 am

Nonstop5h 10m

$251

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 12/15

7:10 am-1:47 pm

Nonstop4h 37m

Punta Cana

Mon 12/22

6:49 pm-9:59 pm

Nonstop5h 10m

$252

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 4/11

11:27 am-5:12 pm

Nonstop4h 45m

Punta Cana

Sat 4/18

5:47 am-9:57 am

Nonstop5h 10m

$254

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 2/14

6:00 am-2:56 pm

1 stop6h 56m

Punta Cana

Sat 2/21

4:11 pm-11:25 pm

1 stop9h 14m

$328

ChicagoPuerto Plata

ORD - POP

ORDPOP

Chicago O'Hare Intl

Thu 1/8

5:30 am-3:53 pm

1 stop8h 23m

Puerto Plata La Union

Mon 1/12

5:08 pm-11:59 pm

1 stop8h 51m

$388

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Thu 2/5

6:00 am-2:21 pm

1 stop6h 21m

Santo Domingo Las Americas

Fri 2/6

3:46 pm-10:22 pm

1 stop8h 36m

$390

ChicagoPuerto Plata

ORD - POP

ORDPOP

Chicago O'Hare Intl

Sat 2/7

8:50 pm-2:32 pm

2 stops15h 42m

Puerto Plata La Union

Sat 2/14

4:36 pm-11:06 pm

1 stop8h 30m

$392

ChicagoPuerto Plata

ORD - POP

ORDPOP

Chicago O'Hare Intl

Thu 1/8

6:05 am-2:32 pm

1 stop6h 27m

Puerto Plata La Union

Mon 1/12

4:42 pm-11:06 am

1 stop20h 24m

$397

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to the Dominican Republic from

How to get the cheapest flight ticket from Chicago to Dominican Republic

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Dominican Republic?

In general, August is the cheapest month to fly from Chicago to Dominican Republic. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $459. If you are unable to visit Dominican Republic during the month of August, then departing from Chicago during the month January is also very affordable. Most momondo users find prices during this month for around $467.

What is the cheapest day to depart on your flight to Dominican Republic?

The cheapest day to depart on your flight to Dominican Republic is on a Monday when prices can be found for as low as $492. This is often the case because there is less demand to fly during this day of the week. Flights from Chicago to Dominican Republic on a Thursday will generally be more expensive and average around $546. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Dominican Republic?

Flying to Dominican Republic from Chicago at noon is the least expensive time of day to depart. momondo users have found prices as low as $321 when looking at flights departing at noon. Flights in the morning are often more expensive with an average ticket price of $522.

What is the cheapest Chicago to Dominican Republic flight route?

Fly from Chicago O'Hare Intl to Punta Cana for the best Chicago - Dominican Republic flight prices

How far in advance should I book a flight to Dominican Republic?

You are more likely to see cheaper flights to Dominican Republic from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Dominican Republic for around $503 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Dominican Republic from Chicago for as low as $459 on momondo.

What cabin class options are available on Chicago to Dominican Republic flights?

There are 3 cabin classes available to choose from on Chicago to Dominican Republic flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to Dominican Republic flights?

No. A direct flight is the cheapest option for a flight between Chicago to Dominican Republic.

Cheap Chicago to Dominican Republic flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Dominican Republic

Best Price Found

$179

Fastest flight time

4h 15m

Direct flights

Every day

Airports in Dominican Republic

1 airport
The best one-way flight to Dominican Republic from Chicago in the past 72 hours is $179. The best round-trip flight deal from Chicago to Dominican Republic found on momondo in the last 72 hours is $344.
The fastest flight from Chicago to Dominican Republic takes 4h 15m
Direct flights go from Chicago to Dominican Republic every day.
There is 1 airport near Dominican Republic: Punta Cana (PUJ)
Search flight deals

  • When did momondo last update prices for flights from Chicago to Dominican Republic?

    Prices for flights from Chicago to Dominican Republic are updated daily.

  • How many operators does momondo search for flights from Chicago to Dominican Republic?

  • How old do you have to be to fly from Chicago to Dominican Republic?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Dominican Republic.

  • What documentation or ID do you need to fly to Dominican Republic?

    The travel and health documents you'll need for your trip to Dominican Republic may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Dominican Republic. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago to Dominican Republic?

Best airlines flying from Chicago to Dominican Republic

Compare and see reviews for airlines that fly from Chicago to Dominican Republic with momondo
Airline
Rating
Free Cancellation
Price
Copa AirlinesPriceFrom $188Free CancellationRating
7.6
1,559 reviews
Search Copa Airlines flights
Spirit AirlinesPriceFrom $208Free CancellationRating
6.3
8,156 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $215Free CancellationRating
7.4
9,063 reviews
Search United Airlines flights
FrontierPriceFrom $224Free CancellationRating
5.8
3,094 reviews
Search Frontier flights
ArajetPriceFrom $236Free CancellationRating
6.9
37 reviews
Search Arajet flights
American AirlinesPriceFrom $274Free CancellationRating
7.2
11,045 reviews
Search American Airlines flights
Air CanadaPriceFrom $335Free CancellationRating
7.1
10,496 reviews
Search Air Canada flights
JetBluePriceFrom $347Free CancellationRating
7.2
2,901 reviews
Search JetBlue flights
DeltaPriceFrom $356Free CancellationRating
7.9
8,011 reviews
Search Delta flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Dominican Republic?

Finding the right flight to Dominican Republic from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Dominican Republic quick and easy, saving you time and money.

Can I find flights from Chicago to Dominican Republic with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Dominican Republic from Chicago with this policy.

How can momondo help me find flights from Chicago to Dominican Republic?

momondo provides multiple filters to help you find the best flight to Dominican Republic from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to Dominican Republic right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Dominican Republic from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Dominican Republic trip

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Find better results for your trip to the Dominican Republic

Popular cities in the Dominican Republic

Popular flights according to clicks in the last 7 days on momondo
Flights to Punta Canafrom $184
Flights to Santo Domingofrom $203
Flights to Santiago de los Caballerosfrom $123
Flights to Puerto Platafrom $254
Flights to Naguafrom $434