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Cheap flights from Chicago to the Dominican Republic from $117

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 12/8. 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
5:45 am - 12:30 pmORD-PUJ
4h 45mnonstop
Multiple Airlines Logo
6:50 pm - 10:00 pmPUJ-ORD
5h 10mnonstop
$257Multiple Airlines
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Wed, Dec 3 - Wed, Dec 10
Multiple Airlines Logo
5:45 am - 12:30 pmORD-PUJ
4h 45mnonstop
Multiple Airlines Logo
6:50 pm - 10:00 pmPUJ-ORD
5h 10mnonstop
$258Multiple Airlines
Find Deal
Wed, Dec 3 - Sun, Dec 7
Frontier Logo
6:45 am - 1:19 pmORD-PUJ
4h 34mnonstop
Frontier Logo
6:50 pm - 10:00 pmPUJ-ORD
5h 10mnonstop
$262Frontier
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Fri, Nov 28 - Fri, Dec 5
Frontier Logo
7:00 am - 1:35 pmORD-PUJ
4h 35mnonstop
Frontier Logo
6:49 pm - 10:01 pmPUJ-ORD
5h 12mnonstop
$263Frontier
Find Deal
Wed, Nov 19 - Wed, Nov 26
Arajet Logo
10:27 am - 5:12 pmORD-PUJ
4h 45mnonstop
Arajet Logo
5:47 am - 8:57 amPUJ-ORD
5h 10mnonstop
$264Arajet
Find Deal
Sat, Dec 6 - Sat, Dec 13
Arajet Logo
5:45 am - 12:30 pmORD-PUJ
4h 45mnonstop
Arajet Logo
6:00 pm - 9:10 pmPUJ-ORD
5h 10mnonstop
$267Arajet
Find Deal
Wed, Dec 3 - Sun, Dec 7
Delta Logo
6:45 am - 3:56 pmORD-POP
7h 11m1 stop
Delta Logo
5:11 pm - 12:01 amPOP-ORD
8h 50m1 stop
$388Delta
Find Deal
Sat, Dec 6 - Fri, Dec 12
American Airlines Logo
10:05 am - 9:46 pmORD-STI
9h 41m1 stop
American Airlines Logo
6:00 am - 3:17 pmSTI-ORD
11h 17m2 stops
$389American Airlines
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Mon, Jan 19 - Wed, Jan 28
American Airlines Logo
6:39 pm - 1:26 pmORD-POP
16h 47m1 stop
American Airlines Logo
4:38 pm - 7:19 amPOP-ORD
16h 41m2 stops
$392American Airlines
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Sat, Dec 6 - Fri, Dec 12
Delta Logo
9:29 am - 1:48 amMDW-SDQ
14h 19m2 stops
Delta Logo
3:57 pm - 11:47 pmSDQ-MDW
9h 50m1 stop
$415Delta
Find Deal
Sat, Dec 6 - Sun, Dec 14

United Airlines flights from Chicago to Dominican Republic

Our best United Airlines deals on Chicago to Dominican Republic flight tickets
United Airlines
Dec 9
ORD6:00 amChicago O'Hare Intl
9h 25m
1 stop
PUJ5:25 pmPunta Cana
Dec 16
PUJ5:20 pmPunta Cana
8h 23m
1 stop
ORD11:43 pmChicago O'Hare Intl
$278
Find similar
United Airlines
Dec 5
ORD9:30 amChicago O'Hare Intl
4h 32m
PUJ4:02 pmPunta Cana
Dec 12
PUJ12:56 pmPunta Cana
12h 48m
1 stop
ORD11:44 pmChicago O'Hare Intl
$298
Find similar
United Airlines
Dec 5
ORD8:45 amChicago O'Hare Intl
6h 40m
1 stop
PUJ5:25 pmPunta Cana
Dec 10
PUJ12:56 pmPunta Cana
12h 47m
1 stop
ORD11:43 pmChicago O'Hare Intl
$303
Find similar

Delta flights from Chicago to Dominican Republic

Our best Delta deals on Chicago to Dominican Republic flight tickets
Delta
Feb 2
MDW6:00 amChicago Midway
6h 20m
1 stop
PUJ2:20 pmPunta Cana
Feb 13
PUJ4:50 pmPunta Cana
7h 54m
1 stop
MDW10:44 pmChicago Midway
$338
Find similar
Delta
Dec 2
MDW6:00 amChicago Midway
6h 25m
1 stop
PUJ2:25 pmPunta Cana
Dec 9
PUJ5:04 pmPunta Cana
8h 43m
1 stop
MDW11:47 pmChicago Midway
$352
Find similar
Delta
Nov 29
MDW6:00 amChicago Midway
7h 38m
1 stop
PUJ3:38 pmPunta Cana
Dec 6
PUJ5:19 pmPunta Cana
8h 28m
1 stop
MDW11:47 pmChicago Midway
$366
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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 November 13, 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

Wed 12/3

5:45 am-12:30 pm

Nonstop4h 45m

Punta Cana

Wed 12/10

6:50 pm-10:00 pm

Nonstop5h 10m

$257

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Wed 12/3

5:45 am-12:30 pm

Nonstop4h 45m

Punta Cana

Sun 12/7

6:50 pm-10:00 pm

Nonstop5h 10m

$258

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Fri 11/28

6:45 am-1:19 pm

Nonstop4h 34m

Punta Cana

Fri 12/5

6:50 pm-10:00 pm

Nonstop5h 10m

$262

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Wed 11/19

7:00 am-1:35 pm

Nonstop4h 35m

Punta Cana

Wed 11/26

6:49 pm-10:01 pm

Nonstop5h 12m

$263

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 12/6

10:27 am-5:12 pm

Nonstop4h 45m

Punta Cana

Sat 12/13

5:47 am-8:57 am

Nonstop5h 10m

$264

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Wed 12/3

5:45 am-12:30 pm

Nonstop4h 45m

Punta Cana

Sun 12/7

6:00 pm-9:10 pm

Nonstop5h 10m

$267

ChicagoPuerto Plata

ORD - POP

ORDPOP

Chicago O'Hare Intl

Sat 12/6

6:45 am-3:56 pm

1 stop7h 11m

Puerto Plata La Union

Fri 12/12

5:11 pm-12:01 am

1 stop8h 50m

$388

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Mon 1/19

10:05 am-9:46 pm

1 stop9h 41m

Santiago de los Caballeros

Wed 1/28

6:00 am-3:17 pm

2 stops11h 17m

$389

ChicagoPuerto Plata

ORD - POP

ORDPOP

Chicago O'Hare Intl

Sat 12/6

6:39 pm-1:26 pm

1 stop16h 47m

Puerto Plata La Union

Fri 12/12

4:38 pm-7:19 am

2 stops16h 41m

$392

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sat 12/6

9:29 am-1:48 am

2 stops14h 19m

Santo Domingo Las Americas

Sun 12/14

3:57 pm-11:47 pm

1 stop9h 50m

$415

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 July is also very affordable. Most momondo users find prices during this month for around $469.

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 $491. 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 $552. 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 $528.

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 $505 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 $447 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

$167

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 $167. The best round-trip flight deal from Chicago to Dominican Republic found on momondo in the last 72 hours is $355.
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
1,565 reviews
Search Copa Airlines flights
FrontierPriceFrom $223Free CancellationRating
5.8
3,110 reviews
Search Frontier flights
United AirlinesPriceFrom $226Free CancellationRating
7.4
9,017 reviews
Search United Airlines flights
ArajetPriceFrom $233Free CancellationRating
7.1
36 reviews
Search Arajet flights
American AirlinesPriceFrom $274Free CancellationRating
7.2
11,052 reviews
Search American Airlines flights
Spirit AirlinesPriceFrom $277Free CancellationRating
6.3
8,138 reviews
Search Spirit Airlines flights
Air CanadaPriceFrom $335Free CancellationRating
7.1
10,448 reviews
Search Air Canada flights
DeltaPriceFrom $356Free CancellationRating
7.9
8,007 reviews
Search Delta flights
JetBluePriceFrom $367Free CancellationRating
7.2
2,907 reviews
Search JetBlue 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.

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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 $205
Flights to Santo Domingofrom $200
Flights to Santiago de los Caballerosfrom $214
Flights to Puerto Platafrom $307
Flights to La Romanafrom $298
Flights to Naguafrom $602