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Cheap flights from Chicago to the Dominican Republic from $86

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 12/2. 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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0 bags

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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.
Spirit Airlines Logo
5:00 am - 3:30 pmORD-SDQ
8h 30m1 stop
Spirit Airlines Logo
4:21 pm - 12:09 amSDQ-ORD
9h 48m1 stop
$288Spirit Airlines
Find Deal
Wed, Dec 3 - Mon, Dec 8
Spirit Airlines Logo
5:00 am - 3:30 pmORD-SDQ
8h 30m1 stop
Spirit Airlines Logo
4:21 pm - 12:09 amSDQ-ORD
9h 48m1 stop
$289Spirit Airlines
Find Deal
Tue, Dec 2 - Tue, Dec 9
Frontier Logo
7:00 am - 1:37 pmORD-PUJ
4h 37mnonstop
Frontier Logo
6:50 pm - 10:00 pmPUJ-ORD
5h 10mnonstop
$301Frontier
Find Deal
Tue, Dec 2 - Mon, Dec 8
United Airlines Logo
8:45 am - 5:25 pmORD-PUJ
6h 40m1 stop
United Airlines Logo
5:20 pm - 11:43 pmPUJ-ORD
8h 23m1 stop
$303United Airlines
Find Deal
Fri, Dec 5 - Tue, Dec 9
United Airlines Logo
8:45 am - 5:25 pmORD-PUJ
6h 40m1 stop
United Airlines Logo
4:25 pm - 7:38 pmPUJ-ORD
5h 13mnonstop
$311United Airlines
Find Deal
Mon, Dec 15 - Fri, Dec 19
Frontier Logo
6:00 am - 3:09 pmORD-PUJ
7h 09m1 stop
Frontier Logo
6:49 pm - 9:59 pmPUJ-ORD
5h 10mnonstop
$328Frontier
Find Deal
Mon, Jan 5 - Fri, Jan 9
Delta Logo
6:10 pm - 1:32 pmORD-PUJ
17h 22m2 stops
Delta Logo
5:19 pm - 8:42 amPUJ-ORD
17h 23m1 stop
$330Delta
Find Deal
Sat, Dec 6 - Sat, Dec 13
Delta Logo
5:30 am - 3:39 pmORD-PUJ
8h 09m1 stop
Delta Logo
3:50 pm - 10:46 pmPUJ-ORD
8h 56m1 stop
$338Delta
Find Deal
Tue, Dec 9 - Wed, Dec 10
American Airlines Logo
7:07 pm - 2:05 pmORD-POP
16h 58m1 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
American Airlines Logo
10:19 am - 10:39 pmORD-SDQ
10h 20m2 stops
American Airlines Logo
11:02 am - 7:40 pmSDQ-ORD
10h 38m2 stops
$394American Airlines
Find Deal
Thu, Feb 5 - Wed, Feb 18

Delta flights from Chicago to Dominican Republic

Our best Delta deals on Chicago to Dominican Republic flight tickets
Delta
Dec 6
ORD6:10 pmChicago O'Hare Intl
17h 22m
2 stops
PUJ1:32 pmPunta Cana
Dec 13
PUJ5:19 pmPunta Cana
17h 23m
1 stop
ORD8:42 amChicago O'Hare Intl
$330
Find similar
Delta
Dec 9
ORD5:30 amChicago O'Hare Intl
8h 09m
1 stop
PUJ3:39 pmPunta Cana
Dec 10
PUJ3:50 pmPunta Cana
8h 56m
1 stop
ORD10:46 pmChicago O'Hare Intl
$338
Find similar
Delta
Dec 5
ORD8:40 pmChicago O'Hare Intl
15h 40m
1 stop
PUJ2:20 pmPunta Cana
Dec 9
PUJ2:57 pmPunta Cana
19h 42m
2 stops
ORD8:39 amChicago O'Hare Intl
$342
Find similar

United Airlines flights from Chicago to Dominican Republic

Our best United Airlines deals on Chicago to Dominican Republic flight tickets
United Airlines
Dec 5
ORD8:45 amChicago O'Hare Intl
6h 40m
1 stop
PUJ5:25 pmPunta Cana
Dec 9
PUJ5:20 pmPunta Cana
8h 23m
1 stop
ORD11:43 pmChicago O'Hare Intl
$303
Find similar
United Airlines
Dec 15
ORD8:45 amChicago O'Hare Intl
6h 40m
1 stop
PUJ5:25 pmPunta Cana
Dec 19
PUJ4:25 pmPunta Cana
5h 13m
ORD7:38 pmChicago O'Hare Intl
$311
Find similar
United Airlines
Nov 11
ORD9:30 amChicago O'Hare Intl
4h 32m
PUJ4:02 pmPunta Cana
Nov 18
PUJ12:56 pmPunta Cana
7h 34m
1 stop
ORD6:30 pmChicago O'Hare Intl
$313
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 October 31, 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

ChicagoSanto Domingo

ORD - SDQ

ORDSDQ

Chicago O'Hare Intl

Wed 12/3

5:00 am-3:30 pm

1 stop8h 30m

Santo Domingo Las Americas

Mon 12/8

4:21 pm-12:09 am

1 stop9h 48m

$288

ChicagoSanto Domingo

ORD - SDQ

ORDSDQ

Chicago O'Hare Intl

Tue 12/2

5:00 am-3:30 pm

1 stop8h 30m

Santo Domingo Las Americas

Tue 12/9

4:21 pm-12:09 am

1 stop9h 48m

$289

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 12/2

7:00 am-1:37 pm

Nonstop4h 37m

Punta Cana

Mon 12/8

6:50 pm-10:00 pm

Nonstop5h 10m

$301

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Fri 12/5

8:45 am-5:25 pm

1 stop6h 40m

Punta Cana

Tue 12/9

5:20 pm-11:43 pm

1 stop8h 23m

$303

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 12/15

8:45 am-5:25 pm

1 stop6h 40m

Punta Cana

Fri 12/19

4:25 pm-7:38 pm

Nonstop5h 13m

$311

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 1/5

6:00 am-3:09 pm

1 stop7h 09m

Punta Cana

Fri 1/9

6:49 pm-9:59 pm

Nonstop5h 10m

$328

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 12/6

6:10 pm-1:32 pm

2 stops17h 22m

Punta Cana

Sat 12/13

5:19 pm-8:42 am

1 stop17h 23m

$330

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 12/9

5:30 am-3:39 pm

1 stop8h 09m

Punta Cana

Wed 12/10

3:50 pm-10:46 pm

1 stop8h 56m

$338

ChicagoPuerto Plata

ORD - POP

ORDPOP

Chicago O'Hare Intl

Sat 12/6

7:07 pm-2:05 pm

1 stop16h 58m

Puerto Plata La Union

Fri 12/12

4:38 pm-7:19 am

2 stops16h 41m

$392

ChicagoSanto Domingo

ORD - SDQ

ORDSDQ

Chicago O'Hare Intl

Thu 2/5

10:19 am-10:39 pm

2 stops10h 20m

Santo Domingo Las Americas

Wed 2/18

11:02 am-7:40 pm

2 stops10h 38m

$394

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 $460. 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 $470.

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 $494. 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 $551. 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 $530.

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 $511 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 $434 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

$191

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 $191. The best round-trip flight deal from Chicago to Dominican Republic found on momondo in the last 72 hours is $383.
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
1,561 reviews
Search Copa Airlines flights
FrontierPriceFrom $223Free CancellationRating
5.8
3,124 reviews
Search Frontier flights
United AirlinesPriceFrom $226Free CancellationRating
7.4
8,995 reviews
Search United Airlines flights
ArajetPriceFrom $233Free CancellationRating
7.1
36 reviews
Search Arajet flights
American AirlinesPriceFrom $274Free CancellationRating
7.2
11,031 reviews
Search American Airlines flights
Spirit AirlinesPriceFrom $277Free CancellationRating
6.3
8,120 reviews
Search Spirit Airlines flights
DeltaPriceFrom $356Free CancellationRating
7.9
7,996 reviews
Search Delta flights
JetBluePriceFrom $367Free CancellationRating
7.2
2,906 reviews
Search JetBlue flights
Air CanadaPriceFrom $388Free CancellationRating
7.1
10,387 reviews
Search Air Canada 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 $207
Flights to Santiago de los Caballerosfrom $214
Flights to Puerto Platafrom $298
Flights to La Romanafrom $298
Flights to Naguafrom $613