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Cheap flights from Chicago to the Dominican Republic from $93

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 11/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Chicago to the Dominican Republic

Cheap round-trip flights

Spirit Airlines Logo
5:05 am - 4:00 pmORD-SDQ
9h 55m1 stop
Spirit Airlines Logo
3:59 pm - 11:45 pmSDQ-ORD
8h 46m1 stop
$270Spirit Airlines
Find Deal
jue., oct. 2 - sáb., oct. 11
Spirit Airlines Logo
5:05 am - 2:54 pmORD-SDQ
8h 49m1 stop
Spirit Airlines Logo
3:59 pm - 11:45 pmSDQ-ORD
8h 46m1 stop
$283Spirit Airlines
Find Deal
sáb., oct. 18 - sáb., oct. 25
United Airlines Logo
9:30 am - 3:02 pmORD-PUJ
4h 32mnonstop
United Airlines Logo
1:55 pm - 6:08 pmPUJ-ORD
5h 13mnonstop
$344United Airlines
Find Deal
lun., oct. 27 - vie., oct. 31
American Airlines Logo
4:28 pm - 10:50 amORD-PUJ
17h 22m1 stop
American Airlines Logo
3:21 pm - 7:36 pmPUJ-ORD
5h 15mnonstop
$347American Airlines
Find Deal
mar., oct. 7 - vie., oct. 10
American Airlines Logo
9:50 am - 4:27 pmORD-PUJ
4h 37mnonstop
American Airlines Logo
1:03 pm - 4:29 pmPUJ-ORD
5h 26mnonstop
$349American Airlines
Find Deal
dom., nov. 9 - vie., nov. 14
Delta Logo
6:00 am - 2:31 pmMDW-PUJ
7h 31m1 stop
Delta Logo
2:49 pm - 10:14 pmPUJ-MDW
8h 25m1 stop
$360Delta
Find Deal
dom., oct. 26 - vie., oct. 31
United Airlines Logo
9:30 am - 4:02 pmORD-PUJ
4h 32mnonstop
United Airlines Logo
5:20 pm - 11:39 pmPUJ-ORD
8h 19m1 stop
$361United Airlines
Find Deal
dom., feb. 1 - mar., feb. 10
Delta Logo
6:00 am - 4:18 pmMDW-PUJ
8h 18m1 stop
Delta Logo
2:38 pm - 11:32 pmPUJ-MDW
10h 54m1 stop
$363Delta
Find Deal
dom., nov. 16 - jue., nov. 20
Frontier Logo
6:15 am - 2:22 pmMDW-PUJ
7h 07m1 stop
Frontier Logo
3:32 pm - 10:47 pmPUJ-MDW
8h 15m1 stop
$383Frontier
Find Deal
sáb., oct. 18 - sáb., oct. 25
Frontier Logo
6:00 am - 3:24 pmMDW-PUJ
7h 24m1 stop
Frontier Logo
4:34 pm - 11:26 pmPUJ-MDW
8h 52m1 stop
$385Frontier
Find Deal
sáb., ene. 10 - sáb., ene. 17

Copa Airlines flights from Chicago to Dominican Republic

Our best Copa Airlines deals on Chicago to Dominican Republic flight tickets
Copa Airlines
Oct 10
ORD3:07 pmChicago O'Hare Intl
10h 06m
1 stop
PUJ2:13 amPunta Cana
Oct 15
PUJ5:17 amPunta Cana
20h 04m
1 stop
ORD12:21 amChicago O'Hare Intl
$345
Find similar
Copa Airlines
Nov 12
ORD6:56 amChicago O'Hare Intl
8h 43m
1 stop
PUJ5:39 pmPunta Cana
Nov 19
PUJ6:36 pmPunta Cana
20h 10m
1 stop
ORD12:46 pmChicago O'Hare Intl
$351
Find similar

Southwest flights from Chicago to Dominican Republic

Our best Southwest deals on Chicago to Dominican Republic flight tickets
Southwest
Nov 9
MDW5:05 amChicago Midway
8h 05m
1 stop
PUJ3:10 pmPunta Cana
Nov 18
PUJ2:40 pmPunta Cana
8h 25m
1 stop
MDW9:05 pmChicago Midway
$357
Find similar
Southwest
Nov 9
MDW7:35 pmChicago Midway
17h 35m
2 stops
PUJ3:10 pmPunta Cana
Nov 18
PUJ2:40 pmPunta Cana
8h 25m
1 stop
MDW9:05 pmChicago Midway
$362
Find similar
Southwest
Nov 16
MDW5:50 amChicago Midway
7h 10m
1 stop
PUJ3:00 pmPunta Cana
Nov 22
PUJ3:25 pmPunta Cana
5h 00m
MDW6:25 pmChicago Midway
$379
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 septiembre 17, 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

jue. 10/2

5:05 am-4:00 pm

1 stop9h 55m

Santo Domingo Las Americas

sáb. 10/11

3:59 pm-11:45 pm

1 stop8h 46m

$270

ChicagoSanto Domingo

ORD - SDQ

ORDSDQ

Chicago O'Hare Intl

sáb. 10/18

5:05 am-2:54 pm

1 stop8h 49m

Santo Domingo Las Americas

sáb. 10/25

3:59 pm-11:45 pm

1 stop8h 46m

$283

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

lun. 10/27

9:30 am-3:02 pm

Nonstop4h 32m

Punta Cana

vie. 10/31

1:55 pm-6:08 pm

Nonstop5h 13m

$344

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

mar. 10/7

4:28 pm-10:50 am

1 stop17h 22m

Punta Cana

vie. 10/10

3:21 pm-7:36 pm

Nonstop5h 15m

$347

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

dom. 11/9

9:50 am-4:27 pm

Nonstop4h 37m

Punta Cana

vie. 11/14

1:03 pm-4:29 pm

Nonstop5h 26m

$349

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

dom. 10/26

6:00 am-2:31 pm

1 stop7h 31m

Punta Cana

vie. 10/31

2:49 pm-10:14 pm

1 stop8h 25m

$360

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

dom. 2/1

9:30 am-4:02 pm

Nonstop4h 32m

Punta Cana

mar. 2/10

5:20 pm-11:39 pm

1 stop8h 19m

$361

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

dom. 11/16

6:00 am-4:18 pm

1 stop8h 18m

Punta Cana

jue. 11/20

2:38 pm-11:32 pm

1 stop10h 54m

$363

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

sáb. 10/18

6:15 am-2:22 pm

1 stop7h 07m

Punta Cana

sáb. 10/25

3:32 pm-10:47 pm

1 stop8h 15m

$383

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

sáb. 1/10

6:00 am-3:24 pm

1 stop7h 24m

Punta Cana

sáb. 1/17

4:34 pm-11:26 pm

1 stop8h 52m

$385

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 $473.

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 $498. 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 $563. 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 $534.

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 $526 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 $441 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

$126

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 $126. The best round-trip flight deal from Chicago to Dominican Republic found on momondo in the last 72 hours is $381.
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
1,533 reviews
Search Copa Airlines flights
United AirlinesPriceFrom $215Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights
FrontierPriceFrom $223Free CancellationRating
5.8
3,173 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $231Free CancellationRating
6.3
8,023 reviews
Search Spirit Airlines flights
ArajetPriceFrom $234Free CancellationRating
7.0
35 reviews
Search Arajet flights
American AirlinesPriceFrom $274Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
Air CanadaPriceFrom $335Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights
JetBluePriceFrom $367Free CancellationRating
7.2
2,914 reviews
Search JetBlue flights
DeltaPriceFrom $375Free CancellationRating
7.9
7,961 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.

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Find better results for your trip to the Dominican Republic

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Popular flights according to clicks in the last 7 days on momondo
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