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Cheap flights from Chicago to the Dominican Republic from $109

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 9/16. 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
3:47 pm - 10:48 pmSDQ-ORD
8h 01m1 stop
$240Spirit Airlines
Find Deal
Wed, Sep 17 - Sat, Sep 20
Spirit Airlines Logo
5:17 pm - 12:15 pmORD-SDQ
17h 58m1 stop
Spirit Airlines Logo
5:05 pm - 9:18 amSDQ-ORD
17h 13m1 stop
$257Spirit Airlines
Find Deal
Mon, Sep 8 - Tue, Sep 9
Spirit Airlines Logo
5:05 am - 2:42 pmORD-SDQ
8h 37m1 stop
Spirit Airlines Logo
3:47 pm - 10:48 pmSDQ-ORD
8h 01m1 stop
$285Spirit Airlines
Find Deal
Sat, Sep 13 - Sat, Sep 20
American Airlines Logo
8:35 am - 2:05 pmORD-PUJ
4h 30mnonstop
American Airlines Logo
4:25 pm - 11:12 pmPUJ-ORD
7h 47m1 stop
$338American Airlines
Find Deal
Tue, Sep 2 - Tue, Sep 9
American Airlines Logo
8:35 am - 2:00 pmORD-PUJ
4h 25mnonstop
American Airlines Logo
3:21 pm - 7:36 pmPUJ-ORD
5h 15mnonstop
$346American Airlines
Find Deal
Mon, Oct 6 - Fri, Oct 10
Delta Logo
5:20 am - 1:24 pmORD-PUJ
7h 04m1 stop
Delta Logo
1:53 pm - 7:50 amPUJ-ORD
18h 57m2 stops
$347Delta
Find Deal
Mon, Oct 27 - Tue, Oct 28
Delta Logo
6:00 am - 2:32 pmMDW-PUJ
7h 32m1 stop
Delta Logo
1:57 pm - 9:48 amPUJ-MDW
20h 51m2 stops
$347Delta
Find Deal
Tue, Sep 23 - Fri, Sep 26
Frontier Logo
6:15 am - 2:22 pmMDW-PUJ
7h 07m1 stop
Frontier Logo
3:32 pm - 10:47 pmPUJ-MDW
8h 15m1 stop
$363Frontier
Find Deal
Sat, Oct 18 - Sat, Oct 25
Frontier Logo
6:15 am - 2:22 pmMDW-PUJ
7h 07m1 stop
Frontier Logo
3:32 pm - 11:25 pmPUJ-MDW
8h 53m1 stop
$364Frontier
Find Deal
Sat, Oct 18 - Sat, Oct 25
United Airlines Logo
7:10 am - 3:12 pmORD-STI
7h 02m1 stop
United Airlines Logo
2:07 pm - 11:25 pmSTI-ORD
10h 18m1 stop
$699United Airlines
Find Deal
Thu, Sep 4 - Mon, Sep 8

Copa Airlines flights from Chicago to Dominican Republic

Our best Copa Airlines deals on Chicago to Dominican Republic flight tickets
Copa Airlines
Aug 25
ORD7:55 amChicago O'Hare Intl
17h 48m
1 stop
SDQ2:43 amSanto Domingo Las Americas
Aug 28
SDQ11:54 amSanto Domingo Las Americas
13h 27m
1 stop
ORD12:21 amChicago O'Hare Intl
$415
Find similar
Copa Airlines
Aug 30
ORD7:55 amChicago O'Hare Intl
8h 42m
1 stop
PUJ5:37 pmPunta Cana
Sep 7
PUJ11:57 amPunta Cana
26h 44m
1 stop
ORD1:41 pmChicago O'Hare Intl
$428
Find similar
Copa Airlines
Aug 27
ORD7:55 amChicago O'Hare Intl
8h 42m
1 stop
PUJ5:37 pmPunta Cana
Sep 2
PUJ2:42 pmPunta Cana
10h 39m
1 stop
ORD12:21 amChicago O'Hare Intl
$470
Find similar

Delta flights from Chicago to Dominican Republic

Our best Delta deals on Chicago to Dominican Republic flight tickets
Delta
Oct 27
ORD5:20 amChicago O'Hare Intl
7h 04m
1 stop
PUJ1:24 pmPunta Cana
Oct 28
PUJ1:53 pmPunta Cana
18h 57m
2 stops
ORD7:50 amChicago O'Hare Intl
$347
Find similar
Delta
Sep 8
ORD5:45 amChicago O'Hare Intl
6h 30m
1 stop
PUJ1:15 pmPunta Cana
Sep 10
PUJ1:50 pmPunta Cana
19h 50m
2 stops
ORD8:40 amChicago O'Hare Intl
$352
Find similar
Delta
Sep 15
MDW6:00 amChicago Midway
7h 32m
1 stop
PUJ2:32 pmPunta Cana
Sep 24
PUJ2:45 pmPunta Cana
7h 51m
1 stop
MDW9:36 pmChicago Midway
$361
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 August 21, 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 9/17

5:05 am-4:00 pm

1 stop9h 55m

Santo Domingo Las Americas

Sat 9/20

3:47 pm-10:48 pm

1 stop8h 01m

$240

ChicagoSanto Domingo

ORD - SDQ

ORDSDQ

Chicago O'Hare Intl

Mon 9/8

5:17 pm-12:15 pm

1 stop17h 58m

Santo Domingo Las Americas

Tue 9/9

5:05 pm-9:18 am

1 stop17h 13m

$257

ChicagoSanto Domingo

ORD - SDQ

ORDSDQ

Chicago O'Hare Intl

Sat 9/13

5:05 am-2:42 pm

1 stop8h 37m

Santo Domingo Las Americas

Sat 9/20

3:47 pm-10:48 pm

1 stop8h 01m

$285

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 9/2

8:35 am-2:05 pm

Nonstop4h 30m

Punta Cana

Tue 9/9

4:25 pm-11:12 pm

1 stop7h 47m

$338

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 10/6

8:35 am-2:00 pm

Nonstop4h 25m

Punta Cana

Fri 10/10

3:21 pm-7:36 pm

Nonstop5h 15m

$346

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 10/27

5:20 am-1:24 pm

1 stop7h 04m

Punta Cana

Tue 10/28

1:53 pm-7:50 am

2 stops18h 57m

$347

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 9/23

6:00 am-2:32 pm

1 stop7h 32m

Punta Cana

Fri 9/26

1:57 pm-9:48 am

2 stops20h 51m

$347

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 10/18

6:15 am-2:22 pm

1 stop7h 07m

Punta Cana

Sat 10/25

3:32 pm-10:47 pm

1 stop8h 15m

$363

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 10/18

6:15 am-2:22 pm

1 stop7h 07m

Punta Cana

Sat 10/25

3:32 pm-11:25 pm

1 stop8h 53m

$364

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Thu 9/4

7:10 am-3:12 pm

1 stop7h 02m

Santiago de los Caballeros

Mon 9/8

2:07 pm-11:25 pm

1 stop10h 18m

$699

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, July 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 $474. If you are unable to visit Dominican Republic during the month of July, then departing from Chicago during the month August is also very affordable. Most momondo users find prices during this month for around $485.

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 Tuesday when prices can be found for as low as $499. 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 $570. 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 $537.

What is the cheapest Chicago to Dominican Republic flight route?

Fly from Chicago Midway 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 $531 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 $446 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?

You could potentially save up to 8% on your flight if you consider stops on a Chicago to Dominican Republic flight.

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 20m

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 $366.
The fastest flight from Chicago to Dominican Republic takes 4h 20m
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 $193Free CancellationRating
7.5
1,512 reviews
Search Copa Airlines flights
FrontierPriceFrom $223Free CancellationRating
5.8
3,207 reviews
Search Frontier flights
United AirlinesPriceFrom $226Free CancellationRating
7.4
8,930 reviews
Search United Airlines flights
Spirit AirlinesPriceFrom $231Free CancellationRating
6.3
8,035 reviews
Search Spirit Airlines flights
ArajetPriceFrom $234Free CancellationRating
7.0
34 reviews
Search Arajet flights
American AirlinesPriceFrom $274Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $334Free CancellationRating
7.9
7,981 reviews
Search Delta flights
Air CanadaPriceFrom $335Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights
JetBluePriceFrom $391Free CancellationRating
7.2
2,916 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.

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
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