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Cheap flights from the Dominican Republic to Chicago from $182

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from the Dominican Republic to Chicago departing on 9/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Find the cheapest flights from the Dominican Republic to Chicago

Recent round-trip flight deals from the Dominican Republic to Chicago

Enter your travel dates to find the best prices.
Arajet Logo
7:30 pm - 11:40 pm
PUJ
-
ORD
5h 10mnonstop
Arajet Logo
5:45 am - 12:30 pm
ORD
-
PUJ
4h 45mnonstop
$343Arajet
Thu, Oct 29 - Fri, Nov 13
Arajet Logo
7:30 pm - 10:40 pm
PUJ
-
ORD
5h 10mnonstop
Arajet Logo
3:20 am - 10:05 am
ORD
-
PUJ
4h 45mnonstop
$349Arajet
Thu, Nov 5 - Sun, Nov 8
Multiple Airlines Logo
3:30 pm - 11:40 pm
SDQ
-
ORD
9h 10m
1 stop
Multiple Airlines Logo
4:30 am - 4:55 pm
ORD
-
SDQ
11h 25m
1 stop
$350Multiple Airlines
Thu, Oct 22 - Mon, Oct 26
Multiple Airlines Logo
1:55 pm - 10:10 pm
SDQ
-
ORD
9h 15m
1 stop
Multiple Airlines Logo
11:27 am - 9:40 pm
ORD
-
SDQ
9h 13m
1 stop
$369Multiple Airlines
Sun, Oct 25 - Sat, Oct 31
JetBlue Logo
4:38 pm - 11:44 pm
SDQ
-
ORD
8h 06m
1 stop
JetBlue Logo
2:35 pm - 11:59 pm
ORD
-
SDQ
8h 24m
1 stop
$375JetBlue
Fri, Jul 24 - Sat, Aug 22
JetBlue Logo
5:01 am - 1:39 pm
SDQ
-
ORD
9h 38m
1 stop
JetBlue Logo
2:35 pm - 11:59 pm
ORD
-
SDQ
8h 24m
1 stop
$377JetBlue
Fri, Jul 24 - Sat, Aug 22
Delta Logo
7:16 pm - 4:48 pm
STI
-
ORD
22h 32m
2 stops
Delta Logo
6:00 am - 5:46 pm
ORD
-
STI
10h 46m
1 stop
$436Delta
Wed, Sep 23 - Wed, Sep 30
American Airlines Logo
1:40 pm - 11:34 pm
STI
-
ORD
10h 54m
2 stops
American Airlines Logo
8:35 pm - 12:10 pm
ORD
-
STI
14h 35m
2 stops
$467American Airlines
Fri, Oct 16 - Tue, Oct 20
American Airlines Logo
3:13 pm - 7:29 am
STI
-
ORD
17h 16m
1 stop
American Airlines Logo
8:55 pm - 2:13 pm
ORD
-
STI
16h 18m
2 stops
$468American Airlines
Sat, Sep 26 - Sat, Oct 3
Delta Logo
2:53 pm - 10:36 pm
SDQ
-
MDW
8h 43m
1 stop
Delta Logo
6:05 am - 1:28 pm
MDW
-
SDQ
6h 23m
1 stop
$585Delta
Tue, Aug 25 - Sat, Sep 5

American Airlines flights from Dominican Republic to Chicago

Our best American Airlines deals on Dominican Republic to Chicago flight tickets
American Airlines
Oct 16
STI1:40 pmSantiago de los Caballeros
10h 54m
2 stops
ORD11:34 pmChicago O'Hare Intl
Oct 20
ORD8:35 pmChicago O'Hare Intl
14h 35m
2 stops
STI12:10 pmSantiago de los Caballeros
$467
American Airlines
Sep 26
STI3:13 pmSantiago de los Caballeros
17h 16m
1 stop
ORD7:29 amChicago O'Hare Intl
Oct 3
ORD8:55 pmChicago O'Hare Intl
16h 18m
2 stops
STI2:13 pmSantiago de los Caballeros
$468
American Airlines
Jul 4
STI1:45 pmSantiago de los Caballeros
11h 56m
1 stop
ORD12:41 amChicago O'Hare Intl
Jul 27
ORD6:10 amChicago O'Hare Intl
14h 19m
1 stop
STI9:29 pmSantiago de los Caballeros
$523

Arajet flights from Dominican Republic to Chicago

Our best Arajet deals on Dominican Republic to Chicago flight tickets
Arajet
Nov 5
PUJ7:30 pmPunta Cana
5h 10m
ORD10:40 pmChicago O'Hare Intl
Nov 8
ORD3:20 amChicago O'Hare Intl
4h 45m
PUJ10:05 amPunta Cana
$349
Arajet
Jul 30
PUJ7:30 pmPunta Cana
5h 10m
ORD11:40 pmChicago O'Hare Intl
Aug 31
ORD5:30 amChicago O'Hare Intl
4h 45m
PUJ11:15 amPunta Cana
$373
Arajet
Aug 13
PUJ7:30 pmPunta Cana
5h 10m
ORD11:40 pmChicago O'Hare Intl
Aug 22
ORD12:12 pmChicago O'Hare Intl
4h 45m
PUJ5:57 pmPunta Cana
$375

momondo Fare Finder

 
Customize your flight search to find flights from Dominican Republic to Chicago 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 June 4, 2026.
Use the filters below to find and compare flights from the Dominican Republic to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 10/29

7:30 pm-11:40 pm

Nonstop5h 10m

Chicago O'Hare Intl

Fri 11/13

5:45 am-12:30 pm

Nonstop4h 45m

$343

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 11/5

7:30 pm-10:40 pm

Nonstop5h 10m

Chicago O'Hare Intl

Sun 11/8

3:20 am-10:05 am

Nonstop4h 45m

$349

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Thu 10/22

3:30 pm-11:40 pm

1 stop9h 10m

Chicago O'Hare Intl

Mon 10/26

4:30 am-4:55 pm

1 stop11h 25m

$350

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Sun 10/25

1:55 pm-10:10 pm

1 stop9h 15m

Chicago O'Hare Intl

Sat 10/31

11:27 am-9:40 pm

1 stop9h 13m

$369

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Fri 7/24

4:38 pm-11:44 pm

1 stop8h 06m

Chicago O'Hare Intl

Sat 8/22

2:35 pm-11:59 pm

1 stop8h 24m

$375

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Fri 7/24

5:01 am-1:39 pm

1 stop9h 38m

Chicago O'Hare Intl

Sat 8/22

2:35 pm-11:59 pm

1 stop8h 24m

$377

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Wed 9/23

7:16 pm-4:48 pm

2 stops22h 32m

Chicago O'Hare Intl

Wed 9/30

6:00 am-5:46 pm

1 stop10h 46m

$436

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Fri 10/16

1:40 pm-11:34 pm

2 stops10h 54m

Chicago O'Hare Intl

Tue 10/20

8:35 pm-12:10 pm

2 stops14h 35m

$467

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Sat 9/26

3:13 pm-7:29 am

1 stop17h 16m

Chicago O'Hare Intl

Sat 10/3

8:55 pm-2:13 pm

2 stops16h 18m

$468

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Tue 8/25

2:53 pm-10:36 pm

1 stop8h 43m

Chicago Midway

Sat 9/5

6:05 am-1:28 pm

1 stop6h 23m

$585

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 Chicago from

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

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 Chicago?

The month of August is, on average, the cheapest month to fly to Chicago from Dominican Republic, with most prices found around $139. If you’re not able to fly to Chicago in August, then January is your next best option. Flight prices from Dominican Republic to Chicago during January average around $160.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $387. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Dominican Republic to Chicago for around $476.

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Dominican Republic to Chicago during this time can be as low as $258. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $485.

What is the cheapest Dominican Republic to Chicago flight route?

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

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

There are 3 cabin classes available to choose from on Dominican Republic to Chicago 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 Dominican Republic to Chicago flights?

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

Cheap Dominican Republic to Chicago flight deals and tips

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

Best Price Found

$228

Fastest flight time

4h 35m

Direct flights

Mon, Wed, Thu, Fri, Sat and Sun

Airports in Chicago

3 airports
The best one-way flight to Chicago from Dominican Republic in the past 72 hours is $228. The best round-trip flight deal from Dominican Republic to Chicago found on momondo in the last 72 hours is $292.
The fastest flight from Dominican Republic to Chicago takes 4h 35m
Direct flights go from Dominican Republic to Chicago on Monday, Wednesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
There are 3 airports in Chicago. From Dominican Republic there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).
Search flight deals

Frequently asked questions about flying from the Dominican Republic to Chicago

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

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

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

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Dominican Republic to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

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

Best airlines flying from Dominican Republic to Chicago

Compare and see reviews for airlines that fly from Dominican Republic to Chicago with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $181Free CancellationRating
5.6
2,914 reviews
Search Frontier flights
ArajetPriceFrom $195Free CancellationRating
6.5
49 reviews
Search Arajet flights
American AirlinesPriceFrom $283Free CancellationRating
7.1
11,642 reviews
Search American Airlines flights
DeltaPriceFrom $449Free CancellationRating
7.8
8,396 reviews
Search Delta flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Saint Joseph
Portage
Benton Harbor
Lansing
Valparaiso
Schererville
Munster
Crown Point
Monticello
Chesterton
Porter
Griffith
Saint John

Why use momondo?

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

Finding the right flight to Chicago from Dominican Republic 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 Chicago quick and easy, saving you time and money.

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

momondo does allow users to show only those flights to Chicago from Dominican Republic which offer a flexible booking policy as well as other useful filters and features.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Dominican Republic to Chicago.

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

Yes momondo offers price alerts on flights to Chicago from Dominican Republic. 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 United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport