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Cheap flights from the Dominican Republic to Chicago from $183

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 9/4. 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

Discover deals from 900+ travel sites with momondo.

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
$279Arajet
Thu, Sep 17 - Fri, Dec 11
Arajet Logo
7:02 am - 11:12 am
PUJ
-
ORD
5h 10mnonstop
Arajet Logo
12:12 pm - 5:57 pm
ORD
-
PUJ
4h 45mnonstop
$307Arajet
Sat, Sep 5 - Sat, Sep 12
Multiple Airlines Logo
3:30 pm - 11:40 pm
SDQ
-
ORD
9h 10m
1 stop
Multiple Airlines Logo
5:45 am - 4:20 pm
ORD
-
SDQ
8h 35m
1 stop
$327Multiple Airlines
Thu, Sep 17 - Fri, Dec 11
Multiple Airlines Logo
7:30 pm - 11:40 pm
PUJ
-
ORD
5h 10mnonstop
Multiple Airlines Logo
3:40 pm - 4:05 pm
ORD
-
PUJ
23h 25m
1 stop
$367Multiple Airlines
Thu, Sep 24 - Thu, Oct 1
Delta Logo
2:50 pm - 9:07 am
PUJ
-
MDW
19h 17m
2 stops
Delta Logo
10:58 am - 12:28 pm
MDW
-
PUJ
24h 30m
2 stops
$397Delta
Thu, Oct 1 - Mon, Oct 19
Delta Logo
4:00 pm - 10:44 pm
PUJ
-
MDW
7h 44m
1 stop
Delta Logo
5:15 pm - 12:28 pm
MDW
-
PUJ
18h 13m
2 stops
$445Delta
Wed, Sep 30 - Mon, Oct 19
American Airlines Logo
10:27 am - 11:30 pm
SDQ
-
ORD
14h 03m
1 stop
American Airlines Logo
5:00 am - 6:44 pm
ORD
-
SDQ
12h 44m
1 stop
$467American Airlines
Thu, Aug 20 - Tue, Aug 25
Southwest Logo
2:35 pm - 9:00 pm
PUJ
-
MDW
7h 25m
1 stop
Southwest Logo
7:55 pm - 1:20 pm
MDW
-
PUJ
16h 25m
2 stops
$471Southwest
Thu, Sep 24 - Mon, Sep 28
American Airlines Logo
2:15 pm - 11:59 pm
SDQ
-
ORD
10h 44m
2 stops
American Airlines Logo
6:59 am - 6:34 pm
ORD
-
SDQ
10h 35m
1 stop
$472American Airlines
Thu, Sep 10 - Sat, Sep 19
Southwest Logo
1:45 pm - 10:40 pm
PUJ
-
MDW
9h 55m
1 stop
Southwest Logo
7:55 pm - 1:20 pm
MDW
-
PUJ
16h 25m
2 stops
$578Southwest
Thu, Aug 20 - Mon, Aug 24

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Air Canada flights from Dominican Republic to Chicago

Our best Air Canada deals on Dominican Republic to Chicago flight tickets
Air Canada
Sep 8
PUJ4:20 pmPunta Cana
17h 40m
1 stop
ORD9:00 amChicago O'Hare Intl
Sep 15
ORD3:40 pmChicago O'Hare Intl
23h 25m
1 stop
PUJ4:05 pmPunta Cana
$457
Air Canada
Sep 8
PUJ4:20 pmPunta Cana
18h 55m
2 stops
ORD10:15 amChicago O'Hare Intl
Sep 15
ORD3:40 pmChicago O'Hare Intl
23h 25m
1 stop
PUJ4:05 pmPunta Cana
$460
Air Canada
Oct 3
PUJ5:05 pmPunta Cana
28h 24m
2 stops
ORD8:29 pmChicago O'Hare Intl
Oct 10
ORD6:21 pmChicago O'Hare Intl
44h 44m
2 stops
PUJ4:05 pmPunta Cana
$470

Copa Airlines flights from Dominican Republic to Chicago

Our best Copa Airlines deals on Dominican Republic to Chicago flight tickets
Copa Airlines
Oct 22
SDQ12:12 pmSanto Domingo Las Americas
26h 47m
1 stop
ORD1:59 pmChicago O'Hare Intl
Oct 26
ORD8:35 amChicago O'Hare Intl
16h 36m
1 stop
SDQ2:11 amSanto Domingo Las Americas
$521
Copa Airlines
Sep 9
SDQ12:42 pmSanto Domingo Las Americas
13h 20m
1 stop
ORD1:02 amChicago O'Hare Intl
Sep 20
ORD3:20 pmChicago O'Hare Intl
19h 22m
1 stop
SDQ11:42 amSanto Domingo Las Americas
$539
Copa Airlines
Sep 10
STI4:12 pmSantiago de los Caballeros
9h 50m
1 stop
ORD1:02 amChicago O'Hare Intl
Sep 18
ORD3:20 pmChicago O'Hare Intl
22h 38m
1 stop
STI2:58 pmSantiago de los Caballeros
$557

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 July 26, 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 9/17

7:30 pm-11:40 pm

Nonstop5h 10m

Chicago O'Hare Intl

Fri 12/11

5:45 am-12:30 pm

Nonstop4h 45m

$279

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 9/5

7:02 am-11:12 am

Nonstop5h 10m

Chicago O'Hare Intl

Sat 9/12

12:12 pm-5:57 pm

Nonstop4h 45m

$307

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Thu 9/17

3:30 pm-11:40 pm

1 stop9h 10m

Chicago O'Hare Intl

Fri 12/11

5:45 am-4:20 pm

1 stop8h 35m

$327

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 9/24

7:30 pm-11:40 pm

Nonstop5h 10m

Chicago O'Hare Intl

Thu 10/1

3:40 pm-4:05 pm

1 stop23h 25m

$367

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 10/1

2:50 pm-9:07 am

2 stops19h 17m

Chicago Midway

Mon 10/19

10:58 am-12:28 pm

2 stops24h 30m

$397

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 9/30

4:00 pm-10:44 pm

1 stop7h 44m

Chicago Midway

Mon 10/19

5:15 pm-12:28 pm

2 stops18h 13m

$445

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Thu 8/20

10:27 am-11:30 pm

1 stop14h 03m

Chicago O'Hare Intl

Tue 8/25

5:00 am-6:44 pm

1 stop12h 44m

$467

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 9/24

2:35 pm-9:00 pm

1 stop7h 25m

Chicago Midway

Mon 9/28

7:55 pm-1:20 pm

2 stops16h 25m

$471

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Thu 9/10

2:15 pm-11:59 pm

2 stops10h 44m

Chicago O'Hare Intl

Sat 9/19

6:59 am-6:34 pm

1 stop10h 35m

$472

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 8/20

1:45 pm-10:40 pm

1 stop9h 55m

Chicago Midway

Mon 8/24

7:55 pm-1:20 pm

2 stops16h 25m

$578

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 February is, on average, the cheapest month to fly to Chicago from Dominican Republic, with most prices found around $375. If you’re not able to fly to Chicago in February, then December is your next best option. Flight prices from Dominican Republic to Chicago during December average around $400.

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 $331. This is often the case because there is less demand to fly during this day of the week. When flying out on a Tuesday, the most expensive travel day of the week, you can expect to see flight prices from Dominican Republic to Chicago for around $502.

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 $297. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $433.

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

$281

Fastest flight time

4h 45m

Direct flights

Mon, Tue, 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 $281. The best round-trip flight deal from Dominican Republic to Chicago found on momondo in the last 72 hours is $299.
The fastest flight from Dominican Republic to Chicago takes 4h 45m
Direct flights go from Dominican Republic to Chicago on Monday, Tuesday, Friday, Saturday and Sunday. The only airline offering direct flights is Arajet.
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
ArajetPriceFrom $237Free CancellationRating
6.3
51 reviews
Search Arajet flights
American AirlinesPriceFrom $283Free CancellationRating
7.1
11,849 reviews
Search American Airlines flights

Traveling to a place near Chicago?

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