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Cheap flights from the Dominican Republic to Chicago from $178

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 10/29. 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 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
2:05 pm - 11:44 pm
PUJ
-
ORD
10h 39m
1 stop
Multiple Airlines Logo
12:12 pm - 5:57 pm
ORD
-
PUJ
4h 45mnonstop
$369Multiple Airlines
Thu, Aug 13 - Sat, Aug 22
JetBlue Logo
1:35 pm - 11:44 pm
SDQ
-
ORD
11h 09m
1 stop
JetBlue Logo
2:35 pm - 11:59 pm
ORD
-
SDQ
8h 24m
1 stop
$383JetBlue
Fri, Jul 17 - Mon, Jul 20
JetBlue Logo
4:30 pm - 11:44 pm
PUJ
-
ORD
9h 14m
1 stop
JetBlue Logo
7:00 am - 3:25 pm
ORD
-
PUJ
6h 25m
1 stop
$389JetBlue
Wed, Nov 4 - Tue, Nov 10
Multiple Airlines Logo
7:30 pm - 10:40 pm
PUJ
-
ORD
5h 10mnonstop
Multiple Airlines Logo
1:55 pm - 6:45 pm
ORD
-
PUJ
26h 50m
1 stop
$391Multiple Airlines
Thu, Nov 5 - Sun, Nov 8
Delta Logo
7:16 pm - 10:04 am
STI
-
ORD
15h 48m
1 stop
Delta Logo
7:05 am - 5:46 pm
ORD
-
STI
9h 41m
2 stops
$436Delta
Fri, Oct 16 - Tue, Oct 20
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
8:31 pm - 12:06 pm
STI
-
ORD
16h 35m
2 stops
Delta Logo
7:10 am - 7:06 pm
ORD
-
STI
10h 56m
2 stops
$511Delta
Fri, Oct 9 - Tue, Oct 13

Delta flights from Dominican Republic to Chicago

Our best Delta deals on Dominican Republic to Chicago flight tickets
Delta
Oct 16
STI7:16 pmSantiago de los Caballeros
15h 48m
1 stop
ORD10:04 amChicago O'Hare Intl
Oct 20
ORD7:05 amChicago O'Hare Intl
9h 41m
2 stops
STI5:46 pmSantiago de los Caballeros
$436
Delta
Oct 9
STI8:31 pmSantiago de los Caballeros
16h 35m
2 stops
ORD12:06 pmChicago O'Hare Intl
Oct 13
ORD7:10 amChicago O'Hare Intl
10h 56m
2 stops
STI7:06 pmSantiago de los Caballeros
$511
Delta
Oct 9
STI8:31 pmSantiago de los Caballeros
16h 35m
2 stops
ORD12:06 pmChicago O'Hare Intl
Oct 13
ORD7:10 amChicago O'Hare Intl
10h 56m
2 stops
STI7:06 pmSantiago de los Caballeros
$539

Air Canada flights from Dominican Republic to Chicago

Our best Air Canada deals on Dominican Republic to Chicago flight tickets
Air Canada
Jun 2
PUJ5:25 pmPunta Cana
17h 53m
1 stop
ORD10:18 amChicago O'Hare Intl
Jun 16
ORD8:20 pmChicago O'Hare Intl
18h 05m
1 stop
PUJ3:25 pmPunta Cana
$424
Air Canada
Jun 2
PUJ5:25 pmPunta Cana
17h 53m
1 stop
ORD10:18 amChicago O'Hare Intl
Jun 16
ORD6:22 pmChicago O'Hare Intl
21h 08m
2 stops
PUJ4:30 pmPunta Cana
$440
Air Canada
Jun 2
PUJ5:25 pmPunta Cana
17h 53m
1 stop
ORD10:18 amChicago O'Hare Intl
Jun 14
ORD8:20 pmChicago O'Hare Intl
14h 35m
1 stop
PUJ11:55 amPunta Cana
$447

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 May 31, 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

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 8/13

2:05 pm-11:44 pm

1 stop10h 39m

Chicago O'Hare Intl

Sat 8/22

12:12 pm-5:57 pm

Nonstop4h 45m

$369

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Fri 7/17

1:35 pm-11:44 pm

1 stop11h 09m

Chicago O'Hare Intl

Mon 7/20

2:35 pm-11:59 pm

1 stop8h 24m

$383

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 11/4

4:30 pm-11:44 pm

1 stop9h 14m

Chicago O'Hare Intl

Tue 11/10

7:00 am-3:25 pm

1 stop6h 25m

$389

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

1:55 pm-6:45 pm

1 stop26h 50m

$391

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Fri 10/16

7:16 pm-10:04 am

1 stop15h 48m

Chicago O'Hare Intl

Tue 10/20

7:05 am-5:46 pm

2 stops9h 41m

$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

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Fri 10/9

8:31 pm-12:06 pm

2 stops16h 35m

Chicago O'Hare Intl

Tue 10/13

7:10 am-7:06 pm

2 stops10h 56m

$511

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

Every day

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 every day.
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
2,924 reviews
Search Frontier flights
ArajetPriceFrom $195Free CancellationRating
6.5
49 reviews
Search Arajet flights
American AirlinesPriceFrom $283Free CancellationRating
7.1
11,644 reviews
Search American Airlines flights
DeltaPriceFrom $449Free CancellationRating
7.9
8,404 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
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
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