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Cheap flights from the Dominican Republic to Chicago from $218

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 8/28. 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
3:20 am - 10:05 am
ORD
-
PUJ
4h 45mnonstop
$315Arajet
Thu, Oct 29 - Sun, Nov 1
Arajet Logo
7:30 pm - 11:40 pm
PUJ
-
ORD
5h 10mnonstop
Arajet Logo
6:45 am - 12:30 pm
ORD
-
PUJ
4h 45mnonstop
$327Arajet
Thu, Sep 3 - Fri, Sep 11
Multiple Airlines Logo
7:30 pm - 11:40 pm
PUJ
-
ORD
5h 10mnonstop
Multiple Airlines Logo
6:21 pm - 11:55 am
ORD
-
PUJ
16h 34m
2 stops
$377Multiple Airlines
Thu, Sep 24 - Sun, Sep 27
Multiple Airlines Logo
7:30 pm - 11:40 pm
PUJ
-
ORD
5h 10mnonstop
Multiple Airlines Logo
8:45 am - 4:05 pm
ORD
-
PUJ
30h 20m
1 stop
$382Multiple Airlines
Thu, Sep 3 - Fri, Sep 11
American Airlines Logo
4:14 pm - 11:44 pm
PUJ
-
ORD
8h 30m
1 stop
American Airlines Logo
8:21 am - 2:05 pm
ORD
-
PUJ
4h 44mnonstop
$383American Airlines
Thu, Aug 27 - Mon, Aug 31
American Airlines Logo
4:14 pm - 11:44 pm
PUJ
-
ORD
8h 30m
1 stop
American Airlines Logo
6:00 am - 3:19 pm
ORD
-
PUJ
8h 19m
1 stop
$387American Airlines
Thu, Aug 27 - Mon, Aug 31
Southwest Logo
2:35 pm - 9:00 pm
PUJ
-
MDW
7h 25m
1 stop
Southwest Logo
5:00 am - 1:40 pm
MDW
-
PUJ
7h 40m
1 stop
$411Southwest
Thu, Aug 27 - Mon, Aug 31
Delta Logo
2:53 pm - 7:56 am
SDQ
-
ORD
18h 03m
2 stops
Delta Logo
6:00 am - 6:06 pm
ORD
-
SDQ
11h 06m
1 stop
$425Delta
Wed, Aug 26 - Sat, Aug 29
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
$425Delta
Tue, Aug 25 - Sat, Sep 5
Southwest Logo
2:35 pm - 9:00 pm
PUJ
-
MDW
7h 25m
1 stop
Southwest Logo
5:10 am - 2:05 pm
MDW
-
PUJ
7h 55m
1 stop
$514Southwest
Thu, Sep 24 - Sun, Sep 27

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Delta flights from Dominican Republic to Chicago

Our best Delta deals on Dominican Republic to Chicago flight tickets
Delta
Sep 17
PUJ4:00 pmPunta Cana
16h 57m
2 stops
ORD7:57 amChicago O'Hare Intl
Sep 21
ORD5:30 amChicago O'Hare Intl
6h 55m
1 stop
PUJ1:25 pmPunta Cana
$392
Delta
Aug 26
SDQ2:53 pmSanto Domingo Las Americas
18h 03m
2 stops
ORD7:56 amChicago O'Hare Intl
Aug 29
ORD6:00 amChicago O'Hare Intl
11h 06m
1 stop
SDQ6:06 pmSanto Domingo Las Americas
$425
Delta
Aug 20
SDQ2:53 pmSanto Domingo Las Americas
18h 03m
2 stops
ORD7:56 amChicago O'Hare Intl
Aug 25
ORD5:30 amChicago O'Hare Intl
11h 36m
2 stops
SDQ6:06 pmSanto Domingo Las Americas
$461

Frontier flights from Dominican Republic to Chicago

Our best Frontier deals on Dominican Republic to Chicago flight tickets
Frontier
Aug 27
PUJ11:39 amPunta Cana
12h 48m
1 stop
ORD11:27 pmChicago O'Hare Intl
Aug 30
ORD12:44 amChicago O'Hare Intl
8h 40m
1 stop
PUJ10:24 amPunta Cana
$394
Frontier
Aug 27
PUJ11:39 amPunta Cana
12h 48m
1 stop
ORD11:27 pmChicago O'Hare Intl
Aug 31
ORD2:25 pmChicago O'Hare Intl
18h 59m
2 stops
PUJ10:24 amPunta Cana
$456
Frontier
Aug 4
PUJ3:31 pmPunta Cana
17h 31m
1 stop
ORD8:02 amChicago O'Hare Intl
Aug 11
ORD12:44 amChicago O'Hare Intl
8h 40m
1 stop
PUJ10:24 amPunta Cana
$483

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 15, 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

Sun 11/1

3:20 am-10:05 am

Nonstop4h 45m

$315

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 9/3

7:30 pm-11:40 pm

Nonstop5h 10m

Chicago O'Hare Intl

Fri 9/11

6:45 am-12:30 pm

Nonstop4h 45m

$327

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 9/24

7:30 pm-11:40 pm

Nonstop5h 10m

Chicago O'Hare Intl

Sun 9/27

6:21 pm-11:55 am

2 stops16h 34m

$377

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 9/3

7:30 pm-11:40 pm

Nonstop5h 10m

Chicago O'Hare Intl

Fri 9/11

8:45 am-4:05 pm

1 stop30h 20m

$382

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 8/27

4:14 pm-11:44 pm

1 stop8h 30m

Chicago O'Hare Intl

Mon 8/31

8:21 am-2:05 pm

Nonstop4h 44m

$383

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 8/27

4:14 pm-11:44 pm

1 stop8h 30m

Chicago O'Hare Intl

Mon 8/31

6:00 am-3:19 pm

1 stop8h 19m

$387

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 8/27

2:35 pm-9:00 pm

1 stop7h 25m

Chicago Midway

Mon 8/31

5:00 am-1:40 pm

1 stop7h 40m

$411

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Wed 8/26

2:53 pm-7:56 am

2 stops18h 03m

Chicago O'Hare Intl

Sat 8/29

6:00 am-6:06 pm

1 stop11h 06m

$425

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

$425

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 9/24

2:35 pm-9:00 pm

1 stop7h 25m

Chicago Midway

Sun 9/27

5:10 am-2:05 pm

1 stop7h 55m

$514

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 Wednesday when prices can be found for as low as $359. 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 $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?

You could potentially save up to 19% on your flight if you consider stops on a Dominican Republic to Chicago flight.

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

$319

Fastest flight time

4h 45m

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 $319. The best round-trip flight deal from Dominican Republic to Chicago found on momondo in the last 72 hours is $377.
The fastest flight from Dominican Republic to Chicago takes 4h 45m
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
ArajetPriceFrom $237Free CancellationRating
6.3
51 reviews
Search Arajet flights
American AirlinesPriceFrom $283Free CancellationRating
7.1
11,807 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
Saint Joseph
Lansing
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