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Cheap flights from the Dominican Republic to Chicago from $188

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 11/13. 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
5:47 am - 9:57 amPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 10mnonstop
Arajet Logo
10:27 am - 5:12 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 45mnonstop
$321Arajet
Sat, Oct 31 - Sat, Nov 7
Arajet Logo
5:47 am - 9:57 amPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 10mnonstop
Arajet Logo
10:27 am - 5:12 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 45mnonstop
$322Arajet
Sat, Oct 31 - Sat, Nov 7
Multiple Airlines Logo
1:40 am - 11:12 amSDQ  Santo Domingo Las Americas-ORD Chicago O'Hare Intl
10h 32m1 stop Punta Cana
Multiple Airlines Logo
5:30 am - 4:55 pmORD  Chicago O'Hare Intl-SDQ Santo Domingo Las Americas
10h 25m1 stop Punta Cana
$327Multiple Airlines
Fri, Sep 18 - Mon, Sep 28
Arajet Logo
7:30 pm - 11:40 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 10mnonstop
Arajet Logo
6:45 am - 12:30 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 45mnonstop
$332Arajet
Thu, Sep 3 - Fri, Sep 11
Multiple Airlines Logo
1:40 am - 11:12 amSDQ  Santo Domingo Las Americas-ORD Chicago O'Hare Intl
10h 32m1 stop Punta Cana
Multiple Airlines Logo
5:30 am - 4:55 pmORD  Chicago O'Hare Intl-SDQ Santo Domingo Las Americas
10h 25m1 stop Punta Cana
$370Multiple Airlines
Fri, Sep 18 - Mon, Sep 28
Multiple Airlines Logo
1:40 am - 11:12 amSDQ  Santo Domingo Las Americas-ORD Chicago O'Hare Intl
10h 32m1 stop Punta Cana
Multiple Airlines Logo
5:30 am - 4:55 pmORD  Chicago O'Hare Intl-SDQ Santo Domingo Las Americas
10h 25m1 stop Punta Cana
$379Multiple Airlines
Fri, Sep 18 - Mon, Sep 28
American Airlines Logo
12:01 pm - 12:33 amPUJ  Punta Cana-ORD Chicago O'Hare Intl
13h 32m1 stop Miami
American Airlines Logo
7:00 pm - 10:58 amORD  Chicago O'Hare Intl-PUJ Punta Cana
14h 58m1 stop Miami
$422American Airlines
Thu, Sep 17 - Fri, Sep 25
American Airlines Logo
4:04 pm - 7:48 amPUJ  Punta Cana-ORD Chicago O'Hare Intl
16h 44m1 stop Miami
American Airlines Logo
6:00 am - 3:02 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
8h 02m1 stop Miami
$422American Airlines
Thu, Sep 24 - Sun, Sep 27
JetBlue Logo
1:32 pm - 11:44 pmSDQ  Santo Domingo Las Americas-ORD Chicago O'Hare Intl
11h 12m1 stop Fort Lauderdale
JetBlue Logo
7:00 am - 3:16 pmORD  Chicago O'Hare Intl-SDQ Santo Domingo Las Americas
7h 16m1 stop Fort Lauderdale
$490JetBlue
Thu, Oct 22 - Mon, Oct 26
JetBlue Logo
9:00 am - 9:56 pmSDQ  Santo Domingo Las Americas-ORD Chicago O'Hare Intl
13h 56m1 stop New York John F Kennedy Intl
JetBlue Logo
2:35 pm - 11:59 pmORD  Chicago O'Hare Intl-SDQ Santo Domingo Las Americas
8h 24m1 stop Fort Lauderdale
$521JetBlue
Sat, Oct 10 - Fri, Oct 16

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Arajet flights from Dominican Republic to Chicago

Our best Arajet deals on Dominican Republic to Chicago flight tickets
Arajet
Oct 31
PUJ5:47 amPunta Cana
5h 10m
ORD9:57 amChicago O'Hare Intl
Nov 7
ORD10:27 amChicago O'Hare Intl
4h 45m
PUJ5:12 pmPunta Cana
$321
Arajet
Oct 31
PUJ5:47 amPunta Cana
5h 10m
ORD9:57 amChicago O'Hare Intl
Nov 7
ORD10:27 amChicago O'Hare Intl
4h 45m
PUJ5:12 pmPunta Cana
$322
Arajet
Sep 3
PUJ7:30 pmPunta Cana
5h 10m
ORD11:40 pmChicago O'Hare Intl
Sep 11
ORD6:45 amChicago O'Hare Intl
4h 45m
PUJ12:30 pmPunta Cana
$332

United Airlines flights from Dominican Republic to Chicago

Our best United Airlines deals on Dominican Republic to Chicago flight tickets
United Airlines
Oct 31
PUJ3:25 pmPunta Cana
5h 16m
ORD7:41 pmChicago O'Hare Intl
Nov 7
ORD9:35 pmChicago O'Hare Intl
16h 29m
1 stop
PUJ4:04 pmPunta Cana
$404
United Airlines
Oct 21
PUJ4:40 pmPunta Cana
17h 20m
1 stop
ORD9:00 amChicago O'Hare Intl
Oct 25
ORD5:30 amChicago O'Hare Intl
8h 34m
1 stop
PUJ3:04 pmPunta Cana
$407
United Airlines
Dec 3
PUJ2:55 pmPunta Cana
5h 13m
ORD6:08 pmChicago O'Hare Intl
Dec 7
ORD9:30 amChicago O'Hare Intl
4h 32m
PUJ4:02 pmPunta Cana
$408

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 August 9, 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 Punta Cana - ORD Chicago O'Hare Intl

PUJORD

Punta Cana

Sat 10/31

5:47 am-9:57 am

Nonstop5h 10m

Chicago O'Hare Intl

Sat 11/7

10:27 am-5:12 pm

Nonstop4h 45m

$321

Punta CanaChicago

PUJ Punta Cana - ORD Chicago O'Hare Intl

PUJORD

Punta Cana

Sat 10/31

5:47 am-9:57 am

Nonstop5h 10m

Chicago O'Hare Intl

Sat 11/7

10:27 am-5:12 pm

Nonstop4h 45m

$322

Santo DomingoChicago

SDQ Santo Domingo Las Americas - ORD Chicago O'Hare Intl

SDQORD

Santo Domingo Las Americas

Fri 9/18

1:40 am-11:12 am

1 stop10h 32m

Chicago O'Hare Intl

Mon 9/28

5:30 am-4:55 pm

1 stop10h 25m

$327

Punta CanaChicago

PUJ Punta Cana - ORD Chicago O'Hare Intl

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

$332

Santo DomingoChicago

SDQ Santo Domingo Las Americas - ORD Chicago O'Hare Intl

SDQORD

Santo Domingo Las Americas

Fri 9/18

1:40 am-11:12 am

1 stop10h 32m

Chicago O'Hare Intl

Mon 9/28

5:30 am-4:55 pm

1 stop10h 25m

$370

Santo DomingoChicago

SDQ Santo Domingo Las Americas - ORD Chicago O'Hare Intl

SDQORD

Santo Domingo Las Americas

Fri 9/18

1:40 am-11:12 am

1 stop10h 32m

Chicago O'Hare Intl

Mon 9/28

5:30 am-4:55 pm

1 stop10h 25m

$379

Punta CanaChicago

PUJ Punta Cana - ORD Chicago O'Hare Intl

PUJORD

Punta Cana

Thu 9/17

12:01 pm-12:33 am

1 stop13h 32m

Chicago O'Hare Intl

Fri 9/25

7:00 pm-10:58 am

1 stop14h 58m

$422

Punta CanaChicago

PUJ Punta Cana - ORD Chicago O'Hare Intl

PUJORD

Punta Cana

Thu 9/24

4:04 pm-7:48 am

1 stop16h 44m

Chicago O'Hare Intl

Sun 9/27

6:00 am-3:02 pm

1 stop8h 02m

$422

Santo DomingoChicago

SDQ Santo Domingo Las Americas - ORD Chicago O'Hare Intl

SDQORD

Santo Domingo Las Americas

Thu 10/22

1:32 pm-11:44 pm

1 stop11h 12m

Chicago O'Hare Intl

Mon 10/26

7:00 am-3:16 pm

1 stop7h 16m

$490

Santo DomingoChicago

SDQ Santo Domingo Las Americas - ORD Chicago O'Hare Intl

SDQORD

Santo Domingo Las Americas

Sat 10/10

9:00 am-9:56 pm

1 stop13h 56m

Chicago O'Hare Intl

Fri 10/16

2:35 pm-11:59 pm

1 stop8h 24m

$521

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 September is your next best option. Flight prices from Dominican Republic to Chicago during September average around $405.

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 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?

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

$253

Fastest flight time

5h 10m

Direct flights

Mon, Fri and Sun

Airports in Chicago

3 airports
The best one-way flight to Chicago from Dominican Republic in the past 72 hours is $253. The best round-trip flight deal from Dominican Republic to Chicago found on momondo in the last 72 hours is $484.
The fastest flight from Dominican Republic to Chicago takes 5h 10m
Direct flights go from Dominican Republic to Chicago on Monday, Friday 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
ArajetPriceFrom $237Free CancellationRating
6.2
53 reviews
Search Arajet flights
American AirlinesPriceFrom $283Free CancellationRating
7.1
11,897 reviews
Search American Airlines flights
JetBluePriceFrom $375Free CancellationRating
7.1
3,030 reviews
Search JetBlue 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