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Cheap flights from the Dominican Republic to Chicago from $209

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 - 10:40 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 10mnonstop
Arajet Logo
3:20 am - 10:05 amORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 45mnonstop
$329Arajet
Thu, Jan 14 - Sun, Jan 31
Arajet Logo
7:30 pm - 11:40 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 10mnonstop
Arajet Logo
11:27 am - 5:12 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 45mnonstop
$349Arajet
Thu, Oct 22 - Sat, Oct 31
Arajet Logo
5:47 am - 8:57 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
$356Arajet
Sat, Nov 7 - Sat, Nov 14
Multiple Airlines Logo
3:30 pm - 11:40 pmSDQ  Santo Domingo Las Americas-ORD Chicago O'Hare Intl
9h 10m1 stop Punta Cana
Multiple Airlines Logo
11:27 am - 9:40 pmORD  Chicago O'Hare Intl-SDQ Santo Domingo Las Americas
9h 13m1 stop Punta Cana
$370Multiple Airlines
Thu, Oct 22 - Sat, Oct 31
Multiple Airlines Logo
7:30 pm - 11:40 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 10mnonstop
Multiple Airlines Logo
2:00 pm - 5:45 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
26h 45m2 stops Toronto Island Montreal Pierre Elliott Trudeau Intl
$387Multiple Airlines
Thu, Oct 22 - Thu, Oct 29
Multiple Airlines Logo
7:30 pm - 11:40 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 10mnonstop
Multiple Airlines Logo
7:05 am - 10:35 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
14h 30m1 stop Montreal Pierre Elliott Trudeau Intl
$387Multiple Airlines
Thu, Oct 22 - Thu, Oct 29
American Airlines Logo
5:34 pm - 9:08 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 34mnonstop
American Airlines Logo
8:10 am - 2:48 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 38mnonstop
$431American Airlines
Thu, Dec 24 - Fri, Jan 1
American Airlines Logo
5:34 pm - 9:08 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 34mnonstop
American Airlines Logo
9:52 am - 4:29 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 37mnonstop
$431American Airlines
Thu, Dec 24 - Thu, Dec 31
JetBlue Logo
3:30 pm - 11:08 pmSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
8h 38m1 stop Fort Lauderdale
JetBlue Logo
7:00 am - 2:47 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
6h 47m1 stop Fort Lauderdale
$524JetBlue
Sat, Oct 3 - Sat, Oct 17
JetBlue Logo
3:30 pm - 11:08 pmSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
8h 38m1 stop Fort Lauderdale
JetBlue Logo
7:00 am - 2:47 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
6h 47m1 stop Fort Lauderdale
$535JetBlue
Thu, Oct 1 - Tue, Oct 20

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Arajet flights from Dominican Republic to Chicago

Our best Arajet deals on Dominican Republic to Chicago flight tickets
Arajet
Jan 14
PUJ7:30 pmPunta Cana
5h 10m
ORD10:40 pmChicago O'Hare Intl
Jan 31
ORD3:20 amChicago O'Hare Intl
4h 45m
PUJ10:05 amPunta Cana
$329
Arajet
Oct 22
PUJ7:30 pmPunta Cana
5h 10m
ORD11:40 pmChicago O'Hare Intl
Oct 31
ORD11:27 amChicago O'Hare Intl
4h 45m
PUJ5:12 pmPunta Cana
$349
Arajet
Nov 7
PUJ5:47 amPunta Cana
5h 10m
ORD8:57 amChicago O'Hare Intl
Nov 14
ORD10:27 amChicago O'Hare Intl
4h 45m
PUJ5:12 pmPunta Cana
$356

JetBlue flights from Dominican Republic to Chicago

Our best JetBlue deals on Dominican Republic to Chicago flight tickets
JetBlue
Oct 3
STI3:30 pmSantiago de los Caballeros
8h 38m
1 stop
ORD11:08 pmChicago O'Hare Intl
Oct 17
ORD7:00 amChicago O'Hare Intl
6h 47m
1 stop
STI2:47 pmSantiago de los Caballeros
$524
JetBlue
Oct 1
STI3:30 pmSantiago de los Caballeros
8h 38m
1 stop
ORD11:08 pmChicago O'Hare Intl
Oct 20
ORD7:00 amChicago O'Hare Intl
6h 47m
1 stop
STI2:47 pmSantiago de los Caballeros
$535
JetBlue
Oct 4
STI3:30 pmSantiago de los Caballeros
8h 38m
1 stop
ORD11:08 pmChicago O'Hare Intl
Oct 17
ORD7:00 amChicago O'Hare Intl
6h 47m
1 stop
STI2:47 pmSantiago de los Caballeros
$538

momondo Fare Finder

 
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

Thu 1/14

7:30 pm-10:40 pm

Nonstop5h 10m

Chicago O'Hare Intl

Sun 1/31

3:20 am-10:05 am

Nonstop4h 45m

$329

Punta CanaChicago

PUJ Punta Cana - ORD Chicago O'Hare Intl

PUJORD

Punta Cana

Thu 10/22

7:30 pm-11:40 pm

Nonstop5h 10m

Chicago O'Hare Intl

Sat 10/31

11:27 am-5:12 pm

Nonstop4h 45m

$349

Punta CanaChicago

PUJ Punta Cana - ORD Chicago O'Hare Intl

PUJORD

Punta Cana

Sat 11/7

5:47 am-8:57 am

Nonstop5h 10m

Chicago O'Hare Intl

Sat 11/14

10:27 am-5:12 pm

Nonstop4h 45m

$356

Santo DomingoChicago

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

SDQORD

Santo Domingo Las Americas

Thu 10/22

3:30 pm-11:40 pm

1 stop9h 10m

Chicago O'Hare Intl

Sat 10/31

11:27 am-9:40 pm

1 stop9h 13m

$370

Punta CanaChicago

PUJ Punta Cana - ORD Chicago O'Hare Intl

PUJORD

Punta Cana

Thu 10/22

7:30 pm-11:40 pm

Nonstop5h 10m

Chicago O'Hare Intl

Thu 10/29

2:00 pm-5:45 pm

2 stops26h 45m

$387

Punta CanaChicago

PUJ Punta Cana - ORD Chicago O'Hare Intl

PUJORD

Punta Cana

Thu 10/22

7:30 pm-11:40 pm

Nonstop5h 10m

Chicago O'Hare Intl

Thu 10/29

7:05 am-10:35 pm

1 stop14h 30m

$387

Punta CanaChicago

PUJ Punta Cana - ORD Chicago O'Hare Intl

PUJORD

Punta Cana

Thu 12/24

5:34 pm-9:08 pm

Nonstop5h 34m

Chicago O'Hare Intl

Fri 1/1

8:10 am-2:48 pm

Nonstop4h 38m

$431

Punta CanaChicago

PUJ Punta Cana - ORD Chicago O'Hare Intl

PUJORD

Punta Cana

Thu 12/24

5:34 pm-9:08 pm

Nonstop5h 34m

Chicago O'Hare Intl

Thu 12/31

9:52 am-4:29 pm

Nonstop4h 37m

$431

Santiago de los CaballerosChicago

STI Santiago de los Caballeros - ORD Chicago O'Hare Intl

STIORD

Santiago de los Caballeros

Sat 10/3

3:30 pm-11:08 pm

1 stop8h 38m

Chicago O'Hare Intl

Sat 10/17

7:00 am-2:47 pm

1 stop6h 47m

$524

Santiago de los CaballerosChicago

STI Santiago de los Caballeros - ORD Chicago O'Hare Intl

STIORD

Santiago de los Caballeros

Thu 10/1

3:30 pm-11:08 pm

1 stop8h 38m

Chicago O'Hare Intl

Tue 10/20

7:00 am-2:47 pm

1 stop6h 47m

$535

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 October is your next best option. Flight prices from Dominican Republic to Chicago during October average around $425.

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 $396. 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 $506.

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 $212. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $499.

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 7% 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

$209

Fastest flight time

5h 04m

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 $209. The best round-trip flight deal from Dominican Republic to Chicago found on momondo in the last 72 hours is $329.
The fastest flight from Dominican Republic to Chicago takes 5h 04m
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
6.1
54 reviews
Search Arajet flights
American AirlinesPriceFrom $283Free CancellationRating
7.1
12,019 reviews
Search American Airlines flights
JetBluePriceFrom $375Free CancellationRating
7.1
3,033 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
Porter
Crown Point
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

Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport