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Cheap flights from the Dominican Republic to Chicago from $186

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
5:45 am - 12:30 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 45mnonstop
$266Arajet
Thu, Jan 14 - Fri, Jan 29
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
$286Arajet
Thu, Nov 19 - Sun, Nov 29
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
$286Arajet
Thu, Nov 12 - Sun, Nov 15
Multiple Airlines Logo
7:30 pm - 10:40 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 10mnonstop
Multiple Airlines Logo
7:25 am - 11:35 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
14h 10m2 stops Toronto Island Montreal Pierre Elliott Trudeau Intl
$367Multiple Airlines
Thu, Dec 3 - Thu, Dec 10
Multiple Airlines Logo
7:30 pm - 10:40 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 10mnonstop
Multiple Airlines Logo
3:45 pm - 6:45 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
25h 00m1 stop Montreal Pierre Elliott Trudeau Intl
$367Multiple Airlines
Thu, Nov 19 - Thu, Nov 26
Multiple Airlines Logo
5:47 am - 8:57 amPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 10mnonstop
Multiple Airlines Logo
7:05 am - 1:45 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
28h 40m1 stop Montreal Pierre Elliott Trudeau Intl
$367Multiple Airlines
Sat, Dec 5 - Sat, Dec 12
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
American Airlines Logo
5:39 pm - 9:12 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 33mnonstop
American Airlines Logo
9:30 am - 4:16 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 46mnonstop
$431American Airlines
Thu, Jan 14 - Sun, Jan 31
JetBlue Logo
4:43 pm - 11:57 pmSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
9h 14m1 stop Fort Lauderdale
JetBlue Logo
7:00 am - 3:23 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
6h 23m1 stop Fort Lauderdale
$524JetBlue
Mon, Nov 2 - Fri, Nov 6
JetBlue Logo
5:29 pm - 11:57 pmSDQ  Santo Domingo Las Americas-ORD Chicago O'Hare Intl
8h 28m1 stop Fort Lauderdale
JetBlue Logo
7:00 am - 4:18 pmORD  Chicago O'Hare Intl-SDQ Santo Domingo Las Americas
7h 18m1 stop Fort Lauderdale
$548JetBlue
Mon, Nov 2 - Sun, Nov 8

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Frontier flights from Dominican Republic to Chicago

Our best Frontier deals on Dominican Republic to Chicago flight tickets
Frontier
Dec 3
SDQ8:19 pmSanto Domingo Las Americas
18h 52m
1 stop
ORD1:11 pmChicago O'Hare Intl
Dec 10
ORD6:15 amChicago O'Hare Intl
10h 49m
1 stop
SDQ7:04 pmSanto Domingo Las Americas
$481
Frontier
Nov 26
SDQ6:29 pmSanto Domingo Las Americas
30h 04m
1 stop
ORD10:33 pmChicago O'Hare Intl
Dec 3
ORD6:15 amChicago O'Hare Intl
10h 49m
1 stop
SDQ7:04 pmSanto Domingo Las Americas
$497
Frontier
Dec 3
SDQ8:19 pmSanto Domingo Las Americas
18h 52m
1 stop
ORD1:11 pmChicago O'Hare Intl
Dec 10
ORD6:15 amChicago O'Hare Intl
10h 49m
1 stop
SDQ7:04 pmSanto Domingo Las Americas
$517

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 29
ORD5:45 amChicago O'Hare Intl
4h 45m
PUJ12:30 pmPunta Cana
$266
Arajet
Nov 12
PUJ7:30 pmPunta Cana
5h 10m
ORD10:40 pmChicago O'Hare Intl
Nov 15
ORD3:20 amChicago O'Hare Intl
4h 45m
PUJ10:05 amPunta Cana
$286
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
$299

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

Fri 1/29

5:45 am-12:30 pm

Nonstop4h 45m

$266

Punta CanaChicago

PUJ Punta Cana - ORD Chicago O'Hare Intl

PUJORD

Punta Cana

Thu 11/19

7:30 pm-10:40 pm

Nonstop5h 10m

Chicago O'Hare Intl

Sun 11/29

3:20 am-10:05 am

Nonstop4h 45m

$286

Punta CanaChicago

PUJ Punta Cana - ORD Chicago O'Hare Intl

PUJORD

Punta Cana

Thu 11/12

7:30 pm-10:40 pm

Nonstop5h 10m

Chicago O'Hare Intl

Sun 11/15

3:20 am-10:05 am

Nonstop4h 45m

$286

Punta CanaChicago

PUJ Punta Cana - ORD Chicago O'Hare Intl

PUJORD

Punta Cana

Thu 12/3

7:30 pm-10:40 pm

Nonstop5h 10m

Chicago O'Hare Intl

Thu 12/10

7:25 am-11:35 pm

2 stops14h 10m

$367

Punta CanaChicago

PUJ Punta Cana - ORD Chicago O'Hare Intl

PUJORD

Punta Cana

Thu 11/19

7:30 pm-10:40 pm

Nonstop5h 10m

Chicago O'Hare Intl

Thu 11/26

3:45 pm-6:45 pm

1 stop25h 00m

$367

Punta CanaChicago

PUJ Punta Cana - ORD Chicago O'Hare Intl

PUJORD

Punta Cana

Sat 12/5

5:47 am-8:57 am

Nonstop5h 10m

Chicago O'Hare Intl

Sat 12/12

7:05 am-1:45 pm

1 stop28h 40m

$367

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

Punta CanaChicago

PUJ Punta Cana - ORD Chicago O'Hare Intl

PUJORD

Punta Cana

Thu 1/14

5:39 pm-9:12 pm

Nonstop5h 33m

Chicago O'Hare Intl

Sun 1/31

9:30 am-4:16 pm

Nonstop4h 46m

$431

Santiago de los CaballerosChicago

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

STIORD

Santiago de los Caballeros

Mon 11/2

4:43 pm-11:57 pm

1 stop9h 14m

Chicago O'Hare Intl

Fri 11/6

7:00 am-3:23 pm

1 stop6h 23m

$524

Santo DomingoChicago

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

SDQORD

Santo Domingo Las Americas

Mon 11/2

5:29 pm-11:57 pm

1 stop8h 28m

Chicago O'Hare Intl

Sun 11/8

7:00 am-4:18 pm

1 stop7h 18m

$548

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 $411.

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?

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

$186

Fastest flight time

5h 10m

Direct flights

Mon, Thu, Fri and Sun

Airports in Chicago

3 airports
The best one-way flight to Chicago from Dominican Republic in the past 72 hours is $186. The best round-trip flight deal from Dominican Republic to Chicago found on momondo in the last 72 hours is $266.
The fastest flight from Dominican Republic to Chicago takes 5h 10m
Direct flights go from Dominican Republic to Chicago on Monday, Thursday, 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).
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
12,039 reviews
Search American Airlines flights
JetBluePriceFrom $375Free CancellationRating
7.1
3,046 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