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Cheap flights from the Dominican Republic to Chicago from $145

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 3/3. 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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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 pm
PUJ
-
ORD
5h 10mnonstop
Arajet Logo
10:27 am - 5:12 pm
ORD
-
PUJ
4h 45mnonstop
$207Arajet
Tue, Feb 24 - Sat, Feb 28
Arajet Logo
5:47 am - 9:57 am
PUJ
-
ORD
5h 10mnonstop
Arajet Logo
11:27 am - 5:12 pm
ORD
-
PUJ
4h 45mnonstop
$211Arajet
Sat, May 16 - Sat, May 23
Arajet Logo
5:47 am - 9:57 am
PUJ
-
ORD
5h 10mnonstop
Arajet Logo
11:27 am - 5:12 pm
ORD
-
PUJ
4h 45mnonstop
$213Arajet
Sat, Apr 18 - Sat, Apr 25
Multiple Airlines Logo
7:30 pm - 10:40 pm
PUJ
-
ORD
5h 10mnonstop
Multiple Airlines Logo
5:15 am - 4:36 pm
ORD
-
PUJ
9h 21m1 stop
$240Multiple Airlines
Tue, Feb 3 - Tue, Feb 10
Spirit Airlines Logo
5:47 pm - 11:47 pm
PUJ
-
ORD
8h 00m1 stop
Spirit Airlines Logo
5:15 am - 4:36 pm
ORD
-
PUJ
9h 21m1 stop
$243Spirit Airlines
Fri, Feb 20 - Fri, Feb 27
Spirit Airlines Logo
4:40 pm - 11:47 pm
STI
-
ORD
9h 07m1 stop
Spirit Airlines Logo
5:15 am - 3:35 pm
ORD
-
STI
8h 20m1 stop
$258Spirit Airlines
Wed, Feb 11 - Wed, Feb 18
Multiple Airlines Logo
11:14 am - 5:52 pm
SDQ
-
ORD
8h 38m1 stop
Multiple Airlines Logo
8:43 pm - 2:27 pm
ORD
-
SDQ
15h 44m1 stop
$278Multiple Airlines
Wed, Jan 21 - Mon, Jan 26
Delta Logo
3:46 pm - 10:22 pm
SDQ
-
MDW
8h 36m1 stop
Delta Logo
10:49 am - 12:32 am
MDW
-
SDQ
11h 43m2 stops
$398Delta
Wed, Feb 11 - Wed, Feb 18
Delta Logo
7:30 am - 5:55 pm
SDQ
-
MDW
12h 25m2 stops
Delta Logo
10:53 am - 12:30 am
MDW
-
SDQ
11h 37m2 stops
$422Delta
Tue, Feb 3 - Sat, Feb 7
Frontier Logo
10:27 am - 8:03 am
SDQ
-
MDW
23h 36m2 stops
Frontier Logo
6:00 am - 11:26 am
MDW
-
SDQ
51h 26m2 stops
$467Frontier
Sat, Jan 17 - Tue, Feb 17

Arajet flights from Dominican Republic to Chicago

Our best Arajet deals on Dominican Republic to Chicago flight tickets
Arajet
Feb 24
PUJ7:30 pmPunta Cana
5h 10m
ORD10:40 pmChicago O'Hare Intl
Feb 28
ORD10:27 amChicago O'Hare Intl
4h 45m
PUJ5:12 pmPunta Cana
$207
Find similar
Arajet
Feb 7
PUJ5:47 amPunta Cana
5h 10m
ORD8:57 amChicago O'Hare Intl
Feb 16
ORD5:45 amChicago O'Hare Intl
4h 45m
PUJ12:30 pmPunta Cana
$210
Find similar
Arajet
May 16
PUJ5:47 amPunta Cana
5h 10m
ORD9:57 amChicago O'Hare Intl
May 23
ORD11:27 amChicago O'Hare Intl
4h 45m
PUJ5:12 pmPunta Cana
$211
Find similar

JetBlue flights from Dominican Republic to Chicago

Our best JetBlue deals on Dominican Republic to Chicago flight tickets
JetBlue
Feb 24
SDQ9:43 pmSanto Domingo Las Americas
16h 21m
2 stops
ORD12:04 pmChicago O'Hare Intl
Feb 28
ORD12:59 pmChicago O'Hare Intl
30h 25m
2 stops
SDQ9:24 pmSanto Domingo Las Americas
$380
Find similar
JetBlue
Feb 26
SDQ9:43 pmSanto Domingo Las Americas
16h 11m
2 stops
ORD11:54 amChicago O'Hare Intl
Mar 4
ORD12:59 pmChicago O'Hare Intl
30h 25m
2 stops
SDQ9:24 pmSanto Domingo Las Americas
$391
Find similar
JetBlue
Feb 5
SDQ6:20 amSanto Domingo Las Americas
15h 11m
1 stop
ORD7:31 pmChicago O'Hare Intl
Feb 7
ORD9:40 amChicago O'Hare Intl
8h 35m
1 stop
SDQ8:15 pmSanto Domingo Las Americas
$427
Find similar

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 December 30, 2025.
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

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Tue 2/24

7:30 pm-10:40 pm

Nonstop5h 10m

Chicago O'Hare Intl

Sat 2/28

10:27 am-5:12 pm

Nonstop4h 45m

$207

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 5/16

5:47 am-9:57 am

Nonstop5h 10m

Chicago O'Hare Intl

Sat 5/23

11:27 am-5:12 pm

Nonstop4h 45m

$211

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 4/18

5:47 am-9:57 am

Nonstop5h 10m

Chicago O'Hare Intl

Sat 4/25

11:27 am-5:12 pm

Nonstop4h 45m

$213

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Tue 2/3

7:30 pm-10:40 pm

Nonstop5h 10m

Chicago O'Hare Intl

Tue 2/10

5:15 am-4:36 pm

1 stop9h 21m

$240

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Fri 2/20

5:47 pm-11:47 pm

1 stop8h 00m

Chicago O'Hare Intl

Fri 2/27

5:15 am-4:36 pm

1 stop9h 21m

$243

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Wed 2/11

4:40 pm-11:47 pm

1 stop9h 07m

Chicago O'Hare Intl

Wed 2/18

5:15 am-3:35 pm

1 stop8h 20m

$258

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Wed 1/21

11:14 am-5:52 pm

1 stop8h 38m

Chicago O'Hare Intl

Mon 1/26

8:43 pm-2:27 pm

1 stop15h 44m

$278

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Wed 2/11

3:46 pm-10:22 pm

1 stop8h 36m

Chicago Midway

Wed 2/18

10:49 am-12:32 am

2 stops11h 43m

$398

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Tue 2/3

7:30 am-5:55 pm

2 stops12h 25m

Chicago Midway

Sat 2/7

10:53 am-12:30 am

2 stops11h 37m

$422

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Sat 1/17

10:27 am-8:03 am

2 stops23h 36m

Chicago Midway

Tue 2/17

6:00 am-11:26 am

2 stops51h 26m

$467

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 $233. If you’re not able to fly to Chicago in February, then May is your next best option. Flight prices from Dominican Republic to Chicago during May average around $299.

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 $354. 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 $521.

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 morning. Flights from Dominican Republic to Chicago during this time can be as low as $286. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $419.

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

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Dominican Republic when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $419 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Dominican Republic for as low as $276 on momondo.

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 1% 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

$235

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 $235. The best round-trip flight deal from Dominican Republic to Chicago found on momondo in the last 72 hours is $350.
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

  • 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
Spirit AirlinesPriceFrom $189Free CancellationRating
6.3
8,238 reviews
Search Spirit Airlines flights
FrontierPriceFrom $216Free CancellationRating
5.7
3,067 reviews
Search Frontier flights
American AirlinesPriceFrom $354Free CancellationRating
7.2
11,074 reviews
Search American Airlines flights
DeltaPriceFrom $449Free CancellationRating
7.9
8,016 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
Benton Harbor
Saint Joseph
Portage
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
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