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Cheap flights from the Dominican Republic to Chicago from $133

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 3/14. 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.
Frontier Logo
6:50 pm - 10:00 pmPUJ-ORD
5h 10mnonstop
Frontier Logo
7:10 am - 1:47 pmORD-PUJ
4h 37mnonstop
$227Frontier
Find Deal
Fri, Dec 5 - Fri, Dec 12
Arajet Logo
5:47 am - 8:57 amPUJ-ORD
5h 10mnonstop
Arajet Logo
10:27 am - 5:12 pmORD-PUJ
4h 45mnonstop
$240Arajet
Find Deal
Sat, Jan 31 - Sat, Feb 7
United Airlines Logo
5:20 pm - 9:36 amPUJ-ORD
18h 16m1 stop
United Airlines Logo
9:30 am - 4:02 pmORD-PUJ
4h 32mnonstop
$272United Airlines
Find Deal
Wed, Dec 3 - Wed, Dec 10
United Airlines Logo
5:20 pm - 9:36 amPUJ-ORD
18h 16m1 stop
United Airlines Logo
6:00 am - 5:25 pmORD-PUJ
9h 25m1 stop
$273United Airlines
Find Deal
Wed, Dec 3 - Wed, Dec 10
Multiple Airlines Logo
5:45 pm - 11:29 pmPUJ-ORD
7h 44m1 stop
Multiple Airlines Logo
10:27 am - 5:12 pmORD-PUJ
4h 45mnonstop
$275Multiple Airlines
Find Deal
Sat, Nov 22 - Sat, Nov 29
Multiple Airlines Logo
5:45 pm - 11:29 pmPUJ-ORD
7h 44m1 stop
Multiple Airlines Logo
10:27 am - 5:12 pmORD-PUJ
4h 45mnonstop
$278Multiple Airlines
Find Deal
Sat, Nov 22 - Sat, Nov 29
Delta Logo
5:04 pm - 11:47 pmPUJ-MDW
8h 43m1 stop
Delta Logo
6:00 am - 2:25 pmMDW-PUJ
6h 25m1 stop
$344Delta
Find Deal
Tue, Dec 2 - Tue, Dec 9
Delta Logo
5:11 pm - 8:54 amPUJ-MDW
17h 43m1 stop
Delta Logo
6:45 pm - 2:30 pmMDW-PUJ
17h 45m1 stop
$368Delta
Find Deal
Thu, Feb 19 - Sun, Feb 22
American Airlines Logo
6:20 am - 12:04 pmSTI-ORD
7h 44m1 stop
American Airlines Logo
12:02 pm - 10:56 pmORD-STI
8h 54m1 stop
$410American Airlines
Find Deal
Mon, Nov 24 - Mon, Dec 1
American Airlines Logo
3:05 pm - 10:59 pmSDQ-ORD
9h 54m1 stop
American Airlines Logo
5:00 am - 2:05 pmORD-SDQ
7h 05m1 stop
$410American Airlines
Find Deal
Fri, Nov 14 - Sun, Nov 16

Frontier flights from Dominican Republic to Chicago

Our best Frontier deals on Dominican Republic to Chicago flight tickets
Frontier
Dec 5
PUJ6:50 pmPunta Cana
5h 10m
ORD10:00 pmChicago O'Hare Intl
Dec 12
ORD7:10 amChicago O'Hare Intl
4h 37m
PUJ1:47 pmPunta Cana
$227
Find similar
Frontier
Dec 4
PUJ6:50 pmPunta Cana
5h 10m
ORD10:00 pmChicago O'Hare Intl
Dec 11
ORD7:10 amChicago O'Hare Intl
4h 37m
PUJ1:47 pmPunta Cana
$328
Find similar
Frontier
Dec 23
SDQ12:35 pmSanto Domingo Las Americas
11h 23m
1 stop
MDW9:58 pmChicago Midway
Jan 1
MDW3:10 pmChicago Midway
18h 10m
1 stop
SDQ11:20 amSanto Domingo Las Americas
$338
Find similar

Arajet flights from Dominican Republic to Chicago

Our best Arajet deals on Dominican Republic to Chicago flight tickets
Arajet
Jan 31
PUJ5:47 amPunta Cana
5h 10m
ORD8:57 amChicago O'Hare Intl
Feb 7
ORD10:27 amChicago O'Hare Intl
4h 45m
PUJ5:12 pmPunta Cana
$240
Find similar
Arajet
Jan 24
PUJ5:47 amPunta Cana
5h 10m
ORD8:57 amChicago O'Hare Intl
Jan 31
ORD10:27 amChicago O'Hare Intl
4h 45m
PUJ5:12 pmPunta Cana
$243
Find similar
Arajet
Nov 22
PUJ5:47 amPunta Cana
5h 10m
ORD8:57 amChicago O'Hare Intl
Nov 29
ORD10:27 amChicago O'Hare Intl
4h 45m
PUJ5:12 pmPunta Cana
$245
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 October 27, 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

Fri 12/5

6:50 pm-10:00 pm

Nonstop5h 10m

Chicago O'Hare Intl

Fri 12/12

7:10 am-1:47 pm

Nonstop4h 37m

$227

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 1/31

5:47 am-8:57 am

Nonstop5h 10m

Chicago O'Hare Intl

Sat 2/7

10:27 am-5:12 pm

Nonstop4h 45m

$240

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 12/3

5:20 pm-9:36 am

1 stop18h 16m

Chicago O'Hare Intl

Wed 12/10

9:30 am-4:02 pm

Nonstop4h 32m

$272

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 12/3

5:20 pm-9:36 am

1 stop18h 16m

Chicago O'Hare Intl

Wed 12/10

6:00 am-5:25 pm

1 stop9h 25m

$273

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 11/22

5:45 pm-11:29 pm

1 stop7h 44m

Chicago O'Hare Intl

Sat 11/29

10:27 am-5:12 pm

Nonstop4h 45m

$275

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 11/22

5:45 pm-11:29 pm

1 stop7h 44m

Chicago O'Hare Intl

Sat 11/29

10:27 am-5:12 pm

Nonstop4h 45m

$278

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Tue 12/2

5:04 pm-11:47 pm

1 stop8h 43m

Chicago Midway

Tue 12/9

6:00 am-2:25 pm

1 stop6h 25m

$344

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 2/19

5:11 pm-8:54 am

1 stop17h 43m

Chicago Midway

Sun 2/22

6:45 pm-2:30 pm

1 stop17h 45m

$368

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Mon 11/24

6:20 am-12:04 pm

1 stop7h 44m

Chicago O'Hare Intl

Mon 12/1

12:02 pm-10:56 pm

1 stop8h 54m

$410

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Fri 11/14

3:05 pm-10:59 pm

1 stop9h 54m

Chicago O'Hare Intl

Sun 11/16

5:00 am-2:05 pm

1 stop7h 05m

$410

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 May is, on average, the cheapest month to fly to Chicago from Dominican Republic, with most prices found around $299. If you’re not able to fly to Chicago in May, then March is your next best option. Flight prices from Dominican Republic to Chicago during March average around $334.

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 Saturday when prices can be found for as low as $321. 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 $478.

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 $306. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $399.

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 $434 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 $283 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.

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

$206

Fastest flight time

4h 55m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Dominican Republic in the past 72 hours is $206. The best round-trip flight deal from Dominican Republic to Chicago found on momondo in the last 72 hours is $195.
The fastest flight from Dominican Republic to Chicago takes 4h 55m
Direct flights go from Dominican Republic to Chicago every day.
There are 2 airports near Chicago: 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
FrontierPriceFrom $181Free CancellationRating
5.8
3,122 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $189Free CancellationRating
6.3
8,110 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $269Free CancellationRating
7.4
8,997 reviews
Search United Airlines flights
American AirlinesPriceFrom $354Free CancellationRating
7.2
11,033 reviews
Search American Airlines flights
DeltaPriceFrom $449Free CancellationRating
7.9
7,996 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
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
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