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Cheap flights from the Dominican Republic to Chicago from $143

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 3/5. 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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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
7:30 pm - 11:40 pm
PUJ
-
ORD
5h 10mnonstop
Arajet Logo
4:30 am - 10:15 am
ORD
-
PUJ
4h 45mnonstop
$230Arajet
Thu, Apr 16 - Mon, Apr 20
Spirit Airlines Logo
5:47 pm - 11:47 pm
PUJ
-
ORD
8h 00m
1 stop
Spirit Airlines Logo
5:15 am - 4:36 pm
ORD
-
PUJ
9h 21m
1 stop
$236Spirit Airlines
Thu, Feb 26 - Sun, Mar 1
Spirit Airlines Logo
3:43 pm - 11:17 pm
STI
-
ORD
8h 34m
1 stop
Spirit Airlines Logo
7:17 am - 2:35 pm
ORD
-
STI
6h 18m
1 stop
$268Spirit Airlines
Thu, Mar 12 - Tue, Mar 17
Multiple Airlines Logo
7:30 pm - 11:40 pm
PUJ
-
ORD
5h 10mnonstop
Multiple Airlines Logo
5:15 am - 1:50 pm
ORD
-
PUJ
7h 35m
1 stop
$275Multiple Airlines
Thu, Apr 16 - Mon, Apr 20
Multiple Airlines Logo
3:37 pm - 9:17 pm
SDQ
-
ORD
30h 40m
1 stop
Multiple Airlines Logo
6:34 pm - 4:29 pm
ORD
-
SDQ
20h 55m
1 stop
$282Multiple Airlines
Mon, May 4 - Tue, May 19
United Airlines Logo
2:55 pm - 6:08 pm
PUJ
-
ORD
5h 13mnonstop
United Airlines Logo
8:47 am - 2:19 pm
ORD
-
PUJ
4h 32mnonstop
$290United Airlines
Fri, Mar 6 - Tue, Mar 10
United Airlines Logo
4:25 pm - 7:38 pm
PUJ
-
ORD
5h 13mnonstop
United Airlines Logo
1:06 pm - 4:25 pm
ORD
-
PUJ
26h 19m
1 stop
$291United Airlines
Fri, Mar 6 - Tue, Mar 10
Delta Logo
3:57 pm - 10:28 pm
PUJ
-
MDW
7h 31m
1 stop
Delta Logo
6:00 am - 1:21 pm
MDW
-
PUJ
6h 21m
1 stop
$380Delta
Thu, Apr 16 - Mon, Apr 20
Frontier Logo
4:08 pm - 8:07 pm
SDQ
-
MDW
28h 59m
1 stop
Frontier Logo
6:30 am - 1:56 pm
MDW
-
SDQ
6h 26m
1 stop
$383Frontier
Wed, Apr 8 - Sat, Apr 11
Frontier Logo
3:32 pm - 7:47 pm
PUJ
-
MDW
29h 15m
1 stop
Frontier Logo
2:56 pm - 2:15 pm
MDW
-
PUJ
22h 19m
1 stop
$412Frontier
Wed, Mar 25 - Tue, Apr 7

Delta flights from Dominican Republic to Chicago

Our best Delta deals on Dominican Republic to Chicago flight tickets
Delta
Apr 16
PUJ3:57 pmPunta Cana
7h 31m
1 stop
MDW10:28 pmChicago Midway
Apr 20
MDW6:00 amChicago Midway
6h 21m
1 stop
PUJ1:21 pmPunta Cana
$380
Delta
Mar 17
STI6:33 amSantiago de los Caballeros
15h 37m
2 stops
ORD9:10 pmChicago O'Hare Intl
Mar 25
ORD10:40 amChicago O'Hare Intl
12h 14m
1 stop
STI11:54 pmSantiago de los Caballeros
$413
Delta
Apr 16
SDQ2:37 pmSanto Domingo Las Americas
8h 51m
1 stop
MDW10:28 pmChicago Midway
Apr 20
MDW6:00 amChicago Midway
6h 12m
1 stop
SDQ1:12 pmSanto Domingo Las Americas
$489

United Airlines flights from Dominican Republic to Chicago

Our best United Airlines deals on Dominican Republic to Chicago flight tickets
United Airlines
Mar 11
PUJ3:25 pmPunta Cana
5h 13m
ORD7:38 pmChicago O'Hare Intl
Mar 18
ORD8:47 amChicago O'Hare Intl
4h 32m
PUJ2:19 pmPunta Cana
$279
United Airlines
Mar 11
PUJ3:25 pmPunta Cana
5h 13m
ORD7:38 pmChicago O'Hare Intl
Mar 18
ORD8:50 amChicago O'Hare Intl
6h 35m
1 stop
PUJ4:25 pmPunta Cana
$283
United Airlines
Mar 6
PUJ2:55 pmPunta Cana
5h 13m
ORD6:08 pmChicago O'Hare Intl
Mar 10
ORD8:47 amChicago O'Hare Intl
4h 32m
PUJ2:19 pmPunta Cana
$290

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 February 13, 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

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 4/16

7:30 pm-11:40 pm

Nonstop5h 10m

Chicago O'Hare Intl

Mon 4/20

4:30 am-10:15 am

Nonstop4h 45m

$230

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 2/26

5:47 pm-11:47 pm

1 stop8h 00m

Chicago O'Hare Intl

Sun 3/1

5:15 am-4:36 pm

1 stop9h 21m

$236

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Thu 3/12

3:43 pm-11:17 pm

1 stop8h 34m

Chicago O'Hare Intl

Tue 3/17

7:17 am-2:35 pm

1 stop6h 18m

$268

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 4/16

7:30 pm-11:40 pm

Nonstop5h 10m

Chicago O'Hare Intl

Mon 4/20

5:15 am-1:50 pm

1 stop7h 35m

$275

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Mon 5/4

3:37 pm-9:17 pm

1 stop30h 40m

Chicago O'Hare Intl

Tue 5/19

6:34 pm-4:29 pm

1 stop20h 55m

$282

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Fri 3/6

2:55 pm-6:08 pm

Nonstop5h 13m

Chicago O'Hare Intl

Tue 3/10

8:47 am-2:19 pm

Nonstop4h 32m

$290

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Fri 3/6

4:25 pm-7:38 pm

Nonstop5h 13m

Chicago O'Hare Intl

Tue 3/10

1:06 pm-4:25 pm

1 stop26h 19m

$291

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 4/16

3:57 pm-10:28 pm

1 stop7h 31m

Chicago Midway

Mon 4/20

6:00 am-1:21 pm

1 stop6h 21m

$380

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Wed 4/8

4:08 pm-8:07 pm

1 stop28h 59m

Chicago Midway

Sat 4/11

6:30 am-1:56 pm

1 stop6h 26m

$383

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 3/25

3:32 pm-7:47 pm

1 stop29h 15m

Chicago Midway

Tue 4/7

2:56 pm-2:15 pm

1 stop22h 19m

$412

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 $270. 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 $345. 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 evening. Flights from Dominican Republic to Chicago during this time can be as low as $258. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $421.

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 5% 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

$186

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 $186. The best round-trip flight deal from Dominican Republic to Chicago found on momondo in the last 72 hours is $184.
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
FrontierPriceFrom $181Free CancellationRating
5.7
3,052 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $189Free CancellationRating
6.3
8,450 reviews
Search Spirit Airlines flights
DeltaPriceFrom $191Free CancellationRating
7.9
8,196 reviews
Search Delta flights
American AirlinesPriceFrom $354Free CancellationRating
7.2
11,281 reviews
Search American Airlines 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
Schererville
Valparaiso
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