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Cheap flights from the Dominican Republic to Chicago from $197

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 11/8. 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
5:47 am - 8:57 am
PUJ
-
ORD
5h 10mnonstop
Arajet Logo
10:27 am - 5:12 pm
ORD
-
PUJ
4h 45mnonstop
$360Arajet
Sat, Nov 7 - Sat, Nov 14
Arajet Logo
7:02 am - 11:12 am
PUJ
-
ORD
5h 10mnonstop
Arajet Logo
12:12 pm - 5:57 pm
ORD
-
PUJ
4h 45mnonstop
$362Arajet
Sat, Sep 26 - Sat, Oct 3
JetBlue Logo
5:01 am - 1:39 pm
SDQ
-
ORD
9h 38m
1 stop
JetBlue Logo
7:00 am - 3:21 pm
ORD
-
SDQ
7h 21m
1 stop
$380JetBlue
Mon, Jul 27 - Sat, Aug 29
JetBlue Logo
4:44 pm - 11:44 pm
SDQ
-
ORD
8h 00m
1 stop
JetBlue Logo
2:35 pm - 11:59 pm
ORD
-
SDQ
8h 24m
1 stop
$383JetBlue
Tue, Sep 1 - Sat, Sep 12
Multiple Airlines Logo
7:30 pm - 11:40 pm
PUJ
-
ORD
5h 10mnonstop
Multiple Airlines Logo
7:00 am - 3:27 pm
ORD
-
PUJ
7h 27m
1 stop
$387Multiple Airlines
Thu, Aug 20 - Sun, Aug 23
Multiple Airlines Logo
3:44 pm - 7:53 am
PUJ
-
ORD
17h 09m
1 stop
Multiple Airlines Logo
7:00 am - 3:27 pm
ORD
-
PUJ
7h 27m
1 stop
$392Multiple Airlines
Wed, Aug 5 - Wed, Aug 12
Frontier Logo
3:44 pm - 11:07 am
PUJ
-
MDW
20h 23m
1 stop
Frontier Logo
6:00 am - 2:34 pm
MDW
-
PUJ
7h 34m
1 stop
$413Frontier
Wed, Aug 5 - Wed, Aug 12
Frontier Logo
11:46 am - 10:08 pm
PUJ
-
MDW
11h 22m
2 stops
Frontier Logo
6:00 am - 2:49 pm
MDW
-
PUJ
7h 49m
1 stop
$424Frontier
Wed, Jul 8 - Tue, Jul 28
American Airlines Logo
7:00 am - 2:56 pm
STI
-
ORD
8h 56m
1 stop
American Airlines Logo
6:10 am - 9:28 pm
ORD
-
STI
14h 18m
1 stop
$525American Airlines
Sat, Jul 4 - Mon, Jul 27
American Airlines Logo
3:31 pm - 7:34 am
STI
-
ORD
17h 03m
1 stop
American Airlines Logo
6:45 am - 9:03 pm
ORD
-
STI
13h 18m
2 stops
$530American Airlines
Thu, Aug 20 - Sun, Aug 23

Frontier flights from Dominican Republic to Chicago

Our best Frontier deals on Dominican Republic to Chicago flight tickets
Frontier
Aug 5
PUJ3:44 pmPunta Cana
20h 23m
1 stop
MDW11:07 amChicago Midway
Aug 12
MDW6:00 amChicago Midway
7h 34m
1 stop
PUJ2:34 pmPunta Cana
$413
Frontier
Jun 9
PUJ3:56 pmPunta Cana
17h 07m
1 stop
ORD8:03 amChicago O'Hare Intl
Jun 13
ORD8:00 pmChicago O'Hare Intl
14h 55m
1 stop
PUJ11:55 amPunta Cana
$421
Frontier
Jul 8
PUJ11:46 amPunta Cana
11h 22m
2 stops
MDW10:08 pmChicago Midway
Jul 28
MDW6:00 amChicago Midway
7h 49m
1 stop
PUJ2:49 pmPunta Cana
$424

Delta flights from Dominican Republic to Chicago

Our best Delta deals on Dominican Republic to Chicago flight tickets
Delta
Oct 9
STI8:31 pmSantiago de los Caballeros
16h 35m
2 stops
ORD12:06 pmChicago O'Hare Intl
Oct 13
ORD7:10 amChicago O'Hare Intl
10h 56m
2 stops
STI7:06 pmSantiago de los Caballeros
$526
Delta
Oct 9
STI8:31 pmSantiago de los Caballeros
16h 35m
2 stops
ORD12:06 pmChicago O'Hare Intl
Oct 13
ORD7:10 amChicago O'Hare Intl
10h 56m
2 stops
STI7:06 pmSantiago de los Caballeros
$547
Delta
May 16
STI6:00 amSantiago de los Caballeros
16h 56m
1 stop
ORD9:56 pmChicago O'Hare Intl
May 19
ORD7:07 amChicago O'Hare Intl
11h 22m
2 stops
STI7:29 pmSantiago de los Caballeros
$567

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 May 14, 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

Cheapest round-trip
Quickest round-trip

Punta CanaChicago

PUJ - ORD

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

$360

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 9/26

7:02 am-11:12 am

Nonstop5h 10m

Chicago O'Hare Intl

Sat 10/3

12:12 pm-5:57 pm

Nonstop4h 45m

$362

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Mon 7/27

5:01 am-1:39 pm

1 stop9h 38m

Chicago O'Hare Intl

Sat 8/29

7:00 am-3:21 pm

1 stop7h 21m

$380

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Tue 9/1

4:44 pm-11:44 pm

1 stop8h 00m

Chicago O'Hare Intl

Sat 9/12

2:35 pm-11:59 pm

1 stop8h 24m

$383

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 8/20

7:30 pm-11:40 pm

Nonstop5h 10m

Chicago O'Hare Intl

Sun 8/23

7:00 am-3:27 pm

1 stop7h 27m

$387

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 8/5

3:44 pm-7:53 am

1 stop17h 09m

Chicago O'Hare Intl

Wed 8/12

7:00 am-3:27 pm

1 stop7h 27m

$392

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 8/5

3:44 pm-11:07 am

1 stop20h 23m

Chicago Midway

Wed 8/12

6:00 am-2:34 pm

1 stop7h 34m

$413

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 7/8

11:46 am-10:08 pm

2 stops11h 22m

Chicago Midway

Tue 7/28

6:00 am-2:49 pm

1 stop7h 49m

$424

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Sat 7/4

7:00 am-2:56 pm

1 stop8h 56m

Chicago O'Hare Intl

Mon 7/27

6:10 am-9:28 pm

1 stop14h 18m

$525

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Thu 8/20

3:31 pm-7:34 am

1 stop17h 03m

Chicago O'Hare Intl

Sun 8/23

6:45 am-9:03 pm

2 stops13h 18m

$530

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 August is, on average, the cheapest month to fly to Chicago from Dominican Republic, with most prices found around $139. If you’re not able to fly to Chicago in August, then January is your next best option. Flight prices from Dominican Republic to Chicago during January average around $160.

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 $387. 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 $476.

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 $482.

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

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

$277

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 $277. The best round-trip flight deal from Dominican Republic to Chicago found on momondo in the last 72 hours is $404.
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

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 $195Free CancellationRating
6.5
48 reviews
Search Arajet flights
American AirlinesPriceFrom $283Free CancellationRating
7.1
11,663 reviews
Search American Airlines flights
DeltaPriceFrom $449Free CancellationRating
7.9
8,453 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
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