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Cheap flights from the Dominican Republic to Chicago from $167

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 5/23. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
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.
Multiple Airlines Logo
3:35 pm - 7:55 am
PUJ
-
ORD
17h 20m
1 stop
Multiple Airlines Logo
5:05 am - 1:30 pm
ORD
-
PUJ
7h 25m
1 stop
$322Multiple Airlines
Sat, May 16 - Mon, May 18
Frontier Logo
4:37 pm - 11:26 pm
PUJ
-
ORD
7h 49m
1 stop
Frontier Logo
7:52 pm - 10:57 am
ORD
-
PUJ
14h 05m
1 stop
$327Frontier
Sat, May 23 - Sat, May 30
Arajet Logo
7:30 pm - 11:40 pm
PUJ
-
ORD
5h 10mnonstop
Arajet Logo
5:30 am - 11:15 am
ORD
-
PUJ
4h 45mnonstop
$353Arajet
Thu, Sep 3 - Mon, Sep 7
Multiple Airlines Logo
3:35 pm - 7:55 am
PUJ
-
ORD
17h 20m
1 stop
Multiple Airlines Logo
4:30 am - 10:15 am
ORD
-
PUJ
4h 45mnonstop
$357Multiple Airlines
Sat, May 16 - Mon, May 18
Arajet Logo
7:30 pm - 11:40 pm
PUJ
-
ORD
5h 10mnonstop
Arajet Logo
11:27 am - 5:12 pm
ORD
-
PUJ
4h 45mnonstop
$359Arajet
Thu, Oct 29 - Sat, Oct 31
Arajet Logo
7:02 am - 11:12 am
PUJ
-
ORD
5h 10mnonstop
Arajet Logo
4:30 am - 10:15 am
ORD
-
PUJ
4h 45mnonstop
$388Arajet
Sat, May 16 - Mon, May 18
Spirit Airlines Logo
3:17 pm - 11:15 pm
STI
-
ORD
8h 58m
1 stop
Spirit Airlines Logo
5:05 am - 2:12 pm
ORD
-
STI
8h 07m
1 stop
$472Spirit Airlines
Sat, May 30 - Sat, Jun 6
Spirit Airlines Logo
3:52 pm - 11:59 pm
STI
-
ORD
9h 07m
1 stop
Spirit Airlines Logo
5:10 am - 3:15 pm
ORD
-
STI
9h 05m
1 stop
$505Spirit Airlines
Sat, Jul 4 - Mon, Jul 27
American Airlines Logo
3:44 pm - 11:30 pm
STI
-
ORD
8h 46m
1 stop
American Airlines Logo
10:00 am - 9:28 pm
ORD
-
STI
10h 28m
1 stop
$530American Airlines
Thu, Jul 2 - Wed, Jul 29
American Airlines Logo
3:44 pm - 11:30 pm
STI
-
ORD
8h 46m
1 stop
American Airlines Logo
8:30 am - 9:28 pm
ORD
-
STI
11h 58m
2 stops
$535American Airlines
Thu, Jul 2 - Wed, Jul 29

Frontier flights from Dominican Republic to Chicago

Our best Frontier deals on Dominican Republic to Chicago flight tickets
Frontier
May 23
PUJ4:37 pmPunta Cana
7h 49m
1 stop
ORD11:26 pmChicago O'Hare Intl
May 30
ORD7:52 pmChicago O'Hare Intl
14h 05m
1 stop
PUJ10:57 amPunta Cana
$327
Frontier
May 23
PUJ4:37 pmPunta Cana
7h 49m
1 stop
ORD11:26 pmChicago O'Hare Intl
May 30
ORD7:52 pmChicago O'Hare Intl
14h 05m
1 stop
PUJ10:57 amPunta Cana
$402
Frontier
Jul 15
PUJ3:44 pmPunta Cana
17h 09m
1 stop
ORD7:53 amChicago O'Hare Intl
Aug 4
ORD1:50 pmChicago O'Hare Intl
23h 44m
1 stop
PUJ2:34 pmPunta Cana
$403

Arajet flights from Dominican Republic to Chicago

Our best Arajet deals on Dominican Republic to Chicago flight tickets
Arajet
Sep 3
PUJ7:30 pmPunta Cana
5h 10m
ORD11:40 pmChicago O'Hare Intl
Sep 7
ORD5:30 amChicago O'Hare Intl
4h 45m
PUJ11:15 amPunta Cana
$353
Arajet
Oct 29
PUJ7:30 pmPunta Cana
5h 10m
ORD11:40 pmChicago O'Hare Intl
Oct 31
ORD11:27 amChicago O'Hare Intl
4h 45m
PUJ5:12 pmPunta Cana
$359
Arajet
May 16
PUJ7:02 amPunta Cana
5h 10m
ORD11:12 amChicago O'Hare Intl
May 18
ORD4:30 amChicago O'Hare Intl
4h 45m
PUJ10:15 amPunta Cana
$388

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 3, 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

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 5/16

3:35 pm-7:55 am

1 stop17h 20m

Chicago O'Hare Intl

Mon 5/18

5:05 am-1:30 pm

1 stop7h 25m

$322

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 5/23

4:37 pm-11:26 pm

1 stop7h 49m

Chicago O'Hare Intl

Sat 5/30

7:52 pm-10:57 am

1 stop14h 05m

$327
Quickest round-trip

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 9/3

7:30 pm-11:40 pm

Nonstop5h 10m

Chicago O'Hare Intl

Mon 9/7

5:30 am-11:15 am

Nonstop4h 45m

$353

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 5/16

3:35 pm-7:55 am

1 stop17h 20m

Chicago O'Hare Intl

Mon 5/18

4:30 am-10:15 am

Nonstop4h 45m

$357

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 10/29

7:30 pm-11:40 pm

Nonstop5h 10m

Chicago O'Hare Intl

Sat 10/31

11:27 am-5:12 pm

Nonstop4h 45m

$359

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 5/16

7:02 am-11:12 am

Nonstop5h 10m

Chicago O'Hare Intl

Mon 5/18

4:30 am-10:15 am

Nonstop4h 45m

$388

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Sat 5/30

3:17 pm-11:15 pm

1 stop8h 58m

Chicago O'Hare Intl

Sat 6/6

5:05 am-2:12 pm

1 stop8h 07m

$472

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Sat 7/4

3:52 pm-11:59 pm

1 stop9h 07m

Chicago O'Hare Intl

Mon 7/27

5:10 am-3:15 pm

1 stop9h 05m

$505

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Thu 7/2

3:44 pm-11:30 pm

1 stop8h 46m

Chicago O'Hare Intl

Wed 7/29

10:00 am-9:28 pm

1 stop10h 28m

$530

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Thu 7/2

3:44 pm-11:30 pm

1 stop8h 46m

Chicago O'Hare Intl

Wed 7/29

8:30 am-9:28 pm

2 stops11h 58m

$535

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 $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 $258. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $437.

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 from the Dominican Republic 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 $447 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 $319 on momondo.

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

$279

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 $279. The best round-trip flight deal from Dominican Republic to Chicago found on momondo in the last 72 hours is $445.
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
Spirit AirlinesPriceFrom $189Free CancellationRating
6.3
8,634 reviews
Search Spirit Airlines flights
ArajetPriceFrom $195Free CancellationRating
6.5
47 reviews
Search Arajet flights
American AirlinesPriceFrom $283Free CancellationRating
7.1
11,673 reviews
Search American Airlines flights
DeltaPriceFrom $449Free CancellationRating
7.9
8,462 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
Monticello
Chesterton
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