Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from the Dominican Republic to Chicago from $151

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 12/2. 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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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
$184Frontier
Find Deal
jue., dic. 4 - mar., dic. 9
Frontier Logo
6:50 pm - 10:00 pmPUJ-ORD
5h 10mnonstop
Frontier Logo
7:10 am - 1:47 pmORD-PUJ
4h 37mnonstop
$201Frontier
Find Deal
dom., dic. 7 - dom., dic. 14
Frontier Logo
6:49 pm - 9:59 pmPUJ-ORD
5h 10mnonstop
Frontier Logo
7:10 am - 1:47 pmORD-PUJ
4h 37mnonstop
$207Frontier
Find Deal
mar., dic. 2 - mar., dic. 9
Multiple Airlines Logo
6:08 pm - 12:09 amPUJ-ORD
8h 01m1 stop
Multiple Airlines Logo
7:10 am - 1:47 pmORD-PUJ
4h 37mnonstop
$214Multiple Airlines
Find Deal
jue., dic. 4 - dom., dic. 7
Frontier Logo
6:49 pm - 9:59 pmPUJ-ORD
5h 10mnonstop
Frontier Logo
7:10 am - 1:47 pmORD-PUJ
4h 37mnonstop
$216Frontier
Find Deal
mié., dic. 24 - mié., dic. 31
Multiple Airlines Logo
3:08 pm - 12:09 amPUJ-ORD
11h 01m2 stops
Multiple Airlines Logo
7:10 am - 1:47 pmORD-PUJ
4h 37mnonstop
$228Multiple Airlines
Find Deal
jue., dic. 4 - jue., dic. 11
Spirit Airlines Logo
3:43 am - 11:08 amSTI-ORD
9h 25m1 stop
Spirit Airlines Logo
3:26 pm - 2:42 amORD-STI
9h 16m1 stop
$310Spirit Airlines
Find Deal
sáb., dic. 6 - vie., dic. 12
Spirit Airlines Logo
4:35 pm - 11:13 pmSDQ-ORD
8h 38m1 stop
Spirit Airlines Logo
5:00 am - 3:23 pmORD-SDQ
8h 23m1 stop
$310Spirit Airlines
Find Deal
mar., dic. 2 - mar., dic. 9
Delta Logo
7:05 am - 10:44 pmSDQ-MDW
17h 39m2 stops
Delta Logo
6:40 pm - 6:35 pmMDW-SDQ
21h 55m2 stops
$422Delta
Find Deal
vie., feb. 13 - mar., feb. 17
Delta Logo
2:45 pm - 9:45 pmSDQ-MDW
8h 00m1 stop
Delta Logo
6:00 am - 1:21 pmMDW-SDQ
6h 21m1 stop
$453Delta
Find Deal
jue., abr. 30 - mié., may. 6

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
$184
Find similar
Frontier
Nov 25
PUJ6:49 pmPunta Cana
5h 12m
ORD10:01 pmChicago O'Hare Intl
Dec 2
ORD7:00 amChicago O'Hare Intl
4h 37m
PUJ1:37 pmPunta Cana
$198
Find similar
Frontier
Nov 23
PUJ6:49 pmPunta Cana
5h 12m
ORD10:01 pmChicago O'Hare Intl
Nov 30
ORD6:45 amChicago O'Hare Intl
4h 34m
PUJ1:19 pmPunta Cana
$199
Find similar

American Airlines flights from Dominican Republic to Chicago

Our best American Airlines deals on Dominican Republic to Chicago flight tickets
American Airlines
Dec 31
STI6:17 pmSantiago de los Caballeros
16h 30m
1 stop
ORD8:47 amChicago O'Hare Intl
Jan 7
ORD8:10 amChicago O'Hare Intl
11h 36m
1 stop
STI9:46 pmSantiago de los Caballeros
$434
Find similar
American Airlines
Dec 31
STI3:24 pmSantiago de los Caballeros
19h 23m
1 stop
ORD8:47 amChicago O'Hare Intl
Jan 7
ORD8:09 amChicago O'Hare Intl
11h 37m
2 stops
STI9:46 pmSantiago de los Caballeros
$438
Find similar
American Airlines
Nov 20
STI4:35 pmSantiago de los Caballeros
10h 02m
1 stop
ORD12:37 amChicago O'Hare Intl
Nov 30
ORD7:00 amChicago O'Hare Intl
13h 56m
1 stop
STI10:56 pmSantiago de los Caballeros
$467
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 noviembre 17, 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

jue. 12/4

6:50 pm-10:00 pm

Nonstop5h 10m

Chicago O'Hare Intl

mar. 12/9

7:10 am-1:47 pm

Nonstop4h 37m

$184

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

dom. 12/7

6:50 pm-10:00 pm

Nonstop5h 10m

Chicago O'Hare Intl

dom. 12/14

7:10 am-1:47 pm

Nonstop4h 37m

$201

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

mar. 12/2

6:49 pm-9:59 pm

Nonstop5h 10m

Chicago O'Hare Intl

mar. 12/9

7:10 am-1:47 pm

Nonstop4h 37m

$207

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

jue. 12/4

6:08 pm-12:09 am

1 stop8h 01m

Chicago O'Hare Intl

dom. 12/7

7:10 am-1:47 pm

Nonstop4h 37m

$214

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

mié. 12/24

6:49 pm-9:59 pm

Nonstop5h 10m

Chicago O'Hare Intl

mié. 12/31

7:10 am-1:47 pm

Nonstop4h 37m

$216

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

jue. 12/4

3:08 pm-12:09 am

2 stops11h 01m

Chicago O'Hare Intl

jue. 12/11

7:10 am-1:47 pm

Nonstop4h 37m

$228

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

sáb. 12/6

3:43 am-11:08 am

1 stop9h 25m

Chicago O'Hare Intl

vie. 12/12

3:26 pm-2:42 am

1 stop9h 16m

$310

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

mar. 12/2

4:35 pm-11:13 pm

1 stop8h 38m

Chicago O'Hare Intl

mar. 12/9

5:00 am-3:23 pm

1 stop8h 23m

$310

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

vie. 2/13

7:05 am-10:44 pm

2 stops17h 39m

Chicago Midway

mar. 2/17

6:40 pm-6:35 pm

2 stops21h 55m

$422

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

jue. 4/30

2:45 pm-9:45 pm

1 stop8h 00m

Chicago Midway

mié. 5/6

6:00 am-1:21 pm

1 stop6h 21m

$453

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 $331. 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 $402.

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 $426 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 14% 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

$230

Fastest flight time

4h 55m

Direct flights

Mon, Wed, Thu, Fri, Sat and Sun

Airports in Chicago

2 airports
The best one-way flight to Chicago from Dominican Republic in the past 72 hours is $230. The best round-trip flight deal from Dominican Republic to Chicago found on momondo in the last 72 hours is $212.
The fastest flight from Dominican Republic to Chicago takes 4h 55m
Direct flights go from Dominican Republic to Chicago on Monday, Wednesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
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
3,106 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $189Free CancellationRating
6.3
8,144 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $269Free CancellationRating
7.4
9,014 reviews
Search United Airlines flights
American AirlinesPriceFrom $354Free CancellationRating
7.2
11,048 reviews
Search American Airlines flights
DeltaPriceFrom $449Free CancellationRating
7.9
8,007 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
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.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
mié. 12/17
mié. 12/24
By creating a price alert you accept our terms of use and privacy policy.

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