Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from the Dominican Republic to Chicago from $108

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 11/15. 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

Arajet Logo
7:30 pm - 10:40 pmPUJ-ORD
5h 10mnonstop
Arajet Logo
4:35 am - 11:20 amORD-PUJ
4h 45mnonstop
$216Arajet
Find Deal
Tue, Nov 25 - Tue, Dec 2
Arajet Logo
7:30 pm - 10:40 pmPUJ-ORD
5h 10mnonstop
Arajet Logo
3:30 am - 10:15 amORD-PUJ
4h 45mnonstop
$219Arajet
Find Deal
Tue, Nov 25 - Sun, Nov 30
American Airlines Logo
3:21 pm - 7:36 pmPUJ-ORD
5h 15mnonstop
American Airlines Logo
8:35 am - 2:05 pmORD-PUJ
4h 30mnonstop
$371American Airlines
Find Deal
Thu, Oct 9 - Mon, Oct 20
United Airlines Logo
2:55 pm - 6:08 pmPUJ-ORD
5h 13mnonstop
United Airlines Logo
8:45 am - 5:25 pmORD-PUJ
6h 40m1 stop
$374United Airlines
Find Deal
Thu, Feb 26 - Tue, Mar 3
American Airlines Logo
3:21 pm - 7:36 pmPUJ-ORD
5h 15mnonstop
American Airlines Logo
5:22 am - 3:45 pmORD-PUJ
9h 23m1 stop
$376American Airlines
Find Deal
Thu, Oct 9 - Mon, Oct 20
United Airlines Logo
2:55 pm - 6:08 pmPUJ-ORD
5h 13mnonstop
United Airlines Logo
3:30 pm - 5:25 pmORD-PUJ
23h 55m1 stop
$381United Airlines
Find Deal
Fri, Nov 21 - Thu, Nov 27
Delta Logo
6:11 am - 10:14 pmSTI-ORD
17h 03m2 stops
Delta Logo
10:30 am - 12:24 amORD-STI
12h 54m2 stops
$386Delta
Find Deal
Sat, Oct 4 - Sat, Oct 18
Delta Logo
7:40 pm - 10:10 amSDQ-ORD
15h 30m2 stops
Delta Logo
9:42 am - 12:27 amORD-SDQ
13h 45m2 stops
$388Delta
Find Deal
Fri, Oct 3 - Mon, Oct 6
Frontier Logo
3:19 pm - 10:03 pmSDQ-MDW
7h 44m1 stop
Frontier Logo
6:20 am - 5:21 pmMDW-SDQ
9h 01m2 stops
$454Frontier
Find Deal
Thu, Oct 30 - Mon, Nov 3
Frontier Logo
3:19 pm - 10:03 pmSDQ-MDW
7h 44m1 stop
Frontier Logo
6:20 am - 5:21 pmMDW-SDQ
9h 01m2 stops
$487Frontier
Find Deal
Thu, Oct 30 - Mon, Nov 3

Spirit Airlines flights from Dominican Republic to Chicago

Our best Spirit Airlines deals on Dominican Republic to Chicago flight tickets
Spirit Airlines
Oct 4
SDQ3:47 pmSanto Domingo Las Americas
8h 01m
1 stop
ORD10:48 pmChicago O'Hare Intl
Oct 11
ORD5:05 amChicago O'Hare Intl
8h 49m
1 stop
SDQ2:54 pmSanto Domingo Las Americas
$282
Find similar
Spirit Airlines
Oct 9
PUJ3:57 pmPunta Cana
8h 48m
1 stop
ORD11:45 pmChicago O'Hare Intl
Oct 20
ORD5:05 amChicago O'Hare Intl
8h 44m
1 stop
PUJ2:49 pmPunta Cana
$289
Find similar
Spirit Airlines
Oct 16
PUJ3:57 pmPunta Cana
8h 48m
1 stop
ORD11:45 pmChicago O'Hare Intl
Oct 25
ORD5:05 amChicago O'Hare Intl
8h 44m
1 stop
PUJ2:49 pmPunta Cana
$290
Find similar

United Airlines flights from Dominican Republic to Chicago

Our best United Airlines deals on Dominican Republic to Chicago flight tickets
United Airlines
Feb 26
PUJ2:55 pmPunta Cana
5h 13m
ORD6:08 pmChicago O'Hare Intl
Mar 3
ORD8:45 amChicago O'Hare Intl
6h 40m
1 stop
PUJ5:25 pmPunta Cana
$374
Find similar
United Airlines
Nov 21
PUJ2:55 pmPunta Cana
5h 13m
ORD6:08 pmChicago O'Hare Intl
Nov 27
ORD3:30 pmChicago O'Hare Intl
23h 55m
1 stop
PUJ5:25 pmPunta Cana
$381
Find similar
United Airlines
Oct 23
SDQ5:45 amSanto Domingo Las Americas
8h 23m
1 stop
ORD1:08 pmChicago O'Hare Intl
Oct 28
ORD12:00 pmChicago O'Hare Intl
9h 46m
1 stop
SDQ10:46 pmSanto Domingo Las Americas
$396
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 September 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

Tue 11/25

7:30 pm-10:40 pm

Nonstop5h 10m

Chicago O'Hare Intl

Tue 12/2

4:35 am-11:20 am

Nonstop4h 45m

$216

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Tue 11/25

7:30 pm-10:40 pm

Nonstop5h 10m

Chicago O'Hare Intl

Sun 11/30

3:30 am-10:15 am

Nonstop4h 45m

$219

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 10/9

3:21 pm-7:36 pm

Nonstop5h 15m

Chicago O'Hare Intl

Mon 10/20

8:35 am-2:05 pm

Nonstop4h 30m

$371

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 2/26

2:55 pm-6:08 pm

Nonstop5h 13m

Chicago O'Hare Intl

Tue 3/3

8:45 am-5:25 pm

1 stop6h 40m

$374

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 10/9

3:21 pm-7:36 pm

Nonstop5h 15m

Chicago O'Hare Intl

Mon 10/20

5:22 am-3:45 pm

1 stop9h 23m

$376

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Fri 11/21

2:55 pm-6:08 pm

Nonstop5h 13m

Chicago O'Hare Intl

Thu 11/27

3:30 pm-5:25 pm

1 stop23h 55m

$381

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Sat 10/4

6:11 am-10:14 pm

2 stops17h 03m

Chicago O'Hare Intl

Sat 10/18

10:30 am-12:24 am

2 stops12h 54m

$386

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Fri 10/3

7:40 pm-10:10 am

2 stops15h 30m

Chicago O'Hare Intl

Mon 10/6

9:42 am-12:27 am

2 stops13h 45m

$388

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 10/30

3:19 pm-10:03 pm

1 stop7h 44m

Chicago Midway

Mon 11/3

6:20 am-5:21 pm

2 stops9h 01m

$454

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 10/30

3:19 pm-10:03 pm

1 stop7h 44m

Chicago Midway

Mon 11/3

6:20 am-5:21 pm

2 stops9h 01m

$487

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 May is, on average, the cheapest month to fly to Chicago from Dominican Republic, with most prices found around $302. If you’re not able to fly to Chicago in May, then December is your next best option. Flight prices from Dominican Republic to Chicago during December average around $351.

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 Sunday when prices can be found for as low as $322. This is often the case because there is less demand to fly during this day of the week. When flying out on a Wednesday, the most expensive travel day of the week, you can expect to see flight prices from Dominican Republic to Chicago for around $448.

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 $413.

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 $432 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 2 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?

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

$306

Fastest flight time

4h 54m

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 $306. The best round-trip flight deal from Dominican Republic to Chicago found on momondo in the last 72 hours is $320.
The fastest flight from Dominican Republic to Chicago takes 4h 54m
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
Spirit AirlinesPriceFrom $189Free CancellationRating
6.3
8,023 reviews
Search Spirit Airlines flights
FrontierPriceFrom $224Free CancellationRating
5.8
3,173 reviews
Search Frontier flights
United AirlinesPriceFrom $269Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights
American AirlinesPriceFrom $354Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $400Free CancellationRating
7.9
7,961 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.

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
Fri 10/17
Fri 10/24
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