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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 5/9. 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
7:02 am - 11:12 am
PUJ
-
ORD
5h 10mnonstop
Arajet Logo
4:30 am - 10:15 am
ORD
-
PUJ
4h 45mnonstop
$261Arajet
Sat, May 16 - Mon, May 18
Multiple Airlines Logo
3:30 pm - 11:40 pm
SDQ
-
ORD
9h 10m
1 stop
Multiple Airlines Logo
4:30 am - 4:55 pm
ORD
-
SDQ
11h 25m
1 stop
$290Multiple Airlines
Thu, Apr 16 - Mon, Apr 27
American Airlines Logo
12:06 pm - 4:25 pm
PUJ
-
ORD
5h 19mnonstop
American Airlines Logo
6:57 am - 4:25 pm
ORD
-
PUJ
8h 28m
1 stop
$330American Airlines
Fri, May 1 - Tue, May 5
American Airlines Logo
12:06 pm - 4:25 pm
PUJ
-
ORD
5h 19mnonstop
American Airlines Logo
9:45 am - 3:24 pm
ORD
-
PUJ
4h 39mnonstop
$331American Airlines
Fri, May 1 - Mon, May 4
United Airlines Logo
4:40 pm - 7:26 am
PUJ
-
ORD
15h 46m
1 stop
United Airlines Logo
11:00 pm - 3:30 pm
ORD
-
PUJ
15h 30m
1 stop
$338United Airlines
Fri, May 1 - Mon, May 4
United Airlines Logo
1:50 pm - 5:59 pm
PUJ
-
ORD
5h 09mnonstop
United Airlines Logo
5:00 am - 1:11 pm
ORD
-
PUJ
7h 11m
1 stop
$339United Airlines
Thu, May 7 - Tue, May 12
Spirit Airlines Logo
3:28 pm - 11:17 pm
STI
-
ORD
8h 49m
1 stop
Spirit Airlines Logo
5:05 am - 2:23 pm
ORD
-
STI
8h 18m
1 stop
$370Spirit Airlines
Wed, Apr 8 - Mon, Apr 13
Spirit Airlines Logo
2:46 am - 5:15 pm
STI
-
ORD
15h 29m
1 stop
Spirit Airlines Logo
5:05 am - 2:23 pm
ORD
-
STI
8h 18m
1 stop
$372Spirit Airlines
Tue, Apr 7 - Mon, Apr 13
Frontier Logo
3:35 pm - 11:12 am
PUJ
-
MDW
20h 37m
1 stop
Frontier Logo
6:00 am - 2:24 pm
MDW
-
PUJ
7h 24m
1 stop
$391Frontier
Wed, May 6 - Tue, May 12
Frontier Logo
4:08 pm - 8:07 pm
SDQ
-
MDW
28h 59m
1 stop
Frontier Logo
5:05 am - 10:07 am
MDW
-
SDQ
28h 02m
1 stop
$397Frontier
Wed, Apr 8 - Sun, Apr 12

Frontier flights from Dominican Republic to Chicago

Our best Frontier deals on Dominican Republic to Chicago flight tickets
Frontier
Apr 18
PUJ3:04 pmPunta Cana
8h 35m
1 stop
ORD10:39 pmChicago O'Hare Intl
May 30
ORD7:52 pmChicago O'Hare Intl
14h 05m
1 stop
PUJ10:57 amPunta Cana
$376
Frontier
May 6
PUJ3:35 pmPunta Cana
20h 37m
1 stop
MDW11:12 amChicago Midway
May 12
MDW6:00 amChicago Midway
7h 24m
1 stop
PUJ2:24 pmPunta Cana
$391
Frontier
Apr 8
SDQ4:08 pmSanto Domingo Las Americas
28h 59m
1 stop
MDW8:07 pmChicago Midway
Apr 12
MDW5:05 amChicago Midway
28h 02m
1 stop
SDQ10:07 amSanto Domingo Las Americas
$397

United Airlines flights from Dominican Republic to Chicago

Our best United Airlines deals on Dominican Republic to Chicago flight tickets
United Airlines
May 1
PUJ4:40 pmPunta Cana
15h 46m
1 stop
ORD7:26 amChicago O'Hare Intl
May 4
ORD11:00 pmChicago O'Hare Intl
15h 30m
1 stop
PUJ3:30 pmPunta Cana
$338
United Airlines
May 7
PUJ1:50 pmPunta Cana
5h 09m
ORD5:59 pmChicago O'Hare Intl
May 12
ORD5:00 amChicago O'Hare Intl
7h 11m
1 stop
PUJ1:11 pmPunta Cana
$339
United Airlines
Apr 23
PUJ3:35 pmPunta Cana
9h 08m
1 stop
ORD11:43 pmChicago O'Hare Intl
Apr 28
ORD8:45 amChicago O'Hare Intl
4h 42m
PUJ2:27 pmPunta Cana
$344

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 March 18, 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 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

$261

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Thu 4/16

3:30 pm-11:40 pm

1 stop9h 10m

Chicago O'Hare Intl

Mon 4/27

4:30 am-4:55 pm

1 stop11h 25m

$290

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Fri 5/1

12:06 pm-4:25 pm

Nonstop5h 19m

Chicago O'Hare Intl

Tue 5/5

6:57 am-4:25 pm

1 stop8h 28m

$330

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Fri 5/1

12:06 pm-4:25 pm

Nonstop5h 19m

Chicago O'Hare Intl

Mon 5/4

9:45 am-3:24 pm

Nonstop4h 39m

$331

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Fri 5/1

4:40 pm-7:26 am

1 stop15h 46m

Chicago O'Hare Intl

Mon 5/4

11:00 pm-3:30 pm

1 stop15h 30m

$338

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 5/7

1:50 pm-5:59 pm

Nonstop5h 09m

Chicago O'Hare Intl

Tue 5/12

5:00 am-1:11 pm

1 stop7h 11m

$339

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Wed 4/8

3:28 pm-11:17 pm

1 stop8h 49m

Chicago O'Hare Intl

Mon 4/13

5:05 am-2:23 pm

1 stop8h 18m

$370

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Tue 4/7

2:46 am-5:15 pm

1 stop15h 29m

Chicago O'Hare Intl

Mon 4/13

5:05 am-2:23 pm

1 stop8h 18m

$372

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 5/6

3:35 pm-11:12 am

1 stop20h 37m

Chicago Midway

Tue 5/12

6:00 am-2:24 pm

1 stop7h 24m

$391

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Wed 4/8

4:08 pm-8:07 pm

1 stop28h 59m

Chicago Midway

Sun 4/12

5:05 am-10:07 am

1 stop28h 02m

$397

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 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 March is your next best option. Flight prices from Dominican Republic to Chicago during March average around $310.

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 $318. 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 $473.

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 $403 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 $328 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 15% 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

$211

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 $211. The best round-trip flight deal from Dominican Republic to Chicago found on momondo in the last 72 hours is $283.
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
3,025 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $189Free CancellationRating
6.3
8,522 reviews
Search Spirit Airlines flights
DeltaPriceFrom $191Free CancellationRating
7.9
8,288 reviews
Search Delta flights
American AirlinesPriceFrom $283Free CancellationRating
7.1
11,469 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
Valparaiso
Schererville
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