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Cheap flights from the Dominican Republic to Chicago from $136

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 2/20. 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.
Spirit Airlines Logo
3:32 pm - 11:47 pm
SDQ
-
ORD
10h 15m
1 stop
Spirit Airlines Logo
5:15 am - 1:20 pm
ORD
-
SDQ
7h 05m
1 stop
$236Spirit Airlines
Wed, Mar 4 - Wed, Mar 11
Spirit Airlines Logo
3:32 pm - 11:47 pm
SDQ
-
ORD
10h 15m
1 stop
Spirit Airlines Logo
8:16 pm - 1:20 pm
ORD
-
SDQ
16h 04m
1 stop
$238Spirit Airlines
Tue, Mar 3 - Tue, Mar 10
Spirit Airlines Logo
5:47 pm - 11:47 pm
PUJ
-
ORD
8h 00m
1 stop
Spirit Airlines Logo
7:00 am - 4:36 pm
ORD
-
PUJ
7h 36m
1 stop
$242Spirit Airlines
Wed, Feb 18 - Wed, Feb 25
United Airlines Logo
1:50 pm - 5:59 pm
PUJ
-
ORD
5h 09mnonstop
United Airlines Logo
8:45 am - 4:30 pm
ORD
-
PUJ
6h 45m
1 stop
$272United Airlines
Thu, Apr 16 - Tue, Apr 21
United Airlines Logo
2:20 pm - 12:45 am
PUJ
-
ORD
11h 25m
1 stop
United Airlines Logo
4:20 pm - 4:30 pm
ORD
-
PUJ
23h 10m
1 stop
$277United Airlines
Thu, Apr 16 - Tue, Apr 21
Multiple Airlines Logo
7:17 am - 10:27 am
PUJ
-
ORD
5h 10mnonstop
Multiple Airlines Logo
7:00 am - 4:36 pm
ORD
-
PUJ
7h 36m
1 stop
$284Multiple Airlines
Sat, Feb 14 - Sun, Feb 15
Multiple Airlines Logo
7:17 am - 10:27 am
PUJ
-
ORD
5h 10mnonstop
Multiple Airlines Logo
5:15 am - 4:36 pm
ORD
-
PUJ
9h 21m
1 stop
$285Multiple Airlines
Sat, Feb 14 - Sun, Feb 15
Delta Logo
7:30 am - 5:37 pm
SDQ
-
MDW
12h 07m
2 stops
Delta Logo
9:34 am - 12:32 am
MDW
-
SDQ
12h 58m
2 stops
$477Delta
Thu, Feb 26 - Mon, Mar 2
Delta Logo
2:37 pm - 10:28 pm
SDQ
-
MDW
8h 51m
1 stop
Delta Logo
9:27 am - 12:17 am
MDW
-
SDQ
13h 50m
2 stops
$529Delta
Fri, Apr 17 - Mon, Apr 20
Frontier Logo
12:34 pm - 10:09 pm
PUJ
-
MDW
10h 35m
2 stops
Frontier Logo
9:16 pm - 2:17 pm
MDW
-
PUJ
16h 01m
2 stops
$952Frontier
Sat, Mar 21 - Sat, Mar 28

United Airlines flights from Dominican Republic to Chicago

Our best United Airlines deals on Dominican Republic to Chicago flight tickets
United Airlines
Apr 16
PUJ1:50 pmPunta Cana
5h 09m
ORD5:59 pmChicago O'Hare Intl
Apr 21
ORD8:45 amChicago O'Hare Intl
6h 45m
1 stop
PUJ4:30 pmPunta Cana
$272
United Airlines
Apr 16
PUJ2:20 pmPunta Cana
11h 25m
1 stop
ORD12:45 amChicago O'Hare Intl
Apr 21
ORD4:20 pmChicago O'Hare Intl
23h 10m
1 stop
PUJ4:30 pmPunta Cana
$277
United Airlines
Mar 5
PUJ5:20 pmPunta Cana
16h 30m
1 stop
ORD7:50 amChicago O'Hare Intl
Mar 8
ORD9:15 pmChicago O'Hare Intl
18h 10m
1 stop
PUJ4:25 pmPunta Cana
$341

Spirit Airlines flights from Dominican Republic to Chicago

Our best Spirit Airlines deals on Dominican Republic to Chicago flight tickets
Spirit Airlines
Mar 4
SDQ3:32 pmSanto Domingo Las Americas
10h 15m
1 stop
ORD11:47 pmChicago O'Hare Intl
Mar 11
ORD5:15 amChicago O'Hare Intl
7h 05m
1 stop
SDQ1:20 pmSanto Domingo Las Americas
$236
Spirit Airlines
Mar 3
SDQ3:32 pmSanto Domingo Las Americas
10h 15m
1 stop
ORD11:47 pmChicago O'Hare Intl
Mar 10
ORD8:16 pmChicago O'Hare Intl
16h 04m
1 stop
SDQ1:20 pmSanto Domingo Las Americas
$238
Spirit Airlines
Feb 18
PUJ5:47 pmPunta Cana
8h 00m
1 stop
ORD11:47 pmChicago O'Hare Intl
Feb 25
ORD7:00 amChicago O'Hare Intl
7h 36m
1 stop
PUJ4:36 pmPunta Cana
$242

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 February 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

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Wed 3/4

3:32 pm-11:47 pm

1 stop10h 15m

Chicago O'Hare Intl

Wed 3/11

5:15 am-1:20 pm

1 stop7h 05m

$236

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Tue 3/3

3:32 pm-11:47 pm

1 stop10h 15m

Chicago O'Hare Intl

Tue 3/10

8:16 pm-1:20 pm

1 stop16h 04m

$238

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 2/18

5:47 pm-11:47 pm

1 stop8h 00m

Chicago O'Hare Intl

Wed 2/25

7:00 am-4:36 pm

1 stop7h 36m

$242

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 4/16

1:50 pm-5:59 pm

Nonstop5h 09m

Chicago O'Hare Intl

Tue 4/21

8:45 am-4:30 pm

1 stop6h 45m

$272

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 4/16

2:20 pm-12:45 am

1 stop11h 25m

Chicago O'Hare Intl

Tue 4/21

4:20 pm-4:30 pm

1 stop23h 10m

$277

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 2/14

7:17 am-10:27 am

Nonstop5h 10m

Chicago O'Hare Intl

Sun 2/15

7:00 am-4:36 pm

1 stop7h 36m

$284

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 2/14

7:17 am-10:27 am

Nonstop5h 10m

Chicago O'Hare Intl

Sun 2/15

5:15 am-4:36 pm

1 stop9h 21m

$285

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 2/26

7:30 am-5:37 pm

2 stops12h 07m

Chicago Midway

Mon 3/2

9:34 am-12:32 am

2 stops12h 58m

$477

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Fri 4/17

2:37 pm-10:28 pm

1 stop8h 51m

Chicago Midway

Mon 4/20

9:27 am-12:17 am

2 stops13h 50m

$529

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 3/21

12:34 pm-10:09 pm

2 stops10h 35m

Chicago Midway

Sat 3/28

9:16 pm-2:17 pm

2 stops16h 01m

$952

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 February is, on average, the cheapest month to fly to Chicago from Dominican Republic, with most prices found around $270. 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 $345. 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 $521.

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 $421.

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 $442 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?

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

$180

Fastest flight time

4h 55m

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 $180. The best round-trip flight deal from Dominican Republic to Chicago found on momondo in the last 72 hours is $236.
The fastest flight from Dominican Republic to Chicago takes 4h 55m
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
3,051 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $189Free CancellationRating
6.3
8,407 reviews
Search Spirit Airlines flights
DeltaPriceFrom $191Free CancellationRating
7.9
8,138 reviews
Search Delta flights
American AirlinesPriceFrom $354Free CancellationRating
7.2
11,218 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
Schererville
Valparaiso
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