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Cheap flights from the Dominican Republic to Chicago from $165

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 2/13. 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.
Multiple Airlines Logo
1:10 pm - 2:55 pm
PUJ
-
MDW
27h 45m1 stop
Multiple Airlines Logo
7:53 pm - 3:36 pm
MDW
-
PUJ
17h 43m1 stop
$314Multiple Airlines
Fri, Feb 13 - Fri, Feb 20
Multiple Airlines Logo
1:10 pm - 2:55 pm
PUJ
-
MDW
27h 45m1 stop
Multiple Airlines Logo
7:53 pm - 3:36 pm
MDW
-
PUJ
17h 43m1 stop
$325Multiple Airlines
Fri, Feb 13 - Fri, Feb 20
Multiple Airlines Logo
1:10 pm - 2:55 pm
PUJ
-
MDW
27h 45m1 stop
Multiple Airlines Logo
7:53 pm - 3:36 pm
MDW
-
PUJ
17h 43m1 stop
$331Multiple Airlines
Fri, Feb 13 - Fri, Feb 20
Multiple Airlines Logo
1:01 pm - 6:54 pm
PUJ
-
MDW
7h 53m1 stop
Multiple Airlines Logo
5:01 pm - 3:01 pm
MDW
-
PUJ
20h 00m1 stop
$338Multiple Airlines
Fri, Jan 16 - Fri, Jan 23
Frontier Logo
12:31 pm - 10:34 pm
SDQ
-
MDW
36h 03m2 stops
Frontier Logo
2:19 pm - 11:56 am
MDW
-
SDQ
19h 37m2 stops
$352Frontier
Thu, Feb 26 - Mon, Mar 2
Frontier Logo
12:31 pm - 6:38 pm
SDQ
-
MDW
32h 07m2 stops
Frontier Logo
6:00 am - 11:56 am
MDW
-
SDQ
27h 56m2 stops
$356Frontier
Thu, Feb 26 - Mon, Mar 2
Frontier Logo
2:37 pm - 8:03 am
SDQ
-
MDW
19h 26m2 stops
Frontier Logo
6:00 am - 11:26 am
MDW
-
SDQ
51h 26m2 stops
$364Frontier
Sat, Jan 17 - Tue, Feb 17
Delta Logo
7:31 am - 5:29 pm
SDQ
-
MDW
11h 58m2 stops
Delta Logo
6:00 am - 2:21 pm
MDW
-
SDQ
6h 21m1 stop
$501Delta
Thu, Jan 22 - Thu, Feb 5
Delta Logo
7:30 am - 5:45 pm
SDQ
-
MDW
12h 15m2 stops
Delta Logo
6:00 am - 2:17 pm
MDW
-
SDQ
6h 17m1 stop
$504Delta
Thu, Feb 26 - Mon, Mar 2
Delta Logo
3:46 pm - 10:22 pm
SDQ
-
MDW
8h 36m1 stop
Delta Logo
6:00 am - 2:21 pm
MDW
-
SDQ
6h 21m1 stop
$519Delta
Thu, Jan 22 - Thu, Feb 5

Frontier flights from Dominican Republic to Chicago Midway Airport

Our best Frontier deals on Dominican Republic to Chicago Midway Airport flight tickets
Frontier
Feb 19
SDQ12:31 pmSanto Domingo Las Americas
27h 55m
1 stop
MDW2:26 pmChicago Midway
Feb 21
MDW8:00 amChicago Midway
23h 39m
1 stop
SDQ9:39 amSanto Domingo Las Americas
$346
Find similar
Frontier
Feb 26
SDQ12:31 pmSanto Domingo Las Americas
36h 03m
2 stops
MDW10:34 pmChicago Midway
Mar 2
MDW2:19 pmChicago Midway
19h 37m
2 stops
SDQ11:56 amSanto Domingo Las Americas
$352
Find similar
Frontier
Feb 26
SDQ12:31 pmSanto Domingo Las Americas
32h 07m
2 stops
MDW6:38 pmChicago Midway
Mar 2
MDW6:00 amChicago Midway
27h 56m
2 stops
SDQ11:56 amSanto Domingo Las Americas
$356
Find similar

Delta flights from Dominican Republic to Chicago Midway Airport

Our best Delta deals on Dominican Republic to Chicago Midway Airport flight tickets
Delta
Jan 22
PUJ3:45 pmPunta Cana
8h 37m
1 stop
MDW10:22 pmChicago Midway
Jan 27
MDW6:00 amChicago Midway
6h 20m
1 stop
PUJ2:20 pmPunta Cana
$377
Find similar
Delta
Jan 14
PUJ3:45 pmPunta Cana
8h 22m
1 stop
MDW10:07 pmChicago Midway
Jan 21
MDW6:00 amChicago Midway
7h 30m
1 stop
PUJ3:30 pmPunta Cana
$412
Find similar
Delta
Dec 29
PUJ4:46 pmPunta Cana
7h 36m
1 stop
MDW10:22 pmChicago Midway
Jan 5
MDW6:45 amChicago Midway
6h 55m
1 stop
PUJ3:40 pmPunta Cana
$438
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Dominican Republic to Chicago Midway Airport 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 December 16, 2025.
Use the filters below to find and compare flights from the Dominican Republic to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 2/13

1:10 pm-2:55 pm

1 stop27h 45m

Chicago Midway

Fri 2/20

7:53 pm-3:36 pm

1 stop17h 43m

$314

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 2/13

1:10 pm-2:55 pm

1 stop27h 45m

Chicago Midway

Fri 2/20

7:53 pm-3:36 pm

1 stop17h 43m

$325

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 2/13

1:10 pm-2:55 pm

1 stop27h 45m

Chicago Midway

Fri 2/20

7:53 pm-3:36 pm

1 stop17h 43m

$331

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 1/16

1:01 pm-6:54 pm

1 stop7h 53m

Chicago Midway

Fri 1/23

5:01 pm-3:01 pm

1 stop20h 00m

$338

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 2/26

12:31 pm-10:34 pm

2 stops36h 03m

Chicago Midway

Mon 3/2

2:19 pm-11:56 am

2 stops19h 37m

$352

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 2/26

12:31 pm-6:38 pm

2 stops32h 07m

Chicago Midway

Mon 3/2

6:00 am-11:56 am

2 stops27h 56m

$356

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Sat 1/17

2:37 pm-8:03 am

2 stops19h 26m

Chicago Midway

Tue 2/17

6:00 am-11:26 am

2 stops51h 26m

$364

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 1/22

7:31 am-5:29 pm

2 stops11h 58m

Chicago Midway

Thu 2/5

6:00 am-2:21 pm

1 stop6h 21m

$501

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 2/26

7:30 am-5:45 pm

2 stops12h 15m

Chicago Midway

Mon 3/2

6:00 am-2:17 pm

1 stop6h 17m

$504

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 1/22

3:46 pm-10:22 pm

1 stop8h 36m

Chicago Midway

Thu 2/5

6:00 am-2:21 pm

1 stop6h 21m

$519

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 Midway Airport

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 Dominican Republic to Chicago Midway flight route?

Fly from Punta Cana to Chicago Midway for the best Dominican Republic - Chicago Midway flight prices

What cabin class options are available on Dominican Republic to Chicago Midway flights?

There is only 1 cabin class available to choose from on Dominican Republic to Chicago Midway 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 Midway Airport flights?

No. A direct flight is the cheapest option for a flight between Dominican Republic to Chicago Midway Airport.

Cheap Dominican Republic to Chicago Midway Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Dominican Republic to Chicago Midway Airport

Fastest flight time

4h 45m

Direct flights

Every day
The fastest flight from Dominican Republic to Chicago Midway Airport takes 4h 45m
Direct flights go from Dominican Republic to Chicago Midway Airport every day.
Search flight deals

  • When did momondo last update prices for flights from Dominican Republic to Chicago Midway Airport?

    Prices for flights from Dominican Republic to Chicago Midway Airport are refreshed on a daily basis.

  • How old do you have to be to fly from Dominican Republic to Chicago Midway Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Dominican Republic to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Dominican Republic to Chicago Midway Airport?

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
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?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Dominican Republic to Chicago for you.

Can I find flights from Dominican Republic to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Dominican Republic with this policy.

How can momondo help me find flights from Dominican Republic to Chicago?

Once all potential Dominican Republic to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Dominican Republic to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Dominican Republic and alert you when they change.

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