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Cheap flights from the Dominican Republic to Chicago from $188

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 5/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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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.
Frontier Logo
3:35 pm - 11:09 am
PUJ
-
MDW
20h 34m
1 stop
Frontier Logo
6:00 am - 2:24 pm
MDW
-
PUJ
7h 24m
1 stop
$269Frontier
Thu, May 7 - Sun, May 10
Frontier Logo
9:29 pm - 3:57 pm
PUJ
-
MDW
19h 28m
2 stops
Frontier Logo
6:00 am - 2:24 pm
MDW
-
PUJ
7h 24m
1 stop
$294Frontier
Thu, May 7 - Sun, May 10
Frontier Logo
9:29 pm - 11:04 am
PUJ
-
MDW
38h 35m
2 stops
Frontier Logo
6:00 am - 2:24 pm
MDW
-
PUJ
7h 24m
1 stop
$317Frontier
Thu, May 7 - Sun, May 10
Frontier Logo
3:35 pm - 11:09 am
PUJ
-
MDW
20h 34m
1 stop
Frontier Logo
6:00 am - 2:24 pm
MDW
-
PUJ
7h 24m
1 stop
$322Frontier
Thu, May 7 - Sun, May 10
Frontier Logo
9:13 pm - 4:13 pm
PUJ
-
MDW
20h 00m
2 stops
Frontier Logo
6:00 am - 8:08 pm
MDW
-
PUJ
13h 08m
2 stops
$351Frontier
Fri, May 1 - Mon, May 4
Frontier Logo
9:13 pm - 10:19 pm
PUJ
-
MDW
26h 06m
2 stops
Frontier Logo
6:00 am - 1:54 pm
MDW
-
PUJ
6h 54m
1 stop
$389Frontier
Wed, Apr 29 - Sat, May 2
Delta Logo
2:49 pm - 9:09 pm
SDQ
-
MDW
7h 20m
1 stop
Delta Logo
6:00 am - 1:12 pm
MDW
-
SDQ
6h 12m
1 stop
$585Delta
Mon, May 11 - Wed, Sep 9
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
$602Delta
Sat, May 2 - Wed, May 6
Delta Logo
2:49 pm - 9:09 pm
SDQ
-
MDW
7h 20m
1 stop
Delta Logo
6:00 am - 6:04 pm
MDW
-
SDQ
11h 04m
2 stops
$613Delta
Mon, May 11 - Wed, Sep 9
Multiple Airlines Logo
6:10 am - 1:00 pm
SDQ
-
MDW
7h 50m
1 stop
Multiple Airlines Logo
6:00 am - 4:29 pm
MDW
-
SDQ
33h 29m
2 stops
$636Multiple Airlines
Thu, Apr 30 - Thu, May 7

Delta flights from Dominican Republic to Chicago Midway Airport

Our best Delta deals on Dominican Republic to Chicago Midway Airport flight tickets
Delta
May 1
PUJ1:00 pmPunta Cana
10h 28m
1 stop
MDW10:28 pmChicago Midway
May 4
MDW6:00 amChicago Midway
6h 21m
1 stop
PUJ1:21 pmPunta Cana
$488
Delta
May 1
PUJ1:00 pmPunta Cana
10h 28m
1 stop
MDW10:28 pmChicago Midway
May 4
MDW6:00 amChicago Midway
7h 32m
1 stop
PUJ2:32 pmPunta Cana
$511
Delta
Sep 16
PUJ2:45 pmPunta Cana
8h 01m
1 stop
MDW9:46 pmChicago Midway
Sep 22
MDW6:00 amChicago Midway
7h 32m
1 stop
PUJ2:32 pmPunta Cana
$556

Frontier flights from Dominican Republic to Chicago Midway Airport

Our best Frontier deals on Dominican Republic to Chicago Midway Airport flight tickets
Frontier
May 7
PUJ3:35 pmPunta Cana
20h 34m
1 stop
MDW11:09 amChicago Midway
May 10
MDW6:00 amChicago Midway
7h 24m
1 stop
PUJ2:24 pmPunta Cana
$269
Frontier
May 7
PUJ9:29 pmPunta Cana
19h 28m
2 stops
MDW3:57 pmChicago Midway
May 10
MDW6:00 amChicago Midway
7h 24m
1 stop
PUJ2:24 pmPunta Cana
$294
Frontier
May 7
PUJ9:29 pmPunta Cana
38h 35m
2 stops
MDW11:04 amChicago Midway
May 10
MDW6:00 amChicago Midway
7h 24m
1 stop
PUJ2:24 pmPunta Cana
$317

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 April 16, 2026.
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

Cheapest round-trip

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 5/7

3:35 pm-11:09 am

1 stop20h 34m

Chicago Midway

Sun 5/10

6:00 am-2:24 pm

1 stop7h 24m

$269

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 5/7

9:29 pm-3:57 pm

2 stops19h 28m

Chicago Midway

Sun 5/10

6:00 am-2:24 pm

1 stop7h 24m

$294

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 5/7

9:29 pm-11:04 am

2 stops38h 35m

Chicago Midway

Sun 5/10

6:00 am-2:24 pm

1 stop7h 24m

$317

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 5/7

3:35 pm-11:09 am

1 stop20h 34m

Chicago Midway

Sun 5/10

6:00 am-2:24 pm

1 stop7h 24m

$322

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 5/1

9:13 pm-4:13 pm

2 stops20h 00m

Chicago Midway

Mon 5/4

6:00 am-8:08 pm

2 stops13h 08m

$351

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 4/29

9:13 pm-10:19 pm

2 stops26h 06m

Chicago Midway

Sat 5/2

6:00 am-1:54 pm

1 stop6h 54m

$389
Quickest round-trip

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Mon 5/11

2:49 pm-9:09 pm

1 stop7h 20m

Chicago Midway

Wed 9/9

6:00 am-1:12 pm

1 stop6h 12m

$585

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Sat 5/2

2:37 pm-10:28 pm

1 stop8h 51m

Chicago Midway

Wed 5/6

9:27 am-12:17 am

2 stops13h 50m

$602

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Mon 5/11

2:49 pm-9:09 pm

1 stop7h 20m

Chicago Midway

Wed 9/9

6:00 am-6:04 pm

2 stops11h 04m

$613

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 4/30

6:10 am-1:00 pm

1 stop7h 50m

Chicago Midway

Thu 5/7

6:00 am-4:29 pm

2 stops33h 29m

$636

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?

You could potentially save up to 22% on your flight if you consider stops on a Dominican Republic to Chicago Midway Airport flight.

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

5h 00m

Direct flights

Mon, Thu and Sun
The fastest flight from Dominican Republic to Chicago Midway Airport takes 5h 00m
Direct flights go from Dominican Republic to Chicago Midway Airport on Monday, Thursday and Sunday. The only airline offering direct flights is Southwest.
Search flight deals

Frequently asked questions about flying from the Dominican Republic to Chicago Midway Airport

  • 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
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?

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.

An easier way to manage your Chicago Midway Airport trip

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