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Cheap flights from the Dominican Republic to Chicago from $182

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 12/10. 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.
Multiple Airlines Logo
3:35 pm - 9:22 pmSDQ-MDW
7h 47m1 stop
Multiple Airlines Logo
8:00 am - 9:45 pmMDW-SDQ
11h 45m1 stop
$352Multiple Airlines
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Sat, Nov 15 - Tue, Dec 9
Multiple Airlines Logo
2:36 pm - 3:30 pmPUJ-MDW
26h 54m1 stop
Multiple Airlines Logo
2:15 pm - 6:00 pmMDW-PUJ
25h 45m1 stop
$353Multiple Airlines
Find Deal
Mon, Dec 8 - Mon, Dec 15
Delta Logo
2:49 pm - 10:14 pmPUJ-MDW
8h 25m1 stop
Delta Logo
6:00 am - 1:24 pmMDW-PUJ
6h 24m1 stop
$365Delta
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Wed, Oct 22 - Wed, Oct 29
Multiple Airlines Logo
9:38 am - 11:17 amPUJ-MDW
26h 39m1 stop
Multiple Airlines Logo
1:37 pm - 3:00 pmMDW-PUJ
24h 23m2 stops
$368Multiple Airlines
Find Deal
Thu, Oct 23 - Thu, Oct 30
Multiple Airlines Logo
1:49 pm - 1:10 pmPUJ-MDW
25h 21m1 stop
Multiple Airlines Logo
2:15 pm - 8:25 pmMDW-PUJ
28h 10m1 stop
$369Multiple Airlines
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Thu, Dec 4 - Thu, Dec 11
Southwest Logo
4:00 pm - 9:55 pmPUJ-MDW
7h 55m1 stop
Southwest Logo
5:05 am - 3:00 pmMDW-PUJ
7h 55m1 stop
$387Southwest
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Tue, Nov 25 - Tue, Dec 2
Delta Logo
2:56 pm - 10:14 pmSDQ-MDW
8h 18m1 stop
Delta Logo
1:08 pm - 12:27 amMDW-SDQ
10h 19m2 stops
$395Delta
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Thu, Oct 23 - Fri, Oct 31
Southwest Logo
2:45 pm - 11:55 pmPUJ-MDW
10h 10m2 stops
Southwest Logo
6:10 am - 1:15 pmMDW-PUJ
6h 05m1 stop
$397Southwest
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Fri, Oct 24 - Fri, Oct 31
Frontier Logo
3:32 pm - 10:47 pmPUJ-MDW
8h 15m1 stop
Frontier Logo
6:15 am - 2:22 pmMDW-PUJ
7h 07m1 stop
$401Frontier
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Sat, Oct 18 - Sat, Oct 25
Frontier Logo
4:40 pm - 11:25 pmPUJ-MDW
8h 45m1 stop
Frontier Logo
6:00 am - 3:29 pmMDW-PUJ
7h 29m1 stop
$409Frontier
Find Deal
Sat, Jan 10 - Sat, Jan 17

Delta flights from Dominican Republic to Chicago Midway Airport

Our best Delta deals on Dominican Republic to Chicago Midway Airport flight tickets
Delta
Oct 22
PUJ2:49 pmPunta Cana
8h 25m
1 stop
MDW10:14 pmChicago Midway
Oct 29
MDW6:00 amChicago Midway
6h 24m
1 stop
PUJ1:24 pmPunta Cana
$365
Find similar
Delta
Oct 23
SDQ2:56 pmSanto Domingo Las Americas
8h 18m
1 stop
MDW10:14 pmChicago Midway
Oct 31
MDW1:08 pmChicago Midway
10h 19m
2 stops
SDQ12:27 amSanto Domingo Las Americas
$395
Find similar
Delta
Oct 21
PUJ3:56 pmPunta Cana
7h 18m
1 stop
MDW10:14 pmChicago Midway
Oct 28
MDW6:00 amChicago Midway
6h 24m
1 stop
PUJ1:24 pmPunta Cana
$396
Find similar

Southwest flights from Dominican Republic to Chicago Midway Airport

Our best Southwest deals on Dominican Republic to Chicago Midway Airport flight tickets
Southwest
Nov 25
PUJ4:00 pmPunta Cana
7h 55m
1 stop
MDW9:55 pmChicago Midway
Dec 2
MDW5:05 amChicago Midway
7h 55m
1 stop
PUJ3:00 pmPunta Cana
$387
Find similar
Southwest
Oct 24
PUJ2:45 pmPunta Cana
10h 10m
2 stops
MDW11:55 pmChicago Midway
Oct 31
MDW6:10 amChicago Midway
6h 05m
1 stop
PUJ1:15 pmPunta Cana
$397
Find similar
Southwest
Jan 15
PUJ2:40 pmPunta Cana
8h 20m
1 stop
MDW9:00 pmChicago Midway
Jan 22
MDW5:00 amChicago Midway
7h 30m
1 stop
PUJ2:30 pmPunta Cana
$416
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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 October 8, 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

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Sat 11/15

3:35 pm-9:22 pm

1 stop7h 47m

Chicago Midway

Tue 12/9

8:00 am-9:45 pm

1 stop11h 45m

$352

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Mon 12/8

2:36 pm-3:30 pm

1 stop26h 54m

Chicago Midway

Mon 12/15

2:15 pm-6:00 pm

1 stop25h 45m

$353

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 10/22

2:49 pm-10:14 pm

1 stop8h 25m

Chicago Midway

Wed 10/29

6:00 am-1:24 pm

1 stop6h 24m

$365

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 10/23

9:38 am-11:17 am

1 stop26h 39m

Chicago Midway

Thu 10/30

1:37 pm-3:00 pm

2 stops24h 23m

$368

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 12/4

1:49 pm-1:10 pm

1 stop25h 21m

Chicago Midway

Thu 12/11

2:15 pm-8:25 pm

1 stop28h 10m

$369

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Tue 11/25

4:00 pm-9:55 pm

1 stop7h 55m

Chicago Midway

Tue 12/2

5:05 am-3:00 pm

1 stop7h 55m

$387

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 10/23

2:56 pm-10:14 pm

1 stop8h 18m

Chicago Midway

Fri 10/31

1:08 pm-12:27 am

2 stops10h 19m

$395

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 10/24

2:45 pm-11:55 pm

2 stops10h 10m

Chicago Midway

Fri 10/31

6:10 am-1:15 pm

1 stop6h 05m

$397

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 10/18

3:32 pm-10:47 pm

1 stop8h 15m

Chicago Midway

Sat 10/25

6:15 am-2:22 pm

1 stop7h 07m

$401

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 1/10

4:40 pm-11:25 pm

1 stop8h 45m

Chicago Midway

Sat 1/17

6:00 am-3:29 pm

1 stop7h 29m

$409

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 55m

Direct flights

Mon, Wed, Thu, Fri, Sat and Sun
The fastest flight from Dominican Republic to Chicago Midway Airport takes 4h 55m
Direct flights go from Dominican Republic to Chicago Midway Airport on Monday, Wednesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
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  • 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
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?

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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