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Cheap flights from the Dominican Republic to Chicago from $159

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 5/8. 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
6:10 am - 1:00 pm
SDQ
-
MDW
7h 50m
1 stop
Multiple Airlines Logo
2:20 pm - 4:29 pm
MDW
-
SDQ
25h 09m
2 stops
$352Multiple Airlines
Tue, May 5 - Tue, May 12
Multiple Airlines Logo
6:10 am - 1:00 pm
SDQ
-
MDW
7h 50m
1 stop
Multiple Airlines Logo
7:30 am - 5:29 am
MDW
-
SDQ
20h 59m
1 stop
$354Multiple Airlines
Tue, May 5 - Tue, May 12
Multiple Airlines Logo
6:10 am - 1:00 pm
SDQ
-
MDW
7h 50m
1 stop
Multiple Airlines Logo
2:15 pm - 9:45 pm
MDW
-
SDQ
30h 30m
2 stops
$392Multiple Airlines
Thu, Apr 23 - Mon, Apr 27
Multiple Airlines Logo
6:10 am - 1:00 pm
SDQ
-
MDW
7h 50m
1 stop
Multiple Airlines Logo
7:30 am - 4:30 pm
MDW
-
SDQ
8h 00m
1 stop
$398Multiple Airlines
Thu, Apr 23 - Mon, Apr 27
Frontier Logo
9:13 pm - 10:26 pm
PUJ
-
MDW
26h 13m
2 stops
Frontier Logo
6:00 am - 1:54 pm
MDW
-
PUJ
6h 54m
1 stop
$400Frontier
Thu, Apr 16 - Sat, Apr 25
Multiple Airlines Logo
9:38 am - 7:31 pm
PUJ
-
MDW
10h 53m
2 stops
Multiple Airlines Logo
7:30 am - 4:19 pm
MDW
-
PUJ
7h 49m
1 stop
$401Multiple Airlines
Tue, Apr 14 - Sun, Apr 19
Frontier Logo
3:04 pm - 7:31 pm
PUJ
-
MDW
29h 27m
1 stop
Frontier Logo
6:00 am - 1:20 pm
MDW
-
PUJ
30h 20m
2 stops
$440Frontier
Sat, Apr 18 - Thu, Apr 23
Southwest Logo
2:05 pm - 12:05 am
PUJ
-
MDW
11h 00m
1 stop
Southwest Logo
9:40 am - 3:00 pm
MDW
-
PUJ
4h 20mnonstop
$522Southwest
Thu, Apr 16 - Sat, Apr 25
Southwest Logo
2:05 pm - 12:05 am
PUJ
-
MDW
11h 00m
1 stop
Southwest Logo
6:10 am - 2:15 pm
MDW
-
PUJ
7h 05m
1 stop
$527Southwest
Thu, Apr 16 - Sat, Apr 25
Delta Logo
3:57 pm - 10:28 pm
PUJ
-
MDW
7h 31m
1 stop
Delta Logo
6:00 am - 2:32 pm
MDW
-
PUJ
7h 32m
1 stop
$575Delta
Tue, Apr 14 - Mon, Apr 20

Delta flights from Dominican Republic to Chicago Midway Airport

Our best Delta deals on Dominican Republic to Chicago Midway Airport flight tickets
Delta
Apr 23
SDQ6:05 amSanto Domingo Las Americas
12h 53m
2 stops
MDW5:58 pmChicago Midway
Apr 27
MDW6:00 amChicago Midway
11h 34m
2 stops
SDQ6:34 pmSanto Domingo Las Americas
$541
Delta
Apr 14
PUJ3:57 pmPunta Cana
7h 31m
1 stop
MDW10:28 pmChicago Midway
Apr 20
MDW6:00 amChicago Midway
7h 32m
1 stop
PUJ2:32 pmPunta Cana
$575
Delta
Apr 20
SDQ6:05 amSanto Domingo Las Americas
12h 53m
2 stops
MDW5:58 pmChicago Midway
Apr 27
MDW1:24 pmChicago Midway
9h 53m
2 stops
SDQ12:17 amSanto Domingo Las Americas
$600

Frontier flights from Dominican Republic to Chicago Midway Airport

Our best Frontier deals on Dominican Republic to Chicago Midway Airport flight tickets
Frontier
Apr 16
PUJ9:13 pmPunta Cana
26h 13m
2 stops
MDW10:26 pmChicago Midway
Apr 25
MDW6:00 amChicago Midway
6h 54m
1 stop
PUJ1:54 pmPunta Cana
$400
Frontier
Apr 18
PUJ3:04 pmPunta Cana
29h 27m
1 stop
MDW7:31 pmChicago Midway
Apr 23
MDW6:00 amChicago Midway
30h 20m
2 stops
PUJ1:20 pmPunta Cana
$440
Frontier
Apr 14
PUJ1:37 pmPunta Cana
43h 27m
2 stops
MDW8:04 amChicago Midway
Apr 19
MDW2:15 pmChicago Midway
28h 53m
2 stops
PUJ8:08 pmPunta Cana
$523

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 February 27, 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

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Tue 5/5

6:10 am-1:00 pm

1 stop7h 50m

Chicago Midway

Tue 5/12

2:20 pm-4:29 pm

2 stops25h 09m

$352

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Tue 5/5

6:10 am-1:00 pm

1 stop7h 50m

Chicago Midway

Tue 5/12

7:30 am-5:29 am

1 stop20h 59m

$354

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 4/23

6:10 am-1:00 pm

1 stop7h 50m

Chicago Midway

Mon 4/27

2:15 pm-9:45 pm

2 stops30h 30m

$392

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 4/23

6:10 am-1:00 pm

1 stop7h 50m

Chicago Midway

Mon 4/27

7:30 am-4:30 pm

1 stop8h 00m

$398

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 4/16

9:13 pm-10:26 pm

2 stops26h 13m

Chicago Midway

Sat 4/25

6:00 am-1:54 pm

1 stop6h 54m

$400

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Tue 4/14

9:38 am-7:31 pm

2 stops10h 53m

Chicago Midway

Sun 4/19

7:30 am-4:19 pm

1 stop7h 49m

$401

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 4/18

3:04 pm-7:31 pm

1 stop29h 27m

Chicago Midway

Thu 4/23

6:00 am-1:20 pm

2 stops30h 20m

$440

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 4/16

2:05 pm-12:05 am

1 stop11h 00m

Chicago Midway

Sat 4/25

9:40 am-3:00 pm

Nonstop4h 20m

$522

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 4/16

2:05 pm-12:05 am

1 stop11h 00m

Chicago Midway

Sat 4/25

6:10 am-2:15 pm

1 stop7h 05m

$527

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Tue 4/14

3:57 pm-10:28 pm

1 stop7h 31m

Chicago Midway

Mon 4/20

6:00 am-2:32 pm

1 stop7h 32m

$575

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 40% 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

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
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?

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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