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Cheap flights from the Dominican Republic to Chicago from $221

1 adult
1 adult, Economy, 0 bags

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
8:19 pm - 7:02 pmSDQ  Santo Domingo Las Americas-MDW Chicago Midway
24h 43m1 stop Orlando
Frontier Logo
8:07 pm - 7:04 pmMDW  Chicago Midway-SDQ Santo Domingo Las Americas
20h 57m1 stop Orlando
$411Frontier
Thu, Dec 24 - Thu, Dec 31
Delta Logo
1:56 pm - 10:54 pmPUJ  Punta Cana-MDW Chicago Midway
10h 58m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 3:30 pmMDW  Chicago Midway-PUJ Punta Cana
7h 30m1 stop Atlanta Hartsfield-Jackson
$416Delta
Fri, Dec 18 - Fri, Jan 8
Southwest Logo
4:05 pm - 11:15 pmPUJ  Punta Cana-MDW Chicago Midway
9h 10m1 stop Baltimore/Washington
Southwest Logo
5:10 am - 3:50 pmMDW  Chicago Midway-PUJ Punta Cana
8h 40m1 stop Orlando
$482Southwest
Thu, Nov 5 - Mon, Nov 9
Southwest Logo
4:50 pm - 11:00 pmPUJ  Punta Cana-MDW Chicago Midway
8h 10m1 stop Orlando
Southwest Logo
5:10 am - 3:50 pmMDW  Chicago Midway-PUJ Punta Cana
8h 40m1 stop Orlando
$482Southwest
Fri, Nov 6 - Mon, Nov 9
Frontier Logo
10:55 am - 12:01 amSDQ  Santo Domingo Las Americas-MDW Chicago Midway
15h 06m2 stops Tampa Atlanta Hartsfield-Jackson
Frontier Logo
8:35 pm - 2:11 pmMDW  Chicago Midway-SDQ Santo Domingo Las Americas
15h 36m1 stop Orlando
$498Frontier
Thu, Dec 24 - Thu, Dec 31
Southwest Logo
4:50 pm - 11:00 pmPUJ  Punta Cana-MDW Chicago Midway
8h 10m1 stop Orlando
Southwest Logo
5:10 am - 3:50 pmMDW  Chicago Midway-PUJ Punta Cana
8h 40m1 stop Orlando
$505Southwest
Fri, Nov 6 - Mon, Nov 9
Delta Logo
4:55 pm - 10:10 pmPUJ  Punta Cana-MDW Chicago Midway
7h 15m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 4:42 pmMDW  Chicago Midway-PUJ Punta Cana
8h 42m1 stop Atlanta Hartsfield-Jackson
$510Delta
Thu, Jan 28 - Mon, Feb 8
Delta Logo
3:40 pm - 10:22 pmPUJ  Punta Cana-MDW Chicago Midway
8h 42m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 4:49 pmMDW  Chicago Midway-PUJ Punta Cana
8h 49m1 stop Atlanta Hartsfield-Jackson
$510Delta
Thu, Dec 24 - Sat, Jan 2
Delta Logo
3:40 pm - 10:22 pmPUJ  Punta Cana-MDW Chicago Midway
8h 42m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 3:24 pmMDW  Chicago Midway-PUJ Punta Cana
7h 24m1 stop Atlanta Hartsfield-Jackson
$510Delta
Thu, Dec 24 - Fri, Jan 1
Frontier Logo
8:19 pm - 7:02 pmSDQ  Santo Domingo Las Americas-MDW Chicago Midway
24h 43m1 stop Orlando
Frontier Logo
8:07 pm - 7:04 pmMDW  Chicago Midway-SDQ Santo Domingo Las Americas
20h 57m1 stop Orlando
$519Frontier
Wed, Dec 23 - Wed, Dec 30

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Southwest flights from Dominican Republic to Chicago Midway Airport

Our best Southwest deals on Dominican Republic to Chicago Midway Airport flight tickets
Southwest
Nov 5
PUJ4:05 pmPunta Cana
9h 10m
1 stop
MDW11:15 pmChicago Midway
Nov 9
MDW5:10 amChicago Midway
8h 40m
1 stop
PUJ3:50 pmPunta Cana
$482
Southwest
Nov 6
PUJ4:50 pmPunta Cana
8h 10m
1 stop
MDW11:00 pmChicago Midway
Nov 9
MDW5:10 amChicago Midway
8h 40m
1 stop
PUJ3:50 pmPunta Cana
$505
Southwest
Oct 22
PUJ2:45 pmPunta Cana
8h 15m
1 stop
MDW10:00 pmChicago Midway
Oct 25
MDW5:10 amChicago Midway
8h 10m
1 stop
PUJ2:20 pmPunta Cana
$511

Frontier flights from Dominican Republic to Chicago Midway Airport

Our best Frontier deals on Dominican Republic to Chicago Midway Airport flight tickets
Frontier
Dec 24
SDQ8:19 pmSanto Domingo Las Americas
24h 43m
1 stop
MDW7:02 pmChicago Midway
Dec 31
MDW8:07 pmChicago Midway
20h 57m
1 stop
SDQ7:04 pmSanto Domingo Las Americas
$411
Frontier
Dec 24
SDQ10:55 amSanto Domingo Las Americas
15h 06m
2 stops
MDW12:01 amChicago Midway
Dec 31
MDW8:35 pmChicago Midway
15h 36m
1 stop
SDQ2:11 pmSanto Domingo Las Americas
$498
Frontier
Dec 23
SDQ8:19 pmSanto Domingo Las Americas
24h 43m
1 stop
MDW7:02 pmChicago Midway
Dec 30
MDW8:07 pmChicago Midway
20h 57m
1 stop
SDQ7:04 pmSanto Domingo Las Americas
$519

momondo Fare Finder

 
Use the filters below to find and compare flights from the Dominican Republic to Chicago Midway Airport that are best for you.

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Price

Cheapest round-trip

Santo DomingoChicago

SDQ Santo Domingo Las Americas - MDW Chicago Midway

SDQMDW

Santo Domingo Las Americas

Thu 12/24

8:19 pm-7:02 pm

1 stop24h 43m

Chicago Midway

Thu 12/31

8:07 pm-7:04 pm

1 stop20h 57m

$411

Punta CanaChicago

PUJ Punta Cana - MDW Chicago Midway

PUJMDW

Punta Cana

Fri 12/18

1:56 pm-10:54 pm

1 stop10h 58m

Chicago Midway

Fri 1/8

6:00 am-3:30 pm

1 stop7h 30m

$416

Punta CanaChicago

PUJ Punta Cana - MDW Chicago Midway

PUJMDW

Punta Cana

Thu 11/5

4:05 pm-11:15 pm

1 stop9h 10m

Chicago Midway

Mon 11/9

5:10 am-3:50 pm

1 stop8h 40m

$482

Punta CanaChicago

PUJ Punta Cana - MDW Chicago Midway

PUJMDW

Punta Cana

Fri 11/6

4:50 pm-11:00 pm

1 stop8h 10m

Chicago Midway

Mon 11/9

5:10 am-3:50 pm

1 stop8h 40m

$482

Santo DomingoChicago

SDQ Santo Domingo Las Americas - MDW Chicago Midway

SDQMDW

Santo Domingo Las Americas

Thu 12/24

10:55 am-12:01 am

2 stops15h 06m

Chicago Midway

Thu 12/31

8:35 pm-2:11 pm

1 stop15h 36m

$498

Punta CanaChicago

PUJ Punta Cana - MDW Chicago Midway

PUJMDW

Punta Cana

Fri 11/6

4:50 pm-11:00 pm

1 stop8h 10m

Chicago Midway

Mon 11/9

5:10 am-3:50 pm

1 stop8h 40m

$505
Quickest round-trip

Punta CanaChicago

PUJ Punta Cana - MDW Chicago Midway

PUJMDW

Punta Cana

Thu 1/28

4:55 pm-10:10 pm

1 stop7h 15m

Chicago Midway

Mon 2/8

6:00 am-4:42 pm

1 stop8h 42m

$510

Punta CanaChicago

PUJ Punta Cana - MDW Chicago Midway

PUJMDW

Punta Cana

Thu 12/24

3:40 pm-10:22 pm

1 stop8h 42m

Chicago Midway

Sat 1/2

6:00 am-4:49 pm

1 stop8h 49m

$510

Punta CanaChicago

PUJ Punta Cana - MDW Chicago Midway

PUJMDW

Punta Cana

Thu 12/24

3:40 pm-10:22 pm

1 stop8h 42m

Chicago Midway

Fri 1/1

6:00 am-3:24 pm

1 stop7h 24m

$510

Santo DomingoChicago

SDQ Santo Domingo Las Americas - MDW Chicago Midway

SDQMDW

Santo Domingo Las Americas

Wed 12/23

8:19 pm-7:02 pm

1 stop24h 43m

Chicago Midway

Wed 12/30

8:07 pm-7:04 pm

1 stop20h 57m

$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 Airport flights?

There is only 1 cabin class available to choose from on Dominican Republic to Chicago Midway Airport 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 36% 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

Best Price Found

$221

Fastest flight time

5h 10m

Direct flights

Tue, Wed, Fri and Sun
The best one-way flight to Chicago Midway Airport from Dominican Republic in the past 72 hours is $221. The best round-trip flight deal from Dominican Republic to Chicago Midway Airport found on momondo in the last 72 hours is $411.
The fastest flight from Dominican Republic to Chicago Midway Airport takes 5h 10m
Direct flights go from Dominican Republic to Chicago Midway Airport on Tuesday, Wednesday, Friday and Sunday. There are no airlines offering direct flights.
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
Portage
Saint Joseph
Benton Harbor
Lansing
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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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