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Cheap flights from the Dominican Republic to Chicago from $255

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 8/18. 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
3:39 pm - 11:09 am
PUJ
-
MDW
20h 30m
1 stop
Frontier Logo
6:00 am - 2:29 pm
MDW
-
PUJ
7h 29m
1 stop
$484Frontier
Tue, Aug 18 - Sat, Aug 29
Frontier Logo
3:35 pm - 11:12 am
PUJ
-
MDW
20h 37m
1 stop
Frontier Logo
6:00 am - 2:29 pm
MDW
-
PUJ
7h 29m
1 stop
$504Frontier
Wed, Aug 19 - Sun, Aug 30
Frontier Logo
11:46 am - 10:03 pm
PUJ
-
MDW
11h 17m
2 stops
Frontier Logo
6:05 am - 2:21 pm
MDW
-
PUJ
7h 16m
1 stop
$517Frontier
Wed, Jul 8 - Tue, Jul 28
Frontier Logo
3:31 pm - 11:07 am
PUJ
-
MDW
20h 36m
1 stop
Frontier Logo
6:05 am - 2:21 pm
MDW
-
PUJ
7h 16m
1 stop
$525Frontier
Mon, Jul 13 - Sat, Jul 18
Frontier Logo
3:39 pm - 11:09 am
PUJ
-
MDW
20h 30m
1 stop
Frontier Logo
6:00 am - 2:25 pm
MDW
-
PUJ
7h 25m
1 stop
$560Frontier
Tue, Aug 18 - Wed, Aug 26
Delta Logo
3:59 pm - 10:25 pm
PUJ
-
MDW
7h 26m
1 stop
Delta Logo
6:05 am - 2:32 pm
MDW
-
PUJ
7h 27m
1 stop
$561Delta
Wed, Sep 23 - Tue, Sep 29
Delta Logo
3:59 pm - 10:25 pm
PUJ
-
MDW
7h 26m
1 stop
Delta Logo
6:05 am - 1:20 pm
MDW
-
PUJ
6h 15m
1 stop
$571Delta
Tue, Sep 22 - Tue, Sep 29
Delta Logo
3:59 pm - 9:07 am
PUJ
-
MDW
18h 08m
2 stops
Delta Logo
10:48 am - 12:32 pm
MDW
-
PUJ
24h 44m
2 stops
$572Delta
Tue, Sep 22 - Tue, Sep 29
Frontier Logo
3:40 pm - 11:07 am
PUJ
-
MDW
20h 27m
1 stop
Frontier Logo
6:05 am - 2:21 pm
MDW
-
PUJ
7h 16m
1 stop
$574Frontier
Sat, Jul 4 - Fri, Jul 10
Frontier Logo
3:31 pm - 11:07 am
PUJ
-
MDW
20h 36m
1 stop
Frontier Logo
12:11 pm - 2:21 pm
MDW
-
PUJ
25h 10m
1 stop
$582Frontier
Wed, Jul 8 - Tue, Jul 28

Southwest flights from Dominican Republic to Chicago Midway Airport

Our best Southwest deals on Dominican Republic to Chicago Midway Airport flight tickets
Southwest
Sep 24
PUJ1:45 pmPunta Cana
9h 55m
1 stop
MDW10:40 pmChicago Midway
Sep 30
MDW6:15 amChicago Midway
6h 05m
1 stop
PUJ1:20 pmPunta Cana
$615
Southwest
Sep 24
PUJ1:45 pmPunta Cana
9h 10m
2 stops
MDW9:55 pmChicago Midway
Sep 30
MDW6:15 amChicago Midway
6h 05m
1 stop
PUJ1:20 pmPunta Cana
$620
Southwest
Jul 4
PUJ1:45 pmPunta Cana
4h 35m
MDW5:20 pmChicago Midway
Jul 10
MDW7:00 amChicago Midway
6h 30m
1 stop
PUJ2:30 pmPunta Cana
$724

Frontier flights from Dominican Republic to Chicago Midway Airport

Our best Frontier deals on Dominican Republic to Chicago Midway Airport flight tickets
Frontier
Aug 18
PUJ3:39 pmPunta Cana
20h 30m
1 stop
MDW11:09 amChicago Midway
Aug 29
MDW6:00 amChicago Midway
7h 29m
1 stop
PUJ2:29 pmPunta Cana
$484
Frontier
Aug 19
PUJ3:35 pmPunta Cana
20h 37m
1 stop
MDW11:12 amChicago Midway
Aug 30
MDW6:00 amChicago Midway
7h 29m
1 stop
PUJ2:29 pmPunta Cana
$504
Frontier
Jul 8
PUJ11:46 amPunta Cana
11h 17m
2 stops
MDW10:03 pmChicago Midway
Jul 28
MDW6:05 amChicago Midway
7h 16m
1 stop
PUJ2:21 pmPunta Cana
$517

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 June 1, 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

Tue 8/18

3:39 pm-11:09 am

1 stop20h 30m

Chicago Midway

Sat 8/29

6:00 am-2:29 pm

1 stop7h 29m

$484

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 8/19

3:35 pm-11:12 am

1 stop20h 37m

Chicago Midway

Sun 8/30

6:00 am-2:29 pm

1 stop7h 29m

$504

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 7/8

11:46 am-10:03 pm

2 stops11h 17m

Chicago Midway

Tue 7/28

6:05 am-2:21 pm

1 stop7h 16m

$517

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Mon 7/13

3:31 pm-11:07 am

1 stop20h 36m

Chicago Midway

Sat 7/18

6:05 am-2:21 pm

1 stop7h 16m

$525

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Tue 8/18

3:39 pm-11:09 am

1 stop20h 30m

Chicago Midway

Wed 8/26

6:00 am-2:25 pm

1 stop7h 25m

$560

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 9/23

3:59 pm-10:25 pm

1 stop7h 26m

Chicago Midway

Tue 9/29

6:05 am-2:32 pm

1 stop7h 27m

$561
Quickest round-trip

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Tue 9/22

3:59 pm-10:25 pm

1 stop7h 26m

Chicago Midway

Tue 9/29

6:05 am-1:20 pm

1 stop6h 15m

$571

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Tue 9/22

3:59 pm-9:07 am

2 stops18h 08m

Chicago Midway

Tue 9/29

10:48 am-12:32 pm

2 stops24h 44m

$572

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 7/4

3:40 pm-11:07 am

1 stop20h 27m

Chicago Midway

Fri 7/10

6:05 am-2:21 pm

1 stop7h 16m

$574

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 7/8

3:31 pm-11:07 am

1 stop20h 36m

Chicago Midway

Tue 7/28

12:11 pm-2:21 pm

1 stop25h 10m

$582

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 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

4h 35m

Direct flights

Every day
The fastest flight from Dominican Republic to Chicago Midway Airport takes 4h 35m
Direct flights go from Dominican Republic to Chicago Midway Airport every day.
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
Monticello
Chesterton
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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