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Cheap flights from Punta Cana to Chicago from $165

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Punta Cana to Chicago departing on 2/13. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Punta Cana to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
1:10 pm - 2:55 pm
PUJ
-
MDW
27h 45m1 stop
Multiple Airlines Logo
7:53 pm - 3:36 pm
MDW
-
PUJ
17h 43m1 stop
$314Multiple Airlines
Fri, Feb 13 - Fri, Feb 20
Multiple Airlines Logo
1:10 pm - 2:55 pm
PUJ
-
MDW
27h 45m1 stop
Multiple Airlines Logo
7:53 pm - 3:36 pm
MDW
-
PUJ
17h 43m1 stop
$325Multiple Airlines
Fri, Feb 13 - Fri, Feb 20
Multiple Airlines Logo
1:10 pm - 2:55 pm
PUJ
-
MDW
27h 45m1 stop
Multiple Airlines Logo
7:53 pm - 3:36 pm
MDW
-
PUJ
17h 43m1 stop
$331Multiple Airlines
Fri, Feb 13 - Fri, Feb 20
Multiple Airlines Logo
1:01 pm - 6:54 pm
PUJ
-
MDW
7h 53m1 stop
Multiple Airlines Logo
5:01 pm - 3:01 pm
MDW
-
PUJ
20h 00m1 stop
$338Multiple Airlines
Fri, Jan 16 - Fri, Jan 23
Multiple Airlines Logo
5:47 pm - 3:19 pm
PUJ
-
MDW
23h 32m2 stops
Multiple Airlines Logo
7:30 am - 8:25 pm
MDW
-
PUJ
10h 55m1 stop
$343Multiple Airlines
Fri, Feb 20 - Fri, Feb 27
Multiple Airlines Logo
4:11 pm - 11:45 am
PUJ
-
MDW
21h 34m1 stop
Multiple Airlines Logo
9:38 am - 6:50 pm
MDW
-
PUJ
31h 12m2 stops
$355Multiple Airlines
Sat, Jan 24 - Sat, Jan 31
Multiple Airlines Logo
1:01 pm - 6:54 pm
PUJ
-
MDW
7h 53m1 stop
Multiple Airlines Logo
5:01 pm - 3:01 pm
MDW
-
PUJ
20h 00m1 stop
$358Multiple Airlines
Fri, Jan 16 - Fri, Jan 23
Multiple Airlines Logo
1:10 pm - 2:55 pm
PUJ
-
MDW
27h 45m1 stop
Multiple Airlines Logo
7:53 pm - 4:36 pm
MDW
-
PUJ
18h 43m2 stops
$360Multiple Airlines
Fri, Feb 13 - Fri, Feb 20
Multiple Airlines Logo
5:47 pm - 10:13 pm
PUJ
-
MDW
30h 26m2 stops
Multiple Airlines Logo
5:01 pm - 3:01 pm
MDW
-
PUJ
20h 00m1 stop
$361Multiple Airlines
Fri, Jan 16 - Fri, Jan 23
Multiple Airlines Logo
1:10 pm - 2:55 pm
PUJ
-
MDW
27h 45m1 stop
Multiple Airlines Logo
7:53 pm - 2:18 pm
MDW
-
PUJ
16h 25m2 stops
$363Multiple Airlines
Fri, Feb 20 - Fri, Feb 27

Frontier flights from Punta Cana to Chicago Midway Airport

Our best Frontier deals on Punta Cana to Chicago Midway Airport flight tickets
Frontier
Dec 25
PUJ11:37 amPunta Cana
12h 35m
1 stop
MDW10:12 pmChicago Midway
Jan 1
MDW6:12 amChicago Midway
6h 57m
1 stop
PUJ3:09 pmPunta Cana
$370
Find similar
Frontier
Dec 24
PUJ4:19 pmPunta Cana
27h 19m
1 stop
MDW5:38 pmChicago Midway
Dec 31
MDW6:12 amChicago Midway
6h 57m
1 stop
PUJ3:09 pmPunta Cana
$371
Find similar
Frontier
Dec 25
PUJ11:37 amPunta Cana
12h 35m
1 stop
MDW10:12 pmChicago Midway
Jan 1
MDW6:12 amChicago Midway
6h 57m
1 stop
PUJ3:09 pmPunta Cana
$373
Find similar

Delta flights from Punta Cana to Chicago Midway Airport

Our best Delta deals on Punta Cana to Chicago Midway Airport flight tickets
Delta
Jan 22
PUJ3:45 pmPunta Cana
8h 37m
1 stop
MDW10:22 pmChicago Midway
Jan 27
MDW6:00 amChicago Midway
6h 20m
1 stop
PUJ2:20 pmPunta Cana
$377
Find similar
Delta
Jan 14
PUJ3:45 pmPunta Cana
8h 22m
1 stop
MDW10:07 pmChicago Midway
Jan 21
MDW6:00 amChicago Midway
7h 30m
1 stop
PUJ3:30 pmPunta Cana
$412
Find similar
Delta
Dec 29
PUJ4:46 pmPunta Cana
7h 36m
1 stop
MDW10:22 pmChicago Midway
Jan 5
MDW6:45 amChicago Midway
6h 55m
1 stop
PUJ3:40 pmPunta Cana
$438
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Punta Cana 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 December 16, 2025.
Use the filters below to find and compare flights from Punta Cana to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 2/13

1:10 pm-2:55 pm

1 stop27h 45m

Chicago Midway

Fri 2/20

7:53 pm-3:36 pm

1 stop17h 43m

$314

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 2/13

1:10 pm-2:55 pm

1 stop27h 45m

Chicago Midway

Fri 2/20

7:53 pm-3:36 pm

1 stop17h 43m

$325

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 2/13

1:10 pm-2:55 pm

1 stop27h 45m

Chicago Midway

Fri 2/20

7:53 pm-3:36 pm

1 stop17h 43m

$331

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 1/16

1:01 pm-6:54 pm

1 stop7h 53m

Chicago Midway

Fri 1/23

5:01 pm-3:01 pm

1 stop20h 00m

$338

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 2/20

5:47 pm-3:19 pm

2 stops23h 32m

Chicago Midway

Fri 2/27

7:30 am-8:25 pm

1 stop10h 55m

$343

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 1/24

4:11 pm-11:45 am

1 stop21h 34m

Chicago Midway

Sat 1/31

9:38 am-6:50 pm

2 stops31h 12m

$355

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 1/16

1:01 pm-6:54 pm

1 stop7h 53m

Chicago Midway

Fri 1/23

5:01 pm-3:01 pm

1 stop20h 00m

$358

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 2/13

1:10 pm-2:55 pm

1 stop27h 45m

Chicago Midway

Fri 2/20

7:53 pm-4:36 pm

2 stops18h 43m

$360

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 1/16

5:47 pm-10:13 pm

2 stops30h 26m

Chicago Midway

Fri 1/23

5:01 pm-3:01 pm

1 stop20h 00m

$361

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 2/20

1:10 pm-2:55 pm

1 stop27h 45m

Chicago Midway

Fri 2/27

7:53 pm-2:18 pm

2 stops16h 25m

$363

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 Punta Cana 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 Punta Cana to Chicago Midway flight route?

Fly from Punta Cana to Chicago Midway for the best Punta Cana - Chicago Midway flight prices

What cabin class options are available on Punta Cana to Chicago Midway flights?

There is only 1 cabin class available to choose from on Punta Cana 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 Punta Cana to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between Punta Cana to Chicago Midway Airport.

When to book flights from Punta Cana to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Punta Cana to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Punta Cana to Chicago Midway Airport (PUJ to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Punta Cana to Chicago Midway Airport

Fastest flight time

4h 45m

Direct flights

Every day
The fastest flight from Punta Cana to Chicago Midway Airport takes 4h 45m
Direct flights go from Punta Cana to Chicago Midway Airport every day.
Search flight deals

  • How far is Punta Cana to Chicago Midway by plane?

    The distance between Punta Cana and Chicago Midway is about 1957.5 mi. Typically, this will take 4h 45m by plane in normal conditions.

  • When did momondo last update prices for flights from Punta Cana Airport to Chicago Midway Airport?

    Prices for flights from Punta Cana Airport to Chicago Midway Airport refresh daily.

  • How old do you have to be to fly from Punta Cana Airport to Chicago Midway Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Punta Cana Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Punta Cana 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
Valparaiso
Schererville
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Punta Cana to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Punta Cana to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Punta Cana to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Punta Cana which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Punta Cana to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Punta Cana.

I’m not ready to book a flight from Punta Cana to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Punta Cana. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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