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Cheap flights from Punta Cana to Chicago from $148

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 12/31. 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
6:08 pm - 5:38 pmPUJ-MDW
25h 30m2 stops
Multiple Airlines Logo
6:12 am - 10:27 amMDW-PUJ
26h 15m1 stop
$306Multiple Airlines
Find Deal
mié., dic. 24 - mié., dic. 31
Multiple Airlines Logo
4:19 pm - 10:12 pmPUJ-MDW
7h 53m1 stop
Multiple Airlines Logo
3:52 pm - 4:31 pmMDW-PUJ
22h 39m1 stop
$309Multiple Airlines
Find Deal
mié., dic. 31 - mié., ene. 7
Multiple Airlines Logo
9:38 am - 9:53 pmPUJ-MDW
14h 15m1 stop
Multiple Airlines Logo
2:16 pm - 7:54 pmMDW-PUJ
27h 38m1 stop
$317Multiple Airlines
Find Deal
jue., dic. 4 - jue., dic. 11
Multiple Airlines Logo
4:19 pm - 10:12 pmPUJ-MDW
7h 53m1 stop
Multiple Airlines Logo
6:00 am - 12:16 pmMDW-PUJ
28h 16m2 stops
$321Multiple Airlines
Find Deal
mié., dic. 31 - mié., ene. 7
Delta Logo
3:50 pm - 11:47 pmPUJ-MDW
9h 57m1 stop
Delta Logo
6:00 am - 3:39 pmMDW-PUJ
7h 39m1 stop
$344Delta
Find Deal
vie., dic. 5 - vie., dic. 12
Delta Logo
5:11 pm - 8:54 amPUJ-MDW
17h 43m1 stop
Delta Logo
6:45 pm - 2:30 pmMDW-PUJ
17h 45m1 stop
$368Delta
Find Deal
jue., feb. 19 - dom., feb. 22
Frontier Logo
4:19 pm - 5:38 pmPUJ-MDW
27h 19m1 stop
Frontier Logo
8:15 am - 10:27 amMDW-PUJ
24h 12m1 stop
$370Frontier
Find Deal
mié., dic. 24 - mié., dic. 31
Southwest Logo
3:20 pm - 6:20 pmPUJ-MDW
5h 00mnonstop
Southwest Logo
8:30 am - 2:50 pmMDW-PUJ
4h 20mnonstop
$379Southwest
Find Deal
sáb., nov. 22 - sáb., nov. 29
Southwest Logo
3:20 pm - 6:20 pmPUJ-MDW
5h 00mnonstop
Southwest Logo
5:25 am - 3:30 pmMDW-PUJ
8h 05m1 stop
$384Southwest
Find Deal
sáb., nov. 22 - sáb., nov. 29
Frontier Logo
3:39 pm - 1:59 pmPUJ-MDW
24h 20m2 stops
Frontier Logo
8:15 am - 10:27 amMDW-PUJ
24h 12m1 stop
$400Frontier
Find Deal
lun., dic. 22 - lun., dic. 29

Southwest flights from Punta Cana to Chicago Midway Airport

Our best Southwest deals on Punta Cana to Chicago Midway Airport flight tickets
Southwest
Nov 22
PUJ3:20 pmPunta Cana
5h 00m
MDW6:20 pmChicago Midway
Nov 29
MDW8:30 amChicago Midway
4h 20m
PUJ2:50 pmPunta Cana
$379
Find similar
Southwest
Nov 22
PUJ3:20 pmPunta Cana
5h 00m
MDW6:20 pmChicago Midway
Nov 29
MDW5:25 amChicago Midway
8h 05m
1 stop
PUJ3:30 pmPunta Cana
$384
Find similar
Southwest
Feb 14
PUJ3:35 pmPunta Cana
5h 00m
MDW6:35 pmChicago Midway
Feb 21
MDW5:40 amChicago Midway
6h 20m
1 stop
PUJ2:00 pmPunta Cana
$388
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
Dec 5
PUJ3:50 pmPunta Cana
9h 57m
1 stop
MDW11:47 pmChicago Midway
Dec 12
MDW6:00 amChicago Midway
7h 39m
1 stop
PUJ3:39 pmPunta Cana
$344
Find similar
Delta
Feb 19
PUJ5:11 pmPunta Cana
17h 43m
1 stop
MDW8:54 amChicago Midway
Feb 22
MDW6:45 pmChicago Midway
17h 45m
1 stop
PUJ2:30 pmPunta Cana
$368
Find similar
Delta
Nov 24
PUJ3:50 pmPunta Cana
9h 50m
1 stop
MDW11:40 pmChicago Midway
Dec 1
MDW6:00 amChicago Midway
6h 25m
1 stop
PUJ2:25 pmPunta Cana
$375
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 octubre 30, 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

mié. 12/24

6:08 pm-5:38 pm

2 stops25h 30m

Chicago Midway

mié. 12/31

6:12 am-10:27 am

1 stop26h 15m

$306

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

mié. 12/31

4:19 pm-10:12 pm

1 stop7h 53m

Chicago Midway

mié. 1/7

3:52 pm-4:31 pm

1 stop22h 39m

$309

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

jue. 12/4

9:38 am-9:53 pm

1 stop14h 15m

Chicago Midway

jue. 12/11

2:16 pm-7:54 pm

1 stop27h 38m

$317

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

mié. 12/31

4:19 pm-10:12 pm

1 stop7h 53m

Chicago Midway

mié. 1/7

6:00 am-12:16 pm

2 stops28h 16m

$321

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

vie. 12/5

3:50 pm-11:47 pm

1 stop9h 57m

Chicago Midway

vie. 12/12

6:00 am-3:39 pm

1 stop7h 39m

$344

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

jue. 2/19

5:11 pm-8:54 am

1 stop17h 43m

Chicago Midway

dom. 2/22

6:45 pm-2:30 pm

1 stop17h 45m

$368

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

mié. 12/24

4:19 pm-5:38 pm

1 stop27h 19m

Chicago Midway

mié. 12/31

8:15 am-10:27 am

1 stop24h 12m

$370

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

sáb. 11/22

3:20 pm-6:20 pm

Nonstop5h 00m

Chicago Midway

sáb. 11/29

8:30 am-2:50 pm

Nonstop4h 20m

$379

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

sáb. 11/22

3:20 pm-6:20 pm

Nonstop5h 00m

Chicago Midway

sáb. 11/29

5:25 am-3:30 pm

1 stop8h 05m

$384

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

lun. 12/22

3:39 pm-1:59 pm

2 stops24h 20m

Chicago Midway

lun. 12/29

8:15 am-10:27 am

1 stop24h 12m

$400

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 55m

Direct flights

Every day
The fastest flight from Punta Cana to Chicago Midway Airport takes 4h 55m
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 5h 00m 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
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 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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1 adult
sáb. 11/29
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