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Cheap flights from Punta Cana to Chicago from $191

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 9/13. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Punta Cana to Chicago

Cheap round-trip flights

Delta Logo
2:40 pm - 9:26 pmPUJ-MDW
7h 46m1 stop
Delta Logo
6:00 am - 2:32 pmMDW-PUJ
7h 32m1 stop
$350Delta
Find Deal
Fri, Sep 5 - Sun, Sep 14
Delta Logo
3:59 pm - 8:40 amPUJ-MDW
17h 41m2 stops
Delta Logo
10:35 am - 12:32 pmMDW-PUJ
24h 57m2 stops
$351Delta
Find Deal
Wed, Sep 24 - Sun, Oct 26
Delta Logo
3:59 pm - 8:40 amPUJ-MDW
17h 41m2 stops
Delta Logo
10:35 am - 12:28 pmMDW-PUJ
24h 53m2 stops
$361Delta
Find Deal
Wed, Sep 24 - Wed, Oct 22
Southwest Logo
3:05 pm - 9:35 pmPUJ-MDW
7h 30m1 stop
Southwest Logo
7:05 am - 2:30 pmMDW-PUJ
6h 25m1 stop
$399Southwest
Find Deal
Thu, Sep 25 - Fri, Oct 24
Frontier Logo
3:25 pm - 1:47 pmPUJ-MDW
23h 22m1 stop
Frontier Logo
8:00 am - 2:23 pmMDW-PUJ
29h 23m1 stop
$408Frontier
Find Deal
Wed, Aug 13 - Wed, Aug 20
Frontier Logo
11:20 am - 11:51 pmPUJ-MDW
13h 31m1 stop
Frontier Logo
10:58 am - 2:19 pmMDW-PUJ
26h 21m1 stop
$443Frontier
Find Deal
Fri, Aug 15 - Fri, Aug 22
Southwest Logo
3:05 pm - 8:05 amPUJ-MDW
18h 00m2 stops
Southwest Logo
7:05 am - 2:30 pmMDW-PUJ
6h 25m1 stop
$458Southwest
Find Deal
Thu, Sep 25 - Fri, Oct 24
Logo
3:05 pm - 4:24 pmPUJ-MDW
26h 19m2 stops
Logo
9:35 am - 1:45 pmMDW-PUJ
27h 10m2 stops
$593
Find Deal
Tue, Sep 9 - Mon, Sep 15
WestJet Logo
12:25 pm - 1:03 pmPUJ-MDW
25h 38m2 stops
WestJet Logo
1:43 pm - 11:29 amMDW-PUJ
20h 46m2 stops
$3,583WestJet
Find Deal
Tue, Sep 16 - Tue, Sep 23
WestJet Logo
7:20 am - 6:07 pmPUJ-MDW
36h 47m2 stops
WestJet Logo
11:48 am - 3:35 pmMDW-PUJ
25h 47m2 stops
$3,650WestJet
Find Deal
Mon, Dec 15 - Wed, Dec 31

Delta flights from Punta Cana to Chicago Midway Airport

Our best Delta deals on Punta Cana to Chicago Midway Airport flight tickets
Delta
Sep 5
PUJ2:40 pmPunta Cana
7h 46m
1 stop
MDW9:26 pmChicago Midway
Sep 14
MDW6:00 amChicago Midway
7h 32m
1 stop
PUJ2:32 pmPunta Cana
$350
Find similar
Delta
Sep 24
PUJ3:59 pmPunta Cana
17h 41m
2 stops
MDW8:40 amChicago Midway
Oct 26
MDW10:35 amChicago Midway
24h 57m
2 stops
PUJ12:32 pmPunta Cana
$351
Find similar
Delta
Sep 24
PUJ3:59 pmPunta Cana
17h 41m
2 stops
MDW8:40 amChicago Midway
Oct 22
MDW10:35 amChicago Midway
24h 53m
2 stops
PUJ12:28 pmPunta Cana
$361
Find similar

Southwest flights from Punta Cana to Chicago Midway Airport

Our best Southwest deals on Punta Cana to Chicago Midway Airport flight tickets
Southwest
Sep 25
PUJ3:05 pmPunta Cana
7h 30m
1 stop
MDW9:35 pmChicago Midway
Oct 24
MDW7:05 amChicago Midway
6h 25m
1 stop
PUJ2:30 pmPunta Cana
$399
Find similar
Southwest
Sep 25
PUJ3:05 pmPunta Cana
18h 00m
2 stops
MDW8:05 amChicago Midway
Oct 24
MDW7:05 amChicago Midway
6h 25m
1 stop
PUJ2:30 pmPunta Cana
$458
Find similar
Southwest
Aug 21
PUJ2:50 pmPunta Cana
17h 20m
2 stops
MDW7:10 amChicago Midway
Aug 29
MDW8:35 pmChicago Midway
16h 10m
2 stops
PUJ1:45 pmPunta Cana
$753
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 August 2, 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 9/5

2:40 pm-9:26 pm

1 stop7h 46m

Chicago Midway

Sun 9/14

6:00 am-2:32 pm

1 stop7h 32m

$350

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 9/24

3:59 pm-8:40 am

2 stops17h 41m

Chicago Midway

Sun 10/26

10:35 am-12:32 pm

2 stops24h 57m

$351

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 9/24

3:59 pm-8:40 am

2 stops17h 41m

Chicago Midway

Wed 10/22

10:35 am-12:28 pm

2 stops24h 53m

$361

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 9/25

3:05 pm-9:35 pm

1 stop7h 30m

Chicago Midway

Fri 10/24

7:05 am-2:30 pm

1 stop6h 25m

$399

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 8/13

3:25 pm-1:47 pm

1 stop23h 22m

Chicago Midway

Wed 8/20

8:00 am-2:23 pm

1 stop29h 23m

$408

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 8/15

11:20 am-11:51 pm

1 stop13h 31m

Chicago Midway

Fri 8/22

10:58 am-2:19 pm

1 stop26h 21m

$443

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 9/25

3:05 pm-8:05 am

2 stops18h 00m

Chicago Midway

Fri 10/24

7:05 am-2:30 pm

1 stop6h 25m

$458

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Tue 9/9

3:05 pm-4:24 pm

2 stops26h 19m

Chicago Midway

Mon 9/15

9:35 am-1:45 pm

2 stops27h 10m

$593

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Tue 9/16

12:25 pm-1:03 pm

2 stops25h 38m

Chicago Midway

Tue 9/23

1:43 pm-11:29 am

2 stops20h 46m

$3,583

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Mon 12/15

7:20 am-6:07 pm

2 stops36h 47m

Chicago Midway

Wed 12/31

11:48 am-3:35 pm

2 stops25h 47m

$3,650

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 are 1 cabin classes 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

Best Price Found

$191

Fastest flight time

7h 18m

Direct flights

Sun
The best one-way flight to Chicago Midway Airport from Punta Cana in the past 72 hours is $191. The best round-trip flight deal from Punta Cana to Chicago Midway Airport found on momondo in the last 72 hours is $350.
The fastest flight from Punta Cana to Chicago Midway Airport takes 7h 18m
Direct flights go from Punta Cana to Chicago Midway Airport on Sunday. The only airline offering direct flights is Southwest.
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 7h 30m 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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