Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Punta Cana to Chicago from $230

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 8/22. 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
1 adult, Economy, 0 bags

Find the cheapest flights from Punta Cana to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
3:31 pm - 9:51 am
PUJ
-
MDW
19h 20m
1 stop
Frontier Logo
6:05 am - 2:21 pm
MDW
-
PUJ
7h 16m
1 stop
$481Frontier
Wed, Aug 5 - Wed, Aug 12
Frontier Logo
3:31 pm - 9:51 am
PUJ
-
MDW
19h 20m
1 stop
Frontier Logo
6:05 am - 2:21 pm
MDW
-
PUJ
7h 16m
1 stop
$539Frontier
Tue, Aug 4 - Tue, Aug 11
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
$549Frontier
Wed, Jul 22 - Sun, Jul 26
Frontier Logo
9:29 pm - 9:51 am
PUJ
-
MDW
37h 22m
2 stops
Frontier Logo
6:05 am - 2:21 pm
MDW
-
PUJ
7h 16m
1 stop
$551Frontier
Wed, Aug 5 - Wed, Aug 12
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
$565Frontier
Thu, Jul 16 - Tue, Jul 21
Frontier Logo
9:29 pm - 9:51 am
PUJ
-
MDW
37h 22m
2 stops
Frontier Logo
6:05 am - 2:21 pm
MDW
-
PUJ
7h 16m
1 stop
$568Frontier
Wed, Aug 5 - Wed, Aug 12
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
$569Frontier
Sat, Jul 18 - Mon, Jul 27
Frontier Logo
3:31 pm - 9:51 am
PUJ
-
MDW
19h 20m
1 stop
Frontier Logo
6:05 am - 8:19 pm
MDW
-
PUJ
13h 14m
2 stops
$570Frontier
Tue, Aug 4 - Tue, Aug 11
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
$576Frontier
Wed, Jul 22 - Sun, Jul 26
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
$589Frontier
Thu, Jul 16 - Tue, Jul 21

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Frontier flights from Punta Cana to Chicago Midway Airport

Our best Frontier deals on Punta Cana to Chicago Midway Airport flight tickets
Frontier
Aug 5
PUJ3:31 pmPunta Cana
19h 20m
1 stop
MDW9:51 amChicago Midway
Aug 12
MDW6:05 amChicago Midway
7h 16m
1 stop
PUJ2:21 pmPunta Cana
$481
Frontier
Aug 4
PUJ3:31 pmPunta Cana
19h 20m
1 stop
MDW9:51 amChicago Midway
Aug 11
MDW6:05 amChicago Midway
7h 16m
1 stop
PUJ2:21 pmPunta Cana
$539
Frontier
Jul 22
PUJ3:31 pmPunta Cana
20h 36m
1 stop
MDW11:07 amChicago Midway
Jul 26
MDW6:05 amChicago Midway
7h 16m
1 stop
PUJ2:21 pmPunta Cana
$549

Southwest flights from Punta Cana to Chicago Midway Airport

Our best Southwest deals on Punta Cana to Chicago Midway Airport flight tickets
Southwest
Jul 18
PUJ11:50 amPunta Cana
8h 30m
1 stop
MDW7:20 pmChicago Midway
Jul 27
MDW8:55 pmChicago Midway
16h 35m
2 stops
PUJ2:30 pmPunta Cana
$662
Southwest
Jul 18
PUJ11:50 amPunta Cana
12h 55m
2 stops
MDW11:45 pmChicago Midway
Jul 27
MDW8:55 pmChicago Midway
16h 35m
2 stops
PUJ2:30 pmPunta Cana
$719
Southwest
Jul 22
PUJ2:35 pmPunta Cana
4h 40m
MDW6:15 pmChicago Midway
Jul 26
MDW5:05 amChicago Midway
9h 55m
1 stop
PUJ4:00 pmPunta Cana
$728

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 June 24, 2026.
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

Cheapest round-trip

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 8/5

3:31 pm-9:51 am

1 stop19h 20m

Chicago Midway

Wed 8/12

6:05 am-2:21 pm

1 stop7h 16m

$481

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Tue 8/4

3:31 pm-9:51 am

1 stop19h 20m

Chicago Midway

Tue 8/11

6:05 am-2:21 pm

1 stop7h 16m

$539

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 7/22

3:31 pm-11:07 am

1 stop20h 36m

Chicago Midway

Sun 7/26

6:05 am-2:21 pm

1 stop7h 16m

$549

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 8/5

9:29 pm-9:51 am

2 stops37h 22m

Chicago Midway

Wed 8/12

6:05 am-2:21 pm

1 stop7h 16m

$551
Quickest round-trip

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 7/16

11:46 am-10:03 pm

2 stops11h 17m

Chicago Midway

Tue 7/21

6:05 am-2:21 pm

1 stop7h 16m

$565

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 8/5

9:29 pm-9:51 am

2 stops37h 22m

Chicago Midway

Wed 8/12

6:05 am-2:21 pm

1 stop7h 16m

$568

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 7/18

3:31 pm-11:07 am

1 stop20h 36m

Chicago Midway

Mon 7/27

6:05 am-2:21 pm

1 stop7h 16m

$569

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Tue 8/4

3:31 pm-9:51 am

1 stop19h 20m

Chicago Midway

Tue 8/11

6:05 am-8:19 pm

2 stops13h 14m

$570

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 7/22

11:46 am-10:03 pm

2 stops11h 17m

Chicago Midway

Sun 7/26

6:05 am-2:21 pm

1 stop7h 16m

$576

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 7/16

3:31 pm-11:07 am

1 stop20h 36m

Chicago Midway

Tue 7/21

6:05 am-2:21 pm

1 stop7h 16m

$589

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 Airport flights?

There is only 1 cabin class available to choose from on Punta Cana 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 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

7h 32m

Direct flights

Every day
The fastest flight from Punta Cana to Chicago Midway Airport takes 7h 32m
Direct flights go from Punta Cana to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from Punta Cana to Chicago Midway Airport

  • 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 32m 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
Portage
Benton Harbor
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Crown Point
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.

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Fri 7/24
Fri 7/31
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago