Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Punta Cana to Chicago from $175

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 10/19. 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

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

Find the cheapest flights from Punta Cana to Chicago

Cheap round-trip flights

Multiple Airlines Logo
9:38 am - 11:27 amPUJ-MDW
26h 49m1 stop
Multiple Airlines Logo
5:28 pm - 11:42 amMDW-PUJ
17h 14m1 stop
$341Multiple Airlines
Find Deal
Thu, Oct 9 - Mon, Oct 20
Southwest Logo
1:40 pm - 10:35 pmPUJ-MDW
9h 55m1 stop
Southwest Logo
5:00 am - 2:30 pmMDW-PUJ
8h 30m1 stop
$386Southwest
Find Deal
Wed, Oct 8 - Mon, Oct 13
Southwest Logo
2:45 pm - 11:55 pmPUJ-MDW
10h 10m2 stops
Southwest Logo
7:05 am - 2:30 pmMDW-PUJ
6h 25m1 stop
$391Southwest
Find Deal
Fri, Oct 10 - Mon, Oct 13
Delta Logo
5:11 pm - 8:54 amPUJ-MDW
17h 43m1 stop
Delta Logo
6:45 pm - 2:30 pmMDW-PUJ
17h 45m1 stop
$396Delta
Find Deal
Thu, Feb 19 - Sun, Feb 22
Multiple Airlines Logo
9:38 am - 11:27 amPUJ-MDW
26h 49m1 stop
Multiple Airlines Logo
10:33 am - 10:50 amMDW-PUJ
23h 17m2 stops
$406Multiple Airlines
Find Deal
Thu, Oct 9 - Mon, Oct 20
Delta Logo
6:05 pm - 9:56 amPUJ-MDW
17h 51m1 stop
Delta Logo
6:45 pm - 2:30 pmMDW-PUJ
17h 45m1 stop
$455Delta
Find Deal
Thu, Feb 19 - Sun, Feb 22
Frontier Logo
12:40 pm - 11:05 pmPUJ-MDW
12h 25m1 stop
Frontier Logo
6:00 am - 3:24 pmMDW-PUJ
7h 24m1 stop
$629Frontier
Find Deal
Thu, Jan 1 - Sat, Jan 10
Frontier Logo
12:40 pm - 11:05 pmPUJ-MDW
12h 25m1 stop
Frontier Logo
6:00 am - 3:24 pmMDW-PUJ
7h 24m1 stop
$697Frontier
Find Deal
Thu, Jan 1 - Sun, Jan 11
WestJet Logo
4:30 pm - 1:08 pmPUJ-MDW
22h 38m2 stops
WestJet Logo
2:00 pm - 1:30 pmMDW-PUJ
21h 30m2 stops
$3,716WestJet
Find Deal
Thu, Feb 26 - Tue, Mar 3
WestJet Logo
4:30 pm - 11:57 amPUJ-MDW
21h 27m2 stops
WestJet Logo
10:35 am - 1:35 pmMDW-PUJ
25h 00m2 stops
$4,258WestJet
Find Deal
Thu, Jan 1 - Sat, Jan 10

Frontier flights from Punta Cana to Chicago Midway Airport

Our best Frontier deals on Punta Cana to Chicago Midway Airport flight tickets
Frontier
Jan 1
PUJ12:40 pmPunta Cana
12h 25m
1 stop
MDW11:05 pmChicago Midway
Jan 10
MDW6:00 amChicago Midway
7h 24m
1 stop
PUJ3:24 pmPunta Cana
$629
Find similar
Frontier
Jan 1
PUJ12:40 pmPunta Cana
12h 25m
1 stop
MDW11:05 pmChicago Midway
Jan 11
MDW6:00 amChicago Midway
7h 24m
1 stop
PUJ3:24 pmPunta Cana
$697
Find similar
Frontier
Jan 1
PUJ12:40 pmPunta Cana
12h 25m
1 stop
MDW11:05 pmChicago Midway
Jan 11
MDW6:00 amChicago Midway
12h 15m
2 stops
PUJ8:15 pmPunta Cana
$760
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
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
$396
Find similar
Delta
Feb 19
PUJ6:05 pmPunta Cana
17h 51m
1 stop
MDW9:56 amChicago Midway
Feb 22
MDW6:45 pmChicago Midway
17h 45m
1 stop
PUJ2:30 pmPunta Cana
$455
Find similar
Delta
Sep 17
PUJ2:45 pmPunta Cana
7h 51m
1 stop
MDW9:36 pmChicago Midway
Sep 22
MDW6:00 amChicago Midway
6h 20m
1 stop
PUJ1:20 pmPunta Cana
$561
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 September 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

Thu 10/9

9:38 am-11:27 am

1 stop26h 49m

Chicago Midway

Mon 10/20

5:28 pm-11:42 am

1 stop17h 14m

$341

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 10/8

1:40 pm-10:35 pm

1 stop9h 55m

Chicago Midway

Mon 10/13

5:00 am-2:30 pm

1 stop8h 30m

$386

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 10/10

2:45 pm-11:55 pm

2 stops10h 10m

Chicago Midway

Mon 10/13

7:05 am-2:30 pm

1 stop6h 25m

$391

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 2/19

5:11 pm-8:54 am

1 stop17h 43m

Chicago Midway

Sun 2/22

6:45 pm-2:30 pm

1 stop17h 45m

$396

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 10/9

9:38 am-11:27 am

1 stop26h 49m

Chicago Midway

Mon 10/20

10:33 am-10:50 am

2 stops23h 17m

$406

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 2/19

6:05 pm-9:56 am

1 stop17h 51m

Chicago Midway

Sun 2/22

6:45 pm-2:30 pm

1 stop17h 45m

$455

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 1/1

12:40 pm-11:05 pm

1 stop12h 25m

Chicago Midway

Sat 1/10

6:00 am-3:24 pm

1 stop7h 24m

$629

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 1/1

12:40 pm-11:05 pm

1 stop12h 25m

Chicago Midway

Sun 1/11

6:00 am-3:24 pm

1 stop7h 24m

$697

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 2/26

4:30 pm-1:08 pm

2 stops22h 38m

Chicago Midway

Tue 3/3

2:00 pm-1:30 pm

2 stops21h 30m

$3,716

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 1/1

4:30 pm-11:57 am

2 stops21h 27m

Chicago Midway

Sat 1/10

10:35 am-1:35 pm

2 stops25h 00m

$4,258

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 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

Mon, Tue and Sun
The fastest flight from Punta Cana to Chicago Midway Airport takes 4h 55m
Direct flights go from Punta Cana to Chicago Midway Airport on Monday, Tuesday and Sunday. There are no airlines offering direct flights.
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
Lansing
Portage
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.

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
Thu 10/16
Thu 10/23
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago