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Cheap flights from Punta Cana to Chicago from $227

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 10/2. 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.
Delta Logo
3:50 pm - 10:56 pm-
9h 06m
Delta Logo
6:00 am - 4:42 pm-
8h 42m
$403Delta
Fri, Dec 18 - Mon, Jan 4
Delta Logo
3:50 pm - 10:56 pm-
9h 06m
Delta Logo
6:00 am - 3:30 pm-
7h 30m
$403Delta
Thu, Dec 17 - Mon, Jan 4
Delta Logo
4:45 pm - 10:10 pm-
7h 25m
Delta Logo
6:00 am - 3:30 pm-
7h 30m
$486Delta
Fri, Dec 25 - Mon, Jan 4
Delta Logo
4:45 pm - 10:10 pm-
7h 25m
Delta Logo
6:00 am - 3:30 pm-
7h 30m
$486Delta
Sat, Dec 19 - Mon, Jan 4
Frontier Logo
3:37 pm - 10:47 pm-
8h 10m
Frontier Logo
6:05 am - 2:27 pm-
7h 22m
$537Frontier
Sat, Aug 29 - Sat, Sep 5
Southwest Logo
4:10 pm - 7:15 pm-
5h 05mnonstop
Southwest Logo
5:05 am - 1:45 pm-
6h 40m
$556Southwest
Sat, Dec 19 - Mon, Jan 4
Southwest Logo
3:20 pm - 12:45 am-
11h 25m
Southwest Logo
5:05 am - 1:45 pm-
6h 40m
$566Southwest
Sat, Dec 19 - Mon, Jan 4
Multiple Airlines Logo
7:35 pm - 11:00 am-
16h 25m
Multiple Airlines Logo
3:20 pm - 5:10 pm-
24h 50m
$585Multiple Airlines
Thu, Sep 17 - Fri, Sep 25
JetBlue Logo
2:50 pm - 10:36 pm-
8h 46m
JetBlue Logo
6:05 am - 2:39 pm-
7h 34m
$590JetBlue
Thu, Aug 20 - Fri, Aug 28

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Southwest flights from Punta Cana to Chicago Midway Airport

Our best Southwest deals on Punta Cana to Chicago Midway Airport flight tickets
Southwest
Dec 19
PUJ4:10 pmPunta Cana
5h 05m
MDW7:15 pmChicago Midway
Jan 4
MDW5:05 amChicago Midway
6h 40m
1 stop
PUJ1:45 pmPunta Cana
$556
Southwest
Dec 19
PUJ3:20 pmPunta Cana
11h 25m
1 stop
MDW12:45 amChicago Midway
Jan 4
MDW5:05 amChicago Midway
6h 40m
1 stop
PUJ1:45 pmPunta Cana
$566
Southwest
Dec 19
PUJ3:20 pmPunta Cana
11h 25m
1 stop
MDW12:45 amChicago Midway
Jan 4
MDW8:25 pmChicago Midway
16h 15m
2 stops
PUJ2:40 pmPunta Cana
$596

Frontier flights from Punta Cana to Chicago Midway Airport

Our best Frontier deals on Punta Cana to Chicago Midway Airport flight tickets
Frontier
Aug 29
PUJ3:37 pmPunta Cana
8h 10m
1 stop
MDW10:47 pmChicago Midway
Sep 5
MDW6:05 amChicago Midway
7h 22m
1 stop
PUJ2:27 pmPunta Cana
$529
Frontier
Aug 29
PUJ3:37 pmPunta Cana
8h 10m
1 stop
MDW10:47 pmChicago Midway
Sep 5
MDW6:05 amChicago Midway
7h 22m
1 stop
PUJ2:27 pmPunta Cana
$541
Frontier
Aug 29
PUJ3:37 pmPunta Cana
8h 10m
1 stop
MDW10:47 pmChicago Midway
Sep 5
MDW6:05 amChicago Midway
7h 22m
1 stop
PUJ2:27 pmPunta Cana
$545

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 4, 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

Fri 12/18

3:50 pm-10:56 pm

1 stop9h 06m

Chicago Midway

Mon 1/4

6:00 am-4:42 pm

1 stop8h 42m

$403

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 12/17

3:50 pm-10:56 pm

1 stop9h 06m

Chicago Midway

Mon 1/4

6:00 am-3:30 pm

1 stop7h 30m

$403

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 12/25

4:45 pm-10:10 pm

1 stop7h 25m

Chicago Midway

Mon 1/4

6:00 am-3:30 pm

1 stop7h 30m

$486

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 12/19

4:45 pm-10:10 pm

1 stop7h 25m

Chicago Midway

Mon 1/4

6:00 am-3:30 pm

1 stop7h 30m

$486

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 8/29

3:37 pm-10:47 pm

1 stop8h 10m

Chicago Midway

Sat 9/5

6:05 am-2:27 pm

1 stop7h 22m

$537
Quickest round-trip

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 12/19

4:10 pm-7:15 pm

Nonstop5h 05m

Chicago Midway

Mon 1/4

5:05 am-1:45 pm

1 stop6h 40m

$556

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 12/19

3:20 pm-12:45 am

1 stop11h 25m

Chicago Midway

Mon 1/4

5:05 am-1:45 pm

1 stop6h 40m

$566

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 9/17

7:35 pm-11:00 am

2 stops16h 25m

Chicago Midway

Fri 9/25

3:20 pm-5:10 pm

1 stop24h 50m

$585

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 8/20

2:50 pm-10:36 pm

1 stop8h 46m

Chicago Midway

Fri 8/28

6:05 am-2:39 pm

1 stop7h 34m

$590
Cheapest one-way

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 10/2

2:08 pm-10:36 am

2 stops21h 28m

$227

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 18 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 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 25m

Direct flights

None
The fastest flight from Punta Cana to Chicago Midway Airport takes 7h 25m
There are no direct flights from Punta Cana to Chicago Midway Airport. Popular non-direct route for this connection is Punta Cana Airport - Chicago Midway Airport.
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 25m 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
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Valparaiso
Schererville
Munster
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Crown Point
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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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