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Cheap flights from Punta Cana to Chicago from $198

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 4/18. 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

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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
9:38 am - 7:31 pm
PUJ
-
MDW
10h 53m
2 stops
Multiple Airlines Logo
7:30 am - 4:19 pm
MDW
-
PUJ
7h 49m
1 stop
$386Multiple Airlines
Tue, Apr 14 - Tue, Apr 21
Frontier Logo
3:35 pm - 11:12 am
PUJ
-
MDW
20h 37m
1 stop
Frontier Logo
6:00 am - 2:24 pm
MDW
-
PUJ
7h 24m
1 stop
$391Frontier
Wed, May 6 - Tue, May 12
Multiple Airlines Logo
9:38 am - 7:31 pm
PUJ
-
MDW
10h 53m
2 stops
Multiple Airlines Logo
7:30 am - 4:19 pm
MDW
-
PUJ
7h 49m
1 stop
$405Multiple Airlines
Tue, Apr 14 - Tue, Apr 21
Multiple Airlines Logo
9:38 am - 7:31 pm
PUJ
-
MDW
10h 53m
2 stops
Multiple Airlines Logo
7:30 am - 4:19 pm
MDW
-
PUJ
7h 49m
1 stop
$420Multiple Airlines
Tue, Apr 14 - Tue, Apr 21
Frontier Logo
9:13 pm - 10:19 pm
PUJ
-
MDW
26h 06m
2 stops
Frontier Logo
12:04 pm - 2:24 pm
MDW
-
PUJ
25h 20m
1 stop
$435Frontier
Wed, Apr 29 - Wed, May 6
Frontier Logo
1:37 pm - 10:14 pm
PUJ
-
MDW
9h 37m
2 stops
Frontier Logo
6:00 am - 2:24 pm
MDW
-
PUJ
7h 24m
1 stop
$442Frontier
Sat, May 2 - Tue, May 5
Multiple Airlines Logo
1:01 pm - 10:02 pm
PUJ
-
MDW
10h 01m
2 stops
Multiple Airlines Logo
6:00 am - 2:24 pm
MDW
-
PUJ
7h 24m
1 stop
$444Multiple Airlines
Wed, May 6 - Tue, May 12
Frontier Logo
1:37 pm - 10:14 pm
PUJ
-
MDW
9h 37m
2 stops
Frontier Logo
6:00 am - 2:24 pm
MDW
-
PUJ
7h 24m
1 stop
$445Frontier
Sat, May 2 - Wed, May 6
Frontier Logo
9:13 pm - 10:26 pm
PUJ
-
MDW
26h 13m
2 stops
Frontier Logo
2:15 pm - 1:54 pm
MDW
-
PUJ
22h 39m
1 stop
$465Frontier
Thu, Apr 23 - Fri, May 1
Frontier Logo
1:37 pm - 10:26 pm
PUJ
-
MDW
9h 49m
2 stops
Frontier Logo
6:00 am - 2:24 pm
MDW
-
PUJ
7h 24m
1 stop
$466Frontier
Fri, May 1 - Fri, May 8

Frontier flights from Punta Cana to Chicago Midway Airport

Our best Frontier deals on Punta Cana to Chicago Midway Airport flight tickets
Frontier
Apr 18
PUJ11:07 amPunta Cana
21h 52m
1 stop
MDW7:59 amChicago Midway
Apr 25
MDW6:00 amChicago Midway
6h 54m
1 stop
PUJ1:54 pmPunta Cana
$383
Frontier
May 6
PUJ3:35 pmPunta Cana
20h 37m
1 stop
MDW11:12 amChicago Midway
May 12
MDW6:00 amChicago Midway
7h 24m
1 stop
PUJ2:24 pmPunta Cana
$391
Frontier
Apr 29
PUJ9:13 pmPunta Cana
26h 06m
2 stops
MDW10:19 pmChicago Midway
May 6
MDW12:04 pmChicago Midway
25h 20m
1 stop
PUJ2:24 pmPunta Cana
$435

Delta flights from Punta Cana to Chicago Midway Airport

Our best Delta deals on Punta Cana to Chicago Midway Airport flight tickets
Delta
May 6
PUJ3:57 pmPunta Cana
21h 45m
2 stops
MDW12:42 pmChicago Midway
May 12
MDW6:36 pmChicago Midway
16h 47m
2 stops
PUJ12:23 pmPunta Cana
$486
Delta
Aug 4
PUJ2:50 pmPunta Cana
7h 55m
1 stop
MDW9:45 pmChicago Midway
Aug 22
MDW6:00 amChicago Midway
6h 27m
1 stop
PUJ1:27 pmPunta Cana
$666
Delta
Apr 29
PUJ3:57 pmPunta Cana
7h 31m
1 stop
MDW10:28 pmChicago Midway
May 6
MDW6:00 amChicago Midway
7h 32m
1 stop
PUJ2:32 pmPunta Cana
$675

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 March 19, 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

Tue 4/14

9:38 am-7:31 pm

2 stops10h 53m

Chicago Midway

Tue 4/21

7:30 am-4:19 pm

1 stop7h 49m

$386

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 5/6

3:35 pm-11:12 am

1 stop20h 37m

Chicago Midway

Tue 5/12

6:00 am-2:24 pm

1 stop7h 24m

$391

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Tue 4/14

9:38 am-7:31 pm

2 stops10h 53m

Chicago Midway

Tue 4/21

7:30 am-4:19 pm

1 stop7h 49m

$405

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Tue 4/14

9:38 am-7:31 pm

2 stops10h 53m

Chicago Midway

Tue 4/21

7:30 am-4:19 pm

1 stop7h 49m

$420

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 4/29

9:13 pm-10:19 pm

2 stops26h 06m

Chicago Midway

Wed 5/6

12:04 pm-2:24 pm

1 stop25h 20m

$435
Quickest round-trip

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 5/2

1:37 pm-10:14 pm

2 stops9h 37m

Chicago Midway

Tue 5/5

6:00 am-2:24 pm

1 stop7h 24m

$442

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 5/6

1:01 pm-10:02 pm

2 stops10h 01m

Chicago Midway

Tue 5/12

6:00 am-2:24 pm

1 stop7h 24m

$444

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 5/2

1:37 pm-10:14 pm

2 stops9h 37m

Chicago Midway

Wed 5/6

6:00 am-2:24 pm

1 stop7h 24m

$445

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 4/23

9:13 pm-10:26 pm

2 stops26h 13m

Chicago Midway

Fri 5/1

2:15 pm-1:54 pm

1 stop22h 39m

$465

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 5/1

1:37 pm-10:26 pm

2 stops9h 49m

Chicago Midway

Fri 5/8

6:00 am-2:24 pm

1 stop7h 24m

$466

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 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

5h 00m

Direct flights

Tue, Thu, Fri, Sat and Sun
The fastest flight from Punta Cana to Chicago Midway Airport takes 5h 00m
Direct flights go from Punta Cana to Chicago Midway Airport on Tuesday, Thursday, Friday, Saturday 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
Portage
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.

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