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Cheap flights from Punta Cana to Chicago from $136

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 2/20. 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

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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.
Spirit Airlines Logo
5:47 pm - 11:47 pm
PUJ
-
ORD
8h 00m
1 stop
Spirit Airlines Logo
7:00 am - 4:36 pm
ORD
-
PUJ
7h 36m
1 stop
$242Spirit Airlines
Wed, Feb 18 - Wed, Feb 25
Spirit Airlines Logo
5:47 pm - 11:47 pm
PUJ
-
ORD
8h 00m
1 stop
Spirit Airlines Logo
5:15 am - 4:36 pm
ORD
-
PUJ
9h 21m
1 stop
$243Spirit Airlines
Tue, Mar 3 - Wed, Mar 4
Spirit Airlines Logo
5:47 pm - 11:47 pm
PUJ
-
ORD
8h 00m
1 stop
Spirit Airlines Logo
5:15 am - 4:36 pm
ORD
-
PUJ
9h 21m
1 stop
$245Spirit Airlines
Fri, Feb 20 - Sun, Feb 22
United Airlines Logo
1:50 pm - 5:59 pm
PUJ
-
ORD
5h 09mnonstop
United Airlines Logo
8:45 am - 2:27 pm
ORD
-
PUJ
4h 42mnonstop
$272United Airlines
Thu, Apr 16 - Tue, Apr 21
United Airlines Logo
2:20 pm - 12:45 am
PUJ
-
ORD
11h 25m
1 stop
United Airlines Logo
4:20 pm - 4:30 pm
ORD
-
PUJ
23h 10m
1 stop
$277United Airlines
Thu, Apr 16 - Tue, Apr 21
Multiple Airlines Logo
7:17 am - 10:27 am
PUJ
-
ORD
5h 10mnonstop
Multiple Airlines Logo
7:00 am - 4:36 pm
ORD
-
PUJ
7h 36m
1 stop
$284Multiple Airlines
Sat, Feb 14 - Sun, Feb 15
Southwest Logo
2:40 pm - 9:00 pm
PUJ
-
MDW
8h 20m
1 stop
Southwest Logo
5:00 am - 2:30 pm
MDW
-
PUJ
7h 30m
1 stop
$720Southwest
Tue, Mar 3 - Wed, Mar 4
Southwest Logo
2:40 pm - 10:05 pm
PUJ
-
MDW
9h 25m
2 stops
Southwest Logo
5:00 am - 2:30 pm
MDW
-
PUJ
7h 30m
1 stop
$725Southwest
Tue, Mar 3 - Wed, Mar 4
Multiple Airlines Logo
3:22 pm - 10:09 pm
PUJ
-
MDW
7h 47m
1 stop
Multiple Airlines Logo
9:16 pm - 6:38 pm
MDW
-
PUJ
20h 22m
2 stops
$740Multiple Airlines
Sat, Mar 21 - Sat, Mar 28
Frontier Logo
12:34 pm - 10:09 pm
PUJ
-
MDW
10h 35m
2 stops
Frontier Logo
9:16 pm - 2:17 pm
MDW
-
PUJ
16h 01m
2 stops
$952Frontier
Sat, Mar 21 - Sat, Mar 28

Spirit Airlines flights from Punta Cana to Chicago

Our best Spirit Airlines deals on Punta Cana to Chicago flight tickets
Spirit Airlines
Feb 18
PUJ5:47 pmPunta Cana
8h 00m
1 stop
ORD11:47 pmChicago O'Hare Intl
Feb 25
ORD7:00 amChicago O'Hare Intl
7h 36m
1 stop
PUJ4:36 pmPunta Cana
$242
Spirit Airlines
Mar 3
PUJ5:47 pmPunta Cana
8h 00m
1 stop
ORD11:47 pmChicago O'Hare Intl
Mar 4
ORD5:15 amChicago O'Hare Intl
9h 21m
1 stop
PUJ4:36 pmPunta Cana
$243
Spirit Airlines
Feb 20
PUJ5:47 pmPunta Cana
8h 00m
1 stop
ORD11:47 pmChicago O'Hare Intl
Feb 22
ORD5:15 amChicago O'Hare Intl
9h 21m
1 stop
PUJ4:36 pmPunta Cana
$245

United Airlines flights from Punta Cana to Chicago

Our best United Airlines deals on Punta Cana to Chicago flight tickets
United Airlines
Apr 16
PUJ1:50 pmPunta Cana
5h 09m
ORD5:59 pmChicago O'Hare Intl
Apr 21
ORD8:45 amChicago O'Hare Intl
6h 45m
1 stop
PUJ4:30 pmPunta Cana
$272
United Airlines
Apr 16
PUJ2:20 pmPunta Cana
11h 25m
1 stop
ORD12:45 amChicago O'Hare Intl
Apr 21
ORD4:20 pmChicago O'Hare Intl
23h 10m
1 stop
PUJ4:30 pmPunta Cana
$277
United Airlines
Mar 5
PUJ5:20 pmPunta Cana
16h 30m
1 stop
ORD7:50 amChicago O'Hare Intl
Mar 8
ORD9:15 pmChicago O'Hare Intl
18h 10m
1 stop
PUJ4:25 pmPunta Cana
$341

momondo Fare Finder

 
Customize your flight search to find flights from Punta Cana to Chicago 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 February 3, 2026.
Use the filters below to find and compare flights from Punta Cana to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 2/18

5:47 pm-11:47 pm

1 stop8h 00m

Chicago O'Hare Intl

Wed 2/25

7:00 am-4:36 pm

1 stop7h 36m

$242

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Tue 3/3

5:47 pm-11:47 pm

1 stop8h 00m

Chicago O'Hare Intl

Wed 3/4

5:15 am-4:36 pm

1 stop9h 21m

$243

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Fri 2/20

5:47 pm-11:47 pm

1 stop8h 00m

Chicago O'Hare Intl

Sun 2/22

5:15 am-4:36 pm

1 stop9h 21m

$245

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 4/16

1:50 pm-5:59 pm

Nonstop5h 09m

Chicago O'Hare Intl

Tue 4/21

8:45 am-2:27 pm

Nonstop4h 42m

$272

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 4/16

2:20 pm-12:45 am

1 stop11h 25m

Chicago O'Hare Intl

Tue 4/21

4:20 pm-4:30 pm

1 stop23h 10m

$277

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 2/14

7:17 am-10:27 am

Nonstop5h 10m

Chicago O'Hare Intl

Sun 2/15

7:00 am-4:36 pm

1 stop7h 36m

$284

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Tue 3/3

2:40 pm-9:00 pm

1 stop8h 20m

Chicago Midway

Wed 3/4

5:00 am-2:30 pm

1 stop7h 30m

$720

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Tue 3/3

2:40 pm-10:05 pm

2 stops9h 25m

Chicago Midway

Wed 3/4

5:00 am-2:30 pm

1 stop7h 30m

$725

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 3/21

3:22 pm-10:09 pm

1 stop7h 47m

Chicago Midway

Sat 3/28

9:16 pm-6:38 pm

2 stops20h 22m

$740

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 3/21

12:34 pm-10:09 pm

2 stops10h 35m

Chicago Midway

Sat 3/28

9:16 pm-2:17 pm

2 stops16h 01m

$952

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

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 month to fly to Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from Punta Cana, with most prices found around $270. If you’re not able to fly to Chicago in February, then May is your next best option. Flight prices from Punta Cana to Chicago during May average around $299.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $345. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Punta Cana to Chicago for around $521.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Punta Cana to Chicago during this time can be as low as $258. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $421.

What is the cheapest Punta Cana to Chicago flight route?

Fly from Punta Cana to Chicago O'Hare Intl for the best Punta Cana - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Punta Cana when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $442 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Punta Cana for as low as $276 on momondo.

What cabin class options are available on Punta Cana to Chicago flights?

There are 3 cabin classes available to choose from on Punta Cana to Chicago 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 flights?

No. A direct flight is the cheapest option for a flight between Punta Cana to Chicago.

How have Punta Cana to Chicago flight prices changed over time?

As of February 2026, prices for Punta Cana to Chicago flights are approximately 5% more expensive when compared to flights at the same time last year.

When to book flights from Punta Cana to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Punta Cana to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Punta Cana to Chicago (PUJ to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Punta Cana to Chicago

Best Price Found

$180

Fastest flight time

4h 55m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Punta Cana in the past 72 hours is $180. The best round-trip flight deal from Punta Cana to Chicago found on momondo in the last 72 hours is $236.
The fastest flight from Punta Cana to Chicago takes 4h 55m
Direct flights go from Punta Cana to Chicago every day.
There are 3 airports in Chicago. From Punta Cana there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).
Search flight deals

  • How far is Punta Cana to Chicago by plane?

    A flight from Punta Cana to Chicago will travel around 1958.2 mi. Flights usually cover this in 4h 55m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Punta Cana Airport to Chicago?

    Prices for flights from Punta Cana Airport to Chicago are updated daily.

  • How many operators does momondo search for flights from Punta Cana Airport to Chicago?

  • How old do you have to be to fly from Punta Cana Airport to Chicago?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Punta Cana Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Punta Cana to Chicago?

  • What is the most popular airline from Punta Cana to Chicago?

Best airlines flying from Punta Cana to Chicago

Compare and see reviews for airlines that fly from Punta Cana to Chicago with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $181Free CancellationRating
5.7
3,051 reviews
Search Frontier flights
American AirlinesPriceFrom $354Free CancellationRating
7.2
11,212 reviews
Search American Airlines flights

  • American Airlines Flights From Punta Cana to Chicago

    Across 11 American Airlines flights from Punta Cana to Chicago this week, the average price was $507, with the best American Airlines deals starting from $354 round-trip. 11,212 users have rated American Airlines on momondo, with an average score of 7.2/10.

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
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?

Finding the right flight to Chicago from Punta Cana is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Punta Cana to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Punta Cana to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Punta Cana to Chicago?

momondo helps you find the best flight between Punta Cana and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Punta Cana to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Punta Cana to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport