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Cheap flights from Punta Cana to Chicago from $152

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 2/26. 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.
Arajet Logo
5:47 am - 9:57 am
PUJ
-
ORD
5h 10mnonstop
Arajet Logo
11:27 am - 5:12 pm
ORD
-
PUJ
4h 45mnonstop
$245Arajet
Sat, Apr 18 - Sat, Apr 25
United Airlines Logo
1:55 pm - 6:08 pm
PUJ
-
ORD
5h 13mnonstop
United Airlines Logo
9:05 pm - 3:14 pm
ORD
-
PUJ
17h 09m1 stop
$263United Airlines
Tue, Mar 17 - Tue, Mar 24
United Airlines Logo
4:25 pm - 7:38 pm
PUJ
-
ORD
5h 13mnonstop
United Airlines Logo
9:05 pm - 3:14 pm
ORD
-
PUJ
17h 09m1 stop
$265United Airlines
Wed, Mar 4 - Wed, Mar 11
Multiple Airlines Logo
5:47 pm - 11:46 pm
PUJ
-
ORD
7h 59m1 stop
Multiple Airlines Logo
5:45 am - 12:30 pm
ORD
-
PUJ
4h 45mnonstop
$270Multiple Airlines
Mon, Jan 26 - Mon, Feb 2
Spirit Airlines Logo
5:47 pm - 11:46 pm
PUJ
-
ORD
7h 59m1 stop
Spirit Airlines Logo
7:20 am - 4:36 pm
ORD
-
PUJ
7h 16m1 stop
$275Spirit Airlines
Fri, Jan 30 - Fri, Feb 6
Spirit Airlines Logo
5:47 pm - 11:46 pm
PUJ
-
ORD
7h 59m1 stop
Spirit Airlines Logo
5:15 am - 4:36 pm
ORD
-
PUJ
9h 21m1 stop
$278Spirit Airlines
Mon, Jan 26 - Mon, Feb 2
Multiple Airlines Logo
5:47 pm - 11:46 pm
PUJ
-
ORD
7h 59m1 stop
Multiple Airlines Logo
10:27 am - 5:12 pm
ORD
-
PUJ
4h 45mnonstop
$282Multiple Airlines
Sat, Jan 17 - Sat, Jan 24
Southwest Logo
2:40 pm - 9:00 pm
PUJ
-
MDW
8h 20m1 stop
Southwest Logo
5:00 am - 2:30 pm
MDW
-
PUJ
7h 30m1 stop
$292Southwest
Wed, Jan 21 - Wed, Jan 28
Frontier Logo
4:11 pm - 11:25 pm
PUJ
-
MDW
9h 14m1 stop
Frontier Logo
6:00 am - 2:56 pm
MDW
-
PUJ
6h 56m1 stop
$341Frontier
Sat, Feb 14 - Sat, Feb 21
Frontier Logo
4:19 pm - 5:38 pm
PUJ
-
MDW
27h 19m1 stop
Frontier Logo
6:12 am - 3:09 pm
MDW
-
PUJ
6h 57m1 stop
$345Frontier
Wed, Dec 24 - Wed, Dec 31

Arajet flights from Punta Cana to Chicago

Our best Arajet deals on Punta Cana to Chicago flight tickets
Arajet
Apr 18
PUJ5:47 amPunta Cana
5h 10m
ORD9:57 amChicago O'Hare Intl
Apr 25
ORD11:27 amChicago O'Hare Intl
4h 45m
PUJ5:12 pmPunta Cana
$245
Find similar
Arajet
Jan 17
PUJ5:47 amPunta Cana
5h 10m
ORD8:57 amChicago O'Hare Intl
Jan 24
ORD10:27 amChicago O'Hare Intl
4h 45m
PUJ5:12 pmPunta Cana
$268
Find similar
Arajet
Jan 31
PUJ5:47 amPunta Cana
5h 10m
ORD8:57 amChicago O'Hare Intl
Feb 7
ORD10:27 amChicago O'Hare Intl
4h 45m
PUJ5:12 pmPunta Cana
$287
Find similar

American Airlines flights from Punta Cana to Chicago

Our best American Airlines deals on Punta Cana to Chicago flight tickets
American Airlines
Mar 3
PUJ5:57 pmPunta Cana
16h 51m
1 stop
ORD8:48 amChicago O'Hare Intl
Mar 10
ORD9:59 amChicago O'Hare Intl
4h 31m
PUJ3:30 pmPunta Cana
$288
Find similar
American Airlines
Jan 13
PUJ6:07 pmPunta Cana
16h 58m
1 stop
ORD9:05 amChicago O'Hare Intl
Jan 20
ORD7:30 pmChicago O'Hare Intl
17h 25m
1 stop
PUJ2:55 pmPunta Cana
$292
Find similar
American Airlines
Jan 22
PUJ6:02 pmPunta Cana
8h 28m
1 stop
ORD12:30 amChicago O'Hare Intl
Jan 27
ORD4:14 pmChicago O'Hare Intl
17h 46m
1 stop
PUJ12:00 pmPunta Cana
$301
Find similar

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 December 8, 2025.
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

Sat 4/18

5:47 am-9:57 am

Nonstop5h 10m

Chicago O'Hare Intl

Sat 4/25

11:27 am-5:12 pm

Nonstop4h 45m

$245

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Tue 3/17

1:55 pm-6:08 pm

Nonstop5h 13m

Chicago O'Hare Intl

Tue 3/24

9:05 pm-3:14 pm

1 stop17h 09m

$263

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 3/4

4:25 pm-7:38 pm

Nonstop5h 13m

Chicago O'Hare Intl

Wed 3/11

9:05 pm-3:14 pm

1 stop17h 09m

$265

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Mon 1/26

5:47 pm-11:46 pm

1 stop7h 59m

Chicago O'Hare Intl

Mon 2/2

5:45 am-12:30 pm

Nonstop4h 45m

$270

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Fri 1/30

5:47 pm-11:46 pm

1 stop7h 59m

Chicago O'Hare Intl

Fri 2/6

7:20 am-4:36 pm

1 stop7h 16m

$275

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Mon 1/26

5:47 pm-11:46 pm

1 stop7h 59m

Chicago O'Hare Intl

Mon 2/2

5:15 am-4:36 pm

1 stop9h 21m

$278

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 1/17

5:47 pm-11:46 pm

1 stop7h 59m

Chicago O'Hare Intl

Sat 1/24

10:27 am-5:12 pm

Nonstop4h 45m

$282

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 1/21

2:40 pm-9:00 pm

1 stop8h 20m

Chicago Midway

Wed 1/28

5:00 am-2:30 pm

1 stop7h 30m

$292

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 2/14

4:11 pm-11:25 pm

1 stop9h 14m

Chicago Midway

Sat 2/21

6:00 am-2:56 pm

1 stop6h 56m

$341

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 12/24

4:19 pm-5:38 pm

1 stop27h 19m

Chicago Midway

Wed 12/31

6:12 am-3:09 pm

1 stop6h 57m

$345

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 $233. 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 $359. 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 $513.

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 morning. Flights from Punta Cana to Chicago during this time can be as low as $286. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $408.

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 $415 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.

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

As of December 2025, prices for Punta Cana to Chicago flights are approximately 44% cheaper 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

$172

Fastest flight time

4h 45m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Punta Cana in the past 72 hours is $172. The best round-trip flight deal from Punta Cana to Chicago found on momondo in the last 72 hours is $184.
The fastest flight from Punta Cana to Chicago takes 4h 45m
Direct flights go from Punta Cana to Chicago every day.
There are 2 airports near Chicago: 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 5h 00m, 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 $216Free CancellationRating
5.8
3,087 reviews
Search Frontier flights
United AirlinesPriceFrom $315Free CancellationRating
7.4
9,078 reviews
Search United Airlines flights
American AirlinesPriceFrom $354Free CancellationRating
7.2
11,044 reviews
Search American Airlines flights

  • United Airlines Flights From Punta Cana to Chicago

    Across 8 United Airlines flights from Punta Cana to Chicago this week, the average price was $433, with the best United Airlines deals starting from $315 round-trip. 9,078 users have rated United Airlines on momondo, with an average score of 7.4/10.

  • American Airlines Flights From Punta Cana to Chicago

    Across 11,044 American Airlines reviews on momondo, the average score is 7.2/10. American Airlines flies from Punta Cana to Chicago about 12 times each week, with ticket deals ranging from $354 to $506. Price data is based on momondo searches in the last 72 hours.

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
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?

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