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Cheap flights from Punta Cana to Chicago from $109

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 11/15. 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

Arajet Logo
7:30 pm - 10:40 pmPUJ-ORD
5h 10mnonstop
Arajet Logo
4:35 am - 11:20 amORD-PUJ
4h 45mnonstop
$216Arajet
Find Deal
mar., nov. 25 - mar., dic. 2
Arajet Logo
7:30 pm - 10:40 pmPUJ-ORD
5h 10mnonstop
Arajet Logo
3:30 am - 10:15 amORD-PUJ
4h 45mnonstop
$219Arajet
Find Deal
mar., nov. 25 - dom., nov. 30
Multiple Airlines Logo
7:30 pm - 10:40 pmPUJ-ORD
5h 10mnonstop
Multiple Airlines Logo
5:59 pm - 12:16 pmORD-PUJ
16h 17m1 stop
$266Multiple Airlines
Find Deal
mar., nov. 25 - mié., dic. 3
Spirit Airlines Logo
3:57 pm - 11:45 pmPUJ-ORD
8h 48m1 stop
Spirit Airlines Logo
5:05 am - 2:49 pmORD-PUJ
8h 44m1 stop
$289Spirit Airlines
Find Deal
jue., oct. 9 - lun., oct. 20
Spirit Airlines Logo
3:57 pm - 11:45 pmPUJ-ORD
8h 48m1 stop
Spirit Airlines Logo
5:05 am - 2:49 pmORD-PUJ
8h 44m1 stop
$290Spirit Airlines
Find Deal
jue., oct. 16 - sáb., oct. 25
Multiple Airlines Logo
12:50 pm - 11:18 amPUJ-ORD
24h 28m1 stop
Multiple Airlines Logo
4:35 am - 11:20 amORD-PUJ
4h 45mnonstop
$295Multiple Airlines
Find Deal
mié., nov. 26 - mar., dic. 2
United Airlines Logo
2:55 pm - 6:08 pmPUJ-ORD
5h 13mnonstop
United Airlines Logo
8:45 am - 5:25 pmORD-PUJ
6h 40m1 stop
$374United Airlines
Find Deal
jue., feb. 26 - mar., mar. 3
United Airlines Logo
2:55 pm - 6:08 pmPUJ-ORD
5h 13mnonstop
United Airlines Logo
3:30 pm - 5:25 pmORD-PUJ
23h 55m1 stop
$381United Airlines
Find Deal
vie., nov. 21 - jue., nov. 27
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
jue., ene. 1 - dom., ene. 11
Frontier Logo
12:40 pm - 11:05 pmPUJ-MDW
12h 25m1 stop
Frontier Logo
6:00 am - 8:15 pmMDW-PUJ
12h 15m2 stops
$760Frontier
Find Deal
jue., ene. 1 - dom., ene. 11

United Airlines flights from Punta Cana to Chicago

Our best United Airlines deals on Punta Cana to Chicago flight tickets
United Airlines
Feb 26
PUJ2:55 pmPunta Cana
5h 13m
ORD6:08 pmChicago O'Hare Intl
Mar 3
ORD8:45 amChicago O'Hare Intl
6h 40m
1 stop
PUJ5:25 pmPunta Cana
$374
Find similar
United Airlines
Nov 21
PUJ2:55 pmPunta Cana
5h 13m
ORD6:08 pmChicago O'Hare Intl
Nov 27
ORD3:30 pmChicago O'Hare Intl
23h 55m
1 stop
PUJ5:25 pmPunta Cana
$381
Find similar
United Airlines
Oct 24
PUJ3:15 pmPunta Cana
9h 15m
1 stop
ORD11:30 pmChicago O'Hare Intl
Oct 31
ORD9:30 amChicago O'Hare Intl
4h 32m
PUJ3:02 pmPunta Cana
$408
Find similar

Spirit Airlines flights from Punta Cana to Chicago

Our best Spirit Airlines deals on Punta Cana to Chicago flight tickets
Spirit Airlines
Oct 9
PUJ3:57 pmPunta Cana
8h 48m
1 stop
ORD11:45 pmChicago O'Hare Intl
Oct 20
ORD5:05 amChicago O'Hare Intl
8h 44m
1 stop
PUJ2:49 pmPunta Cana
$289
Find similar
Spirit Airlines
Oct 16
PUJ3:57 pmPunta Cana
8h 48m
1 stop
ORD11:45 pmChicago O'Hare Intl
Oct 25
ORD5:05 amChicago O'Hare Intl
8h 44m
1 stop
PUJ2:49 pmPunta Cana
$290
Find similar
Spirit Airlines
Oct 3
PUJ3:19 pmPunta Cana
8h 29m
1 stop
ORD10:48 pmChicago O'Hare Intl
Oct 11
ORD7:43 pmChicago O'Hare Intl
18h 06m
1 stop
PUJ2:49 pmPunta Cana
$321
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 septiembre 17, 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

mar. 11/25

7:30 pm-10:40 pm

Nonstop5h 10m

Chicago O'Hare Intl

mar. 12/2

4:35 am-11:20 am

Nonstop4h 45m

$216

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

mar. 11/25

7:30 pm-10:40 pm

Nonstop5h 10m

Chicago O'Hare Intl

dom. 11/30

3:30 am-10:15 am

Nonstop4h 45m

$219

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

mar. 11/25

7:30 pm-10:40 pm

Nonstop5h 10m

Chicago O'Hare Intl

mié. 12/3

5:59 pm-12:16 pm

1 stop16h 17m

$266

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

jue. 10/9

3:57 pm-11:45 pm

1 stop8h 48m

Chicago O'Hare Intl

lun. 10/20

5:05 am-2:49 pm

1 stop8h 44m

$289

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

jue. 10/16

3:57 pm-11:45 pm

1 stop8h 48m

Chicago O'Hare Intl

sáb. 10/25

5:05 am-2:49 pm

1 stop8h 44m

$290

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

mié. 11/26

12:50 pm-11:18 am

1 stop24h 28m

Chicago O'Hare Intl

mar. 12/2

4:35 am-11:20 am

Nonstop4h 45m

$295

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

jue. 2/26

2:55 pm-6:08 pm

Nonstop5h 13m

Chicago O'Hare Intl

mar. 3/3

8:45 am-5:25 pm

1 stop6h 40m

$374

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

vie. 11/21

2:55 pm-6:08 pm

Nonstop5h 13m

Chicago O'Hare Intl

jue. 11/27

3:30 pm-5:25 pm

1 stop23h 55m

$381

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

jue. 1/1

12:40 pm-11:05 pm

1 stop12h 25m

Chicago Midway

dom. 1/11

6:00 am-3:24 pm

1 stop7h 24m

$697

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

jue. 1/1

12:40 pm-11:05 pm

1 stop12h 25m

Chicago Midway

dom. 1/11

6:00 am-8:15 pm

2 stops12h 15m

$760

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 typical price of a round-trip flight between Punta Cana and Chicago?

What is the cheapest month to fly to Chicago?

The month of May is, on average, the cheapest month to fly to Chicago from Punta Cana, with most prices found around $302. If you’re not able to fly to Chicago in May, then December is your next best option. Flight prices from Punta Cana to Chicago during December average around $351.

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 Sunday when prices can be found for as low as $322. This is often the case because there is less demand to fly during this day of the week. When flying out on a Wednesday, the most expensive travel day of the week, you can expect to see flight prices from Punta Cana to Chicago for around $448.

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 $306. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $413.

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 $432 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 $283 on momondo.

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

There are 2 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 September 2025, prices for Punta Cana to Chicago flights are approximately 49% 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

$306

Fastest flight time

4h 54m

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 $306. The best round-trip flight deal from Punta Cana to Chicago found on momondo in the last 72 hours is $320.
The fastest flight from Punta Cana to Chicago takes 4h 54m
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 $224Free CancellationRating
5.8
3,173 reviews
Search Frontier flights
United AirlinesPriceFrom $269Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights
American AirlinesPriceFrom $354Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

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?

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