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Cheap flights from Punta Cana to Chicago from $206

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 11/3. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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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
7:30 pm - 11:40 pm
PUJ
-
ORD
5h 10mnonstop
Arajet Logo
5:30 am - 11:15 am
ORD
-
PUJ
4h 45mnonstop
$315Arajet
Thu, Aug 13 - Mon, Aug 17
Arajet Logo
7:30 pm - 11:40 pm
PUJ
-
ORD
5h 10mnonstop
Arajet Logo
6:45 am - 12:30 pm
ORD
-
PUJ
4h 45mnonstop
$355Arajet
Thu, Oct 8 - Fri, Oct 30
Arajet Logo
7:30 pm - 11:40 pm
PUJ
-
ORD
5h 10mnonstop
Arajet Logo
6:45 am - 12:30 pm
ORD
-
PUJ
4h 45mnonstop
$358Arajet
Thu, Sep 10 - Fri, Sep 18
Arajet Logo
7:02 am - 11:12 am
PUJ
-
ORD
5h 10mnonstop
Arajet Logo
12:12 pm - 5:57 pm
ORD
-
PUJ
4h 45mnonstop
$365Arajet
Sat, Aug 15 - Sat, Aug 29
Arajet Logo
7:30 pm - 11:40 pm
PUJ
-
ORD
5h 10mnonstop
Arajet Logo
12:12 pm - 5:57 pm
ORD
-
PUJ
4h 45mnonstop
$368Arajet
Thu, Aug 13 - Sat, Aug 22
Multiple Airlines Logo
2:05 pm - 11:44 pm
PUJ
-
ORD
10h 39m
1 stop
Multiple Airlines Logo
5:30 am - 11:15 am
ORD
-
PUJ
4h 45mnonstop
$400Multiple Airlines
Thu, Aug 13 - Mon, Aug 17
Multiple Airlines Logo
7:02 am - 11:12 am
PUJ
-
ORD
5h 10mnonstop
Multiple Airlines Logo
7:00 am - 3:24 pm
ORD
-
PUJ
7h 24m
1 stop
$406Multiple Airlines
Sat, Aug 15 - Sat, Aug 29
Frontier Logo
3:59 pm - 11:07 am
PUJ
-
MDW
20h 08m
1 stop
Frontier Logo
6:00 am - 2:34 pm
MDW
-
PUJ
7h 34m
1 stop
$485Frontier
Thu, Aug 13 - Mon, Aug 17
Frontier Logo
3:59 pm - 10:08 pm
PUJ
-
MDW
31h 09m
1 stop
Frontier Logo
6:00 am - 2:49 pm
MDW
-
PUJ
7h 49m
1 stop
$511Frontier
Thu, Aug 6 - Tue, Aug 11
Frontier Logo
3:44 pm - 11:07 am
PUJ
-
MDW
20h 23m
1 stop
Frontier Logo
6:00 am - 2:29 pm
MDW
-
PUJ
7h 29m
1 stop
$513Frontier
Sat, Aug 15 - Sat, Aug 29

Air Canada flights from Punta Cana to Chicago

Our best Air Canada deals on Punta Cana to Chicago flight tickets
Air Canada
Jul 26
PUJ4:20 pmPunta Cana
22h 02m
1 stop
ORD1:22 pmChicago O'Hare Intl
Aug 12
ORD9:50 amChicago O'Hare Intl
28h 35m
1 stop
PUJ3:25 pmPunta Cana
$428
Air Canada
Jun 2
PUJ5:25 pmPunta Cana
17h 53m
1 stop
ORD10:18 amChicago O'Hare Intl
Jun 16
ORD8:20 pmChicago O'Hare Intl
18h 05m
1 stop
PUJ3:25 pmPunta Cana
$454
Air Canada
Jun 2
PUJ5:25 pmPunta Cana
17h 53m
1 stop
ORD10:18 amChicago O'Hare Intl
Jun 16
ORD6:22 pmChicago O'Hare Intl
21h 08m
2 stops
PUJ4:30 pmPunta Cana
$456

Arajet flights from Punta Cana to Chicago

Our best Arajet deals on Punta Cana to Chicago flight tickets
Arajet
Aug 13
PUJ7:30 pmPunta Cana
5h 10m
ORD11:40 pmChicago O'Hare Intl
Aug 17
ORD5:30 amChicago O'Hare Intl
4h 45m
PUJ11:15 amPunta Cana
$315
Arajet
Oct 8
PUJ7:30 pmPunta Cana
5h 10m
ORD11:40 pmChicago O'Hare Intl
Oct 30
ORD6:45 amChicago O'Hare Intl
4h 45m
PUJ12:30 pmPunta Cana
$355
Arajet
Sep 10
PUJ7:30 pmPunta Cana
5h 10m
ORD11:40 pmChicago O'Hare Intl
Sep 18
ORD6:45 amChicago O'Hare Intl
4h 45m
PUJ12:30 pmPunta Cana
$358

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 May 19, 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

Cheapest round-trip
Quickest round-trip

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 8/13

7:30 pm-11:40 pm

Nonstop5h 10m

Chicago O'Hare Intl

Mon 8/17

5:30 am-11:15 am

Nonstop4h 45m

$315

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 10/8

7:30 pm-11:40 pm

Nonstop5h 10m

Chicago O'Hare Intl

Fri 10/30

6:45 am-12:30 pm

Nonstop4h 45m

$355

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 9/10

7:30 pm-11:40 pm

Nonstop5h 10m

Chicago O'Hare Intl

Fri 9/18

6:45 am-12:30 pm

Nonstop4h 45m

$358

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 8/15

7:02 am-11:12 am

Nonstop5h 10m

Chicago O'Hare Intl

Sat 8/29

12:12 pm-5:57 pm

Nonstop4h 45m

$365

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 8/13

7:30 pm-11:40 pm

Nonstop5h 10m

Chicago O'Hare Intl

Sat 8/22

12:12 pm-5:57 pm

Nonstop4h 45m

$368

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 8/13

2:05 pm-11:44 pm

1 stop10h 39m

Chicago O'Hare Intl

Mon 8/17

5:30 am-11:15 am

Nonstop4h 45m

$400

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 8/15

7:02 am-11:12 am

Nonstop5h 10m

Chicago O'Hare Intl

Sat 8/29

7:00 am-3:24 pm

1 stop7h 24m

$406

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 8/13

3:59 pm-11:07 am

1 stop20h 08m

Chicago Midway

Mon 8/17

6:00 am-2:34 pm

1 stop7h 34m

$485

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 8/6

3:59 pm-10:08 pm

1 stop31h 09m

Chicago Midway

Tue 8/11

6:00 am-2:49 pm

1 stop7h 49m

$511

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 8/15

3:44 pm-11:07 am

1 stop20h 23m

Chicago Midway

Sat 8/29

6:00 am-2:29 pm

1 stop7h 29m

$513

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 August is, on average, the cheapest month to fly to Chicago from Punta Cana, with most prices found around $154. If you’re not able to fly to Chicago in August, then December is your next best option. Flight prices from Punta Cana to Chicago during December average around $181.

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 $387. 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 $476.

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 $482.

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

Can stopping save me money on Punta Cana to Chicago flights?

You could potentially save up to 16% on your flight if you consider stops on a Punta Cana to Chicago flight.

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

As of May 2026, prices for Punta Cana to Chicago flights are approximately 24% 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

$279

Fastest flight time

4h 45m

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 $279. The best round-trip flight deal from Punta Cana to Chicago found on momondo in the last 72 hours is $404.
The fastest flight from Punta Cana to Chicago takes 4h 45m
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

Frequently asked questions about flying from Punta Cana to Chicago

  • 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 45m, 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
ArajetPriceFrom $195Free CancellationRating
6.5
48 reviews
Search Arajet flights
American AirlinesPriceFrom $283Free CancellationRating
7.1
11,646 reviews
Search American Airlines flights

  • American Airlines Flights From Punta Cana to Chicago

    Across 3 American Airlines flights from Punta Cana to Chicago this week, the average price was $448, with the best American Airlines deals starting from $283 round-trip. 11,646 users have rated American Airlines on momondo, with an average score of 7.1/10.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
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