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Cheap flights from Chicago to Punta Cana from $96

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Punta Cana 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.
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0 bags

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Find the cheapest flights from Chicago to Punta Cana (CHI-PUJ)

Cheap round-trip flights

Spirit Airlines Logo
5:05 am - 3:00 pmORD-PUJ
8h 55m1 stop
Spirit Airlines Logo
3:19 pm - 10:48 pmPUJ-ORD
8h 29m1 stop
$228Spirit Airlines
Find Deal
Wed, Sep 3 - Wed, Sep 10
Spirit Airlines Logo
5:05 am - 3:00 pmORD-PUJ
8h 55m1 stop
Spirit Airlines Logo
3:19 pm - 10:48 pmPUJ-ORD
8h 29m1 stop
$231Spirit Airlines
Find Deal
Wed, Sep 3 - Sat, Sep 6
Arajet Logo
4:35 am - 11:20 amORD-PUJ
4h 45mnonstop
Arajet Logo
7:30 pm - 10:40 pmPUJ-ORD
5h 10mnonstop
$245Arajet
Find Deal
Tue, Jan 13 - Tue, Jan 20
Arajet Logo
10:27 am - 5:12 pmORD-PUJ
4h 45mnonstop
Arajet Logo
6:00 pm - 9:10 pmPUJ-ORD
5h 10mnonstop
$246Arajet
Find Deal
Sat, Jan 31 - Sun, Feb 8
Southwest Logo
5:10 am - 2:05 pmMDW-PUJ
7h 55m1 stop
Southwest Logo
3:05 pm - 9:35 pmPUJ-MDW
7h 30m1 stop
$343Southwest
Find Deal
Mon, Sep 1 - Fri, Sep 5
Delta Logo
12:48 pm - 12:28 pmMDW-PUJ
22h 40m2 stops
Delta Logo
3:56 pm - 10:14 pmPUJ-MDW
7h 18m1 stop
$347Delta
Find Deal
Tue, Oct 14 - Wed, Oct 22
Frontier Logo
6:10 am - 2:07 pmMDW-PUJ
6h 57m1 stop
Frontier Logo
3:22 pm - 11:09 pmPUJ-MDW
8h 47m1 stop
$363Frontier
Find Deal
Sat, Oct 18 - Sat, Oct 25
Delta Logo
6:00 am - 2:34 pmMDW-PUJ
7h 34m1 stop
Delta Logo
2:45 pm - 9:36 pmPUJ-MDW
7h 51m1 stop
$368Delta
Find Deal
Tue, Sep 2 - Tue, Sep 23
Frontier Logo
6:21 am - 4:34 pmMDW-PUJ
9h 13m1 stop
Frontier Logo
3:22 pm - 11:09 pmPUJ-MDW
8h 47m1 stop
$383Frontier
Find Deal
Sun, Oct 19 - Sat, Oct 25
Southwest Logo
6:15 am - 1:55 pmMDW-PUJ
6h 40m1 stop
Southwest Logo
1:40 pm - 10:35 pmPUJ-MDW
9h 55m1 stop
$389Southwest
Find Deal
Tue, Sep 23 - Tue, Oct 7

Southwest flights from Chicago to Punta Cana

Our best Southwest deals on Chicago to Punta Cana flight tickets
Southwest
Sep 1
MDW5:10 amChicago Midway
7h 55m
1 stop
PUJ2:05 pmPunta Cana
Sep 5
PUJ3:05 pmPunta Cana
7h 30m
1 stop
MDW9:35 pmChicago Midway
$343
Find similar
Southwest
Sep 23
MDW6:15 amChicago Midway
6h 40m
1 stop
PUJ1:55 pmPunta Cana
Oct 7
PUJ1:40 pmPunta Cana
9h 55m
1 stop
MDW10:35 pmChicago Midway
$389
Find similar
Southwest
Aug 22
MDW5:10 amChicago Midway
7h 55m
1 stop
PUJ2:05 pmPunta Cana
Aug 26
PUJ2:50 pmPunta Cana
7h 50m
1 stop
MDW9:40 pmChicago Midway
$423
Find similar

Spirit Airlines flights from Chicago to Punta Cana

Our best Spirit Airlines deals on Chicago to Punta Cana flight tickets
Spirit Airlines
Sep 3
ORD5:05 amChicago O'Hare Intl
8h 55m
1 stop
PUJ3:00 pmPunta Cana
Sep 10
PUJ3:19 pmPunta Cana
8h 29m
1 stop
ORD10:48 pmChicago O'Hare Intl
$228
Find similar
Spirit Airlines
Sep 3
ORD5:05 amChicago O'Hare Intl
8h 55m
1 stop
PUJ3:00 pmPunta Cana
Sep 6
PUJ3:19 pmPunta Cana
8h 29m
1 stop
ORD10:48 pmChicago O'Hare Intl
$231
Find similar
Spirit Airlines
Sep 9
ORD5:05 amChicago O'Hare Intl
8h 09m
1 stop
PUJ2:14 pmPunta Cana
Sep 13
PUJ3:19 pmPunta Cana
8h 29m
1 stop
ORD10:48 pmChicago O'Hare Intl
$257
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Punta Cana 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 August 6, 2025.
Use the filters below to find and compare flights from Chicago to Punta Cana that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Wed 9/3

5:05 am-3:00 pm

1 stop8h 55m

Punta Cana

Wed 9/10

3:19 pm-10:48 pm

1 stop8h 29m

$228

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Wed 9/3

5:05 am-3:00 pm

1 stop8h 55m

Punta Cana

Sat 9/6

3:19 pm-10:48 pm

1 stop8h 29m

$231

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 1/13

4:35 am-11:20 am

Nonstop4h 45m

Punta Cana

Tue 1/20

7:30 pm-10:40 pm

Nonstop5h 10m

$245

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 1/31

10:27 am-5:12 pm

Nonstop4h 45m

Punta Cana

Sun 2/8

6:00 pm-9:10 pm

Nonstop5h 10m

$246

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 9/1

5:10 am-2:05 pm

1 stop7h 55m

Punta Cana

Fri 9/5

3:05 pm-9:35 pm

1 stop7h 30m

$343

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 10/14

12:48 pm-12:28 pm

2 stops22h 40m

Punta Cana

Wed 10/22

3:56 pm-10:14 pm

1 stop7h 18m

$347

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 10/18

6:10 am-2:07 pm

1 stop6h 57m

Punta Cana

Sat 10/25

3:22 pm-11:09 pm

1 stop8h 47m

$363

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 9/2

6:00 am-2:34 pm

1 stop7h 34m

Punta Cana

Tue 9/23

2:45 pm-9:36 pm

1 stop7h 51m

$368

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sun 10/19

6:21 am-4:34 pm

1 stop9h 13m

Punta Cana

Sat 10/25

3:22 pm-11:09 pm

1 stop8h 47m

$383

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 9/23

6:15 am-1:55 pm

1 stop6h 40m

Punta Cana

Tue 10/7

1:40 pm-10:35 pm

1 stop9h 55m

$389

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 Punta Cana from

How to get the cheapest flight ticket from Chicago to Punta Cana

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 Chicago and Punta Cana?

What is the cheapest month to fly to Punta Cana?

If you’re not able to fly to Punta Cana in July, then January is your next best option. Flight prices from Chicago to Punta Cana during January average around $486.

What is the cheapest day to depart on your flight to Punta Cana?

The cheapest day to depart from Chicago to Punta Cana is on a Tuesday when prices can be found for as low as $500. Be sure to avoid booking your departure on a Thursday as prices are generally higher than usual. According to our data, the average ticket price to Punta Cana on Thursday is $581.

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

At noon is the cheapest time of day to fly from Chicago to Punta Cana when you can find flight prices for as low as $341. Flying to Punta Cana at noon is an ideal time because this is during off-peak travel hours. In the morning is when there is more demand to fly to Punta Cana, so prices are often more expensive at around $551 per ticket.

What is the cheapest Chicago to Punta Cana flight route?

Fly from Chicago Midway to Punta Cana for the best Chicago - Punta Cana flight prices

How far in advance should I book a flight to Punta Cana?

You are more likely to see cheaper flights to Punta Cana from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Punta Cana for around $535 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Punta Cana from Chicago for as low as $457 on momondo.

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

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

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

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

As of August 2025, prices for Chicago to Punta Cana flights are approximately 20% more expensive when compared to flights at the same time last year.

When to book flights from Chicago to Punta Cana

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

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

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

Best Price Found

$96

Fastest flight time

4h 25m

Direct flights

Every day

Airports in Punta Cana

1 airport
The best one-way flight to Punta Cana from Chicago in the past 72 hours is $96. The best round-trip flight deal from Chicago to Punta Cana found on momondo in the last 72 hours is $228.
The fastest flight from Chicago to Punta Cana takes 4h 25m
Direct flights go from Chicago to Punta Cana every day.
There is 1 airport near Punta Cana: Punta Cana (PUJ)
Search flight deals

  • How far is Chicago to Punta Cana by plane?

    Chicago and Punta Cana are 1958.2 mi apart from one another. A reasonable flight in good conditions will take 4h 45m.

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

    Prices for flights from Chicago to Punta Cana Airport refresh daily.

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

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

  • What documentation or ID do you need to fly to Punta Cana Airport?

    The required travel and health documents for your Punta Cana 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 Punta Cana 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 Chicago to Punta Cana?

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

Best airlines flying from Chicago to Punta Cana

Compare and see reviews for airlines that fly from Chicago to Punta Cana with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $223Free CancellationRating
5.8
3,232 reviews
Search Frontier flights
ArajetPriceFrom $235Free CancellationRating
6.9
33 reviews
Search Arajet flights
Spirit AirlinesPriceFrom $270Free CancellationRating
6.3
8,051 reviews
Search Spirit Airlines flights
Air CanadaPriceFrom $335Free CancellationRating
7.1
9,890 reviews
Search Air Canada flights
United AirlinesPriceFrom $343Free CancellationRating
7.4
8,916 reviews
Search United Airlines flights
American AirlinesPriceFrom $359Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $386Free CancellationRating
8.0
7,985 reviews
Search Delta flights
SouthwestPriceFrom $495Free CancellationRating
8.0
4,246 reviews
Search Southwest flights
AviancaPriceFrom $615Free CancellationRating
6.7
2,394 reviews
Search Avianca flights

  • United Airlines Flights From Chicago to Punta Cana

    Across 7 United Airlines flights from Chicago to Punta Cana this week, the average price was $633, with the best United Airlines deals starting from $343 round-trip. 8,916 users have rated United Airlines on momondo, with an average score of 7.4/10.

  • American Airlines Flights From Chicago to Punta Cana

    Across 10,000 American Airlines reviews on momondo, the average score is 7.2/10. American Airlines flies from Chicago to Punta Cana about 7 times each week, with ticket deals ranging from $359 to $597. Price data is based on momondo searches in the last 72 hours.

Traveling to a place near Punta Cana?

Book flights to Punta Cana if you plan to visit one of these locations
Bavaro

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Punta Cana?

It is quick and easy to find Chicago to Punta Cana flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Punta Cana that suits you.

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

momondo does allow users to show only those flights to Punta Cana from Chicago which offer a flexible booking policy as well as other useful filters and features.

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

momondo provides multiple filters to help you find the best flight to Punta Cana from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Yes momondo offers price alerts on flights to Punta Cana from Chicago. 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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