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Flight Deals from Chicago to Punta Cana from $108

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Stops

  • Nonstop
    from $251
  • Up to 1 stop
    $334
  • Up to 2 stops
    $588

Airlines

  • Air Canada
    $554
  • American Airlines
    $424
  • COPA Airlines
    $540
  • Delta Air Lines
    $334
  • Frontier Airlines
    $251
  • JetBlue
    $450
  • Spirit Airlines
    $562
  • United Airlines
    $349

Cabin Class

  • Economy
    $251

Departure Airports

  • Chicago Midway Airport
    $446
  • Chicago O Hare Airport
    $251

Arrival Airports

  • Punta Cana International Airport
    $251

Layover Airports

  • Charlotte Douglas International Airport
    $424
  • Dallas Fort Worth International Airport
    $722
  • Fort Lauderdale Hollywood International Airport
    $562
  • General Edward Lawrence Logan International Airport
    $555
  • George Bush Intercontinental Houston Airport
    $465
  • Hartsfield Jackson Atlanta International Airport
    $334
  • Miami International Airport
    $523
  • Montreal Trudeau Airport
    $588
  • New York John F Kennedy Airport
    $450
  • Newark Liberty Airport
    $478
  • Orlando International Airport
    $446
  • Philadelphia International Airport
    $446
  • Tocumen International Airport
    $540
  • Toronto Pearson Airport
    $554
  • Washington Dulles Airport
    $408

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Frontier Airlines Logo
Frontier Airlines

07/16/25

ORD
5h 40m
Direct

07/16/25

PUJ
Frontier Airlines Logo
Frontier Airlines

07/30/25

PUJ
4h 8m
Direct

07/30/25

ORD
$251
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

07/29/25

ORD
7h 52m
ATL

07/29/25

PUJ
Delta Air Lines Logo
Delta Air Lines

08/12/25

PUJ
8h
ATL

08/12/25

ORD
$334
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

07/13/25

ORD
5h 42m
Direct

07/13/25

PUJ
United Airlines Logo
United Airlines

07/16/25

PUJ
4h 5m
Direct

07/16/25

ORD
$349
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

07/08/25

ORD
7h 52m
ATL

07/08/25

PUJ
Delta Air Lines Logo
Delta Air Lines

07/22/25

PUJ
7h 53m
ATL

07/23/25

ORD
$358
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

07/14/25

ORD
5h 40m
Direct

07/14/25

PUJ
Frontier Airlines Logo
Frontier Airlines

07/28/25

PUJ
4h 8m
Direct

07/28/25

ORD
$382
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

07/13/25

ORD
15h 9m
IAD

07/14/25

PUJ
United Airlines Logo
United Airlines

07/16/25

PUJ
4h 5m
Direct

07/16/25

ORD
$408
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

07/29/25

ORD
14h 16m
CLT

07/30/25

PUJ
American Airlines Logo
American Airlines

08/12/25

PUJ
18h 29m
CLT

08/13/25

ORD
$424
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

07/25/25

MDW
7h 50m
ATL

07/25/25

PUJ
Frontier Airlines Logo
Frontier Airlines

08/08/25

PUJ
12h 31m
PHL

08/08/25

MDW
$446
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

07/26/25

MDW
11h 42m
MCO

07/27/25

PUJ
Frontier Airlines Logo
Frontier Airlines

07/28/25

PUJ
12h 31m
PHL

07/28/25

MDW
$446
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

07/18/25

MDW
11h 42m
MCO

07/19/25

PUJ
Frontier Airlines Logo
Frontier Airlines

08/01/25

PUJ
7h 47m
ATL

08/01/25

MDW
$446
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

07/09/25

ORD
5h 35m
Direct

07/09/25

PUJ
American Airlines Logo
American Airlines

07/23/25

PUJ
7h 7m
PHL

07/23/25

ORD
$449
Free cancellation within 83 hours of booking
JetBlue Logo
JetBlue

07/09/25

ORD
12h 6m
JFK

07/09/25

PUJ
JetBlue Logo
JetBlue

07/23/25

PUJ
10h 10m
JFK

07/23/25

ORD
$450
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

07/29/25

ORD
5h 42m
Direct

07/29/25

PUJ
United Airlines Logo
United Airlines

08/12/25

PUJ
11h 2m
IAH

08/12/25

ORD
$465
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

07/08/25

ORD
5h 42m
Direct

07/08/25

PUJ
United Airlines Logo
United Airlines

07/22/25

PUJ
28h 43m
EWR

07/23/25

ORD
$478
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

07/09/25

ORD
15h 9m
IAD

07/10/25

PUJ
United Airlines Logo
United Airlines

07/23/25

PUJ
4h 5m
Direct

07/23/25

ORD
$479
Free cancellation within 83 hours of booking
JetBlue Logo
JetBlue

07/23/25

ORD
12h 6m
JFK

07/23/25

PUJ
JetBlue Logo
JetBlue

08/06/25

PUJ
12h 18m
JFK

08/06/25

ORD
$483
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

07/08/25

ORD
8h 45m
CLT

07/08/25

PUJ
American Airlines Logo
American Airlines

07/22/25

PUJ
9h 9m
MIA

07/22/25

ORD
$523
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

07/23/25

ORD
8h 2m
MIA

07/23/25

PUJ
American Airlines Logo
American Airlines

08/06/25

PUJ
8h 39m
CLT

08/06/25

ORD
$523
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

07/29/25

ORD
18h 25m
IAH

07/30/25

PUJ
United Airlines Logo
United Airlines

08/12/25

PUJ
11h 2m
IAH

08/12/25

ORD
$524
Free cancellation within 83 hours of booking
COPA Airlines Logo
COPA Airlines

07/22/25

ORD
11h 50m
PTY

07/22/25

PUJ
COPA Airlines Logo
COPA Airlines

08/13/25

PUJ
30h 41m
PTY

08/14/25

ORD
$540
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

07/23/25

ORD
9h 35m
EWR

07/23/25

PUJ
United Airlines Logo
United Airlines

08/06/25

PUJ
15h 14m
IAD

08/07/25

ORD
$543
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

07/09/25

ORD
27h 45m
YYZ

07/10/25

PUJ
Air Canada Logo
Air Canada

07/14/25

PUJ
26h 37m
YYZ

07/15/25

ORD
$554
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

07/21/25

ORD
17h 20m
YYZ

07/22/25

PUJ
Air Canada Logo
Air Canada

07/25/25

PUJ
24h 14m
YYZ

07/26/25

ORD
$554
Free cancellation within 83 hours of booking
JetBlue Logo
JetBlue

07/24/25

ORD
12h 6m
JFK

07/24/25

PUJ
JetBlue Logo
JetBlue

08/07/25

PUJ
28h 56m
BOS

08/08/25

ORD
$555
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

07/19/25

ORD
11h 24m
FLL

07/19/25

PUJ
Spirit Airlines Logo
Spirit Airlines

08/02/25

PUJ
16h 20m
FLL

08/03/25

ORD
$562
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

07/07/25

ORD
17h
YYZ
YUL

07/08/25

PUJ
Air Canada Logo
Air Canada

07/22/25

PUJ
24h 14m
YYZ

07/23/25

ORD
$588
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

07/11/25

ORD
22h 10m
YUL
YYZ

07/12/25

PUJ
Air Canada Logo
Air Canada

07/16/25

PUJ
24h 14m
YYZ

07/17/25

ORD
$588
Free cancellation within 83 hours of booking
COPA Airlines Logo
COPA Airlines

07/09/25

ORD
24h 55m
PTY

07/10/25

PUJ
COPA Airlines Logo
COPA Airlines

07/14/25

PUJ
11h 42m
PTY

07/15/25

ORD
$632
Free cancellation within 83 hours of booking
JetBlue Logo
JetBlue

07/16/25

ORD
12h 6m
JFK

07/16/25

PUJ
JetBlue Logo
JetBlue

07/30/25

PUJ
16h 10m
BOS

07/31/25

ORD
$641
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

07/19/25

ORD
9h 59m
MIA

07/19/25

PUJ
American Airlines Logo
American Airlines

08/02/25

PUJ
14h 20m
DFW

08/03/25

ORD
$722
Free cancellation within 83 hours of booking

Top Deals on flights from Chicago to Punta Cana

Chicago, US (CHI) - Punta Cana, DO (PUJ)

Frontier Airlines Logo
Frontier Airlines

May 25

ORD
5h 41m
Direct

May 25

PUJ

as low as

$108

Chicago, US (CHI) - Punta Cana, DO (PUJ)

Spirit Airlines Logo
Spirit Airlines

May 27

ORD
9h 12m
FLL

May 27

PUJ

as low as

$134

Chicago, US (CHI) - Punta Cana, DO (PUJ)

American Airlines Logo
American Airlines

May 25

ORD
26h 40m
PHL

May 26

PUJ

as low as

$157

Chicago, US (CHI) - Punta Cana, DO (PUJ)

American Airlines Logo
American Airlines

May 20

ORD
8h 10m
CLT

May 20

PUJ

as low as

$160

Chicago, US (CHI) - Punta Cana, DO (PUJ)

American Airlines Logo
American Airlines

May 31

ORD
18h
JFK

Jun 1

PUJ

as low as

$164

Chicago, US (CHI) - Punta Cana, DO (PUJ)

United Airlines Logo
United Airlines

May 19

ORD
5h 42m
Direct

May 19

PUJ

as low as

$185

Chicago, US (CHI) - Punta Cana, DO (PUJ)

Frontier Airlines Logo
Frontier Airlines

May 31

MDW
11h 34m
MCO

Jun 1

PUJ

as low as

$203

Chicago, US (CHI) - Punta Cana, DO (PUJ)

Frontier Airlines Logo
Frontier Airlines

May 27

MDW
7h 51m
ATL

May 27

PUJ

as low as

$203

Chicago, US (CHI) - Punta Cana, DO (PUJ)

JetBlue Logo
JetBlue

May 31

ORD
18h 25m
JFK

Jun 1

PUJ

as low as

$242

Chicago, US (CHI) - Punta Cana, DO (PUJ)

American Airlines Logo
American Airlines

May 16

ORD
18h 19m
MIA

May 17

PUJ

as low as

$246

Chicago, US (CHI) - Punta Cana, DO (PUJ)

Delta Air Lines Logo
Delta Air Lines

May 20

ORD
7h 40m
ATL

May 20

PUJ

as low as

$252

Chicago, US (CHI) - Punta Cana, DO (PUJ)

 Logo

May 31

ORD
5h 50m
Direct

May 31

PUJ

as low as

$256

Frequently Asked Questions

What is the typical flight duration from Chicago to Punta Cana?
Flights from Chicago to Punta Cana typically take between 4 to 5 hours if you catch a direct service. However, connections can extend travel times to 6 or 7 hours depending on layovers and weather conditions. It’s best to account for potential delays when planning your itinerary. Ensure you check with carriers for exact durations during your travel period, as seasonal variations may slightly alter these times. Planning ahead can help you adjust your schedule for arriving comfortably at your tropical destination.
Are there any direct flights from Chicago to Punta Cana?
Yes, there are direct flights available from Chicago to Punta Cana, although their availability can vary seasonally. Direct options tend to offer shorter travel times, usually in the 4 to 5-hour range, compared to connecting flights that can take longer. Plans might fluctuate based on the time of year and airline schedules. It is best to check with major airlines and travel aggregators for current direct flight frequencies and prices, which can range broadly depending on advance booking and demand.
What are the best transportation options from Punta Cana airport to local resorts or downtown?
The best transportation options from Punta Cana airport include airport shuttles, taxis, and car rentals. Taxis typically cost between $20 and $50 depending on the destination, while shared shuttles range from $15 to $40 per person for a more economical ride. Car rental services are also available with daily rates from $30 to $80, offering flexibility if you wish to explore independently. Many resorts provide complimentary shuttle services, so it’s a good idea to verify with your accommodation when planning your arrival.
What are the must-see attractions in Punta Cana for travelers arriving from Chicago?
Travelers arriving from Chicago should consider visiting iconic attractions such as Bavaro Beach for its exquisite sands and turquoise waters, and the Indigenous Eyes Ecological Park for its natural beauty. Other highlights include the adventure parks at Scape Park and excursions to Hoyo Azul, a natural water sinkhole. These sites offer unique tropical experiences and cultural insights into the region. Exploring these landmarks can offer a balanced mix of relaxation and adventure during your stay, ensuring a memorable trip with varied activities.
Which local dishes should travelers from Chicago try when visiting Punta Cana?
Travelers from Chicago should sample local dishes that highlight the rich Dominican flavors. The traditional meal known as 'La Bandera' – a combination of rice, beans, and meat – is a must-try, along with fresh seafood specialties and stewed goat. Other regional favorites include mangú for breakfast and sancocho, a hearty stew. These dishes are found in local eateries and beachside restaurants, with prices usually ranging from $8 to $20 per dish, allowing you to indulge in authentic culinary experiences without breaking the bank.
What are the best family-friendly activities in Punta Cana for visitors from Chicago?
Family-friendly activities in Punta Cana include safe, well-supervised water parks, guided eco-tours at the Indigenous Eyes Ecological Park, and interactive experiences at adventure parks like Scape Park. Many resorts also offer children’s clubs, beach activities, and pool games with professional supervision. Additionally, organized boat tours and snorkeling trips cater to families and typically cost between $30 and $70 per person. These activities provide both fun and educational experiences while ensuring a comfortable environment for all ages.
Are there any seasonal events in Punta Cana that travelers from Chicago should not miss?
Yes, seasonal events in Punta Cana provide a vibrant insight into local culture. Notably, the Carnival season features parades, dancing, and colorful costumes, while local music and cultural festivals usually take place in the winter and spring. Additionally, occasional food festivals and beach events can be found, offering unique experiences to visitors. These events often include performances and local culinary showcases with ticket prices ranging between $10 and $40. Checking local event calendars prior to travel is recommended to ensure you don’t miss these cultural highlights.
What are the most affordable dining options in Punta Cana for travelers from Chicago?
Affordable dining options in Punta Cana include local paladares, street food vendors, and small family-owned restaurants offering traditional Dominican cuisine. Meals here typically range from $5 to $15, allowing you to enjoy authentic flavors without overspending. Look for local dishes like ricas empanadas and hearty stews in neighborhood eateries. These spots often provide the most authentic taste of the region. Additionally, many tourist areas have midday specials that offer great value, so it pays to explore beyond the more expensive, high-end resort restaurants.
What are the best car rental options in Punta Cana for travelers from Chicago?
Car rental in Punta Cana is a viable option, with international and local companies available. Reputable brands such as Avis and Budget offer vehicles at daily rates typically ranging between $30 and $80, although local agencies may offer competitive rates. Renting a car provides flexibility to explore areas beyond the main resort zones, though be aware of potential additional charges such as insurance and fuel costs. It’s advisable to book in advance and compare prices online, checking reviews to select a service that suits your itinerary and comfort level.
What cultural tips should travelers from Chicago be aware of when visiting Punta Cana?
When visiting Punta Cana, travelers should know that local customs emphasize warm greetings, often with a handshake or light cheek kiss among acquaintances. The pace of life may be slower with a midday siesta, and punctuality is more relaxed compared to larger cities like Chicago. Dress modestly when venturing away from resort areas and learn a few Spanish phrases to connect better with locals. It’s also respectful to ask before taking photos of people. These cultural tips can help ensure positive interactions and a smoother travel experience.
Is there a specific time of year when Punta Cana is best visited by travelers from Chicago?
Yes, the best time to visit Punta Cana from Chicago is typically between December and April when the weather is pleasantly warm, and the region experiences its dry season. This period offers clear skies and calm seas, ideal for beach activities and water sports. However, peak season can also mean higher prices and more crowds, so early bookings are advisable. Alternatively, the shoulder months of May and November provide a good balance between favorable weather and lower travel costs, making them attractive for budget-conscious travelers.
What are the customs requirements for travelers flying from Chicago to Punta Cana?
Travelers leaving from Chicago to Punta Cana should have a passport valid for at least six months beyond their travel dates. In addition, most visitors are required to purchase a Dominican tourist card, which can cost between $10 and $15, sometimes included in airline fees. Be prepared for customs declarations on arrival, and avoid carrying prohibited items such as excessive cash or certain electronic devices without proper documentation. It’s important to verify these details with official sources prior to travel, as requirements can change occasionally.
What unique airport amenities can travelers expect at Punta Cana airport when arriving from Chicago?
Punta Cana International Airport offers several unique amenities designed for comfort and convenience. Travelers can enjoy duty-free shopping with a variety of local and international brands, comfortable VIP lounges for relaxation, and readily available currency exchange services. The airport also features dining areas with local food selections and free Wi-Fi in many areas. These facilities are intended to provide a smooth arrival and transit experience. Additionally, rental car counters and travel assistance kiosks are conveniently located within the terminal, making your entry seamless and stress-free.
What are the best shopping areas for souvenirs in Punta Cana for travelers from Chicago?
For memorable souvenirs, visitors should explore local artisan markets and specialty shopping centers near the resort areas. Popular destinations include the markets near Bavaro and smaller local shops along busy streets, where handcrafted items, local art, and authentic Dominican products are offered. Prices typically range from $5 to $50 depending on the item. As you stroll these areas, be sure to compare prices and negotiate politely if appropriate. This approach can yield unique items that capture the essence of the local culture and create lasting memories of your visit.
Are there any health precautions travelers from Chicago should take before visiting Punta Cana?
Travelers from Chicago should take several health precautions when visiting Punta Cana. It is advisable to consult a travel clinic for recommended immunizations, such as Hepatitis A, typhoid, and other routine vaccines, with costs usually ranging from $50 to $150 for a complete set. Use mosquito repellent to prevent bites, as the tropical climate can carry mosquito-borne illnesses. Additionally, carry sunscreen and stay hydrated. Checking the latest health advisories and travel insurance that covers medical emergencies can add an extra layer of protection during your trip.

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