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Flight Deals from Punta Cana to Chicago from $131

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Stops

  • Nonstop
    from $350
  • Up to 1 stop
    $343

Airlines

  • Air Canada
    $620
  • American Airlines
    $343
  • COPA Airlines
    $480
  • Delta Air Lines
    $371
  • Frontier Airlines
    $350
  • JetBlue
    $492
  • Spirit Airlines
    $363
  • United Airlines
    $419

Cabin Class

  • Economy
    $343

Departure Airports

  • Punta Cana International Airport
    $343

Arrival Airports

  • Chicago Midway Airport
    $479
  • Chicago O Hare Airport
    $343

Layover Airports

  • Charlotte Douglas International Airport
    $353
  • Dallas Fort Worth International Airport
    $343
  • Fort Lauderdale Hollywood International Airport
    $363
  • General Edward Lawrence Logan International Airport
    $492
  • George Bush Intercontinental Houston Airport
    $424
  • Hartsfield Jackson Atlanta International Airport
    $371
  • Miami International Airport
    $400
  • New York John F Kennedy Airport
    $399
  • Newark Liberty Airport
    $447
  • Orlando International Airport
    $444
  • Philadelphia International Airport
    $472
  • Tampa International Airport
    $515
  • Tocumen International Airport
    $480
  • Toronto Pearson Airport
    $620
  • Washington Dulles Airport
    $419

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American Airlines Logo
American Airlines

05/20/25

PUJ
4h 20m
Direct

05/20/25

ORD
American Airlines Logo
American Airlines

05/27/25

ORD
9h 49m
DFW

05/27/25

PUJ
$343
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

06/08/25

PUJ
4h 9m
Direct

06/08/25

ORD
Frontier Airlines Logo
Frontier Airlines

06/22/25

ORD
5h 44m
Direct

06/22/25

PUJ
$350
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/20/25

PUJ
9h 59m
CLT

05/21/25

ORD
American Airlines Logo
American Airlines

05/27/25

ORD
9h 49m
DFW

05/27/25

PUJ
$353
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

06/10/25

PUJ
7h 42m
FLL

06/10/25

ORD
Spirit Airlines Logo
Spirit Airlines

06/24/25

ORD
9h 5m
FLL

06/24/25

PUJ
$363
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/02/25

PUJ
9h 19m
ATL

05/02/25

ORD
Delta Air Lines Logo
Delta Air Lines

05/09/25

ORD
9h 15m
ATL

05/09/25

PUJ
$371
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

05/13/25

PUJ
7h 42m
FLL

05/13/25

ORD
Spirit Airlines Logo
Spirit Airlines

05/27/25

ORD
9h 12m
FLL

05/27/25

PUJ
$385
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/20/25

PUJ
4h 20m
Direct

05/20/25

ORD
American Airlines Logo
American Airlines

05/27/25

ORD
5h 30m
Direct

05/27/25

PUJ
$385
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/16/25

PUJ
9h 59m
CLT

05/17/25

ORD
American Airlines Logo
American Airlines

05/30/25

ORD
18h
JFK

05/31/25

PUJ
$399
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/02/25

PUJ
11h
MIA

05/02/25

ORD
American Airlines Logo
American Airlines

05/09/25

ORD
16h 42m
MIA

05/10/25

PUJ
$400
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/02/25

PUJ
4h 5m
Direct

05/02/25

ORD
United Airlines Logo
United Airlines

05/09/25

ORD
18h 45m
IAD

05/10/25

PUJ
$419
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/05/25

PUJ
9h 55m
IAH

05/06/25

ORD
United Airlines Logo
United Airlines

05/12/25

ORD
5h 42m
Direct

05/12/25

PUJ
$424
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/10/25

PUJ
18h 14m
JFK

05/11/25

ORD
American Airlines Logo
American Airlines

05/17/25

ORD
18h
JFK

05/18/25

PUJ
$427
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

05/08/25

PUJ
7h 21m
MCO

05/08/25

ORD
Spirit Airlines Logo
Spirit Airlines

05/12/25

ORD
9h 12m
FLL

05/12/25

PUJ
$444
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/20/25

PUJ
4h 5m
Direct

05/20/25

ORD
United Airlines Logo
United Airlines

05/27/25

ORD
15h 9m
IAD

05/28/25

PUJ
$447
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/13/25

PUJ
4h 5m
Direct

05/13/25

ORD
United Airlines Logo
United Airlines

05/27/25

ORD
9h 35m
EWR

05/27/25

PUJ
$447
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

06/10/25

PUJ
15h 54m
EWR

06/11/25

ORD
United Airlines Logo
United Airlines

06/24/25

ORD
5h 42m
Direct

06/24/25

PUJ
$454
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

06/06/25

PUJ
4h 6m
Direct

06/06/25

ORD
Frontier Airlines Logo
Frontier Airlines

06/20/25

ORD
5h 44m
Direct

06/20/25

PUJ
$455
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/14/25

PUJ
10h 53m
ATL

05/14/25

ORD
Delta Air Lines Logo
Delta Air Lines

05/28/25

ORD
9h 15m
ATL

05/28/25

PUJ
$465
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/09/25

PUJ
8h 31m
CLT

05/10/25

ORD
American Airlines Logo
American Airlines

05/16/25

ORD
17h 40m
PHL

05/17/25

PUJ
$472
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/05/25

PUJ
9h 55m
IAH

05/06/25

ORD
United Airlines Logo
United Airlines

05/12/25

ORD
17h 35m
IAH

05/13/25

PUJ
$475
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

06/06/25

PUJ
7h 32m
PHL

06/06/25

MDW
Frontier Airlines Logo
Frontier Airlines

06/06/25

MDW
13h 39m
MCO

06/07/25

PUJ
$479
Free cancellation within 83 hours of booking
COPA Airlines Logo
COPA Airlines

06/10/25

PUJ
23h 51m
PTY

06/11/25

ORD
COPA Airlines Logo
COPA Airlines

06/24/25

ORD
11h 6m
PTY

06/25/25

PUJ
$480
Free cancellation within 83 hours of booking
JetBlue Logo
JetBlue

06/10/25

PUJ
15h 20m
BOS

06/11/25

ORD
JetBlue Logo
JetBlue

06/24/25

ORD
10h 15m
JFK

06/24/25

PUJ
$492
Free cancellation within 83 hours of booking
COPA Airlines Logo
COPA Airlines

05/30/25

PUJ
10h 40m
PTY

05/31/25

ORD
COPA Airlines Logo
COPA Airlines

06/13/25

ORD
11h 6m
PTY

06/14/25

PUJ
$498
Free cancellation within 83 hours of booking
JetBlue Logo
JetBlue

05/14/25

PUJ
10h 28m
JFK

05/14/25

ORD
JetBlue Logo
JetBlue

05/28/25

ORD
9h 18m
JFK

05/28/25

PUJ
$508
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

06/29/25

PUJ
12h 15m
TPA

06/29/25

MDW
Frontier Airlines Logo
Frontier Airlines

07/13/25

MDW
7h 50m
ATL

07/13/25

PUJ
$515
Free cancellation within 83 hours of booking
JetBlue Logo
JetBlue

05/24/25

PUJ
15h 20m
BOS

05/25/25

ORD
JetBlue Logo
JetBlue

06/07/25

ORD
9h 21m
JFK

06/07/25

PUJ
$527
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

06/22/25

PUJ
12h 15m
TPA

06/22/25

MDW
Frontier Airlines Logo
Frontier Airlines

07/06/25

MDW
7h 50m
ATL

07/06/25

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

06/10/25

PUJ
18h 30m
YYZ

06/11/25

ORD
Air Canada Logo
Air Canada

06/24/25

ORD
18h 55m
YYZ

06/25/25

PUJ
$620
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

06/18/25

PUJ
22h 39m
YYZ

06/19/25

ORD
Air Canada Logo
Air Canada

07/02/25

ORD
30h 41m
YYZ

07/03/25

PUJ
$663
Free cancellation within 83 hours of booking

Top Deals on flights from Punta Cana to Chicago

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

Frontier Airlines Logo
Frontier Airlines

May 16

PUJ
4h 3m
Direct

May 16

ORD

as low as

$131

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

Spirit Airlines Logo
Spirit Airlines

Jun 4

PUJ
7h 42m
FLL

Jun 4

ORD

as low as

$166

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

Spirit Airlines Logo
Spirit Airlines

May 23

PUJ
7h 21m
MCO

May 23

ORD

as low as

$178

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

American Airlines Logo
American Airlines

Jun 4

PUJ
9h 43m
PHL

Jun 4

ORD

as low as

$179

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

American Airlines Logo
American Airlines

May 30

PUJ
8h 31m
CLT

May 31

ORD

as low as

$179

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

American Airlines Logo
American Airlines

Jun 10

PUJ
21h 32m
JFK

Jun 11

ORD

as low as

$186

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

United Airlines Logo
United Airlines

Jun 11

PUJ
4h 5m
Direct

Jun 11

ORD

as low as

$199

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

Frontier Airlines Logo
Frontier Airlines

Jun 1

PUJ
12h 15m
TPA

Jun 1

MDW

as low as

$248

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

Frontier Airlines Logo
Frontier Airlines

Jun 6

PUJ
7h 51m
ATL

Jun 6

MDW

as low as

$248

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

Frontier Airlines Logo
Frontier Airlines

May 25

PUJ
10h 15m
MCO

May 25

MDW

as low as

$248

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

COPA Airlines Logo
COPA Airlines

Jun 5

PUJ
20h 36m
PTY

Jun 6

ORD

as low as

$249

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

United Airlines Logo
United Airlines

May 16

PUJ
14h 48m
EWR

May 17

ORD

as low as

$278

Frequently Asked Questions

What is the typical flight duration from Punta Cana to Chicago?
The typical flight duration between Punta Cana and Chicago generally ranges from 5 to 7 hours when considering connecting flights. Although direct flights, when available, might take closer to 4 to 5 hours, most journeys involve layovers which can extend travel time. It is advisable to arrive at the airport at least 2 hours early, as additional time is needed for boarding and security checks. Flight durations can vary based on the airline, weather conditions, and the specific route taken, so always check the latest schedule details.
Are there any direct flights from Punta Cana to Chicago?
Yes, direct flights from Punta Cana to Chicago do exist occasionally, though they are often seasonal and offered by a limited number of carriers. These non-stop options are generally the fastest and most convenient choice. Many travelers planning this route benefit from monitoring airline announcements or using travel comparison tools to catch these limited opportunities. In the event that a direct flight is not available, well-coordinated connecting flights provide a reliable alternative, albeit with slightly longer travel times.
What are the best transportation options from Chicago airport to downtown?
Chicago offers several convenient transportation options from its airports to downtown. The CTA train is a popular choice with fares ranging from $5 to $10 and travel times of about 30 to 45 minutes. Additionally, ride-sharing services such as Uber or Lyft typically cost between $20 to $40, depending on traffic conditions and exact locations. Taxis are another alternative, but can be pricier. For a balance of cost and convenience, compare these options before departure to select the best match for your travel schedule.
What are the must-see attractions in Chicago for travelers arriving from Punta Cana?
Chicago boasts a wide array of attractions that cater to diverse interests. Iconic landmarks include Millennium Park, the Art Institute, and Navy Pier, each offering distinctive cultural and scenic experiences. Additionally, a river architecture boat tour provides a unique view of the city's skyline and history. For travelers interested in museums, the Field Museum and Museum of Science and Industry offer intriguing displays. Planning an itinerary around these spots ensures a memorable visit, with each location serving as a gateway to understanding the city’s rich heritage.
What are the most affordable dining options in Chicago for travelers from Punta Cana?
Chicago’s dining scene is both diverse and affordable for visitors from Punta Cana. Budget-friendly options include local diners and neighborhood eateries where meals can typically range from $10 to $20 per person. Enjoy regional specialties such as deep-dish pizza or try ethnic cafes offering Latin American flavors. Food trucks and street vendors scattered across popular areas provide quick and delicious bites for about $5 to $10. For those on a tight budget, exploring lunch specials or local markets can yield great meals without compromising on quality or experience.
Is there a specific time of year when Chicago is best visited by travelers from Punta Cana?
Yes, many travelers find late spring through early fall to be the most ideal time to visit Chicago. During these seasons, temperatures tend to be moderate, typically ranging between 55°F to 75°F, which is comfortable for sightseeing. Moreover, the city hosts a variety of outdoor events and festivals during these months. While summer offers vibrant street life, it can be busy, and winter may bring colder conditions. Therefore, planning a visit during the shoulder seasons can provide a balance of pleasant weather, fewer crowds, and a chance to experience local happenings.
What are the top cultural experiences in Chicago for visitors from Punta Cana?
Chicago is rich in cultural experiences that cater to travelers from Punta Cana. The city’s museums, such as the Field Museum, the Art Institute, and the Museum of Science and Industry, provide dynamic exhibits and historical insights. Neighborhoods like Pilsen add a vibrant Latin cultural influence with street art and local cuisine. Additionally, live performance venues hosting jazz, blues, and theatre reveal the city’s artistic heartbeat. Consider booking guided tours for a more contextual understanding of these attractions, and check local listings to time your visits with cultural festivals or special exhibits.
What are the best family-friendly activities in Chicago for travelers arriving from Punta Cana?
Chicago presents an assortment of activities that cater to families. Interactive destinations like the Museum of Science and Industry and the Shedd Aquarium engage both adults and children with hands-on exhibits and educational displays. Expansive green spaces such as Millennium Park and Maggie Daley Park offer outdoor recreation, while Navy Pier features rides and kid-friendly attractions. To maximize convenience and budget, consider purchasing a city pass covering multiple attractions. Each environment is designed to entertain and educate, ensuring an enjoyable experience for family travelers seeking both fun and cultural enrichment.
Are there any local events or festivals in Chicago that travelers from Punta Cana should not miss?
Chicago’s calendar is filled with energetic festivals and events ideal for travelers from Punta Cana. Annual celebrations like Taste of Chicago and the Chicago Air and Water Show offer rich experiences through food, music, and spectacular displays. Cultural neighborhood festivals, particularly in areas like Pilsen and Little Italy, highlight local traditions and diverse communities. These events generally occur during the summer and early fall, creating festive atmospheres throughout the city. It is recommended to review local event listings ahead of time to align your visit with these celebrations and enjoy immersive local experiences.
What are the customs requirements for travelers flying from Punta Cana to Chicago?
Yes, when flying from Punta Cana to Chicago, customs requirements must be met as it is an international journey. Travelers will need to present a valid passport along with any required visas or travel authorizations upon entry into the United States. Forms provided during the flight need to be completed accurately, often including a declaration of items being brought into the country. It is essential to review the latest guidelines provided by U.S. Customs and Border Protection prior to travel. This preparation helps ensure a smooth entry process and avoids unexpected delays at immigration.
What are the best shopping areas in Chicago for travelers from Punta Cana?
Chicago boasts several top shopping districts appealing to travelers from Punta Cana. The Magnificent Mile provides a high-end retail experience with a range of luxury and mainstream stores where products span from $25 to several hundred dollars. For more eclectic tastes, neighborhoods like Wicker Park and Logan Square offer charming boutiques, vintage shops, and artisan markets. These areas not only provide diverse merchandise but also capture the local culture. Planning a day around these shopping hubs allows for a mix of browsing, dining, and cultural exploration, ensuring an enjoyable retail experience.
What health precautions should travelers from Punta Cana consider before visiting Chicago?
Before traveling from Punta Cana to Chicago, it is wise to take several health precautions. Make sure routine vaccinations, including those for the flu and tetanus, are up to date. Considering travel insurance that covers medical emergencies is advisable, with estimated costs ranging between $50 to $100 per week depending on coverage. Carry essential medications and a small first-aid kit, particularly if you have specific health needs. Check local health advisories and weather conditions, as Chicago’s climate can vary greatly. Preparing in advance ensures a smoother and safer travel experience.
Are there any budget-friendly hotels in Chicago for visitors from Punta Cana?
Yes, Chicago offers a variety of budget-friendly accommodations suitable for travelers from Punta Cana. Affordable options can range from $80 to $150 per night depending on the area and season. Neighborhoods in the Loop and near O’Hare often provide access to economical hotels with basic but comfortable amenities. Booking early or using discount travel websites may secure even better rates. Researching recent guest reviews can also help ensure that the hotel meets your expectations in terms of cleanliness and service, making your stay both cost-effective and pleasant.
What unique airport amenities are available in Chicago for travelers arriving from Punta Cana?
Chicago’s airports provide several unique amenities designed to enhance the traveler experience. Modern lounges equipped with comfortable seating, free high-speed Wi-Fi, and a variety of dining options are available. Retail outlets and art installations reflecting the local culture create an inviting atmosphere. Additionally, many terminals offer multilingual information desks and designated relaxation zones, which are particularly useful during transit. These features help minimize the stress of travel and allow passengers to enjoy a seamless, convenient arrival experience. Checking the airport’s official app can also provide real-time updates on services and amenities.
What are the best solo travel activities in Chicago for travelers arriving from Punta Cana?
Solo travelers in Chicago can relish a wide range of engaging activities that foster both exploration and introspection. Walking tours through vibrant neighborhoods allow for personal discovery of local history and architecture. Cultural landmarks like the Art Institute and the Field Museum offer enriching experiences, often enhanced by self-guided audio tours. Local cafes, bookstores, and parks provide ideal spots for relaxation and reflection. Additionally, public transport offers a convenient way to navigate between attractions, making it easy to craft a flexible itinerary. Embracing local tours and events can also provide opportunities to connect with the city’s dynamic cultural scene.

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