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Flight Deals from Punta Cana to Chicago O Hare Airport from $131

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Stops

  • Nonstop
    from $271
  • Up to 1 stop
    $359

Airlines

  • Aeromexico
    $902
  • Air Canada
    $705
  • American Airlines
    $455
  • AVIANCA
    $773
  • COPA Airlines
    $577
  • Delta Air Lines
    $359
  • Frontier Airlines
    $271
  • JetBlue
    $496
  • Spirit Airlines
    $699
  • United Airlines
    $366

Cabin Class

  • Economy
    $271

Departure Airports

  • Punta Cana International Airport
    $271

Arrival Airports

  • Chicago O Hare Airport
    $271

Layover Airports

  • Charlotte Douglas International Airport
    $455
  • Detroit Metropolitan Airport
    $603
  • El Dorado International Airport
    $773
  • Fort Lauderdale Hollywood International Airport
    $699
  • General Edward Lawrence Logan International Airport
    $618
  • George Bush Intercontinental Houston Airport
    $449
  • Hartsfield Jackson Atlanta International Airport
    $359
  • Licenciado Benito Juarez International Airport
    $902
  • Miami International Airport
    $455
  • Montreal Trudeau Airport
    $705
  • New York John F Kennedy Airport
    $496
  • Newark Liberty Airport
    $406
  • Philadelphia International Airport
    $476
  • Tocumen International Airport
    $577
  • Toronto Pearson Airport
    $705
  • Washington Dulles Airport
    $393

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Frontier Airlines Logo
Frontier Airlines

08/01/25

PUJ
4h 8m
Direct

08/01/25

ORD
Frontier Airlines Logo
Frontier Airlines

08/15/25

ORD
5h 40m
Direct

08/15/25

PUJ
$271
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

07/23/25

PUJ
8h 24m
ATL

07/23/25

ORD
Delta Air Lines Logo
Delta Air Lines

08/06/25

ORD
7h 51m
ATL

08/06/25

PUJ
$359
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

07/23/25

PUJ
4h 5m
Direct

07/23/25

ORD
United Airlines Logo
United Airlines

08/06/25

ORD
5h 42m
Direct

08/06/25

PUJ
$366
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

07/22/25

PUJ
7h 53m
ATL

07/23/25

ORD
Delta Air Lines Logo
Delta Air Lines

08/05/25

ORD
7h 51m
ATL

08/05/25

PUJ
$387
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

07/23/25

PUJ
15h 14m
IAD

07/24/25

ORD
United Airlines Logo
United Airlines

08/06/25

ORD
5h 42m
Direct

08/06/25

PUJ
$393
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

07/29/25

PUJ
15h 23m
EWR

07/30/25

ORD
United Airlines Logo
United Airlines

08/12/25

ORD
5h 42m
Direct

08/12/25

PUJ
$406
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

07/31/25

PUJ
4h 8m
Direct

07/31/25

ORD
Frontier Airlines Logo
Frontier Airlines

08/14/25

ORD
5h 40m
Direct

08/14/25

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

07/25/25

PUJ
6h 55m
IAD

07/25/25

ORD
United Airlines Logo
United Airlines

08/08/25

ORD
5h 42m
Direct

08/08/25

PUJ
$425
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

07/31/25

PUJ
4h 5m
Direct

07/31/25

ORD
United Airlines Logo
United Airlines

08/14/25

ORD
18h 25m
IAH

08/15/25

PUJ
$449
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

07/22/25

PUJ
16h 52m
MIA

07/23/25

ORD
American Airlines Logo
American Airlines

08/05/25

ORD
10h 35m
CLT

08/05/25

PUJ
$455
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

08/11/25

PUJ
15h 40m
PHL

08/12/25

ORD
American Airlines Logo
American Airlines

08/25/25

ORD
5h 40m
Direct

08/25/25

PUJ
$476
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

07/23/25

PUJ
15h 14m
IAD

07/24/25

ORD
United Airlines Logo
United Airlines

08/06/25

ORD
9h 25m
IAH

08/06/25

PUJ
$481
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

07/31/25

PUJ
4h 4m
Direct

07/31/25

ORD
American Airlines Logo
American Airlines

08/14/25

ORD
8h 40m
CLT

08/14/25

PUJ
$491
Free cancellation within 83 hours of booking
JetBlue Logo
JetBlue

07/23/25

PUJ
12h 18m
JFK

07/23/25

ORD
JetBlue Logo
JetBlue

08/06/25

ORD
12h 6m
JFK

08/06/25

PUJ
$496
Free cancellation within 83 hours of booking
JetBlue Logo
JetBlue

08/05/25

PUJ
12h 18m
JFK

08/05/25

ORD
JetBlue Logo
JetBlue

08/19/25

ORD
12h 6m
JFK

08/19/25

PUJ
$496
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

08/11/25

PUJ
15h 40m
PHL

08/12/25

ORD
American Airlines Logo
American Airlines

08/25/25

ORD
8h 5m
MIA

08/25/25

PUJ
$501
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

08/13/25

PUJ
4h 5m
Direct

08/13/25

ORD
United Airlines Logo
United Airlines

08/27/25

ORD
9h 25m
EWR

08/27/25

PUJ
$502
Free cancellation within 83 hours of booking
COPA Airlines Logo
COPA Airlines

07/29/25

PUJ
20h 31m
PTY

07/30/25

ORD
COPA Airlines Logo
COPA Airlines

08/12/25

ORD
9h 43m
PTY

08/12/25

PUJ
$577
Free cancellation within 83 hours of booking
COPA Airlines Logo
COPA Airlines

08/05/25

PUJ
30h 41m
PTY

08/06/25

ORD
COPA Airlines Logo
COPA Airlines

08/19/25

ORD
9h 43m
PTY

08/19/25

PUJ
$577
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

07/19/25

PUJ
17h 19m
DTW

07/20/25

ORD
Delta Air Lines Logo
Delta Air Lines

08/02/25

ORD
10h 15m
ATL

08/02/25

PUJ
$603
Free cancellation within 83 hours of booking
JetBlue Logo
JetBlue

08/07/25

PUJ
28h 56m
BOS

08/08/25

ORD
JetBlue Logo
JetBlue

08/21/25

ORD
12h 6m
JFK

08/21/25

PUJ
$618
Free cancellation within 83 hours of booking
JetBlue Logo
JetBlue

07/29/25

PUJ
28h 56m
BOS

07/30/25

ORD
JetBlue Logo
JetBlue

08/12/25

ORD
12h 6m
JFK

08/12/25

PUJ
$618
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

08/09/25

PUJ
16h 20m
FLL

08/10/25

ORD
Spirit Airlines Logo
Spirit Airlines

08/23/25

ORD
9h 29m
FLL

08/23/25

PUJ
$699
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

07/21/25

PUJ
17h 9m
YYZ

07/22/25

ORD
Air Canada Logo
Air Canada

08/04/25

ORD
28h 45m
YUL

08/05/25

PUJ
$705
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

07/22/25

PUJ
18h 19m
YYZ

07/23/25

ORD
Air Canada Logo
Air Canada

08/05/25

ORD
18h 55m
YYZ

08/06/25

PUJ
$706
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

08/05/25

PUJ
16h 44m
YYZ

08/06/25

ORD
Air Canada Logo
Air Canada

08/19/25

ORD
23h 17m
YUL

08/20/25

PUJ
$736
Free cancellation within 83 hours of booking
AVIANCA Logo
AVIANCA

08/13/25

PUJ
19h 35m
BOG

08/14/25

ORD
AVIANCA Logo
AVIANCA

08/27/25

ORD
20h 5m
BOG

08/28/25

PUJ
$773
Free cancellation within 83 hours of booking
AVIANCA Logo
AVIANCA

08/05/25

PUJ
19h 35m
BOG

08/06/25

ORD
AVIANCA Logo
AVIANCA

08/19/25

ORD
20h 5m
BOG

08/20/25

PUJ
$773
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

07/19/25

PUJ
16h 20m
FLL

07/20/25

ORD
Spirit Airlines Logo
Spirit Airlines

08/02/25

ORD
11h 24m
FLL

08/02/25

PUJ
$818
Free cancellation within 83 hours of booking
Aeromexico Logo
Aeromexico

08/13/25

PUJ
21h 19m
MEX

08/14/25

ORD
Aeromexico Logo
Aeromexico

08/27/25

ORD
23h 25m
MEX

08/28/25

PUJ
$902
Free cancellation within 83 hours of booking

Top Deals on flights from Punta Cana to Chicago O Hare Airport

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 29

PUJ
7h 21m
MCO

May 29

ORD

as low as

$178

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 4

PUJ
9h 43m
PHL

Jun 4

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)

COPA Airlines Logo
COPA Airlines

Jun 5

PUJ
23h 51m
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

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

United Airlines Logo
United Airlines

May 23

PUJ
12h 3m
IAH

May 24

ORD

as low as

$278

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

United Airlines Logo
United Airlines

Jun 4

PUJ
15h 27m
IAD

Jun 5

ORD

as low as

$284

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

Delta Air Lines Logo
Delta Air Lines

May 31

PUJ
7h 7m
ATL

May 31

ORD

as low as

$298

Frequently Asked Questions

What is the typical flight duration from Punta Cana to Chicago?
Typically, the flight duration between Punta Cana and Chicago ranges from 6 to 9 hours. Direct flights, when available, may take closer to 5-6 hours, but most itineraries include one or more layovers, extending travel time. Factors like airline scheduling, weather conditions, and transit procedures can further influence the duration. For the best experience, check multiple options and reviews, and consider travel times when planning your journey between these two vibrant cities.
Are there any direct flights from Punta Cana to Chicago O'Hare Airport?
Direct flights between Punta Cana and Chicago O'Hare Airport are not very common and tend to appear only during peak seasons or as promotional offerings. Most itineraries require at least one stopover, resulting in a longer total journey. It’s advisable to research current flight schedules and use flight comparison tools to monitor available direct connections. Travelers should also consider signing up for alerts or checking with multiple airlines to secure the most convenient option during the desired travel period.
What are the best transportation options from Chicago O'Hare Airport to downtown Chicago?
Travelers arriving at Chicago O'Hare Airport have several efficient transportation options to reach downtown Chicago. One popular choice is the CTA Blue Line, costing between $5 and $10 and taking approximately 30 to 45 minutes. Taxis and rideshare services offer another convenient option, with fares typically ranging from $30 to $50 depending on traffic and time of day. Additionally, airport shuttles and rental car services are available. Each option provides a balance of cost, convenience, and travel time based on personal preferences and schedules.
What are the must-see attractions in Chicago for travelers arriving from Punta Cana?
For travelers from Punta Cana, Chicago offers an abundance of must-see attractions blending art, culture, and urban charm. Iconic sites include Millennium Park, Navy Pier, and the Art Institute of Chicago, where history and contemporary exhibitions meet. The Magnificent Mile provides a bustling shopping and dining experience, while architecture tours reveal the city’s renowned skyline. Exploring diverse neighborhoods also offers local culinary experiences and street art. Each attraction delivers an immersive view of Chicago’s cultural mix and vibrant city life.
Which local dishes should travelers from Punta Cana try when visiting Chicago?
Visitors from Punta Cana should indulge in Chicago’s distinctive culinary offerings that contrast with Caribbean flavors. Signature dishes include deep-dish pizza with its hearty, cheesy base, Italian beef sandwiches loaded with savory juices, and Chicago-style hot dogs garnished with unique toppings. Exploring neighborhoods like Pilsen or Wicker Park can introduce you to local fusion cuisine and artisanal treats. These dining experiences offer an authentic taste of Chicago’s diverse food scene, making each meal both a culinary adventure and a chance to appreciate the city’s vibrant culture.
What are the best family-friendly activities in Chicago for visitors from Punta Cana?
Chicago offers numerous family-friendly activities that cater to various interests. Notable attractions include interactive experiences at the Museum of Science and Industry, the captivating exhibits at the Shedd Aquarium, and animal encounters at Lincoln Park Zoo. Outdoor spaces like Grant Park and Maggie Daley Park provide ample room for play and relaxation. These venues offer an engaging blend of education, culture, and outdoor fun. Families can also explore local neighborhoods, enjoy seasonal festivals, and sample diverse cuisine, ensuring that visitors from Punta Cana have a varied and memorable experience.
Are there any budget-friendly hotels in Chicago for travelers from Punta Cana?
Yes, Chicago provides several budget-friendly hotel options suitable for travelers from Punta Cana. In many neighborhoods near downtown, accommodations range from $100 to $200 per night depending on the season and booking time. Options include well-known chains offering essential amenities as well as boutique hotels tailored for cost-conscious visitors. It’s advisable to use online platforms for reviews and to check for special deals or discounts. Booking during off-peak times can further secure lower rates while still offering convenient access to the city’s major attractions.
What are the customs requirements for travelers flying from Punta Cana to Chicago?
Travelers flying from Punta Cana to Chicago should be prepared to comply with U.S. customs and immigration procedures. All passengers must present a valid passport along with a visa or an approved ESTA under the Visa Waiver Program when eligible. Additionally, it might be necessary to provide details such as proof of onward travel, travel itinerary, or financial resources. Given occasional updates to protocols, it is important to review the latest U.S. customs guidelines before departure to ensure a smooth arrival and to avoid any last-minute complications during your travel between these destinations.
What are the top cultural experiences in Chicago for visitors from Punta Cana?
Chicago’s rich cultural tapestry offers visitors a robust and engaging experience. Highlights include a visit to the Art Institute for an extensive collection of artworks, live theater performances in noted districts, and engaging architectural tours that showcase landmark buildings. Neighborhood festivals and local art scenes provide further insight into the city’s dynamic heritage. For those traveling from Punta Cana, these experiences strike a balance between modern urban life and historical traditions, offering cultural immersion that is both authentic and educational. Advance bookings for tours and events are often recommended.
Is there a specific time of year when Chicago is best visited by travelers from Punta Cana?
Yes, the optimal time to visit Chicago largely depends on your preferences. The city's late spring through early fall, roughly May to September, offers pleasant weather, open-air festivals, and numerous cultural events that enhance the visitor experience. However, winter bring its own charm with festive holiday markets and indoor events, though temperatures drop and snow can impact travel. Consider the type of activities you enjoy and check event calendars ahead of time. This timeframe advice ensures travelers from Punta Cana can plan a visit that best suits their interests and comfort levels.
What are the best shopping areas in Chicago for travelers from Punta Cana?
Chicago boasts a wide range of shopping experiences that cater to diverse tastes. The Magnificent Mile is famous for upscale retail stores and luxury brands, while areas like Wicker Park and the South Loop offer unique boutiques and vintage stores. Additionally, seasonal street fairs and flea markets provide opportunities to discover local art, handmade crafts, and one-of-a-kind souvenirs. For travelers from Punta Cana looking for both high-end and affordable options, these shopping districts present a well-rounded blend of contemporary fashion, local craftsmanship, and potentially great bargains.
What health precautions should travelers from Punta Cana consider before visiting Chicago?
Travelers heading from Punta Cana to Chicago should prepare by ensuring all routine vaccinations, such as influenza and tetanus, are up-to-date. Given Chicago’s varying seasonal weather and urban settings, carrying adequate medications and travel health insurance is advisable. It is also important to practice good hygiene and be aware of local advisories, especially during colder months when respiratory illnesses are more prevalent. Additionally, consider checking water quality in public venues and having a small first-aid kit available. Consulting with a healthcare professional prior to travel can further tailor precautions to personal health needs.
Are there any seasonal events in Chicago that travelers from Punta Cana should not miss?
Chicago hosts an array of seasonal events that offer enriching experiences for visitors from Punta Cana. During the summer, events like Taste of Chicago and outdoor concerts create festive atmospheres, while winter features holiday markets, ice skating rinks, and vibrant light displays. Spring and fall typically bring art festivals, food fairs, and local parades that highlight the city’s diverse culture. These events often draw large crowds and offer unique local flavors, so planning ahead and purchasing tickets early may enhance your overall experience. Checking an event calendar before arrival is highly recommended.
What are the best solo travel activities in Chicago for travelers arriving from Punta Cana?
Solo travelers can embrace a variety of activities in Chicago that foster both self-discovery and social interactions. Exploring cultural districts, such as those hosting museums and independent art galleries, offers enriching experiences. City tours focusing on architectural history or local cuisine are also popular and provide opportunities to meet other travelers. Additionally, the city’s café culture and public parks present ideal settings for reflective time or casual encounters. Utilizing efficient public transport and joining group events can enhance safety and connectivity, ensuring visitors from Punta Cana enjoy a balanced, engaging, and independent travel experience.
What unique airport amenities can travelers expect at Chicago O'Hare Airport?
Chicago O'Hare Airport features numerous modern amenities designed to elevate the travel experience. Visitors can expect comfortable lounges, an array of dining choices—from quick service to sit-down restaurants—and diverse retail outlets offering essentials and souvenirs. Free Wi-Fi, charging stations, and digital information boards are scattered throughout the terminals. The airport also showcases art installations reflecting local culture and may offer spa services or quiet zones for relaxation. These amenities ensure that transitioning between flights or waiting for luggage is as pleasant as possible for fellow travelers coming from Punta Cana.

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