CHI - PUJ

$162 Find Cheap Flights from Chicago to Punta Cana - Compare and Save

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Everything you should know

Cheapest round-trip
$346
Typical prices: $407-$723
Arajet
Wed 10/24Wed 10/31
ORD - PUJ • Non-stop
Cheapest one-way
$162
Typical prices: $181-$360
Arajet
Wed 9/26
ORD - PUJ • Non-stop
Nonstop flights
You can fly direct with American Airlines, United Airlines and Arajet. Average duration is 4h 42m
Direct flights
+1
Direct flights
+1
Top routes
Cheapest • 8% average savings
Most popular
Insights
Insights
Avoid delays
Most punctual • 82% on-time
Best time • Fewest delays
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 19% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 25% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $336 (round-trip)
Shortest trip • 7h 18m (one-way)
Insights
Insights
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We hope you love your trip to Punta Cana!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Chicago to Punta Cana (CHI-PUJ)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Punta Cana

Sat, Oct 24 - Sat, Oct 31
Arajet Logo
12:12 pm - 5:57 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 45mnonstop
Arajet Logo
5:47 am - 9:57 amPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 10mnonstop
$346Arajet
Fri, Nov 13 - Thu, Nov 19
Arajet Logo
5:45 am - 12:30 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 45mnonstop
Arajet Logo
7:30 pm - 10:40 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 10mnonstop
$347Arajet
Sun, Oct 25 - Thu, Oct 29
Multiple Airlines Logo
3:45 pm - 10:35 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
29h 50m1 stop Montreal Pierre Elliott Trudeau Intl
Multiple Airlines Logo
7:30 pm - 11:40 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 10mnonstop
$378Multiple Airlines
Fri, Oct 16 - Thu, Oct 22
Multiple Airlines Logo
2:00 pm - 4:05 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
49h 05m2 stops Toronto Island Montreal Pierre Elliott Trudeau Intl
Multiple Airlines Logo
7:30 pm - 11:40 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 10mnonstop
$378Multiple Airlines
Sun, Aug 30 - Sat, Sep 5
Frontier Logo
12:44 am - 7:19 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
17h 35m1 stop San Juan Luis Munoz Marin Intl
Frontier Logo
11:39 am - 11:27 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
12h 48m1 stop San Juan Luis Munoz Marin Intl
$386Frontier
Sat, Aug 29 - Sat, Sep 5
Frontier Logo
12:44 am - 7:19 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
17h 35m1 stop San Juan Luis Munoz Marin Intl
Frontier Logo
11:39 am - 11:27 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
12h 48m1 stop San Juan Luis Munoz Marin Intl
$391Frontier
Tue, Oct 27 - Tue, Nov 3
United Airlines Logo
9:17 am - 2:57 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 40mnonstop
United Airlines Logo
2:55 pm - 6:10 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 15mnonstop
$395United Airlines
Sun, Nov 15 - Sat, Nov 21
United Airlines Logo
7:38 am - 2:15 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 37mnonstop
United Airlines Logo
2:55 pm - 6:10 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 15mnonstop
$395United Airlines
Sun, Oct 25 - Sun, Nov 1
Air Canada Logo
3:45 pm - 5:45 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
25h 00m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
12:35 pm - 11:07 amPUJ  Punta Cana-ORD Chicago O'Hare Intl
24h 32m1 stop Montreal Pierre Elliott Trudeau Intl
$395Air Canada
Sat, Oct 24 - Sat, Oct 31
Air Canada Logo
8:45 am - 12:45 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
27h 00m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
6:45 pm - 3:52 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
22h 07m1 stop Montreal Pierre Elliott Trudeau Intl
$403Air Canada
Booking Insights

Price, demand and travel trends for Chicago to Punta Cana flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Chicago to Punta Cana with more confidence.

How much is a round-trip flight from Chicago to Punta Cana?

Round-trip flights from Chicago to Punta Cana start at $346. Prices are below average for this route right now, with typical round-trip fares ranging from $407 to $723. The lowest price found in the past 5 days was $346 on Arajet.

What is the cheapest Chicago to Punta Cana flight route?

Chicago O'Hare Intl Airport (ORD) to Punta Cana (PUJ) is the cheapest Chicago to Punta Cana route, averaging $551 round-trip. Other Chicago to Punta Cana routes average $619, based on KAYAK data over the past 12 months.

What's the cheapest day of the week to fly from Chicago to Punta Cana?

Monday is the cheapest day of the week to fly from Chicago to Punta Cana, it is 9% cheaper than the average day. Sunday is the most expensive day with flight prices 12% higher than average. Based on deals found by KAYAK users in the last 12 months.

What is the cheapest month to fly from Chicago to Punta Cana?

  • September is the cheapest month to fly from Chicago to Punta Cana at $417 round-trip.
  • June ($657) and March ($604) are the most expensive months.
  • The price difference between flying in the cheapest and most expensive months is 57% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are prices from Chicago to Punta Cana the cheapest?

Flights from Chicago to Punta Cana are cheapest 3 weeks before departure. Booking in this window typically costs about 19% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Expert advice

Expert advice for your flight from Chicago to Punta Cana

 
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Stefanie Waldek

Stefanie Waldek

Expert on United Airlines, Frontier and ORD

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Mark Chesnut

Mark Chesnut

Expert on PUJ

Mark Chesnut is a travel writer and public speaker with more than 30 years of experience. The 2019 winner of the NLGJA Excellence in Travel Writing Award, Mark is the author of the book “Prepare for Departure” and has covered air travel for multiple top consumer and trade media outlets.

Key details for Chicago to Punta Cana flights

Low season

September

Cheapest flight

$162
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly with an average 9% increase in price.
Flight from Chicago O'Hare Intl Airport to Punta Cana

When to book flights from Chicago to Punta Cana

Are your dates flexible? Find out the best times to travel from Chicago to Punta Cana based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Chicago to Punta Cana flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • Does Chicago Midway International Airport offer family services?

    Yes. If you’re traveling with your baby to Punta Cana, use the baby changing facilities in most washrooms or use the baby care room to breastfeed and a washing area at Concourse C. In most restaurants at MDW, kids have their menus and are also supplied with high chairs. The Family Lanes at MDW allows families with small children to go through the security checkpoint easily.

  • What are the transport options from Punta Cana International Airport?

    To get to Santa Domingo and other locations from PUJ are buses, airport transfer services, free hotel shuttles, car rentals, and taxi and ride apps. To get to Punta Cana from PUJ either use, the Punta Cana Airport shuttle that costs around RD$110 ($2) to around RD$810 ($15) for a 7min ride, taxis that charge around RD$1080 ($20), a taxi that costs around RD$400 ($8) or car rentals that cost around RD$1080 ($20) per day.

  • Does Punta Cana International Airport have accessible services?

    PUJ is well equipped to cater to the needs of travelers with disabilities and special needs. Wheelchair users receive VIP treatment at PUJ through priority check-in upon request and dedicated queues for wheelchair users at the Arrivals area and Departures area. The airport has access ramps all over to ensure wheelchair users in PUJ have an easy time navigating the airport.

  • Where can I sleep at Punta Cana International Airport?

    PUJ allows customers to sleep within the terminals like Terminals A and B, on benches, and on the grass. For undisturbed sleep, book a room at nearby hotels like Four Points by Sheraton.

  • Which airlines offer extra legroom and free seat selection on Chicago to Punta Cana flights?

    Among airlines operating Chicago to Punta Cana flights:

    • Arajet: offers extra legroom; offers free seat selection
    • United Airlines: offers extra legroom; offers free seat selection
    • American Airlines: offers extra legroom; offers free seat selection
    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • What airlines are available from Chicago to Punta Cana?

    3 airlines operate flights between Chicago and Punta Cana. The airlines offering nonstop flights on this route include:
    • American Airlines
    • United Airlines
    • Arajet

  • Which airports can I use when flying from Chicago to Punta Cana?

    Flights from Chicago to Punta Cana may depart from several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD). Flights usually arrive at Punta Cana (PUJ).

  • Which airlines include bags at no extra cost on Chicago to Punta Cana flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • United Airlines: a cabin bag and a checked bag in Economy Class
    • American Airlines: a cabin bag and a checked bag in Economy Class
    • Hahn Air: a cabin bag and a checked bag in Economy Class

    Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

  • What cabin classes can I book on flights from Chicago to Punta Cana?

    Three cabin classes are available on flights from Chicago to Punta Cana:

    • Economy Class
    • Premium Economy Class
    • Business Class

  • How much can I save by taking a layover when flying from Chicago to Punta Cana?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $336 round-trip via Boston Logan Intl (BOS), compared to $556 for nonstop.

  • What is the standard checked-bag allowance on flights from Chicago to Punta Cana?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $25–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which airports do connecting flights from Chicago to Punta Cana pass through?

    One-stop flights from Chicago to Punta Cana most commonly connect through:

    • Atlanta Hartsfield-Jackson (ATL) - 17% of one-stop connections
    • Fort Lauderdale (FLL) - 16% of one-stop connections
    • New York John F Kennedy Intl (JFK) - 15% of one-stop connections
    • Chicago O'Hare Intl (ORD) - 12% of one-stop connections

    Atlanta Hartsfield-Jackson (ATL) handles the largest share of one-stop connections on this route.

  • Can I save money by using flexible dates for flights from Chicago to Punta Cana?

    Yes. Being flexible with your travel dates can save you up to 19% on the Chicago to Punta Cana route. Monday is the cheapest departure day at $508 round-trip on average, while Sunday is the most expensive at $622, a difference of $114. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • At what point is a flight considered delayed from Chicago to Punta Cana?

    A flight is considered delayed when it departs 15 minutes or more after its scheduled time. This is the standard used by the US Department of Transportation and most airline industry reporting. On the Chicago to Punta Cana route, 22% of flights were delayed in the past 3 months, with delays averaging 2 hours 18 minutes.

  • How are flight departures from Chicago to Punta Cana spread across the day?

    Morning is the busiest departure period on Chicago to Punta Cana flights, with 100% of flights leaving in that window. Afternoon departures account for 0%, evening flights for 0%, and night flights for 0%.

  • What popular places can I visit in Punta Cana?

    Some of the most popular sights in Punta Cana are Catalonia Caribe Golf Club, Playa Juanillo and Punta Espada Golf Course. These are among the most viewed places in Punta Cana on KAYAK.

  • How long is a flight from Chicago to Punta Cana?

    A nonstop flight from Chicago to Punta Cana takes 4h 42m, covering 1,967 miles.

  • What are the earliest and latest flights from Chicago to Punta Cana?

    These are the earliest and latest flight times available from Chicago to Punta Cana:

    • Earliest: departs at 3:20 am and lands at 8:02 am
    • Latest: departs at 12:12 pm and lands at 4:54 pm.

    The flight takes about 4h 42m.

  • How expensive are last-minute Chicago to Punta Cana flights?

    Last-minute fares on this route - booked within 2 weeks of departure - run 3% above the route average of $554. Book 3 weeks before departure for the lowest fares.

  • Do I need a passport to fly from Chicago to Punta Cana?

    Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

  • How are flight prices from Chicago to Punta Cana looking right now?

    One-way fares from Chicago to Punta Cana are currently lower than usual. Average one-way flight prices are about $170, which is 34% below the typical average for this route.

  • How does American Airlines’s on-time performance compare to other airlines on Chicago to Punta Cana flights?

    American Airlines is slightly above the route average for timely arrivals, while United Airlines has a lower on-time arrival rate. On-time arrival rates on Chicago to Punta Cana flights are:

    • American Airlines: 82% on time
    • United Airlines: 81% on time
    • Frontier: 71% on time

    Overall, flights on this route are on time 78% of the time on average.

  • How do delay rates compare for morning and evening flights from Chicago to Punta Cana?

    Morning flights have the fewest delays on this route. Delays tend to pile up throughout the day as one late flight pushes the next, so earlier departures are usually more reliable.

  • How much time can I save by choosing a different layover airport from Chicago to Punta Cana?

    Flying via Orlando (MCO) gives the shortest average 1-stop total travel time at 7h 18m, compared with 7h 28m via Washington, D.C. Dulles Intl (IAD) and 7h 29m via Charlotte Douglas (CLT).

  • What is the time difference between Chicago and Punta Cana?

    Punta Cana is 1 hour ahead of Chicago (Atlantic Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

  • What car rental options are available at Punta Cana Airport (PUJ)?

    Punta Cana Airport (PUJ) hosts 5 major car rental companies, with daily rates starting from around $3 for economy cars. Top options include:
    · Infinity Car Rental
    · Zezgo
    · Alamo
    · Routes Car & Truck Rentals
    · Europcar

  • How much should I expect to pay for a Chicago to Punta Cana flight?

    Round-trip flights from Chicago to Punta Cana range from $407 to $723, with an average of $554 over the past 12 months. Anything below $407 counts as a good deal.

  • Which airlines offer Wi-Fi on Chicago to Punta Cana flights?

    Two airlines offer in-flight Wi-Fi on Chicago to Punta Cana flights:

    • • American Airlines
    • • JetBlue

    Pricing varies by airline and fare class. Some plans are included with the ticket or loyalty program; others are paid add-ons priced by flight length.

Your guide to booking Chicago to Punta Cana flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates can be flexible, aim for a Monday departure instead of Sunday. On this route, Monday flights average $508 - about $114 less than Sunday (18% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 3 weeks before you fly. On this route, that window historically saves about 19% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Chicago to Punta Cana trip for September. Fares historically average $417 round-trip in that month - typically $240 less than the most expensive month, which is June (based on the last 12 months).
  • If arriving on time is high on your priority list, American Airlines is the strongest pick on this route. 82% of American Airlines flights from Chicago to Punta Cana arrived on time in the past 3 months, slightly above the route's average on-time arrival rate of 78%. When flights on this route do arrive late, the average delay is 2 hours 18 minutes, so choosing a carrier with strong on-time performance can make a difference on tight schedules.
  • If you have the time, taking a 1-stop flight through Boston Logan Intl Airport (BOS) can be cheaper than flying direct. The cheapest layover option averages $336 round-trip on this route - about $220 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Punta Cana Airport.
    - Four Points by Sheraton Puntacana Village
  • Chicago Midway International Airport (MDW) is one of the busiest airports in Chicago located 11 miles from downtown Chicago and consists of one two-leveled terminal at 3 concourses, Concourses A, B, and C. The two buildings at the airport are connected by a pedestrian bridge and the concourses are near each other hence no need for inter-terminal transport.
  • Chicago Midway International Airport caters to the potty needs of your pet by providing two pet relief areas within the airport. They are found outside the lower level(Baggage Claim) of the terminal building at the north end and in the concessions area on the path to Gate A4A.
  • The VIP Lounge at Punta Cana International Airport (PUJ) found on the 2nd floor of both Terminals A and B, Airside can be accessed by passengers in Punta Cana. Passengers either pay for a lounge pass or get an annual membership to get access to the lounges. Here, they can enjoy air conditioning, complimentary alcoholic drinks, refreshments, TV access, newspapers and magazines, and showers.
  • At Chicago Midway International Airport, there is a chapel at the Mezzanine Level of Concourse C with prayer rugs, books, and rosaries. Before their flight, passengers can go there to pray and calm their minds and spirits as they wait for departure.
  • Both Chicago Midway International Airport and Chicago O’Hare International Airport (ORD) have airlines that offer direct flights from Chicago to Punta Cana. ORD is bigger and busier than Midtown making it easier to get car rentals but has longer waiting times. MDW is closer to downtown Chicago, easier to get to, and is more preferred for domestic flights.

Prefer to fly direct from Chicago to Punta Cana?

 
Find which airlines fly direct from Chicago to Punta Cana Airport, which days they fly and book direct flights.

Direct departures

Chicago to Punta Cana

Monday

American Airlines,Arajet,United Airlines

American Airlines,Arajet, +1 more

Tuesday

American Airlines,United Airlines

American Airlines,United Airlines

Wednesday

American Airlines,United Airlines

American Airlines,United Airlines

Thursday

American Airlines,United Airlines

American Airlines,United Airlines

Friday

American Airlines,Arajet,United Airlines

American Airlines,Arajet, +1 more

Saturday

American Airlines,Arajet,United Airlines

American Airlines,Arajet, +1 more

Sunday

American Airlines,United Airlines

American Airlines,United Airlines

See more direct flights

Direct returns

Punta Cana to Chicago

Monday

American Airlines,United Airlines

American Airlines,United Airlines

Tuesday

American Airlines,United Airlines

American Airlines,United Airlines

Wednesday

American Airlines,United Airlines

American Airlines,United Airlines

Thursday

American Airlines,Arajet,United Airlines

American Airlines,Arajet, +1 more

Friday

American Airlines,United Airlines

American Airlines,United Airlines

Saturday

American Airlines,Arajet,United Airlines

American Airlines,Arajet, +1 more

Sunday

American Airlines,Arajet,United Airlines

American Airlines,Arajet, +1 more

See more direct flights

Everything you need to know for your flight from Chicago to Punta Cana

Information on your arrival and departure airports