Sample trip plan · a winter escape for two

Four ways to escape the Chicago winter

Thu, Feb 4 – Mon, Feb 8, 2027 · 4 nights 2 adults · from O’Hare All-inclusive Schedule a call(opens in a new tab)

This is a real trip plan I built for a couple this week, shared with their names removed. Want one built for you? Book a free 15-minute call.

A note from Troy

Sun, sand and maybe some whales.

This couple asked about Aruba and the Dominican Republic, flying from Chicago, so I priced both, plus Costa Rica and the whale trip to Samaná. Every option is all-inclusive, and the Punta Cana suites are in a private adults-only section. I chose nonstop flights wherever they exist.

Every option is priced the same way: 4 nights, Thursday February 4 to Monday February 8, with travel protection included. That first night usually goes to recovering from the travel day, so 4 nights gives you three full days in the sun. Pricing them all alike means you’re comparing apples to apples and seeing the real cost of the trip.

Troy HaleyTraveling Wahoo · Fora Travel advisor

Option 1 · Dominican Republic · Adults only

Punta Cana

The easiest trip of the four: nonstop flights from O’Hare, about 30 minutes from the airport, and big ocean-front suites in a private adults-only section.

Why this is my pick

I’ve walked this resort myself, more than once.

I’ve personally toured Paradisus Palma Real several times, and I don’t recommend places I haven’t seen with my own eyes. Here’s why it’s the best value on this page:

  • A real suite, right on the ocean. Even the starting suite is 517 sq ft and ocean front. Most resorts at this price give you a standard room with a partial view.
  • Adults-only, without giving anything up. The Reserve is its own private section with its own pool, beach area, lounge and concierge, inside a big resort with even more restaurants and bars.
  • Extras that cost money elsewhere. About $200 in spa, food and drink, and room-upgrade credits, 50% off golf, and free entry to the Fun Republic entertainment park.
  • Low risk. Free cancellation until January 28, and I book it directly with Meliá.
  • It books fast. Because it’s such a good deal, these suites sell out. Right now February 4–8 is the only stretch left, so if you like it, don’t wait.
  • Easy to get to. Nonstop from O’Hare and about 30 minutes to the resort, so you’re on the beach the day you land.
The Suite Ocean Front View bedroom and living area, looking out to the oceanThe view from the suite's balcony: beach, palm trees and turquoise water

Best value

The Reserve Suite Ocean Front

Paradisus Palma Real · Adults only · 517 sq ft

8.8 out of 10 on Expedia · 1,693 guest reviews

$3,870 for two

about $1,935 per person

An ocean-front suite with a king bed, sitting area and a bathroom with a freestanding tub. Same Reserve perks and resort credits. Free cancellation until January 28.

The Grand Suite Ocean Front at Paradisus Palma Real, with a king bed facing the beach and oceanThe Grand Suite's ocean-front terrace with an outdoor tub and lounge chairs

My pick

The Reserve Grand Suite Ocean Front

Paradisus Palma Real · Adults only · 807 sq ft

8.8 out of 10 on Expedia · 1,693 guest reviews

$4,400 for two

about $2,200 per person

A big ocean-front suite in The Reserve, Paradisus Palma Real’s private adults-only section on Bávaro Beach, with its own pool, beach area, lounge, restaurants and concierge. Your terrace has an outdoor tub facing the sea.

Includes resort credits for the spa, food and drinks and a room upgrade, plus 50% off golf and free access to the Fun Republic entertainment park. Free cancellation until January 28.

The Presidential Suite's ocean-view terrace with a jacuzzi and lounge chairsThe Presidential Suite living room opening onto an ocean-view balcony

Want to go big?

The Reserve Presidential Suite Ocean Front

Paradisus Palma Real · Adults only · 1,668 sq ft

8.8 out of 10 on Expedia · 1,693 guest reviews

$5,825 for two

about $2,915 per person

More than twice the space: a separate living room, a bedroom, a bathroom with a soaking tub, and a wide ocean-front terrace with a jacuzzi. Same Reserve perks and resort credits. Free cancellation until January 28.

How it’s booked: I book the suite directly with Meliá and your flights separately. Thursday, February 4 to Monday, February 8 (4 nights), the only dates these suites are available. Nonstop on United out Thursday and home Monday. Totals include the hotel with taxes, round-trip flights for two (about $1,160), a private airport transfer and travel insurance (estimated at about 7% of the trip).

Option 2 · Costa Rica · Guanacaste

Costa Rica

Beach plus nature: volcanoes, wildlife and zip lines are all within reach. Liberia is a nonstop flight from Chicago.

Aerial view of Riu Guanacaste on Matapalo BeachThe pool at Riu Guanacaste

Best value

Riu Guanacaste

All-inclusive · Matapalo Beach

3.9 out of 5 on Tripadvisor · 10,878 reviews

$3,875 for two

about $1,940 per person

A big, easygoing beach resort on Matapalo Beach with lots of pools and dining. Great value for Costa Rica, but families stay here too.

Riu Palace Costa RicaThe pool at Riu Palace Costa Rica

Riu Palace Costa Rica

All-inclusive · Matapalo Beach

3.9 out of 5 on Tripadvisor

$4,300 for two

about $2,150 per person

The upscale sister next door, with more refined rooms and restaurants on the same beach. The adults-only Occidental Papagayo has no rooms left for these dates.

Flights: United nonstop out Thursday at 7:46 AM, landing 12:56 PM. The flight home connects; I’ll try for a nonstop at booking. Totals include transfers and Travel Protection Plus.

Option 3 · Dominican Republic · Whale season

Samaná: the whale trip

Every winter, thousands of humpback whales come to Samaná Bay to mate and give birth, and February is peak season. This one I know firsthand: I’ve been to Cayo Levantado Resort and I’ve been out on the water with the whales myself. Every photo here is mine.

Nothing prepares you for a 40-ton humpback launching itself out of the water a few hundred feet from the boat, or the sound of a mother and calf surfacing together. It’s one of the best things I’ve ever done.

A humpback whale breaching in Samaná Bay A humpback whale tail rising out of the water A humpback whale waving its pectoral fin
Aerial view of Cayo Levantado Resort on its private islandAnother view of Cayo Levantado Resort

Island luxury · I’ve been here

Cayo Levantado Resort

All-inclusive · private island in Samaná Bay

9.8 out of 10 on Expedia · 300 reviews · guests rave about the staff

A small luxury resort on its own island, right in the bay where the whales gather. I’ve been there: it’s quiet, beautiful and you can sometimes spot whales from the beach. Fully refundable rate.

Want to go ashore? The resort’s boat runs to Samaná town. I have restaurant recommendations on the mainland from my own trips, so just ask.

Wyndham Alltra Samaná on the beach in Las GalerasAnother view of Wyndham Alltra Samaná

Best value

Wyndham Alltra Samaná

All-inclusive · on the beach in Las Galeras · relaxed and quiet

8.4 out of 10 on Expedia · 556 reviews

A relaxed, quiet beach resort at the tip of the Samaná Peninsula, about 45 minutes from the whale boats in Samaná town. It’s open to all ages, but it’s far off the family-vacation track, so the crowd skews toward couples looking to unwind. A much lower price than the island, with a fully refundable rate.

The whale tour

Whale Samaná

$65 per adult

Whale watching in Samaná since 1983, on a 55-foot double-deck boat. Tours leave at 9:00 AM and 1:30 PM in February. If you don’t see whales, your next trip is free.

Getting to the boat: from Cayo Levantado, the resort’s boat takes you across to the Samaná town dock. From Wyndham Alltra, I include a private driver to the dock and back, about 45 minutes each way.

Samaná, for two, 4 nightsCayo LevantadoWyndham Alltra
Resort, all-inclusive, fully refundable, taxes included$3,480$1,442
Flights, Chicago to Santo Domingo, round trip (Delta, 1 stop in Atlanta, about 6 hr 45 min)about $1,040about $1,040
Private car from Santo Domingo airport and backabout $300 (about 2.5 hr each way)about $350 (about 3 hr each way)
Whale tour with Whale Samaná ($65 per person)$130$130
Getting to the whale boat in Samaná townResort boatabout $90 private driver, round trip
Travel insurance (estimated at about 7% of the trip)about $345about $215
Totalabout $5,295
about $2,650 per person
about $3,265
about $1,635 per person

Honest note: there’s no nonstop to Samaná from Chicago. The best routing is an early Delta flight through Atlanta, landing in Santo Domingo around 2:15 PM, then about 2.5 hours by car, so the first day is all travel. It’s worth it for the whales, and it’s even better as a longer trip or as 2 extra nights added to Punta Cana.

Option 4 · Aruba

Aruba

Dry, sunny and outside the hurricane belt, with some of the calmest water in the Caribbean. It’s a great island. It’s just not a budget one.

Straight talk: Aruba is out of budget for this trip, and that’s just the reality of Aruba. There are no low-cost all-inclusive resorts on the island. The cheapest all-inclusive I can find for these dates is a family resort at about $5,955 for two, and the adults-only option is about $7,120. Most Aruba hotels aren’t all-inclusive at all, so you’d be paying Aruba restaurant prices on top. Secrets Baby Beach, the newest adults-only resort on the island, has no rooms left for February 4–8.

For less money, Punta Cana gets you an ocean-front suite in a private adults-only section. I’ve included Aruba so you can see the difference for yourself.

Riu Palace Antillas in ArubaThe pool at Riu Palace Antillas

Adults only

Riu Palace Antillas

Adults only · all-inclusive · Palm Beach

4.0 out of 5 on Tripadvisor · 6,539 reviews

about $7,120 for two

about $3,560 per person

Right on Palm Beach, walking distance to shops, restaurants and the high-rise strip.

Barceló Aruba on Palm BeachAnother view of Barceló Aruba

Lowest all-inclusive price

Barceló Aruba

All-inclusive · families welcome · Palm Beach

4.2 out of 5 on Tripadvisor · 13,267 reviews

about $5,955 for two

about $2,980 per person

The least expensive all-inclusive on Aruba for these dates, and it isn’t adults only.

Flights: the package flights connect through Panama. Totals include switching you to the United nonstop out of O’Hare (about $1,010 more), plus package transfers and Travel Protection Plus.

Side by side

All four, for two people

Destination and resortTotal for twoPer personFlight from O’Hare
Samaná · Wyndham Alltra Samanáabout $3,265about $1,6351 stop + 3 hr drive
Punta Cana · Paradisus Reserve Suite Ocean Front$3,870$1,935Nonstop, about 4.5 hr
Costa Rica · Riu Guanacaste$3,875$1,940Nonstop out, about 5 hr
Costa Rica · Riu Palace Costa Rica$4,300$2,150Nonstop out, about 5 hr
Punta Cana · Paradisus Reserve Grand Suite (my pick)$4,400$2,200Nonstop, about 4.5 hr
Samaná · Cayo Levantadoabout $5,295about $2,6501 stop + 2.5 hr drive
Punta Cana · Paradisus Reserve Presidential Suite$5,825$2,915Nonstop, about 4.5 hr
Aruba · Barceló Aruba (families)about $5,955about $2,980Nonstop, about 5.5 hr
Aruba · Riu Palace Antillas (adults only)about $7,120about $3,560Nonstop, about 5.5 hr

Every price is for 2 adults, all-inclusive, 4 nights (Thursday Feb 4 to Monday Feb 8), and includes taxes, flights, airport transfers and travel protection. These are today’s prices; they aren’t held until the trip is paid in full.

Good to know before you book

Terms and disclosures

Here are the key points in plain English. The Costa Rica and Aruba packages are booked through Travel Impressions, a brand of ALG Vacations Corp., and their terms apply. Punta Cana and Samaná are booked directly with the hotels and airlines, and each supplier’s terms apply. I’ll send the full terms with your booking.

Prices

  • All prices are in U.S. dollars and include mandatory government, airline and hotel taxes and fees.
  • Some charges may be payable at the resort, such as resort fees, energy surcharges, environmental levies and departure taxes. They can change with exchange rates.
  • Prices aren’t held until the trip is paid in full. Once it’s paid, your price is locked.
  • Every total on this page includes travel protection.

Payment in full at booking

  • Trips are paid in full when you book. I don’t take deposits or offer payment plans.
  • Airlines and resorts are paid upfront the moment I book, so your full payment is what locks in your flights, your room and your price.
  • Payment is taken by phone, never on the web.

Changes and cancellations

  • Packages: canceling 4 or more days before departure costs $100 per person, plus any airline, hotel or excursion penalties.
  • Within 3 days of departure, or not showing up: 100% nonrefundable.
  • Changing dates, flights, names or destination counts as a change and the same fees apply.
  • Once the trip begins, there are no refunds for unused parts.
  • Cancel and rebook within 7 days and the Travel Impressions fee is waived (supplier penalties may still apply).

Flights

  • Basic Economy fares are nonrefundable. No changes, upgrades or seat selection, and a change or cancellation forfeits the ticket.
  • Checked bags are extra and paid to the airline. Airline credit card perks like free bags don’t apply on package bookings.
  • I can price a standard Economy fare if you want more flexibility.

Travel protection

  • I strongly recommend travel protection, so it’s included in every price on this page.
  • Costa Rica and Aruba packages: Travel Impressions Travel Protection Plus, about $115 per person. It covers cancellation and change fees as a future travel credit; a cash-refund plan costs more. It doesn’t cover nonrefundable hotel rates.
  • Punta Cana and Samaná: a separate travel insurance policy, estimated at about 7% of the trip. I’ll get you an exact quote at booking.
  • Protection is bought when you book and isn’t refundable. Without it, money back after penalties is limited, and on packages it comes as a future travel credit.

Documents

  • Names must match your passports exactly. TSA requires full name, date of birth and gender at booking.
  • A valid passport is required for all four destinations. Each traveler is responsible for entry requirements.

Punta Cana

  • Punta Cana isn’t a package. The suite is booked directly with Meliá, and flights, the airport transfer and travel insurance are booked separately, each with its own terms.
  • All three suites are quoted at Meliá’s flexible rates: paid in full at booking, with free cancellation until January 28, 2027. A non-refundable rate is a little less.
  • Only February 4–8 is available in these suites right now, and they book fast.
  • At check-in, the cardholder who made the reservation must show the card and a photo ID.
  • Hotel totals include taxes. Final prices are confirmed at booking.
  • Resort credits, golf discount and Fun Republic access are Meliá offers and subject to their conditions.

Samaná

  • Samaná isn’t a package. The resort, flights, cars, whale tour and travel insurance are booked separately, and each has its own terms.
  • The Cayo Levantado and Wyndham Alltra rates shown are fully refundable under each hotel’s cancellation policy and include taxes.
  • The whale tour is paid to Whale Samaná and runs January 15 to March 31.

Next steps

February is peak season.

Prices for February rise as rooms and nonstop seats fill up, and the Paradisus suites book fast. Pick a favorite and I’ll lock it in.

  1. Pick your favoriteChoose a destination and resort, or schedule a call and we’ll talk it through.
  2. Send traveler detailsNames exactly as on your passports, birthdays and contact info, on one secure form.
  3. Pay in full and you’re bookedI call you to take full payment by phone, never on the web, and book everything right away at the confirmed price. No deposits.