Family Friendly Tropical Trip Locations for Chicagoans

I’m here to encourage you to get away from the cold and grey Chicagoland skies and jet off to a fabulous vacation WITH kids in tow. Yes, that’s right, you can have an amazingly enjoyable and fun vacation with your kids. It’s not going to be the same as before they were born (I mean, is anything the same since becoming a parent? I think not.), but it will most definitely be a welcome respite from winter. I’ve chatted with numerous Chicago families and have come up with this list of seven family friendly tropical trip locations for Chicagoans.

To Prepare

But before we get to talking about fun in the sun, let’s be sure that you have your expectations in check. Traveling with kids is always an adventure, with them being off their schedules and away from home you really just have to roll with the punches (it helps if you have a rum punch in hand) and just go with the flow.

If possible, try to stick to home base and make it as comfortable as possible. That might mean shelling out a few more dollars for a suite instead of a standard room but trust me, it makes such a great difference. Be sure to look into Airbnb as well as VRBO to expand your options.

Figure out what YOU want to get out of the trip. For me, it doesn’t feel like a vacation unless I have devoured a great book. So my priority is to make sure I have a book and time to read it. If that means that I read on the balcony while my boys are snoozing and encourage my hubby to go out on an adventure, that’s fine with me. If you really want to go to dinner without kids at least once, be sure to look into hotels and resorts that have reputable and highly acclaimed kids’ clubs and other babysitting services. Spoiler alert: All of the resorts and hotels on this list fulfill this need.

Have a willing aunt or grandparent who would love to help out with the kids and have some fun in the sun?  Bring them along. It will ease stress (hopefully) and an extra set of hands is always helpful. And it will also ensure that you won’t have to take family selfies all vacation long…if you don’t want to, that is.

Look for trips with the most direct route. Skip layovers whenever possible and be sure to look for hotels and resorts that aren’t a long ride from the airport. Speaking of which, I highly recommend bringing your own car seat. Although it is annoying to lug around the seats, they will come in handy when you cannot rent car seats and will keep everyone as safe as possible so you can focus on having an amazing vacation.

Tropical Locations

San Juan Marriott Resort and Stellaris Casino, Puerto Rico

Why moms love it: Travel is a piece of cake with a direct flight and no need for a passport since San Juan is a United States territory. There are tons of beautiful beach front rooms available so this is the perfect place for beach lovers, young and old. And if you can get a break from the kiddos, you can try your luck at the casino.


Iberostar Paraiso Lindo Riviera Maya, Mexico 

Why moms love it: You simply can’t go wrong with an Iberostar resort. The Iberostar Lindo is no exception. This all inclusive resort is a hit with families because it is HUGE and boasts so many things that are perfect for everyone in your family. There are many different activities to choose from and you can see many of these first hand on my Instagram feed in a few weeks when my boys and I visit this popular resort. I. Can’t. Wait.


Finest Playa Mujeres, Cancun, Mexico

Why moms love it: This all inclusive luxury resort is the only one in Cancun that caters to kids just as much as it caters to adults. There are different kids clubs available depending on ages and specific areas that are just for kids, no adults allowed—how cool is that? There are also family suites with childcare included so that you all can experience every moment of vacation (that means no sitting in the dark after bedtime, parents. Hooray!). This resort is very grand and large so if you are looking for a more intimate yet similar resort, look into Beloved Hotel and Resort.


Beaches Turks and Caicos

Why moms love it: This family friendly all inclusive resort has it all. And even better? The kids activities are included in your package price so there is no need to pay additional fees for supervision when you need some time away from the kiddos. There is a waterpark, endless activities featuring Sesame Street characters, and all of this fun is focused around one of the most amazing beaches in the world. It is only a 10 minute ride from the airport to the hotel and there is a quick and easy direct flight from Chicago….basically there is no excuse as to why you aren’t packing your bags right now. Tick tock.


Marriott Aruba Surf Club, Aruba

Why moms love it: If you are looking for spacious accommodations to use while at a beautiful white sand beach, the Marriott Aruba Surf Club is the resort for you. There are tons of beautiful villas to choose from, or you can also rent a time share. There are tons of kids’ activities and the nearby town has lots of things to do and explore as a family. Don’t forget that when booking a villa, you will be able to do some of your own cooking, which might serve your picky kids’ appetites much better than restaurant food.


Barcelo Bavaro Palace Delux Punta Cana, Dominican Republic

Why moms love it: This highly rated and all inclusive resort caters to both the young and old with a plethora of activities. The food is highly regarded, as are the kids’ pools and amenities. Located on Bavaro Beach, one of the most beautiful beaches in the world, it is truly a great way to get away from mundane parenting tasks and simply enjoy your time together as a family.


Sandpiper Bay, Naples, Florida

Why moms love it: Sandpiper Bay is part of Club Med, so you know that they have delicious food and fantastic activities to keep everyone entertained while on vacation. Kids will love the waterpark while parents enjoy the spa, tennis courts, and more. Sit back and relax knowing that all meals and drinks are included, and that there are highly qualified staff to provide childcare if desired.

And if you want your vacation to actually FEEL like a vacation, book with Mickey and head on a Disney Cruise! You can read all about our amazing experience at sea here.

I hope that these tips from local Chicagoland moms inspire you to book a trip, no matter how anxious you might be about traveling with kids. Once you see that crystal blue water and feel the sand in between your toes, it will be totally and utterly worth it.

Looking for travel tips such as must have travel apps? Then this page is for you!

Happy and safe travels!



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    • Amanda says

      We Midwesterners deserve a nice winter vacation, don’t you agree?!? Hopefully the snow will stick to the East coast and away from us!

  1. Fi Ní Neachtáin says

    I am loving the sound of those tropical holiday destinations, I especially really want to visit the Caribbean, it’d be a dream come true! Great tips, especially about skipping layovers where possible and picking a resort not too far from the airport.

  2. Robin Rue (@massholemommy) says

    I live at the beach, so when I travel I usually don’t go to beachy places HOWEVER, it’s been super cold here in Boston this winter, so I would be happy anywhere warm 🙂

  3. Heather Paulding says

    I don’t live in Chicago, but I suppose getting away from the freezy weather would be important. Great information! Southern Florida is a favorite of our family, because it is just like visiting the tropics right here in the USA.

  4. Tara says

    I don’t live anywhere near Chicago, but I am definitely thinking about tropical escapes right about now. We tend to save all of our vacationing for summer (my husband is a teacher), but I’ve been craving winter getaways more and more!

    • Amanda says

      As a former teacher I know how hard it is to get away during the school year…hopefully you two can take a weekend away!

  5. Pam says

    Tropical vacations are my favorite! My family went to Punta Cana last year and had an amazing time. It’s a great way to beat winter!

    • Amanda says

      We don’t have a ton of snow this year (yet) but I really can’t wait to get away from these long and gloomy days.

  6. R U S S says

    I have a lot of friends who travel with their kids and they say that while it is fun, it could also be tiring so the willing aunt or grandparent ( or cousin! ) is a brilliant idea. I live in a tropical country so I see why you love all these tropical paradise.

  7. Denay DeGuzman says

    These are fantastic get-away locales for families with children. When my girls were small my husband and I took them on many international vacations and we all had a fabulous time. For beach resorts I suggest looking for ones that are all-inclusive. For children that are grazers or picky eaters, this option is a life-saver and makes everyone happy, and there is food available around the clock. Also look for resorts that have incredible kids’ clubs. While the kids are having fun the adults can have a bit of relaxing or romantic alone time too!

    • Amanda says

      We are totally taking your tips for our upcoming trip–it is all inclusive and has a great kids’ club. We can’t wait!

  8. Heather Lawrence says

    We have only been back from vacation less than a month and we are looking for where we want to go next. I would love to visit Turks and Caiocos with the kids! We didn’t have a great beach day on out vacation so I need to make up for it right! Lol.

  9. Michelle says

    I could use a getaway right about now! A friend and I were talking just last night that we need to get back to Beaches. Soon. But who flies direct to T&C from Chicago?! I’ve always had layovers – what a joy if someone has added a direct flight! And I’ll second the Marriott in PR. Absolutely gorgeous. There’s a great Embassy Suites there that’s cheaper and right by the beach with chairs set up on the private beach just for you. I miss the sun!

    • Amanda says

      It was a smaller airline that flies from Chicago straight to Turks. I think Spirit, maybe? Thanks for the tip about the Embassy Suites in Puerto Rico!

  10. Rebecca Swenor says

    These are great tips for family friendly tropical trip locations for Chicagoans or anyone for that matter. Sandpiper Bay Naples Florida would be as far as we could go with my parents both being sick right now. Thanks for sharing these tips and locations.

    • Amanda says

      Sorry to hear that your parents are sick. I had to cancel a trip to Paris when my Dad was sick. So glad I was able to spend that extra time with him, however.

  11. Ryan Escat says

    Having a tropical trip is really fun and exciting. I’m sure your family had fun and enjoyment adventure. I would love to go those beaches with my wife, for sure, she would also love it.

    • Amanda says

      I wish money wasn’t a factor, either! But that’s why we tend to go to all inclusive places–much better deal for our family.

  12. XmasDolly says

    Soooooooooooooo perrrrrrrrrrrfect! TAKE ME AWAY, PLEASE! It looks so relaxing and a really great place to have fun. Maybe if I leave pictures all over the house my husband would get the hint… nothing like being subtle. bwahahahaha Thanks for sharing.

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