Chicago to Caribbean with toddler
 

Looking into a winter getaway in February. We'll be traveling with a 15 month old, so a direct flight would be awesome. Any recommendations for islands and resorts (hopefully a resort that has good medical care on premise just in case).

Criteria:
Direct flight
Not too "touristy"
newer/modern resort
kiddie pool
lots of restaurants to choose from

Thanks in advance!

First, just to clarify - I think you really want a "Non-Stop" flight not a "Direct Flight" (which in airline parlance means a flight that makes one or more intermediate stops but you stay on the came plane). I point this out because if when booking if you tell the agent you'll accept a "Direct Flight" that's what you'll get and most likely the flight won't be "Direct" but rather a "Connecting Flight" where you change planes somewhere.

Anyway, there are only a couple of Caribbean islands you can reach Non-stop from Chicago - namely Puerto Rico and the Dominican Republic. All other destinations will require at least one "Connecting Flight" through either Miami, Atlanta, Charlotte or perhaps San Juan.

So, would you consider destinations requiring one or more "Connecting Flight"? Keep in mind that both of those destinations will be fairly "touristy".

Second, before anyone can make meaningful hotel/resort recommendations we need to know what type of budget you have. Please give us a dollar range not some nebulous terms like "affordable", "not too expensive" or "won't break the bank" as we have no idea what those terms mean without a point of reference.

Also, please clarify if by "lots of restaurants" you mean an island with plenty of dining options to are you seeking a resort with multiple "on-site" dining options. The answer could make a big difference on the recommendations you receive.

Thanks for your input. I guess I did mean "non stop" - I wasn't aware of the difference, but I would consider a quick connecting flight.

Budget is 4k for 4 nights (including airfare)

Seeking resorts with on site dining options.

I was originally thinking of Exuma, Bahamas but was wondering if anyone had any other ideas!

Thanks!

You won't find any non-stops to Exuma and since that's part of the Bahamas and fairly far north it could be cool or even cold in February. You'd be wise going further south at that time of year.

Check out Beaches Resort on Providenciales in the Turks & Caicos

Oops! Hit submit too soon!

Meant to add:
Check out Beaches Resort on Providenciales in the Turks & Caicos. It's very popular with families and has everything you are seeking.

Also, look at Four Seasons on Nevis (fly into St. Kitts via MIA then a short water taxi or ferry ride to the Nevis) - they have an excellent reputation for dealing with families with young children.

Lastly, look at Caneel Bay, on St. John. Fly into St. Thomas than a short ferry ride to St. John. It has all you are seeking but the "kiddie pool".

Thank you! I will look into it :)