I am planning a surprise trip to the Caribbean next February for my first anniversary and need help determining where to go. I am travelling from Chicago and only have five nights so I need somewhere that is somewhat easy to access. My criteria include amazing resort, great food, and beautiful beaches/weather. If you have any suggestions as to which island to visit, I would GREATLY appreciate it (and so will my husband when he finds out where we're going)! Thanks in advance for any responses!

Not sure about your flights from Chicago but I'd pick one that maybe has a non-stop. Do some research on some of the major carriers that use Chicago as their hub. Check their sites first and then go to a discount site like Expedia, Travelocity, etc. to see if you can find a package. Sometimes, the airline websites offer better deals on their own sites, especially package deals. If you're traveling in February, however, it's not too early to book. Very busy in the Caribbean. Some spots close to US are Bermuda, Turks & Caicos, Bahamas to name a few.

Think about Puerto Rico. There are, or were, three flights a day from O'Hare direct to San Juan on American. If the trip is a suprise you won't have any stumbling blocks re: passports.

I also live right out of Chicago and I would suggest Jamaica...the flight is only 3 1/2 hrs and your there. Try looking into Sandals, we have been to all of these resorts and aregoing back in Feb for 2 weeks to Sandals Negril.If youhave any specific ? feel free to email me.

while bermuda, t&c and bahamas are fast flights they will not be warm enough in feb. bermuda might be in the 50's. t&c warm air but water too cool to stay in long for swimming/snorkeling.
jamaica is a good idea. nice resorts, lots to do. i know 2 couples who have been to couples swept away numerous times. one couple 20's, adventurous and into diving the other in 50's and pretty laid back. they both love swept away.
or you might consider the all-inclusive resorts south of cancun. cheaper air than to jam. this site will show you most of what's available : http://www.locogringo.com/dynamic/lo...usive%20Resort
lg also has a comprehensive list of what there is to do, but diving/snorkeling, atv jungle tours, eco-marine parks, ruins, zip-line, shopping, golf, cenotes. great food! near playa del carmen is busy; near akumal laid back; further south - down right quiet.
and WOW i was just checking flts on kayak.com - there are some really cheap flights from ord to sju - san juan pureto rico. big island - loads to do.
aren't you nice to take on the planning of the honeymoon surprise.

The Westin Our Lacuya, in Freeport, Bahamas. Awesome resort, easy to get to. The food at the resort is boring, but there are lots of great choices just across the street in the little tourist village.

The weather is similar to Florida, so it is not blazing hot sunshine in February, but it will feel great compared to Chicago.

What a great lady your husband married! Jamaica is an easy flight from Chicago and is a beautiful Caribbean Island. The sightseeing/shopping and cultural exposure is incredible. The beaches are a unique experience. Dunn's River is a must. It is a national park and one of the most beautiful spots on Earth! It is a natural waterfall of clear, cool mountain water that goes down the side of the mountain right into the ocean. The cuisine is delicious. We stayed at Sandals MoBay and were very happy with the resort. There are a number of AI's on the island as well as villa's.