ORD > Oranjestad, Aruba: $264 round-trip – Nov-Jan

Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a nice hotel, and called Michelle saying “What are we doing the third week of July?”.
“Nothing, why?” she said.
“Because we can fly there AND stay at the Renaissance for about $700 each.”

The renaissance, BTW, has their own private beautiful island with one quiet beach for adults only, and another (also quiet and safe) beach for families. You can feed the flamingos, snorkel with thousands of fish, and not worry about the kids because it’s all inside a protective reef.

While there, be sure to check out the Flying Fishbone restaurant. It’s both of our favorite dining experiences EVER. (Get there a couple hours before sunset. It’s easily a 3 to 4 hour experience, and worth every minute. Apparently their reputation precedes them because we watched two couples get engaged there.

 * There only appear to be a few seats at this price and availability is spotty. It will take a little digging to find dates other than the dates I found, but at this price, it’s well worth digging for.

Chicago to Oranjestad, Aruba: 7 night trip. (But can be changed.)
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Flight Options
Best price I found: Sat, Dec 07 to Sat, Dec 14.
Flight Alone: $264. (Normal price: $750.00)

Lodging options:
Want to customize your hotel choice? Watch this video.

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  • User assumes all responsibility for researching details before purchasing flights or hotels on the travel site of their choice and fares found are only good until airline sells those seats.
  • All package prices are per-person & assume double occupancy. Single travelers can expect to pay 5% to 30% more for packages. 3 or 4 travelers sharing a room can expect to spend 5% to 40% less per person.<
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