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Chicago
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Let the windy city sweep you off your feet with its incredible dining, drinking and nature-meets-urban personality. There’s always a new restaurant to try, a drink to be had and of course, you can never get enough of the stunning Lake Michigan views and friendly Midwest hospitality.

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Fun, sceney restaurant, chef is from Mykonos! Great for celebrations, they bring out sparklers etc.

Delicious food and drinks! You can even eat on the river when the weather is nice. Mediterranean cuisine and it does not disappoint.

The outdoor space is absolutely beautiful at night and the food was delicious both times I visited!

Upscale Italian with a remarkable food. Pasta trip is a must try. Very intimate inside and would be perfect for date night/special occasion

The first time we stayed here, we were absolutely obsessed. However, this StayPineapple has gone downhill since our last visit. When we arrived the fr...

It’s one of the best aquariums for a reason. Great for a rainy day activity