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So this year, I’ve was determined to stay put, and when Starwood Hotels offered me the chance to take a mini staycation as part of their My Summer Story campaign, I jumped at the opportunity.
It was great to get away without having to deal with any airports or other travel nuisances and it was the perfect excuse to explore my own city.I stayed at the W Chicago Lakeshore which is a funky high-rise hotel with sweeping views of Lake Michigan, and nearby attractions like Navy Pier and the beach (see the photo at the top of the post). What’s nice is that even if you don’t get a room with a lake view, you can still soak it all in from the indoor pool or from one of the hotel’s several bars.The furniture and lighting all has that boutique-y designer feel to it and I saw lots of guests taking advantage of the bar, restaurant, and chill-out area near the lobby. But being right downtown, the hotel was also a great base for exploring everything Chicago has to offer.
Here are a few of the things that I’ve been up to…Living It Up At Music & Street FestivalsThere must be hundreds of music and street festivals each summer in Chicago – I think because we go into hibernation for so much of the year, come summertime, we go a little overboard with the outdoor events. Not that I’m complaining.One festival that I made it to for the first time this year was Lollapalooza. I realize my lack of attendance in prior years is kind of blasphemous given that people travel from all over the country to see their favorite bands at this massive three-day festival, but I finally got my act together early enough to buy tickets this year and join in the fray.Of course, there are plenty of free festivals in Chicago too, covering every niche you can think of.
A couple I made it too included the Wicker Park Green Music Fest (featuring all things sustainable and eco-friendly), the Randolph Street Market (filled to the brim with all manner of antiques and vintage goods), and Taste of Randolph (a street fair with food, music, and random stalls selling everything from vintage posters to jewelry).But the award for the most bizarre festival I came across this year had to go to the Scottish Festival and Highland Games, which took place in the Chicago suburbs. There was a haggis hurling contest, a knobbly knees competition, and of course lots of physical events like caber tossing (that’s where men dressed in kilts flip giant tree trunks into the air) and sheaf tossing (where bales of hay are hurled over a tall bar).
But living in a city where it’s cold and frosty so much of the year, it wouldn’t make much sense, even if I could afford it.

In fact, the Chicago Electric Boat Company will let you rent a boat and drive it yourself (as long as you’re over 21 and not drinking while you drive) so you really get that “ah, I own the waterways” kind of feeling.
The views along the Chicago River are spectacular to say the least and a boat ride is one of the best ways to take in the architecture the city is so famous for (plus, if you hit the water on a Wednesday night like I did, you can catch the regularly scheduled fireworks near Navy Pier).Watching Live ComedySecond City is another Chicago institution I’m embarrassed to admit I’d never made to before, so I was determined to set things right this summer.
For such a well known comedy club, I’m blown away by how affordable tickets to shows are (most performances cost $23-28 although I’ve seen tickets for as little as $12) and if you want to make a night of it, you can also get some great pre-theater dinner deals at nearby restaurants.
And although summer is the perfect time to sit outside and enjoy brunch, I have a hard time stomaching the idea of super greasy or super sugary foods for my first meal of the day. So what better than picnicking with millions of others at Grant Park during Taste of Chicago, a giant outdoor food festival (the biggest in the country, actually)? The food holds up exceptionally well if you’re buying it to eat on the plane, but there’s often a 15-20 minute wait since the place is so popular – allow extra time!Make sure you save room for dessert at Xoco because the churros with a shot of dipping chocolate are incredible. I couldn’t even wait long enough to take a photo before digging in.Hitting The BeachAnd last but not least, there’s the beach.
Growing up in Australia where there’s a strong beach-centric culture, I used to think living in Chicago would mean having to give up the sun and sand. But despite being inland, the Windy City actually has some great lakefront strips of beach with pretty spectacular skyline views to boot.The Ohio Street Beach was easy to access from the W Hotel where I was staying and the tall buildings nearby cast shadows across the sand, providing welcome respite from the heat.
I also love the North Avenue Beach since the music blasting from Castaways (a bar and grill shaped like a ship) always reminds me of fun European beach clubs.What have you been up to this summer?

Let me know below and by tweeting me with the hashtag #mysummerstoryYour Chance To Win!As part of the My Summer Story campaign, Starwood is giving one lucky reader the chance to experience their own amazing hotel stay. You’ll get 16,000 Starwood points that you can redeem at any participating Starwood hotel around the world (that includes brands like Sheraton, W, Le Meridien, and St Regis, among others). Depending on where you choose to stay, that could be up to one week free in a luxurious hotel! Good luck!a Rafflecopter giveawayMy stay at the W Chicago Lakeshore was courtesy of Starwood. I had no idea you were from Chicago, so we’ll have to get together when I’m home next summer! Chicago in summertime is really one of the best times to be there I guess – would love to visit again soon!

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