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Chicago the ‘Windy City’, the songs are true, you’re deemed a bad hair day but hey, who needs nice locks when you have high rises by your side 😉

As most of  you know I have just a few days ago completed the ultimate bucket list road trip that is Route 66. With a few days in each state along the famous route I have decided to break the trip up and post about as many of the locations as I can and then include some 66 specifics in-between.

Chicago marks the official start of Route 66 and I have to admit it was one of the cities I was most excited to see. I love built up industrial locations, high rise buildings and wide roads do to me what beaches and palm trees do to others 😉

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Have breakfast by the River Walk, there’s a number of cute cafes and larger chain eateries situated on the river bank with the breath taking views of Chicago’s famed skyscrapers to start the day in the thick of things 🙂 As a more industrial and populated city there’s something and somewhere for everyone regardless of your food tastes.

After Breakfast take a leisurely stroll towards Millennium park, the streets are easy to navigate thanks to the handy American grid system so it’s almost impossible to get lost, grab a map from your hotel front desk or pull up your google maps. If you book your hotel in the right location (we’ll come to that later) you shouldn’t need to use anything but your own two feet to get around.

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Millennium Park is the perfect place to head to to visit a number of the city’s great sculptures and attractions. If you arrive from your river walk breakfast you’ll first walk past the famous silver bean, otherwise and correctly known as Cloud Gate. This fantastic metallic sculpture is open to the public and a fun sight to see. If you’re looking for the perfect picture get your butt there first thing in the morning to avoid the crowds but if you are wanting to enjoy the marvel of the sculpture then just before lunch is better for people watching and sharing the fun 😉

You can have a play with the echoes and the comical mirror images of yourself as well as enjoying that amazing view, only this time with you in the frame 😉

From here you can move on to the park where there is even more quirky architecture to marvel at. The show space itself is incredibly impressive to see, as a working outdoor auditorium it’s worth checking out if there is any activity happening during your stay. You can see the schedule here. 

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From the park follow the signs to the Lake Front, here you can stroll along the edge of Lake Michigan and watch the sail boats and budding sailors take to the water for the day. Even on a windy day (as photo above) we were able to watch a number of water-sports taking place and the view of the city with the backdrop of the lake is incredible.

I can only imagine how beautiful this place would be during the day. If you visit be sure to email me a picture please 😀 You can then follow the water front all the way round to the Navy Pier. The entire walk is signposted so keep your eye out if you aren’t travelling with that trusty map. The walk is a pretty one that takes you not just along the lake front but also through and above (via bridges) the bustling city itself.

The Navy Pier is a great place for a spot of lunch, it’s quite the city attraction with countless restaurants, bars and souvenir shops, inside and out. There’s also  a number of fair rides and boat trips (bookable in advance) from this very pier. During the summer it’s a great spot for a stroll and even during the colder months as long as the sky is clear it’s well worth a walk to the end to see Michigan in the distance.

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After strolling by the water and grabbing some lunch by the pier we personally wanted to enjoy and explore the inner city once again for a spot of shopping. Knowing that we were going to be out in the sticks for two weeks meant an obligatory Sephora and Forever 21 was needed! 😉 We walked from the Pier a few blocks west to meet Washington Street, one of the best places for a leisurely retail stroll. 

We then headed back to our hotel for a quick freshen up before the evening’s activities. We stayed at the Kimpton Hotel Allegro and even though this is the only place I’ve had the pleasure of staying at in Chicago I can’t imagine there is a better hotel in the City!

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First of all the location of the hotel was perfect. As I mentioned earlier we were able to walk absolutely everywhere apart from our evening plans.  Then the actual hotel itself was a genuine, memorable and delightful experience. The interior decor is luxurious and minimal, fresh white walls and floors with rich velvet fabrics and metallic fixtures. Stunning art work and a complimentary prosecco cart from 5-6pm in the lobby was our welcome to the building – quite the first impression!

The rooms were in keeping with the overall decor and sizeable for an inner city stay, the bed however, was unfortunately way to comfortable – not what you need to when you need to fight jet lag 😉

The hotel staff were so sweet and courteous throughout our stay, the concierge was so helpful in helping us with our itinerary and there’s even free coffee in the mornings – I honestly couldn’t recommend this hotel more. I made a special mention to it on my instagram after such a sweet gesture from the guest services manager, click here to see what it was.

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After a little R&R in the hotel room it’s time to explore the evening. We were lucky enough to be in town whilst the Chicago Bulls were playing, which leads me to my next recommendation; Go to a Basket Ball Game!

As luck would have it we were able to watch the mighty Bulls play against Cleveland in the iconic United Center. If you have a chance, head to a game for sure, the tickets are pricey but the experience of watching the game is amazing. Even if you are not into sports (insert hands up emoji!) the atmosphere is electric! There’s so much more than just the game; cheerleaders, competitions, audience participation, the famous kissing cam and then, of course, the obligatory thick base Chicago pizza and beer that must be consumed whilst cheering on the boys!

We ate at the game and headed straight back to the hotel to enjoy the comfy bed before our big drive the next day but in terms of dinner recommendations I have heard amazing things about RPM, I may be a little biased as it’s part own by ultimate E! Host Giuliana Rancic but I spoke to a number of people about the restaurant at the hotel and they all said that the steak restaurant was amazing, so it may be worth a try if you are in town.

If you do venture to any of the above be sure to let me know about it in the comments below 🙂 As for C&C next stop………St Louis!

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My Outfit is this post:

Denim Jacket – Missguided/Jeans – Topshop/T-Shirt – Reiss/Boots – Nasty Gal/Bag – Gucci

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