An Instagram Guide to Chicago

Having already visited Chicago twice with work, this time around I decided to do a bit more exploring and put together a little “Instagram Hotspot” guide.

I did some research before I left, and saved a few places on Google Maps to pay a visit whilst there. I was a little too optimistic and didn’t quite manage to fit them all in, but if you have a bit more time than I did (and don’t stop too often to drink bellinis…) you might just be able to fit them all in in 48 hours.

Cloud Gate & Millenium Park

Of course, you can’t come to Chicago and not go and see The Bean. The official name of this sculpture is Cloud Gate, but due to the shape it has been nicknamed The Bean. Whatever you prefer to call it, make sure to stop by and admire your reflection.

Surrounding the area is Millennium Park, which boasts a variety of public art. Take a stroll admiring the beautiful greenery and flowers – the springtime tulips were in full bloom, and there were trees with blossom floating off at every corner.

Stan’s Donuts

Strolling up the “Magnificent Mile”, it won’t be hard to spot this coffee and donut joint, and I’m sure it won’t be hard to resist one of their delicious donuts either!

I went for the classic cinnamon and sugar coated donut, with an iced latte to cool down.

What I didn’t realise, is that Stan’s Donuts is actually a chain, and the one I’d bookmarked on my maps was actually a little bit further up the road, and has a super cute instagrammable pink front door! If you’re really dedicated to the ‘gram, get those few extra steps in and keep walking to find it.

Though this location didn’t have the pink door, it did have donuts decorating the ceiling, and a fun pink interior.

Flamingo Mural at The Flamingo Rum Club

Fuelled up from a strong coffee, it was time to visit another pink hotspot – the flamingo mural! I’d seen this pop up on Instagram, and luckily it’s just a short stroll from the magnificent mile.

A super cool mural that you really have to stand across the street to see all of, this is actually located on the exterior of a Cuban eatery and rum bar. Since it was daytime, we just stopped to take a few snaps outside.

3 Arts Café at Restoration Hardware

Who would have ever thought there would be a fantastic café tucked away inside a furniture shop?! From the outside you’d have no idea this place is even here, though once you step inside you’re greeted by an airy, open space, with beautiful furnishings, and greenery all over.

The café serves up breakfast, sharing dishes, fresh salads and larger main meals, as well as having an espresso and wine bar. Since there was a bit of a wait for a table, and we were still feeling full from the decadent donuts, we decided to grab a drink from the wine bar, and head up to the rooftop.

You can purchase drinks from the bar and take them anywhere in the store, which is definitely something new for me, and I loved it! The café was bustling and busy, and we took the lift up to the 5th floor where we relaxed on a comfy sofa and enjoyed a bellini in the sunshine.

The Hampton Social

From here it was a beautiful stroll through the city, soaking up the sunshine on the way to our next stop.

The Hampton Social is a gorgeous restaurant inspired by The Hamptons – think nautical vibes, whitewashed walls, and of course the motto, rosé all day. While we were there, there was live music going on, which added to the chilled out atmosphere.

We managed to get inside just in time, as the clouds suddenly appeared and it started to pour down with rain!

Happy hour is 3-6pm Monday – Friday, where you can enjoy the house rosé and pizzas for half price, an absolute bargain.

We devoured the pizzas between us in no time, and the rosé was chilled and crisp. The perfect spot to end a day of exploring Chicago!

One last place that I didn’t quite manage to squeeze in, was the Garfield Park Conservatory, one of the largest greenhouse conservatories in the US. Located slightly outside of the main city area, although not difficult to reach via public transport,  I will have to tick this one off my list next time I’m in the city. It’s full of pretty plants and flowers, as well as a beautiful glass structure and a traditional Moroccan fountain inside.

P.s. Follow me on Instagram, Facebook & Twitter for more day-to-day updates of where I am in the world! 🙂


  1. Asher
    May 15, 2018 / 4:41 am

    It was such a treat to read about the Windy City through your words. Chicago truly is one of the top notch cities of the world. It has got so much to offer to just about every one. You are very lucky to have been able to visit this world class city…..there are many millions who can’t in this day and age.

    • thedubaidiaries
      May 16, 2018 / 12:50 pm

      Thanks Asher, glad you enjoyed reading my take on Chicago!

  2. Valerie G
    May 14, 2018 / 8:46 pm

    Hi Rachel,
    Wow! I’ve been to Chicago so many times and it looks so different in your blog with such lovely pictures.You have a gift for writing. Do you know Chicago actually has beaches? Visit next time. xx

    • thedubaidiaries
      May 16, 2018 / 12:49 pm

      Thanks so much Valerie! Glad you enjoyed reading my take on Chicago. I did actually, and I was planning to go to one on the last day but just ran out of time. Hopefully I can come back in summer and enjoy the beach! xx

  3. Abbey
    May 13, 2018 / 11:45 pm

    Nice post and pictures. Well done , I always enjoy reading your post. Have a wonderful week ahead.

    • thedubaidiaries
      May 16, 2018 / 12:48 pm

      Thanks so much Abbey! xx

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