Windy Ways: Chicago, Illinois

In tune with short getaways, we recently made our way to Chicago, Illinois.  Going there for the first time we were pleasantly greeted by amazing weather, all american optimism in the air and some lovely people. So here a guide to my Chicago essentials:

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We stayed at the The Palmer House Hilton in downtown which was a vintage- esque hotel. I would also recommend an Airbnb in or close to ‘the loop’ which is the main downtown district.


We mainly walked around and used the subway or CTA system which is brilliant and should help you get around easily. This is also the best way to get to and from  O’Hare airport to downtown Chicago. For late nights there was Uber or Lyft.

Also, bike rentals or bikeshares like Divvy are spread all across the city, which is quite biker friendly.


First, we jumped on board the architectural river cruise organised by the Chicago Architecture Foundation (CAF). It was super fun –  to be guided into Chicago’s story through its buildings old & new, floating under the 24 bridges and wafting briefly though the aroma of melting chocolate. In Chi-town ‘less is more’ and ‘less is bore’ happily co-exist together. If the weather is good this is really a tour worth taking even for peeps not that into in architecture or design.

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We also took the walking tour Chicago Masterworks – Connecting Old & New again by CAF. We saw up close how the works of Ludwig Mies van der Rohe , Frank Gehry, Helmut Jahn, Renzo Piano & many more, all making for a unique and eloquent cityscape. My favourites were Chicago Federal Center by Mies van der Rohe decorated by the Flamingo sculpture by Alexander Calder and the James R. Thompson Center – designed by Helmut Jahn – where you can actually watch your government at work!

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Next was  Millennium Park. That’s were Cloud Gate sculpture by Anish Kapoor stands interacting with so many people everyday. After floating around ‘the Bean’ (Cloud Gate) we strolled to the Jay Pritzker Pavilion designed by Frank Gehry. We were lucky to catch a band practicing there feeling the music thundering around us. Yay for brilliant acoustics! This is a Chi-town venue for many a free concerts and picnicking is encouraged.

Finally we walked towards Lake Michigan for a calming lakeside stroll, enjoying the beautiful view of blue water and bobbing sailboats.

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Next morning was dedicated to the SkyDeck at Willis tower (erstwhile Sears towers).

We were lucky to avoid the lines as we went there as it opened at 9am. A 60 second elevator ride up took us to the tallest building in Chicago (and once in the world). The craziest part is the glass balcony that make you feel like you are floating in the clouds. The views from here are of course stunning! A bit freaky if you are afraid of heights.

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Then we popped into the Art Institute of Chicago Museum, which boasts an impressive collection of art and design exhibits. Here again, the building itself is a treasure along with the awesome new wing designed by Renzo Piano.

At night we headed to Old Town for an evening comedy at The Second City MainStage. The show – FOOL ME TWICE, DÉJÀ VU was perfectly sarcastic and hilarious!


Last but not the least, I wanted to check out Oak Park for a tour of architect Frank Lloyd Wright’s home and studio but didn’t get enough time. So thats on the list for the next visit!


Chi-town food is da bomb!

We started the trip with a sumptuous lunch of pork & ginger dumplings and spicy piri piri chicken (fatracha style) at Fat Rice near Logan Square.

At night the mood was Japanese at Momotaro. We had some amazing cocktails at the Izakaya bar (delicious Momo -ritas) while we waited for a table enjoying the easy breezy energy. The food was fab and the favourites were the Negima chicken skewers with an insane shishito pepper sauce, the wagyu donburi, the chili mentaiko spaghetti, and the sweet cotton cake…

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The next day it was breakfast at Eastman Egg for ridiculously mouthwatering sandwiches and craft coffee. Lunch was late (we had stuffed ourselves at Eastman) but delectable at The Purple Pig. The sommelier gladly paired our food and drinks and the must haves here were the pork shoulder entree and the chorizo sandwich.

The evening was dedicated to strolling around the riverwalk and catching up with old friends at the Tiny Hatt bar. The scenery and casual ambience makes for a lovely Friday evening.

We ended the trip with Saturday brunch at The Publican at the Fulton District Market with some brilliant avocado toast, warm scones, sausages and pecan sticky buns! Brunch happens here only on the weekends but I’ve heard the dinner here is awesome sauce too.

Reservations are recommended especially if its a busy night and we didn’t have the foresight to reserve at two Chicago institutions Alinea and Girl & the Goat. We missed those but hopefully next time…


Chicago is flooded with the usual shopping suspects and the Magnificent Mile is the area to browse for the key high street and luxury brands.

If you are a Chicago Bulls/ Michael Jordan fan there is a Jordan Brand Experience store on State street worth checking out. If you love home decor stop by the Design Center at the gorgeous Merchandise Mart Plaza and finally pick up souvenirs at the Chicago Architecture Foundation store right opposite the Art Institute Museum.

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Here’s saluting a city that actually made its river flow backwards, with a quote from Mark Twain…

“She is novelty; for she is never the Chicago you saw when you passed through the last time.” 

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