Chicago was never my go-to place. To be honest, the United States was always at the bottom of my ‘must-absolutely-[without question]-visit’ list. Reason being that the US is has a fairly young history and a culture that isn’t too different to what I’m familiar with.


I am absolutely thrilled that I got the chance to explore this American gem all courtesy to my wonderful boyfriend who booked this holiday as my birthday gift.

It’s quite extraordinary that when I told friends and family that I was heading to Chicago, I usually got a very specific reaction – a puzzled look.

Why Chicago?

Well, I probably gave Marco the same puzzled look. But as I dug deeper, I realised that it didn’t deserve to be the underdog.

Chicago is bursting with architectural wonders, incredible artworks and a fire-blazing, gangster-ridden history. The architecture, the jazz scene, the speakeasies and Chicago’s trendier neighbourhoods, all speak for the State’s ability to marry old with new.

Chicago Picasso, 1967

Although Chicago is the third largest city in the US, we found it easy to get around, well connected and not crowded at all. The busiest areas are within the Loop, which refers to both the elevated (L) rail as well as downtown.

The Rail Loop

Downtown comprises the financial district, Broadway and the infamous Jay Pritzker Pavilion located at the Millenial Park. Not to mention Cloud Gate (a.k.a The Bean).

The Mirror Ball

What I absolutely loved about Chicago was that there was also an abundance of landscaping, gardens and parks.

Never knew I dressed like a tulip garden until this very day

But the real question is, is Chicago a foodie destination.  YES – it definitely has potential. And my blog post will give you my top recommendations, should you happen to be passing by.


DAY 1: After the River Cruise Tour by Shoreline Sightseeing, which was a brilliant way to be introduced to Chicago’s architecture, we had our first lunch. It HAD to be deep dish pizza.

The closest I ever got to deep dish pizza was Pizza Hut. Then I encountered Gino’s East – and it changed everything. Really. EVERYTHING.

We got the dish for two (with four slices in total) and we were able to mix and match different pizzas on offer. We got the Spinach Margherita and the Meaty Legend. [Be prepared to wait 45 minutes to an hour for the pizza to be prepared and cooked – they do warn you in advance.]

The best by far was the Spinach Margherita – the tomato sauce was rich, the dough was buttery and the cheese was well, cheesy. We found the Meaty Legend had too much going on, so our vote goes for… the Spinach Margherita.

Gino’s East Meaty Legend

Because we enjoyed this deep dish pizza so much we tried another local haunt called, Lou Malnati. We ordered the Malnati Chicago Classic and the Lou. The Lou was not meant to be too different from Gino’s Spinach Margherita but it was overly garlicky and the crust wasn’t as delicious. Sorry, Lou!


That same day with dined at Alinea, a 3 Michelin Star Restaurant I had discovered through Chef’s Table. There are three menus available and we chose the Salon Menu with 12 courses.  On the whole, it was a special multi-sensory experience, where you are challenged to think about what you are eating based on its appearance, flavour and texture. We were also invited to the kitchen to witness the chefs at work, guided by Head Chef Grant. There, we also witnessed the making of a cocktail, mixed by a rare cocktail shaker (1 in 30 in the world, modelled after the Victorian shakers).  Some pictures of the experience below.



DAY 2: Because a 15-course dish isn’t enough to push the thought of food out of my mind, I decided to treat myself to Xoco‘s Pork Belly Chilaquiles made out of crunchy tortillas, tomatillo-serrano sauce, poblano rajas,  pork belly chunks, cheese, and a sunny-side-up egg. It was DIVINE. Ridiculously heavy for breakfast, but it was certainly my most important meal of the day.

Never skip Xoco breakfast.

And don’t leave without trying their Aztec hot chocolate.

Or their bacon popcorn.

Xoco’s Pork Belly Chilaquiles

And Marco’s less exciting Chorizo variation.

Xoco’s Scramble with Chorizo

As holiday’s are not just about food (something I need to remind myself), that day we visited the world-class Art Institute of Chicago which houses plenty of notable artworks from various periods, as well as modern installations.

Little Dancer of Fourteen Years (Degas)
Woman in Tub (Jeff Koons)

That day’s lunch menu involved a Chicago-style hot dog from the infamous Portillo’s – a local favourite, retro-style chain, selling fast food. The Chicago-style hot dog includes mustard, relish, celery salt,  onions, sliced tomatoes, kosher pickle and ‘sport’ peppers piled onto a steamed poppy seed bun. Chicagoans call this “dragging the dog through the garden.” Nice.

Portillo’s Restaurants
Chicago-style Classic Hot Dog

The weather remained poor (thanks Chicago!), so we spent the rest of the afternoon walking along the Magnificent Mile and taking shelter within the many high-street and high-end shops. On the bright side, the rain left a few lovely reflections in return.

‘You Know What You Should Do’ Mural  (2011) Jeff Zimmerman

We then closed the evening with a historical tour on Chicago’s architecture and entertainment, which took us to a few Speakeasies and infamous watering holes known for their relation to Al Capone.

We then headed to our local speakeasy – The Drifter –  which is hidden within the Green Door Tavern. A classic speakeasy serving cocktails and wild entertainment.

The Drifter

DAY 3: The following day was classified as Museum Day, as it was bitterly cold and windy, looking exactly like this.

Museum Campus Skyline View

We visited the Shedd Aquarium and The Field Museum (a natural history museum). They were both wonderful, with the aquarium being my favourite as I feel right at home. [Not saying I’m a fish, but I’m not a fish out of water when I’m at an aquarium that’s all.]

OK, moving on.


Fish in Water?


We also had no other opportunity other than that day to observe the Chicago from up high. This is what stubbornness amounts to (both from our side and the clouds’). Do visit the Skydeck or the 360 on a GOOD day. Unless you really like clouds.

Dinner was booked at the Untitled Supper Club, a vintage-inspired, high-end venue with a dress code and live jazz. They claim to have one of the best whiskey bars in Chicago. We had cocktails.

The weather remained shoddy, so we decided to spruce things up with some jazz at the famous Green Mill, where legendary figures such as Von Freeman, Franz Jackson and Wilbur Campbell, as well as young lions Kurt Elling, Eric Alexander and Orbert Davis, played. It has not strayed far from the atmosphere of the early ’30s and ’40s in service, price and music. Shades of Al Capone’s heyday are found in the wall memorabilia as you enter and in the famous booth where he and his henchmen could keep a cautious eye on both doors. Make sure to catch the late night show (midnight – 5am) with Sabertooth. Don’t let the jet lag get to you (now that Al Capone isn’t around). It sure got me.

DAY 4: On day 4, we decided to head north towards Lincoln Park, a beautiful, sizeable park hosting a free zoo. I’m not an advocate of zoos and me being there, confirmed it. Animals, especially large animals should be roaming free and not be confined to such small spaces. However, I can’t hide that I was especially happy to see this fellow.

Lincoln Park Zoo

In the afternoon, we headed towards Old Town which is known for its 20th-century style, pastel coloured houses – all rebuilt since the great fire of 1971.


At lunch, we were lucky to get ourselves a seat at The Twin Anchors, a well-known establishment serving barbequed ribs. They were sticky and sweet and came with a choice of sauce, side and coleslaw.


We closed off the evening at the Steppenwolf Theatre – showing great productions since 1974.


Day 5: This day was nice and easy. We explored the West Loop and Greek Town. The West loop is undergoing a period of transformation. Old establishments like the French Market continues to run, although don’t expect it to be very…French.

The French Market

Fulton Market is pretty much completely under development but comes alive at night, with young, trendy folk. Rumour has it that gentrification is slowly driving its previous tenants, mostly Art Galleries, out of the picture as a result.

DSC_0263The Greek Town was a disappointment, as all it was was a string of Greek Restaurants and the National Hellenic Museum, which we didn’t have time to enter.

Thankfully we ended the holiday on a very sweet note. I may have found one of my favourite smokehouses – Green Street Smoked Meats. We ordered half a pound each of smoked brisket and smoked pastrami with a side of creamed corn with cilantro and paprika. Washed down with Chicago’s best Pale Ale – Daisy Cutter.


If you’ve visited Chicago or will be visiting Chicago, I’d love to hear your thoughts.