It’s long overdue, but I’m pretty excited to be posting my very first travel guide! It’s kind of ironic that this is my first, considering travel is one of my passions. On average, I take at least one, but often times two, big trips per year. But, with all the developments over the last 6-8 months, like getting engaged and now saving for our wedding, my fiancé and I have barely traveled for the year. Apart from this trip to Chicago, we don’t have any other travel plans on the horizon until next year (which makes me really sad).

My fiancé had the opportunity to attend International Telecoms Week for work, which is held every year in Chicago. So, we decided at the last minute that we may as well turn it into a little vacation for us. Anyone I had spoken to about Chicago had nothing but great things to say. “Clean”, “neat”, and “diverse” are just a few adjectives used to describe it, and I would certainly agree. As with all my other trips, I picked up a Lonely Planet guide book in advance (which tends to become my bible and never leaves my side on a trip), which helped me with a lot of the planning.

They really weren’t kidding when they named this place the “Windy City”, and unfortunately, with the exception of a couple sunny and warm days, our 5 days there were cloudy and rainy. Pro-tip: if you’re planning a trip to Chicago, go during the summer months! Nevertheless, the weather didn’t stop us from getting out and seeing all that Chicago has to offer. I’ve put together my short list of the things we did and what I recommend for Chicago below.


We stayed at Hyatt Centric The Loop Chicago, which was centrally located in the Loop (financial district) and very close to many major sights and public transportation. We were thoughtfully greeted with a lovely gift from the hotel: Garrett Popcorn (if you haven’t tried this yet, you NEED to), chocolates, and a Chicago, Then and Now book. The rooms were modern and minimalist with very, very comfy beds. I was also pleasantly surprised by the Bee Kind bath products, which are free of parabens and other artificial ingredients, and the Drybar blow dryer, which uses nanoionic technology and dried my hair in a fraction of the time it usually takes without damaging it (very essential, given that I rely heavily on heat to style my hair, even when on vacation). We got to check out the rooftop bar, Aire, which wasn’t even open yet, for a private tour. You could say we were “blown away” by the views from up there! Hyatt Centric The Loop Chicago also has a first-class French bistro inside called Cochon Volant, where we enjoyed lunch one day (more on that below).


We did a lot in the 5 days we were in Chicago, including: Cloud Gate (a.k.a. “The Bean”) & Millennium Park, The Museum of Contemporary ArtRiverwalk (a designated walking area alongside the Chicago River), Magnificent Mile (the famed 13-block stretch of Michigan Avenue filled with upscale boutiques), Navy Pier (which is soooo touristy, but is a Chicago landmark), and Wrigleyville (not my personal fave, but it’s iconic and I could see how it would be fun for baseball lovers). Chicago is most known for its architecture, and there is no better way to see and learn about the history behind Chicago’s famous buildings than on one of the architectural boat cruises (we did ours aboard Chicago’s First Lady). This was one of the highlights of our trip, and I don’t think any trip to Chicago would be complete without one of these cruises along the Chicago River! Second to the architecture, the atmosphere in the various neighbourhoods also impressed me. Even though it’s small, I could spend hours or even a full day eating and bar hopping in West Loop, which was my favourite neighbourhood by far (think of this as Chicago’s hipster neighbourhood).


The title might be a little misleading, since I’m not referring to alcohol. When I say “drink”, I mean my other favourite beverage: coffee! But, if you are looking for a nice place to grab a drink, I highly recommend Cindy’s rooftop bar in the Chicago Athletic Association Hotel, which is a modern and chic place to take in some views of the city. Going up to the Signature Lounge on the 96th floor of the John Hancock Center (the 4th tallest building in Chicago) was once a good alternative to Skydeck at the Willis Tower (the tallest building in Chicago), because you could see the skyline for free if you order a drink (versus paying at the observation deck). But, it seems that people have caught on to this trick, since we waited for close to an hour in line on the day that we did this.

But back to coffee. Chicago has an ABUNDANCE of great cafes, and they all have their own funky vibe, not to mention good beans and matcha, in some cases! Coffee shop hopping was a major activity on the trip, and my to-do list was comprised equally of places to see, eat, and grab a coffee. Intelligentsia is the most well-known coffee brand in Chicago. There are several locations, their beans are served at lots of places all over the city, and there is a roasting facility that you could tour, if that interests you. We checked out the Millennium Park location, which was busy, but did not disappoint. La Colombe was a convenient pit stop after we got ice cream in Wicker Park. One of the Asado Coffee locations is in the cutest little lane in the Loop (Pickwick Lane). The “COFFEE” sign above the door would have made for many more photo ops, had it not been dark and raining when I visited. But it wasn’t a problem because I shared a coffee with the lovely photographer/entrepreneur, Amy Mokris (@amymokris), of Le Coeur Watches. C.C. Ferns is worth the trek all the way out to Humboldt Park. I took a bus for more than 45 minutes to get there and over an hour and a half to get back, but it was worth it because I got to have coffee with Rachel Bires (, fellow lawyer and Chicago-based Instagrammer and photographer extraordinaire! My favourite of all, not just because it’s located in West Loop, is Sawada Coffee. First, the matcha is AMAZING. Second, do-nut get me started on the baked goods (I don’t even eat donuts (or “doughnuts”) and I really enjoyed the camouflage/military donut). Third, it shares space with Green Street Smoked Meats, so if you want to grab a bite to eat before or after your coffee, you can just go down the stairs and you’re in the restaurant – you just have to see for yourself how cool the space is!


Naturally, I saved the best part for last! We might as well have been on an eating adventure because our itinerary was essentially made up of our brunch/lunch and dinner options each day! I’ll give you the run-down, in the order in which we ate.

As pedestrian as it may seem, if you go to Chicago, you must try the deep dish pizza, so this was our first stop. There are many debates about who started this pizza pie phenomenon. Our research told us that Lou Malnati’s was the best in town. But, you’d still get the same effect, I’m sure, if you went to another well-known place, like Giordano’s or Uno. The deep dish pizza debate wasn’t one we cared to engage in – we just wanted some ‘za, and man, did Lou’s ever hit the spot! The Purple Pig is another Chicago institution, which serves up tapas-style dishes. Our only regret was that we were still full from the deep dish pizza, so we only had a light bite to eat here. Brunch at Little Goat (the sister restaurant to Girl and the Goat) is recommended. I had the shrimp and grits, which was pretty spot on but could have been more substantial! We only grazed on charcuterie and cheese (and, of course, sipped a glass of wine) at Terzo Piano in the Art Institute of Chicago. You can see what was a priority on our agenda, since that’s the only part of the museum we saw! Longman & Eagle was a must-try for us. I mean, anything Anthony Bourdain approved must be good, right? And it doesn’t hurt that it has a michelin star! As mentioned, Cochon Volant in Hyatt Centric The Loop was really, really good! The portions here were huge (we had to take doggie bags), which differed from most other restaurants we went to in Chicago. If you’re a cupcake lover, you can’t visit Chicago without a trip to the Sprinkles Cupcake ATM. I have to admit that this was pretty cool, even though my fiancé was the one who ate the cupcake! Tre Soldi is a pretty solid, no fuss, rustic Italian restaurant. Go here if you want a filling and delicious pasta or pizza (the carbonara was pretty awesome). At the same time, Eataly is the perfect Italian marketplace, with lots to eat in or take away, including gelato, various desserts, savoury foods, and wine. Yolk is a breakfast/brunch option for families, but don’t go here for the ambiance. IMHO, Jeni’s Splendid Ice Creams is the best in Chicago (we went to the Wicker Park location). I had the sweet cream flavour, and I easily could have had 3 more scoops! We had another good dinner at The Publican, a bit of an upscale gastro-pub, which featured communal style tables. On our last night, we treated ourselves to the Michelin-starred Blackbird. The attention to detail was noteworthy here, as were the menu items. However, the portions were too small and we probably would have benefited more from a tasting menu (but not our wallets!).

Sorry, I did say “short list” of things to see and do in Chicago. But as you can see, the Windy City really has a lot to offer! Happy travels, and if you have any questions at all, feel free to drop me a line!

Also, if you managed to get all the way through this travel guide, let me know what you think!