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Wanderlust Wednesday: The Windy City

This week’s Wanderlust Wednesday feature is by Tiffany from My Happy Coincidence.  Tiffany is a Toronto based blogger, photographer, and writer who loves exploring new places both within her city and the across the globe. You can explore Tiffany’s work on her blog (My Happy Coincidence) and see her photos on Instagram.


“Chicago is, my kind of town. My kind of people too!” Frank Sinatra knew what was up for sure! I fell in love with this neat city on my recent summer excursion. Among its many highlights, the city boast great food, friendly people, and fantastic walk-ability.

Here are my tips, tricks, and highlights for those of you who plan to visit The Windy City…

1) Hancock Centre (875 N Michigan Ave)IMG_0322

Don’t pay for the observation deck! Enter from the north street-level entrance of the Hancock Centre (off E Delaware Pl) and tell them you are going to the “Signature Lounge” (they will ask for ID before letting you up the elevator). Dessert is around $10 and you get great views of the city from both the north and south facing lounges.

I found the view from the Hancock Centre  way better than the Willis Tower’s as well, though its hard to beat the allure of those fun glass cubes!

Do you ever wish you could have a local show you around their city? This is exactly what the Chicago Greeter program gives you. Visit their website 10 days in advance, select the themes or neighbourhoods that interests you, and Chicago Greeter will pair you with a local accordingly. The program is completely free, includes transit if necessary, and has a strict no-tipping policy.

3) Chicago Cultural Centre (78 E Washington St)
If you meet-up with a Chicago Greeter he or she will likely meet you here or, if you meet at your hotel, you may stop here to collect a transit pass. This short pit-stop will only be a tease though and you will certainly want to make another stop. Originally the city’s first library, the Chicago Cultural Centre plays host to variety of stain-glass ceilinged rooms and halls of intricate tile work.

4) Chicago Athletic Association (12 S Michigan Ave)
This gorgeous building is just a little south of Cloud Gate and The Bean. Now the home of an ultra hip hotel, this historic site is absolutely gorgeous inside. The rooftop restaurant has phenomenal views of the skyline from inside the city and if you ask nicely they will let you out on the balcony even if you don’t eat there.


5) Harold Washington Library (400 S State St)

The outside architecture of this site is breathtaking and the intricate ironwork makes a bold statement. Visit the 9th floor Winter Garden for a beautiful, utopian escape from the city.


Speaking of eating… 

1) Garret’s Popcorn
The caramel and cheese combination of Garret’s famous “Chicago Mix” may sound a bit off, but it is the best pop-corn I’ve ever eaten! They have many locations all over the city.

2) Cafecito (7 N Wells St, near Harold Washington Library)
This cute stop has amazing Cuban style coffee and sandwiches; their pastries are also very tasty! We did take-out and walked over to Millennium Park to eat and people watch.

3) The Purple Pig (500 N Michigan Ave)
Tapas style eating and wine bar with amazing flavours! The wait on a weekday evening can be a tad long so show up, get put your name on the list, and wander the area a bit.

5) Lou Malnati’s PizzaIMG_0277
The much heated “best pizza place in Chicago” debate is a difficult one to navigate. Our Chicago Greeter assured us that Lou Malnati’s was the real day and it was very good. They too have locations all over the city.

6) Hash House a Go Go (1212 N State St)
If you want breakfast that will fill you for the whole day this is the place. Very yummy, not too expensive, and with great  portions. We affectionately called our plates “Freedom Breakfast” if that give you any idea of how typically American this tasty stop is.


7) Max’s Take Out (20 E Adams Street)
If having a Chicago Style Hot-dog is on your list, Max does it right. No ketchup unless you are under 18, a fully loaded, Chicago-style Vienna Beef dog won’t cost you much and makes a very satisfying lunch! There isn’t much seating inside so be prepared to opt for carry-out.

Handy Websites… 

Chicago Magazine’s Neighbourhood Guide  highlights the attractions in Chicago’s many diverse neighbourhoods. Consider exploring this site before booking your Chicago Greeter to inform your theme and neighbourhood choices.


More about Tiffany

IMG_1416Tiffany is a recent graduate from York University’s English M.A. program and also holds a B.A. in English from York. She is editor-in-chief of My Happy Coincidence: A Bog for Art, Literature, & Life where she also writes book and theatre reviews along with life and career advice articles. She loves photography and is rarely found without a camera in her hand.


  1. Pingback: Wanderlust Wednesday: The Windy City — Eco Chic Cayman | My Happy Coincidence

  2. Chicago is one of my favourite cities! My boyfriend lives there (I live in England) and I love visiting him. I loved reading about Chicago on your blog. I have a blog post about the Windy City as well, I hope you will like it at least half as much as I liked yours 🙂