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Chicago Diary

Chicago Diary

“Road trip?” he said. Umm…ok! And that’s how my summer of road trippin’ began. I have to admit, the very attractive part of travelling in your car is that you can take whatever you want with you. No weight restriction is a sexy thought to me. Seven pairs of shoes? No problem. And those were just his.  Actually for my road trip to Chicago this wasn’t exactly the case. We had to stuff two teenagers and their baggage…I mean luggage in the back seat.  So we all had to cut down to five pairs of shoes. What can I say? We’re a shoe family!

The drive from Toronto to Chicago is fairly straightforward.  We stopped for a night along the shores of beautiful Lake Huron for a quick visit with the Rents.  The next day was a bright an early start for a weekend in the Windy City.

Must see sights:

Millennium Park

Located in The Loop community of Chicago, Millennium Park is a must see for an Insta worthy photo op with the Cloud Gate sculpture – more commonly known as ‘The Bean’ because of it’s shape.  Designed by artist Anish Kapoor in 2006, Cloud Gate is made of 168 Stainless Steel plates that have been welded together and highly polished so no seams are visible. It’s truly a piece of public art to be seen. My suggestion is to try and go early in the morning if you’re looking for the very best photo op. The crowds get big and the selfie op’s diminish by mid day.   



If you’re lucky, or really great at planning (I’m not that good) you might catch a concert at the Frank Gehry designed Pritzker Pavilion. The Pritzker is an outdoor bandshell and home to the Grank Park Symphony Orchestra. The free outdoor summer music festival fills up quickly and is a great opportunity to grab a picnic and listen to some great music by sunset. 



Chicago River Cruise

My favorite ‘attraction’ in Chicago was definitely the Chicago River Cruise operated by the Chicago Architecture Foundation (CAF). This is the architectural cruise to take.  The CAF is a non-profit cultural organization; so all proceeds from your admission go to supporting the educational mission of the organization. The cruise guides are all volunteers who dedicate their time to learning (hundreds of hours) the extensive history of the architecture of Chicago and the storied river they sit on.   I was completely taken in by Marina City built in 1967 by Bertrand Goldberg who happened to be a student of Mies van der Rohe. This complex sits proudly besides Mies’ last designed building the AMA plaza.  The juxtapositioning of these two buildings was truly a wonder.  I’m kicking myself for not doing this tour twice, there’s just too much information to take in all in one cruise.



Navy Pier

To really take in the beauty of Lake Michigan go for a stroll down Navy Pier.  The 3, 300 foot long pier is home to gardens, restaurant’s, The Chicago Children’s Museum and family attractions including the brand new (2016) giant Ferris wheel, which offers an outstanding view of the city.  Did you know that George Ferris designed the Ferris wheel in Chicago in 1893? Fun fact, right?  Many sightseeing tours depart from the Pier – my favorite being a lake tour on the Tall Ship “Windy.” The Pier is a fabulous place to watch the sunset and take in the beauty of Chicago.




Museum of Science and Industry

 If you’re with kids (teens), it’s worth the trip down to the Museum of Science and Industry. I was completely taken in by the beauty of the Beaux Arts building. One of the most popular of the permanent exhibits at the museum is the German submarine U-505 captured during WW II. Also very cool is the Apollo 8 Spacecraft, which was the vessel that transported the first humans to orbit the Moon in 1968, but those are among the 2000 exhibits displayed in 75 major halls. If you’re a lover or museums – this one is worth a full day of your itinerary.


Magnificent Mile

 Fashion Blogger who was totally agitated on the Mag Mile. That’s exactly what I am. The Mag Mile is a bit like Times Square to me…loads of people and nothing I haven’t seen before.  This ‘upscale’ section of Michigan Avenue is Chicago’s largest shopping area which ranges from mid to upscale shops.   I personally don’t like elbowing through crowds to do my shopping…but you should probably take a stroll down (or up) the Mag Mile, just to say you’ve done it. My hus tipped me off to Water Tower Place, a shopping mall on the street that made me happy because it had a CUSP by Neman Marcus in it.  I always like peeking in a CUSP when I can. But that’s pretty much where the Mag Mile ended forme. I know…sad, right?


Off the Beaten Path

 Frank Lloyd Wright Historic Site Tour

Chicago is an absolute treasure for architecture lovers, and not just for the buildings along the river. My favourite architect Frank Lloyd Wright (FLW) happens to hail from the windy city and seeing that the first home he designed for himself and his first wife, and subsequent homes in the surrounding area of Oak Park Chicago was bucket list (I don’t actually have a ‘bucket list’ – but if I did this would have been on it) item for me.

Oak Park is small subdivision about 15 minutes west of downtown Chicago. It’s famous for housing the highest concentration of FLW designed homes in the US and is the birthplace of his legendary Prairie style.  2017 also happens to be the 150th Anniversary of FLW’s birth, it’s a special year in his architecture.  I chose the ‘self-guided’ tour of Oak Park and enjoyed strolling the streets taking in each home’s unique beauty.  What drives me crazy is that I was so enveloped in FLW that I completely missed the birthplace of one of my favourite authors Ernest Hemmingway.  Talk about the biggest F-up ever. Well…guess it means I’ll just have to return.  Sorry Hem!


Where to Stay:

 Because I was travelling with my children, I chose a hotel close to all the amenities of downtown Chicago.  The Kimpton Palomar - Chicago was a great choice.  I had never stayed at a Kimpton Hotel, so it was good to try a new chain.  It had a pool…so when the boys wanted a bit of down time; they had something to keep them occupied. I will admit, I did let them venture off on their own a couple of times. They’re teenage boys (17 &14) with Siri, Google and city street smarts on their side.  They loved and appreciated the freedom, which made for happy kids.   And we all know happy kids are soooo much better to travel with.

The Kimpton is also one of the only larger hotels that offered a suite room AND rollaway cot.  Many of the hotels I contacted wouldn’t provide a cot for the room. To my surprise, the cot was more like a twin bed! Everyone was happy.


Kimpton Palomar

505 North State Street

Chicago, Il



If you’re not keen on staying in one of the big hotel chains, Chicago has a ton of fab Air BnB’s to choose from.  Air Bn’B is a great option when travelling - don’t overlook it.

Where to Eat:

 Staying so close to the Magnificent Mile there’s a cornucopia of resto choice to enjoy with your kids. Here are my suggestions:


Weber Grill Restaurant – if they love The Keg, and who doesn’t?

539 N State Street.



43 E Ohio Street. 

True Food Kitchen – Um, not my kids – but maybe your kids!

1 W Erie Street.


Shake Shack – great for lunch - check website for all locations.

66 E Ohio Street. 


Pizzaria Uno – for classic Chicago Deep Dish.

29 E Ohio Street


Smile for the Camera

Smile for the Camera

Caring for your Cosmetic Brushes

Caring for your Cosmetic Brushes