Chicago By Mat, By Board, and By Rooftop

The black hole of content from August of 2016 to April of 2017 — when I jumped forward to blog the summer of 2017 as it was happening — have been haunting me. I’m so excited the time has finally come for me to catch up on them! I can’t wait to turn my detailed notes and journals into blog posts from Canada, the United Kingdom, Hawaii, Thailand and Bali! But first, a few final briefings from the continental US, picking up where I left off with my August 2016 trip to Illinois…

My apologies for any confusion with the timeline, and thanks for sticking with me!

I’ve been lucky to write about some truly exotic and far-flung adventures with my family in the six years I’ve been full-time blogging. But I’ve also shared that as travel-crazed as my clan is these days, when I was growing up, we kept things simple. Until I hit college, my family rotated through a familiar trio of destinations: Martha’s Vineyard, our favorite summer getaway; Florida, where my dad’s family lives; and Illinois, where my mom’s family lives.

Once I hit middle school, I was deemed old enough to get on the plane by myself to go visit my beloved cousin Kirsten solo, where I’d spend spring break hanging out in her classroom or tagging along on the church group excursions she chaperoned. I absolutely loved my regular trips to both Decatur, the small town where my mom grew up and most of the family still lives, and Chicago, where my cousin had moved after college.

So I don’t really know how five years flew by without me making my way back to the Land of Lincoln! This trip was very, very long overdue, so when I finally made it happen, we hit the ground running — Kirsten instructed me to wear yoga pants on my 6am flight, and picked me up from the airport with a mat in hand.

We were straight to the free Sunday series CorePower Yoga in the Park at Rosemont Financial Park. Kirsten recently did her yoga teacher training at CorePower, and I was excited to try the popular chain of studios, especially since they offer a free week of classes to first time students. A whole free week of yoga and barre? CorePower is all over the US — that’s a hot fitness travel tip if I’ve ever heard one! (And if you’re one of those people that things yoga is boring or easy or you want a tougher workout, I challenge you to heated Yoga Sculpt at CorePower. It burns!)

After post-flow brunch at Flo — where no, I could not in fact resist ordering the famous fruity pebble french toast for the table — we were off to meet Kirsten’s then-fiancé (now husband!) at their boat dock. Now, this will always be remembered as a very momentous summer in my life: the summer I learned that going and sitting on your boat while it’s docked, and not actually turning the boat on or going anywhere, is very much a thing.

Before this awakening, I was under the impression that people enjoyed their boats by, well, boating them somewhere! But suddenly it seemed like everyone I knew had gotten a boat or was dating someone with a boat, and all said people wanted to do was roll up at the dock, crack open a bottle of wine, and chat with fellow boat dock sitters. As someone who is both a fan of sitting on boats and doing nothing, I did not hate this.

For the next few days, Kirsten worked on getting her classroom set up for the new fall class and I swapped between helping her where I could and crunching through my own to-do lists — with plenty of breaks for CorePower classes, of course.

But these two asana addicts can never get enough yoga! We also snuck away one night for my most anticipated event of the trip — SUP yoga on Lake Michigan.

Chicago’s urban beaches are without question my absolute favorite aspect of the city, and so I was thrilled to check out a new one when we pulled up to Montrose Beach. Paddling out as the sun began to set over the skyline was epic! Unfortunately, my gushing ends there.

At $50, this was one of the most expensive SUP Yoga classes I’ve ever taken — and I’ve been lucky to take them across the US and around the world.  In previous classes, life-jackets have either been optional, not even offered as an option, or sometimes required to have on the board — but never, in my experience, required to be worn throughout the class. I actually gave a lot of pushback on this when the teacher made the announcement in our introduction — even asking if I could sign a waiver that I’m a certified divemaster and registered rescue diver and was opting out of the life jacket. The answer was no.

I found it pretty hard to enjoy the class after that. We were anchored in waist-deep water in a calm lake, largely enclosed by a nearby fishing pier, and you try doing a chaturanga with three inches of foam between you and your board. It’s pointless.

I absolutely have the utmost respect for water safety and I understand that life jackets can be literal life savers in many situations. But this was one of the most expensive yoga classes of my life and I spent it frustrated by my restricted movement and uncomfortable chafing. They were unnecessary given the conditions and we should have been allowed to make our own choices about wearing the jackets or keeping them on our boards. In retrospect, I wish I’d asked for a refund and left.

I will look for more SUP yoga classes next time in Chicago so I have a great one to recommend — and I’ll be sure to ask ahead about their life jacket policy, next time.

Back to dry land! On our last day in the city, we decided to take a true Chicago field trip: a day of playing tourists in The Loop.

Despite my many, many trips to Chicago, I couldn’t actually remember every ticking some of these iconic sights off my list. So we set off to hit all the big ones, starting with the iconic Bean sculpture in Millennium Park. To me, it’s perhaps the most iconic image of the city — aside from perhaps a slice of deep dish pizza.

We were loving this beautiful late-summer day in Millennium Park and so we decided to enjoy it a little longer with lunch from Cindy’s Rooftop. While Cindy’s can be one of the hottest reservations in town, we lucked out with it being a mid-week late afternoon and walked right into seats at the bar for salads and craft cocktails.

I’m not sure what we loved more — the perfectly designed interiors of the chic and retro restaurant, or the views from its deck. Okay, it was the deck.

I loved Cindy’s so much it was top of my list for my next trip — I returned the next year in all my wedding finery the day Kirsten said “I do!” And I’ll come back again — I’d still love to try their weekend brunch menu, if I can score a reservation someday.

Next up on our day of tourist-ing out? The Centennial Wheel at Navy Pier! For $15 a ticket, we hopped in a pod and soaked up the views, took selfies, and chatted with the cute family we were seated across from.

Having enjoyed the main attraction, we skipped the other rides at Navy Pier in favor of moving onto our next stop — Tilt at the 360 Chicago Observation Deck. This is Chicago’s answer to The Empire State Building or Top of The Rock… and it can have the lines to match! Again we lucked out with no crowds, and splurged and went for a package that included admission, a round on the Tilt ride, and a drink from the bar for $32.

Having already had two great views that day, I wasn’t exactly expecting to be blown away by a third. But I was wrong — this was far and away the best vantage point over Chicago I’ve ever seen, including incredible views onto the city’s beloved beaches. If you’re only going to get one aerial view over The Windy City, make it this one.

As for the Tilt itself, it was actually very cool! Basically, you and seven other people walk up to a special portion of the window and grab onto handle bars. Then, the window tilts outward thirty degrees, leaving you squealing like a crazy person a thousand feet above street level on the Magnificent Mile.

360 Chicago has some very cool programming throughout the week — a skytop yoga class on Saturday mornings, a “hoppy hour” of local craft beers on Thursday evenings, and an art night for painting the view every Wednesday. How fun is that?!

And heads up, Chicago residents — there’s a sweet 50% off deal for anyone who’s a local resident! And fear not if you’re from afar — you can still get 10% off by ordering online. Ironically, this was probably the item on our agenda I would have been most likely to cut, but it ended up being my favorite.

What a literal high note to end the trip on! And as much as I’d loved my time in the big city, it was time to head to a small town.

Next stop, Decatur…

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