Sunday, November 4, 2012

Trading Monday for Chicago

 It's Monday, and by nature - that means that most of us are sitting at our desks, depressed, sipping coffee and imagining what life would be like if the weekend never ended. It's some hoggggggwash. And when I need to escape the reality of the 40-hour work week that faces me on those cruel Monday mornings, I escape to what a perfect day would be in my favorite city of all time:
Image VIA 1 | 2

EARLY: Wake-up and bask in the unrivaled aesthetics at the Hotel Sax Chicago. Enjoy a room service breakfast while looking out over Marina City- one of my very favorite architectural designs I've ever witnessed.
Images VIA:  1 | 2 | 3

SEMI-EARLY: Grab a cab and head to Wicker Park. Known for its subculture and artistic whimsy; I'd navigate area shops with an appreciation I inherited from Portland's enthusiasm for this vibe.
Image VIA
Noon: Be a shameless tourist and head over to the Art Institute of Chicago. I'd lose myself in a way that would even make cultural icon Ferris Bueller proud.
Images VIA 1 | 2

Afternoon: After filling my soul with art, I'd gladly contrast that with a decadent shopping trip on Michigan Ave. I'd pop from shop to cafe spending money like the world is about to end (this is all hypothetical mind you).
Images VIA 1 | 2
Late Afternoon: Enjoy a stroll alongside Lake Michigan. This Lake seriously makes my jaw drop- it's just like an ocean!
Image VIA

Happy Hour: Visit the John Hancock observatory. Might be the less noticeable, tall, black building in Chicago- but I think it's got a lot of street cred on its own and provides just as amazing of views as the Willis/Sears Tower.
Images VIA 1 | 2

Dinner: One word: Alinea. Noted as one of the best restaurants in the country by many reviewers, I am simply dying to try it out myself. If for no other reason than the amazing presentation of the food. But as I've heard- this is definitely an ALL STYLE, ALL SUBSTANCE situation.
Images VIA 1 | 2

Late: Go to "The Whistler" for late-night cocktails and live music - a combination that few I know would pass up.
Images VIA 1 | 2

Way late: End the night at The Wiener's Circle- but not because I want a hot dog. Working here is what I imagine every food service employee dreams about: the employees b*tch out the patrons...incessantly. Don't believe me? See for yourself HERE. Next time I go to Chicago, I'm going to put on my big-girl boots and take a verbal beating at this joint- just so I can say I did.
Images VIA 1 | 2

So that's my 'happy place' for today- what helps cure your Monday blues?
And Chicago Natives/Locals - any thoughts to my list above (good or bad) are welcomed!



Unknown said...

I dont know if i have ever loved a place as much as you love Chicago. All these posts about it have me dying to visit it :)
P.S. My Christmas present DSLR was purchased on the weekend :) weeeeeee! I showed my mum your post about your new camera bag and warned her that that was what i wanted next haha

Anonymous said...

I loved the view from the Hancock Observatory. Didn't go to the Sears tower though, so can't compare them.

I think Monday will be spent recuperating. Saturday night was a long one!

Brooke said...

Looks fantastic! I would love to visit that city! Great pictures!



Kate Sparkles said...

I am so very jealous of how well you know Chicago. I spent a lovely week there a few years ago but it was very touristy.. I liked what I was but felt like I didn't really get to know the city. if that makes sense?

What a perfect cure for mondayitis.

erika sorocco said... I've decided that I'm totally going to live vicariously through you today, and imagine that I am visiting each and every one of these places. LOVE Chicago!

Happy, Happy Monday, Caitlin!! :)

Bravoe Runway said...

You pretty much would love where I live since it is about 1/2 a block from marina towers. I would love to eat at Alina or at grant's recent creation, next. A new menu and decor every 3 months!

Pat Hatt said...

Sounds like you love Chicago a ton. That is one vacation I'd even give a run, have to make Bueller proud haha

Ashleigh said...

This post made me teary! I do love this city so much and seeing all of this reconfirms how incredible it is. Every time I drive into downtown I put the skyline between my fingers and "hug" it. (Hubby thinks I'm ridiculous. :) I was once in your shoes, dreaming of Chicago from a small town in Tennessee, and sometimes I still have to pinch myself that I moved here, and have called it home for nearly 7 years. It's bittersweet because I know we won't be here forever, so I soak up as much as I can and play shameless tourist as often as possible. I hope I still live here when you do. If not, I'd be happy to pass my life over to you, condo near the lake, amazing friends, and all :) At least come visit before I go!

HollyGoGlam said...

Ha! I am doing exactly that..I am in my office at work and putting off a pile of files while browsing blogs.. sipping my Starbuck's thinking about this coming weekend. Ahh Mondays. I have never been to Chicago. It is def. on my top America destination list! I have heard so many cool things about that city..and I LOVE cities! Can't get enough of the buzz of a downtown!

Mandy @ In the Fashion Lane said...

Can I go with you? Haha. I have never been to Chicago and I am dying to go. When I do, I will be contacting you. I hope to love it as much as you do! It looks like an incredible place to live. :)

Amanda @ Life with A.Co said...

That's cute! What a cool blog post idea, sure seems like a perfect and ideal day in Chi-town!! :D

PS - your comments are always THE NICEST, C, thanks SO MUCH, they really make my day!! xoxox

Harriet said...

One of my favorite things I've ever done in Chicago was going to Park Grill (right outside of Millenium Park) for some drinks. It was perfect-- the bean was only a few hundred yards from us, and we had some delicious cocktails while recovering from the half marathon we did earlier that day. Ooh... maybe sign up for the Rock 'n Roll half there next year? (Or really any other race.) It'll give you an excuse to head out there, AND training for the race will help get (or keep) you moving. :) [Also, ditto to what A. Co said-- you're one of the nicest commenters ever!]

Kara said...

You haavveeeeeee to try this place called La Scarola a few blocks from's a bit off the beaten path but the character is just sooooo worth it. Plus, the italian is great :)

naghmeh said...

aaahh you've made me fall in love with Chicago! visiting your blog regularly has made me want to go there so badly and it's going to happen some time soon, it just has too!
thanks for the little guide you've put up too :)

my Monday blues are easily cured by good cup of coffee and a book I love :)

| C AND C | Sarmin said...

You totally make me want to book a ticket to Portland, & Chicago. Both cites never been to, well I was O'Hara on my way to NY, but yeah I shouldn't count that in. Can I come visit you? I will bring cupcakes...

erica said...

Oh how these pictures make me miss Chicago. Maybe i`ll have to talk some friends into going after Christmas. xx