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Saucy manages to dash in and out of Chicago pretty regularly and for that, she is very fortunate and grateful. For some reason, as a kid she always wanted to go there. When asked where she wanted to travel it was always at the top of her list and often this response grew quizzical stares from friends and relatives. From the first trip she made there almost ten years ago, Saucy felt like she'd found a very dear friend.

Now that she somewhat knows what to do, Saucy can "do" Chicago in three days. In a mere seventy two hours, she can accomplish what she needs to do, and she usually arrives with a list. This past weekend was no different. With tight time constraints, this is how Saucy and her crew get things done.

Friday evening: check into the James Hotel on Ontario Street. It's a haven for hipsters and those who frequent Hotwire.com (Veto). Steps away from the shopping on the famous "magnificent mile," and there's only a few hours allotted for moving around there, so let's get this party started.



Hungry? Grab a quick bite and some evening dessert at the Grande Lux Cafe. It's been a long day of traveling and since The Warden and The Inmate are staying at a hotel on the other side of Michigan Avenue, this is a great place to meet up after having a quick drink in the lobby of The James. Sure, it's a chain, but it's around the corner, it's handy, and there's a table ready. That doesn't happen often but there's bad weather rolling in and people seem to be staying home.



On the way back to the hotel for the night, Saucy makes a clean sweep of TJ Maxx and Home Goods and even though she's had a chocolate martini or three, she still bags a few bargains and gathers up some giant pearl baking sixlets.



On Saturday morning the alarm is set for... early. Saucy and The Inmate are meeting at Blowtique (a blow dry salon on Huron Avenue) for shampoo/blow outs that leave Saucy's hair as bouncy as she's ever had it in her entire life. This one stop of the weekend ensures good hair for the duration of the trip. Indeed, even the ladies at Tory Burch later in the day stop and compliment on her tousled locks. A well-spent thirty five dollars.



After the blow outs, meet up with the boys and meander through Nordstrom Rack for a quick scour. Saucy scores a Kate Spade dress, reading glasses and a few Christmas gifts.


These glasses, right here.


This dress, right here. 

Anthropologie is right next door. Let's pick up those little felted mice tree ornaments, Saucy has a plan for them in the new year. She's pretty excited that mice could look so cute... and so fake. She's had some mice issues lately. These mice are okay. 



Before the group breaks off into boy/girl shopping buddies, have a lunch break at the seriously crowded (for good reason) RL Grille in the world's largest Ralph Lauren Polo store. Over the years, the baked cheese plate gets more and more delicious and when followed with a lobster clubhouse sandwich, you will be immediately fortified to cross the street and brave the shopping at The Water Tower. It's the only place to find American Girl and the Lego store, so get it done now while you're still a little tipsy from the champagne lunch and your fluffy hairdo.



With The Water Tower crossed off your list, head over to the 900 Shops (900 North Michigan Ave). Scope out worldly trends at LK Bennett and Karen Millan, where after a glass of free champagne you will actually begin to think you might be Kate Middleton when you catch a reflection of your hair in the mirror. 

Scoot out of Bloomingdale's and hit the highbrow boutiques on Oak Street. It's still early but surprisingly dark outside, you love that about Chicago in December. Dash in and out of Juicy Couture, Kate Spade, Tom Ford and Tory Burch (where you are so delirious over the hair compliments from other customers that you purchase the orange nylon tote bag - but don't worry, it's deeply discounted).



On the way back to the hotel to get changed for dinner, make quick pit stops into Urban Outfitters (a glittery vintage headband for Loopy) and Argo Tea.



Dinner on Saturday night is a tad disappointing at Howells & Hood in the Tribune Building. Televisions are blaring not just in the bar but also throughout the dining room. The food and the service are bland, and you make a mental note that even though you try something new every time you visit, it might not always be a home run. Proceed to the lobby of the Intercontinental Hotel for a nightcap and a "flight of chocolate," whatever that means. The men will order desserts from Micheal Jordan's Steak House that are as lacklustre as you would expect them to be. 

It's time for bed, anyway. You've only been at this for thirty hours and you're already exhausted.

On Sunday morning, get up early to ensure a good seat at Hash House a Go Go on State Street. It's one of Loopy's favourite stops (the pancakes are the diameter of a truck tire) but she's not with you so go ahead and have the grapefruit mimosa laced with St. Germain and basil. For actual food, order (to share) the chicken and waffles.



There's bacon cooked inside those giant waffles, friends. And that is enough chicken to feed an entire family. It's at this stop that Veto orders an extra biscuit with his breakfast and earns the nickname "Biscuit Benny" for the rest of the weekend. It was a lot of biscuits.

Hop on the Kennedy Expressway and make your way toward O'Hare. At Rosemont you will find the new outlet stores.



Go inside and find the items you wanted that you saw on Oak Street yesterday for a fraction of the price. Don't you love it when that happens?


Like these boots from Steve Madden...

and these ones, too... it's BOGO after all!

Shoes to go with the Kate Spade dress!

Sensible Kate Spade shoes!

A sparkly J Crew sweater

J Crew with embellishment

J Crew tunic with sequins

J Crew sweatshirt with beads
Saucy also got a pink oxford shirt and some accessories... and left the store for under one hundred and forty dollars! 

After some serious damage is done at the fashion outlets, make your way back into the city by detouring through Lincoln Park to hit some street shopping and Restoration Hardware, Pottery Barn and West Elm. Saucy picked up a luxury fuzzy throw at RH and a few gifts.



Back in the city, after recharging at the hotel, it's time for a quiet and relaxing dinner at the Capital Grille. 


It's hard to even imagine being hungry after brunch but you cannot resist the siren song of the lobster mac and cheese.


Apparently the Dallas Cowboys cannot resist it either, they're in town for Monday Night Football and are all dining at the Grille. They're staying at the Hyatt adjacent to the restaurant so head there for a nightcap and some gawking/stalking afterwards, even though you are stuffed.

On Monday morning, time is of the essence. You only have a few hours left to accomplish what's on your list: buy groceries and booze at Jewel/Osco, help Veto change hotels (he has meetings at the Hyatt Regency this week) and scoot around State Street. Around "The Loop" you can hit another Nordstrom Rack, TJ Maxx and Macy's. Stop for a sugar fix at Magnolia Bakery and head into Sephora with Loopy's list of must-haves (items the small store at home doesn't carry). 

Saucy picked up one last bottle of the Jennifer Aniston perfume at the discounted price. It will be off the shelves soon.
Duck into Target to pick up grocery items you can't find at home. This includes several different flavours of Goldfish crackers and some ice cream (it's going to be your supper so enjoy it).


And... that's about it. You still have to get back to the hotel and pack this all up before catching your flight home. It's been a whirlwind of a weekend. You realize that you didn't really try anything new or exciting, but it was awesome. You spent a weekend with family that you enjoy calling friends. You ate, you drank, you found bargains. You wisely skipped the lineup on Michigan Avenue for the Garrett's popcorn because you can grab it in Terminal 2 before you board. You've got this down.

This is your kind of town, Chicago is your kind of town.

6 comments:

K :) said...

Love, love, love visiting Chicago. Planning to add the fashion outlets and Capital Grille to my list for my next trip to the Windy City.

Thanks so much for sharing.

Amy said...

You should be able to get the Scotchy Scotch Scotch here, Walmart in Regina has it anyways :)

Anonymous said...

Those RH throws are the best! I have two but might want one more, so everyone has their own!

sassy said...

Oh the school of Saucy is so educational! Thank you dear cousin! The Cowboys! The waffles! The blowout!! The shopping- oh the shopping!!!!
I love hearing about your glamorous adventures as I fold laundry, pour milk upon demand, drive to soccer and enforce piano practices.

Green Girl in Wisconsin said...

What a trip!

Anonymous said...

Oh Sasha, the Grand Lux is one of my favorite restaurants in the states!!!!!
Jennifer