The Ultimate Weekend in Chicago

Ah, the windy city! The most amazing place in the Midwest to have a quick girls trip. The Ultimate weekend in Chicago doesn’t have to be overdone or too full of plans, take it easy and follow along if you want to hit the right spots and see what the city has to offer. From the best views, parks, restaurants, and hotels, Chicago truly has it all for all taste and budgets. I think of it as an understated, clean and chilled version of NYC. Have you been?

I’ve rounded up in this post the places I went to and loved, with my buddy boo Kathleen Post from the Lemon Blonde the weekend before the fourth of July.

We were invited by The Gettys Group to spend a couple of summer nights at one of their finest properties in Chicago, The Blackstone Hotel. Needless to say, we were thrilled and decided to explore the best of what the city has to offer – and report it all back to you!!

THE ULTIMATE WEEKEND IN CHICAGO!

I’d love to start with 7 reasons you want to stay at The Blackstone:

1. Just steps away from the Cultural Mile, Grant Park and Lake Michigan.
2. Known as the “Hotel of Presidents” The Blackstone has hosted US presidents, foreign dignitaries, political and mob exchanges, actors and more.
3. If you like history, you’ll get a kick out of this place. It hosted Al Capone every time he was in the city. He even had his own barber chair where he used to get his grooming at! A few movies were filmed on the property as well. One of the chicest hotels in the city, it has a lot of history behind its name and you can visit the beautifully curated spaces recently redesigned by The Gettys Group. If you’re an art lover or simply appreciate it, you’ll find more than 1,600 original artworks, primarily by Chicago artists and curated by NINE Dot ARTS. Plus the lobby has been recently updated with locally sourced, unique furniture and décor pieces that reimagine, yet pay homage to the property’s colorful past.
4. Besides the perfect location, our room had amazing Skyline views, as well as the Lake Michigan and Navy Pier.
5. Amazing beds are essential but the all white marble bathroom is a huge plus. A fabulous shower (I’m a sucker for a good shower head!!), super clean and prompt room service.
6. Stay for breakfast by booking the Stay for Breakfast package (weekends only) or enjoy breakfast at the 1600 Club featuring some great coffee, pancakes, bacon fresh seasonal fruit and more at the cutest little breakfast room 🙂
7. They have a happy hour mini bar in the lobby with a bartender making cocktails that are available for purchase for the guests that are chilling on the cool chairs, waiting to go somewhere or coming back for the night. I grabbed a glass of cab before heading up for the night, such a nice little treat!

I bought this gummy bear gauze woven jammies in Chicago and they came in super handy for after my surgery! Super soft and they have the cutest styles for $22. Go up a size for a loose comfy feel 🙂

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Oh, the bathroom. Perfect lighting!

I like to travel light when it comes to beauty too, so I select products that I can multi-task. Like this Charlotte Tilbury Film Star bronze & glow that works as my eyeshadow as well!!

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The first day we met up with our friend Ali Stone at the Barrio for a quick drink and some delish chips & guac!

After catching up for a bit we headed to our Chicago First Lady’s Cruises Boat tour, a must for a weekend in Chicago. This tour is an architecture tour in the river that lasts a little over an hour and has such a cool perspective of the buildings by the water. We got rained on twice, blame July’s heat, but we were able to see so much of the city from one end of the river to the other! The boat has a full bar for those who truly want to sit back and enjoy the ride!

Wore this Vici Collection blouse / Vici shorts (sold out) / Vici Coronado Sandals / Gucci bag (similar) / sunnies / hat

Talking about the river we got to enjoy dinner at The Kitchen bistro right by the river with a stunning view of the water and the city’s buildings. The kitchen is owned by Kimbal Musk, whose primary goal is to serve real food sourced by American farmers at every price point. Besides the delicious hearty food and yummy craft cocktails, The Kitchen has a relaxed yet chic atmosphere. The open kitchen concept is seen here just like at their sister restaurant here in Indy, the Hedge Row Bistro. Which btw is one of my favorites in town!!

We had delicious fried cheese curds and braised lamb gnocchi (to die for), we were so full from these two appetizers we couldn’t order an entree. BUT we managed to fit in dessert!

May I introduce you to Sticky Toffee Pudding – pecans and buttermilk ice cream, an explosion of yumminesssss

We loved their outdoor space, bummer they were closed that evening due to storm warnings. But we got a little sneak peek of it for ya!!

I wore a Vici Collection stripped jumpsuit (sold out sorry!)/ Vici Coronado sandals / straw bag / Gorjana crescent necklace 

Day 2: you can’t plan the ultimate weekend in Chicago without paying a visit to the Skydeck Chicago. If you’re not familiar this is what the experience entails: step outside the tallest building in the Western Hemisphere. At 1,353 feet in the air, the Ledge’s glass boxes extend out 4.3 feet from the Skydeck. Lines are long but it’s such a cool experience! I couldn’t look down much because that is some serious highs but the feeling is like you’re floating!!! The Skydeck is open 365 days a year and you can get a discount if you use the Chicago City Pass.

Vici Jumpsuit (comes in black too) / vici sandals / straw bag

The views from the building are stunning!

Brunch at the Summer House Santa Monica is a must while in town. They have such a cool atmosphere! Think Cali vibe beach house style with hanging plants, a retractable glass ceiling long silky curtains. The menu is California inspired and focuses on market-driven ingredients, local and sustainable farming, and seasonal specialties, all complemented by a carefully curated list of California and Pacific North Coast wines. The Market counter, shared with Stella Barra Pizzeria, offers a variety of our signature fresh-baked pastries, cookies, sourdough English muffins, along with locally sourced coffee and specialty espresso drinks. – Summer House. 

Vici Jumpsuit (comes in black too) / vici sandals / straw bag / sunnies

After brunch we headed to the hotel to freshen up and change and then shopping we went, after all, that’s what the Magnificent Mile is for my friends!!! The MM is Chicago’s premier commercial district. They have just about any store you can name for every taste and budget, from fast-fashion to couture. It’s just FAB!!! We hit Forever 21  (where I bought the cute gummy bear pj’s up there!) and my fave Zara and surprisingly I didn’t buy much…they had awesome sales but I think I’m ready for fall shopping…anyone with me?!

Another must-do while planning your weekend in Chicago is to pay a visit to the Navy Pier. I love the fun vibe, attractions for all ages and budgets, fair food, bars and restaurants that line up by the sidewalk with a view of the lake. The Ferris Wheel views are one of the best views in the whole city, we didn’t get to go this time around but see this post from a trip I took with my daughter Bella last year, for all the cool views and an overview of the Navy Pier!

Outfit by Vici Collection (sold out) sorry guys it took me a while to get this up and going so I apologize for sold out items!! / sandals / sunnies / necklace

Fisk and Co. is inspired by Belgian Bistros. Think mussels, beers, and an amazing oyster bar! They call themselves casual but they are upscale in the most casual way 🙂 beautiful indoors and the outdoor is in a perfect city corner with a fun and energetic street scenery!

We had a feast at Fisk & Co. I started with their jumbo shrimp cocktail (which I failed to snap a pic…ugh!) we had the Kale Caesar, Gnocchi Cacio E Pepe (to die for), frites with different aioli and sauces accompanied by delicious glasses of vino!

This cheesecake was the BEST one I had this far in my life….no joke. the crust is moist and nutty and the top is fluffy and airy. Must try my friends!!

bb dakota pant / bb dakota top / sunnies / bamboo bag(size large!)  

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The recently remodeled lobby at The Blackstone was the perfect spot to relax and chill before our departure.

 

ASTR The Label Marissa dress / wedges / bag / sunnies

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Is it just me or this decor is stunning?

We meant to stop at Cindy’s Rooftop but failed to do so since our days were so busy. That’s on the to-do list for next visit. I’d love to know if you’ve been and if you love it!! Finally, I hope you enjoyed this post and that it helps you plan your first or next visit to the Windy City! Any thoughts on what’s missing in this post I’d love to hear them!!

For more must-visit places on Chicago check out this partnership I did with Holly & Tanager last year at a few great touristic attractions in the city.

Beijos,

-K