A weekend or two ago, myself and four of the loveliest little ladies ventured off to Chicago for a complete girls weekend getaway. It all happened because of our recent 200,000 Facebook follower giveaway where the idea was to pick one winner and a person of their choice to join us [the LIY team] for a fun filled weekend in Chicago! After selecting our winner(s) at random, the sweetest girl Sarah and her sister all the way from California, we were ready to roll! Bringing two strangers from states away for a weekend away could have been a very scary/risky thing [what if the people had zero personality? what if they only ate kale? what if they didn’t get my humor? what if they didn’t like alcohol?] basically, a lot was on the line. Fortunately, our personalities couldn’t have meshed better and we had such a fun time. Or at least I had a fun time. I think they did too but you know what assuming does…

Regardless, I thought it would be fun if I shared the complete itinerary of what we did, where we stayed, where we ate, etc because in my personal opinion it was the prime time of all girls weekends. Everything we did we loved, where we stayed was amazing, the food we devoured was delicious and the activities we ventured off to were a lot of fun. If you and your girls are planning a trip to Chicago in the near future, consider this your ultimate guide. And if you aren’t, consider this your motivation to get it booked.

Let’s start with the most important detail of the weekend — where we stayed. When selecting which hotel we wanted to be at, it was all about a) location b) atmosphere and vibe of hotel and c) amenities. Fortunately, we found a spot that rated A+ in all of these areas, The Dana Hotel And Spa. We knew we wanted a place that was close to shopping, close to some awesome restaurants and a place that had a spa because hello, massages. The Dana Hotel And Spa is a boutique style hotel located in River North which is my favorite neighborhood of Chicago. You are literally just a couple blocks away [which means about a 2-5 minute walk] from the heart of all of the shopping on Magnificent Mile, right around the corner from my all-time favorite restaurant, RPM Italian. As far as the hotel itself goes, it has such a cool unique vibe. I am somewhat of a hotel snob so I can be quite picky about where we stay and this place did not disappoint in any regard. The rooms with the floor to ceiling windows showcasing the views of the city were super chic, the restaurants located in the hotel were delicious [we ate at Porthsmith for breakfast one morning outside and loved the avocado toast with a side of people watching], they have a rooftop bar, Apogee Lounge, which makes some of the most unique crazy drinks you’ve ever experienced [we’re talking cotton candy, edible flowers, cocktails served out of huge shells, it was nuts] all while overlooking the amazing Chicago city at night. The next best thing about the hotel? The onsite full-service Spa at Dana. The fact that you can walk from your room to the spa, get a massage or facial, manicure or pedicure, body wrap or whatever the heck you want and then turn around and go right back up to your room is sorta [okay, very] fabulous. Basically, to sum it all up, The Dana Hotel And Spa is the perfect spot to stay for any Chicago girls weekend. End of story.

K, now time for the events and what we did and what I would highly highly recommend you do…

After we all got settled into our rooms at the hotel, we hit the ground running with our first stop at The Allis for high tea. The atmosphere of this place is so cute and if you’re like me, you’ve never done a high tea so you have no idea what to expect. Well, here’s what you can expect….All sorts of mini sandwiches, different breads [the scones were amazing] and desserts. We did the Processco lunch because duh, champagne, and it was such a fun time to sit and get to know one another better. Plus, you feel kinda fancy during the whole thing so that’s fun. I would definitely try this at least once just because of the experience. We took our first selfie together and then hit the ground running for more…

Next stop, the architectural boat tour. PLEASE WHATEVER YOU DO, DO THIS! I am not a huge history or architecture buff, but this boat ride is fun and totally worth it! The tour that we did was around 90 minutes and it was so much fun. You get to learn so many things about the buildings all around Chicago, hear some history of the city, sip on a cocktail of your choice, eat a bag of potato chips should you desire [I desired] and take in the city from a different perspective. Highly, highly recommend!

top [40% off, size down, wearing in XS] // jeans [50% off, true to size] // heels [true to size]

After our hair got all whipped around from being on a boat for an hour and a half, we decided it was necessary hit up a DryBar for blowouts [no, not the bathroom kind]. We made appointments prior at DryBar River North [only a few minutes from the hotel] to get all sorts of pampered and pretty before drinks and dinner that night. I have no clue what style I got, other than the fact that I know it was curly. Did I feel like a poodle? Kinda. Do I like poodles? Absolutely. After everybody was lookin’ fresh to death we made the short trip back to the hotel to get ready for our evening out…

First stop? A short ride up our hotel elevator to Apogee Lounge where we each chose a different fruity fun filled drink concoction which did not disappoint. 

From there we went to that restaurant I mentioned earlier that I happen to be somewhat obsessed with….

Just seeing the menu makes my mouth salivate. I love this place because the prices aren’t crazy, Bill & Giuliana frequent [makes sense due to their ownership in the company..I would be so fat] and the vibe is always fun. Yes, it’s always super packed so you do have to try to make reservations beforehand, but I promise you it’s worth it. I’m pretty sure we ordered nearly everything on the menu. Oh, if only I could go there tonight..

And that just completes day one. Moving onward to day two…sweatshirt [true to size, wearing in small! so cozy and soft] // shorts [true to size, wearing in small] // favorite lounge tee [size down if in between]

After deciding to allow some sleep in time [always necessary for girls weekends] we made our way down the stairs [yes, in the outfit above] for some breakfast at Porthsmith. A few cups of coffee, avocado toast and chicken sausage later and we were ready to tackle the day. And by tackle the day I mean shop our hearts out.

Because the hotel is so close to the heart of it all, we were able to easily walk to all of the stores we wanted to hit up, mostly Nordstrom and of course – Eataly for lunch. The place is massive and can be quite overwhelming, until you find your way upstairs and grab a seat, sit down and shove all of the meat and cheese in front of your face and then you know, yes, this is exactly the place you are supposed to be. Funny what cheese can do for your mental state. After enjoying that heavenly goodness and the most amazing chocolate gelato ever, we headed back to the hotel for afternoon massages. 

OH WAIT! Somewhere in all of this we stopped at Garrett’s Popcorn which write that down on your list. The caramel/cheddar mixture is all sorts of yes in your mouth. K, moving on.

After being all relaxed and massaged, we got ready for our last night in the city together and headed off to eat dinner at a new favorite Chicago spot, The Dearborn Tavern. The atmosphere of this place was awesome and the food was even better. We all loved every single thing we ordered and I can’t wait to go back! If you go, get an order or two of the midwest fried chicken, shishito peppers and parmesan truffle fries to share with the table. Mmmmm, so good. 

After dinner, we uber’d right on over to The United Center to see Cirque Du Soleil LUZIA. IT WAS SO GOOD! And crazy entertaining. The contortionist kinda made me want to throw up and also had me not able to look away because HOW THE HECK DOES THAT HAPPEN? If this show doesn’t happen to be playing when you are in Chicago, definitely check out all of the other options as there is always something great to go see!

And that my friends concludes our girls weekend to Chicago. Special thanks to Sarah and her sister for being the most amazing guests and going along so easily with all that we had planned! Hopefully I covered it all and gave you a few ideas on what to do next time you visit the Windy City. Whatever you do, just go and have fun…I have a pretty good feeling it’s impossible not to accomplish that. Until next time Chicago..until next time.