This past weekend, the boyfriend and I took a little trip to Chicago. We’ve been a million times but somehow never when its been warm. We usually go to Gulf Shores for Hangout Fest but opted out this year last minute and flew to Cali instead. I still need to make a post about that trip actually. Why am I telling you that you ask? Well thats how we ended up in Chicago this weekend! It was my idea to go to California. Skipp agreed with this change as long as we chose another music festival to attend this year! Easy. Lollapoolza. We booked our original hotel through a third party on Trip Advisor, Cancelon. We booked the Kimpton Allegro and were excited to stay there! It look beautiful. We were set to depart on Thursday. Well that Sunday before we are set to leave, I get a phone call that we in fact do not have a reservation. Apparently they were overbooked and we had to find a new reservation. Let me point out incase you didn’t catch this earlier.. this was FIVE DAYS before we were arriving. Let the search begin.. AGAIN. Now, in Cancelon’s defense, they did offer to help us find a new hotel or to give us 10% off a new reservation through them? 10%? No offense, but I’m good. And it wasn’t a code I enter at checkout, it was a refund they would issue days later after I submitted proof of my new reseveration through them. Holy Moly. No. So, I took to trusty Hotwire and rolled the dice. What did I have to lose at this point? I decided to do one where they don’t tell you what you’re gonna get. It just said it would be something similar to the Omni. Sold. I’ll take it. What did we get you ask? Drumroll please…….. INTERCONTINENTAL. Dear Intercontinetal. You were a sweet breathe of fresh air after that fiasco. We arrive for check in Thursday Evening. Valet was $71 a night. We did a hard pass on that since we were staying for four nights. Thankfully I already knew about Spot Hero. Its a wonderful app I will circle back around to cause you should know about it if you don’t. They unloaded our car for us at the hotel and held our things while we found our parking garage from SpotHero! Check-in.. Susan. Susan was so friendly! After random conversation she discovered it was my boyfriends birthday in a few days and part of our reason for being there. She immediately said, well an upgrade is a must then! She upgraded us to a room that was slightly bigger with a much better view! She also gave us complimentary breakfast our first morning and a couple “birthday” drink tickets to use at Michael Jordan’s Steakhouse which is attached to the hotel. After a very wonderful chat with her, we head up to the room to wait for our bags. We get to our room and for some reason, the top part of the window was open. Which was a nice breeze haha but we had a feeling it wasn’t really supposed to be open. We ask the kind bellman how to close it and he agreed it shouldn’t have been open. They call an engineer up. He says he can fix it no problem and to meet someone in the lobby while he fixes it. We get to the lobby and can’t find the gentleman we were supposed to meet but we did find Susan! She apologizes and they send us to the Steakhouse for some cocktails on them (again) while we wait. It is fixed quickly and back to the room we go! Everyone we encountered here was SO nice!! The service was impeccable. The pool was a MUST see. It’s over a hundred years old and stunning. It’s indoor so its perfect year round! There was also a Starbucks in the hotel and a wine bar (which if you know me -score). Intercontintel, we will 100% be back!! Now on to the city itself and our days well spent! Friday was Lollapoolza day!! For Lollapoolza, you can by day passes or the full 4-day pass. We decided to just pick a day since we wanted to be able to really do Chicago in the summer! Lolla his held at Grant Park downtown and the most perfect location for it! You’re right across the street from the lake, have the beautiful fountain in the middle (perfect photo opp peeps) and just the perfect setup! I heard complaints about the bag rules but we didn’t have any issues. I bought a used Vintage Gucci fanny pack from a Louisville local store called Peach Soul. It was the perfect size and met all requirments. We saw Bruno Mars, Dillon Francis, Post Malone, The Neighborhood, James Bay, Bebe Rexha, Chase Atlantic, just to name a few. We are such music festival fans because of the amount of people you get to see for that one ticket price. We broke it down after Hangout one year and it came out to like $10-$15 per person we saw. So worth it when you think about it that way. Besides, theres nothing better than being surrounded by a giant group of people that love it as much as you! It fills my soul!We decided to make Saturday a beach day after hearing about a newer place called the Shore Club located at North Ave. beach. They have an area where you can reserve day beds which we looked into doing Saturday but they were already booked by the time we looked into it. So we decided to just go there and eat and lemme tell you, this place did not disapoint. Reviews I read said it was a little pricey but the food was amazing, and I would agree with that. We both decided it was worth it. They also serve larger drinks for sharing. We obviously stuck with the pineapple that serves 2 people. We didn’t need to get too crazy too quickly haha! After eating and drinking our beautiful gold pineapple filled goodness.. we decided to close out and keep moving.We were planning to go lay out on the beach and relax until we heard some music coming from another place back from where we initially came into the beach area (dont ask me where – courtesy our uber driver’s decision making). So we thought, what the heck!? Let’s go check it out. This brought us to a place called Castaways. It basically looked like a shipwrecked boat turned restaurant. We headed on in not knowing where we were going or what we were doing, just following the dance music. We found our way to the rooftop where it was a straight up dance party. Kiss FM was there broadcasting live. People were dancing in bathing suits, having a good time. Weren’t sure about the vibe at first but the people watching was phenomenal so we decided to get a drink and hang for an hour. Well, about 5 hours later we were still here haha! We had made all kinds of friends. We met a group of guys and ended up hanging out with them all night! They were from San Francisco all on vaca together! We left Castaways together and all headed to the J Parker – a rooftop bar at Hotel Lincoln in Lincoln Park area which is close to where North Ave Beach is. I somehow got zero pictures here. Which honestly, isn’t the worst thing, we were all just enjoying each others company so much and getting to know eachother! From J Parker we headed to a pizza place called Homeslice. If you wanna look them up – I have to share this because their website name is AMAZINGGGGG – getsomehomie.com – HAHA You have no sense of humor if that doesn’t make you chuckle. We basically took all the servers suggestions seriously and ordered what she told us to. We were not disappointed. Sunday we slept in and then ventured out for Brunch. We decided to try Beatrix (several locations – we did N St Clair location since it was a block off magnificent mile and close to our hotel – the intercontinental) Again – not disappointed. Beautiful atmosphere, wonderful food, great service. We then ventured to magnificent mile to do some shopping. We passed the Conrad Hotel and I requested to step inside. I had never been there but saw beautiful pictures of the inside. We end up stumbling upon a rooftop bar/restaurant they have there called Noyane. Noyane had a bit of a Japanese flair to it. What we didn’t know til we sat, was that they had spiked Snowballs. SPIKED SNOWBALLS. So legit, Shaved Ice in 4 different flavors. UH YEAH! I have to have it. Skipp got the Bourbon Peach and I got the Passionfruit Gin. BOTH WERE AMAZING with amazing views. One of those things that we were like, “Yeah, this is why visiting Chicago in the summer was a must!Sunday night we just had a low key dinner at Michael Jordans steakhouse then ventured out to meet our friends that were also in town for Lollapalooza. Monday was our day to head home. We weren’t in a rush to leave this amazing city however – so we decided to stop by the 3 Arts Cafe at Restoration Hardware before leaving town. We had heard they always say an hour wait but it never actually ends up being an hour. We waited every bit of one hour – but that was A-Okay! You can get drinks (champagne, coffee, fresh juice, etc.) and just walk around and look at all the beautiful furniture. They also have a really nice rooftop. Once we had a wonderful little lunch there, it was time to hit the road and hit the stop button on our nice little weekend. I hope this helps you guys find some things to do when you’re in Chicago next!