Since New York and Boston, Jenny, Cassie, Ashley and I have been meaning to travel together again but our busy schedules made it hard to schedule. Finally with one of us pregnant, we had to do it this year or else it’ll be even harder to plan. 

Day 1 – Thursday, May 25 2017

After reuniting in our hotel room, we quickly made way to Parachute, a one Michelin star restaurant serving modern Korean food. The food was very good and had interesting flavour combinations. But the best part of the dinner was catching up and sharing stories as if we were never apart. 

After dinner, we decided to find a cafe to hangout and continue the conversations. Ashley found Kibbitznest, a really cute book cafe that had no wifi to discourage technology use and promote face-to-face interactions. It was a pleasant surprise and a great spot to chill.

Day 2 – Friday, May 26 2017

We started the day slow and slept in until 10am. With lunch reservations at 11:45, we decided to find a cafe close to the restaurant. We found Doughnut Vault and it was the most adorable doughnut shop I’ve ever seen. Oh, and these doughnuts were fluffy, light and delicious. We loved it. 

We had lunch shortly after at Frontera Grill by Rick Bayless, a top chef but while it was good, I wasn’t overly impressed. The churro next door at XOCO was also overly sweet and crunchy. Not a fan…

We went to a bridal store after where I got to try on some gowns and model for these gals. They had fun watching and were chatting it up with another bride whom seem to have found her dress. 

After that, we headed to Cloud Gate, more popularly known as the Bean, for some photos and selfies. Super touristy and busy spot but it does photograph really well. 

We wandered and shopped a bit before heading back to our hotel to get ready for our fancy 12-course dinner at El Ideas, another Michelin spot. The restaurant was a hip and interactive experience. Each dish was beautifully plated and had unique flavors. Our first dish, chawanmushi (waygu beef, black garlic etc.) was meant to be eaten without hands or utensils. We had to slurp and lick the plate.

Midway through the courses was a dessert called ‘french fries & ice cream’ and once you stab into it, a reaction of liquid nitrogen occurs. Too cool. I also liked the ‘tomato soup’ dish which was like grilled cheese bread on a spoon that bursts tomato soup when you bite into it. 

Cassie and I were heading to a rooftop lounge until we decide to go to a Korean Spa instead. King’s Spa was huge and had a good-sized bath area, stream room and multiple hot saunas. There was even a large restaurant on site where Ashley and I ended up ordering some late night food. It was very relaxing and the perfect way to end the day.

Day 3 – Saturday, May 27 2017

With a open morning, we slept in even later and left the hotel around 11:30. We headed to Lou Malnati’s for deep dish pizza. It was really good and I like the cheesiness paired with tangy tomato sauce and topped with spiced sausage. 

We tried to go up to Sky Deck but the wait was 3 hours! We decided to leave and try again first thing next morning. We went to Wicker Park and wandered about. We ate donuts at Stan’s and then got nails done at Zazazoo. 

We took a cab to Fat Rice in the middle of nowhere for fusion Asian food. It was very good and different than typical fusion Asian.

Ashley, Cassie and I watched fireworks at the Navy Pier and it was a nice brisk stroll by the water with the Chicago skyline behind us. The fireworks were surprisingly pretty good for a weekly event. I started a running joke about how they should pair the fireworks with Phil Collin’s song ‘You’ll be in my heart’ and the girls wondered why that song… I had no reason. It’s just a good song that popped in my head. 

Day 4 – Sunday, May 28 2017

We woke up early and left the hotel around 7:45am to get to Sky Deck before it opens at 9:00. To our surprise, it opened early and we were able to go right up with no wait and minimal crowds at the top. We took endless selfies and photos in the glass boxes, which were very photogenic and fun. It was an unexpectedly great experience. 

We had breakfast at Cochon Volant nearby and it was a charming french spot with good corned beef hash. 

Jenny and Cassie went back for a long nap while Ashley and I made way to Lincoln Park area. We explored some of the cute shops and ate ice cream at Jenis. It was really creamy and the almond butter brittle was fantastic. 

As we were shopping, there was a flash thunderstorm where it started to pour but it didn’t last long and we walked to Lincoln Park Zoo to meet Cassie. We were impressed at this free zoo in the middle of the park. There were lions, polar bears, giraffes, gorillas and more! 

We ate dinner at The Purple Pig and it was fantastic. Every dish was delicious. I loved the roasted garlic broccoli and the milk braised pork. 

We walked back to our hotel along Magnificent Mile but wanted to do something for our last night. Debating between boat tours and rooftop lounges, we instead ended up at a bubble tea spot called Cassava Cafe and we put together a puzzle. It was a nice simple activity for our last night together. Jenny got to demonstrate her skills with her ‘puzzle queen’ title from work. 

On our walk back, Cassie stated it’ll be a while before us four are together traveling again. Jenny’s perfect response in a monotone voice was “You’ll be in my heart”. We were cracking up and then had to listen to the song back at the hotel room. We also put on animal beauty face masks, which was the most hideous but funniest thing. 

Day 5 – Monday, May 29 2017

Ashley was the first to leave that morning and I said my goodbye half-asleep. Jenny came with Cassie and I to get doughnuts from Doughnut Vault. Yes, it was that good that we wanted to try other flavors. We got a little overboard with four doughnuts but it was so delicious. 

Cassie and I said goodbyes and good luck to Jenny and then walked to Magnificent Mile. But first, we ended up at the photogenic flamingo mural and snapped some pics. We shopped along the mile hitting up common shops like Victoria Secret, Anthropologie and Uniqlo. It was quickly lunch time and we had modern tacos from Velvet Tacos, which our Lyft driver recommended. My Cuban pork and braised beef tacos were very good and I really like the tortilla shell. 

We both left for the airport and parted ways at the gate. This extended long weekend getaway was perfect —great food, weather and city with the best company. I loved our impromptu plans and relaxing activities. It was a nice change of pace from my last trip, Japan. I’ll miss them. Until next time… maybe another five years but hopefully less.