I’m at the age where it seems like I have a wedding to attend every month. At the risk of offending people, it’s bittersweet. Of course it’s a great opportunity to spend time with friends and/or family, catching up and laughing till my face hurts. On the other hand, it’s expensive, and can throw a wrench in my workflow and productivity levels. The good far outweighs any less than good, however, which was exactly the case on mine and Jaclyn’s trip to Chicago this past weekend for one of my oldest friend’s weddings.

Let’s start at the beginning. We – as usual – left later than we should’ve to get to the airport, eventually forcing ourselves to get out of the shuttle and run to our check in counter. We sprinted across LAX, making it to the Virgin America desk two minutes too late for them to check us in (which is an entirely separate frustrating story in and of itself). We almost didn’t get the chance to take the trip at all but thankfully were able to book something on a different airline, landing us in Chicago around 12:30 AM.

We made it to our hotel, the Ambassador Chicago, located in the Gold Coast neighborhood, about three blocks from the lake. The place was understandably empty at this hour, but we were warmly greeted by Jared, the night concierge, who was extremely nice and taught us that the hotel was originally opened in 1938. The place screams with character. The main lobby includes a library with board games and tons of seating options (which would come in handy the next morning).

We tiredly made our way up to our room, 714, having no expectations as to what type of room we’d been set up in. As I opened the door and entered the space, we immediately noticed the modern style space with king sized bed, a sitting chair, as well as a desk with a TV…very nice, plenty for us to enjoy as we were exhausted from a long day of travel, but nothing out of the ordinary from a hotel…or so we thought. A door next to the TV, what we expected to be the connection to the room next door was open and available for us to enter…strange, I thought. We opened the door and revealed a MASSIVE living room with a sitting area and a huge dining table. It felt like I was in an episode of Mad Men, staying at a Don Draper’s corner apartment. We couldn’t believe how spacious and wonderful everything was. By the time we settled down it was around 2 AM and time to get some rest. We snuggled up in our king sized bed and passed out.

The next morning we were awoken to beautiful streams of sunlight leaking in through the curtains and I immediately called room service. It was quick and easy, and we enjoyed some pancakes, eggs, potatoes, and coffee. The perfect start to a busy day ahead.

We’re both trying to be better about working on our business during travel, so we got dressed and busted out our laptops to answer some emails and strategize our day. A quick photoshoot was in order as well as getting some coverage of this beautiful room, so we took care of that and got it done faster than expected. There was a bit of time before we needed to get ready, so I borrowed a chess board from the lobby and we played a quick game. Jac beat me – as usual.

Once it was time to get ready for the wedding, we made sure to save enough time to grab a couple of photos of ourselves in the space. It was so photogenic and comfortable. We got what we needed and headed out to meet our friends.

The wedding took place at vintage furniture store and was one of the more unique venues we’ve ever been to. The entire night was a mix of food, dancing, and drinks. So much so that we didn’t take photos, we just enjoyed ourselves! It was so great to spend time with so many of my oldest and best friends. People that I don’t get to see nearly often enough, but when I do, we don’t skip a beat. That’s how you know you’ve got some truly great friends.

Afterwards, we headed back to the hotel for one last night of rest and relaxation before heading back to LA the next afternoon. Jared was working the desk again and he welcomed us in. We slept hard, not waking up until about 11 the next morning. We packed up our stuff, said our goodbyes to one of the nicest experiences of our lives, and headed for the airport.

If you’ve never had an experience that validates why traveling can be so great, I hope you do soon. This was one of those trips, although extremely short, that reminded both of us how great it can be to escape. Even bringing work with us, it was inspiring to be in such a bright, fashionable, comfortable space like our room at Ambassador Chicago. If you’re ever traveling to Chicago, I highly recommend checking them out. Tell them Parker and Jaclyn sent you. I know we’ll be back!