Day 1: Chicago

Summer time used to be the only time for vacations. Now that I’ve been working for a few years, I’ve tried to take my trips in less busy seasons like the Spring or Fall. However, this summer, my girlfriend and I wanted to take a smaller trip around the US to some popular but new destinations. Having grown up on the West Coast, I’ve never actually visited Eastern North America. This ten-day trip will take us to Chicago and New York City for the first time, while finishing up in one of our favorite places, Las Vegas. Even though we have travelled around the world, this particular trip was going be a little bit more special - stay tuned till the end.


We started our journey at my home airport of Seattle-Tacoma. I’ve been through here many times over the past few years now and more recently have been able to access the American Express Centurion Lounge. We enjoyed some cocktails alongside some McDonald’s that we brought in from next door. We later found out that outside food was not permitted, but I guess the staff that day didn’t mind.

Soon, we boarded our evening flight out to Chicago O’Hare.

The 3 hour flight was pretty uneventful and we landed 6 hours later (due to the time difference) at around midnight Chicago time. Since it was pretty late, I decided to book an overnight at an airport hotel. Airport hotels are typically much cheaper than the ones in the city, so since we just needed a place to sleep, we could use the money we saved here to book a much nicer hotel for the next day.


We stayed at the Renaissance O’Hare, which is part of the Marriott chain. As a platinum member, I got a small upgrade and free breakfast. This particular hotel was unique in that they offered pretty spacious junior suites in even the base rooms. The Renaissance brand also gives it a premium and polished touch - not too shabby at all for an airport hotel.

After a good night of sleep, we woke up to a cloudy day with a bit of sun piercing through. We could see the silhouette of the Chicago skyline from our room.

We started the morning with some breakfast at the hotel restaurant.

Then we checked out and took the subway (Blue Line) directly into the city. We dropped off our luggage at our next hotel and headed out to explore the Magnificent Mile. We were worried that it was going to be really hot, so we didn’t mind the overcast. As we walked down Michigan Avenue, we passed by several landmarks, such as the Water Tower and the John Hancock Center.

As we explored, we felt some raindrops so we took shelter in one of the stores. Soon, there was a torrential downpour, so we moved to one of the many malls that lined this avenue. For someone who loves architecture and legos, this was pretty cool.

At the north end of Michigan Avenue was Oak Street Beach. On this day, the Chicago Air and Water Show was going on, so this area was packed. It was so packed that the beach was closed to additional visitors. On the way back, we stopped by Astor Place, which was a relatively empty but very high end mall.

They had probably the most luxurious food court I’ve ever seen. There was a touch screen ordering system that could access the dozen or so food vendors. I had a Chicago Dog while my girlfriend got some ramen.

I also had some coffee and a pastry before we headed back out. By now, the rain had cleared and the sun was out. We walked back to our hotel, the Gwen, part of Marriott’s Luxury Collection. This was a five-star property, and one of my favorite hotel chains in the world.

The room was newly renovated in a historic building. It wasn’t huge and, unfortunately, we didn’t get a suite upgrade, but the furnishings and decor was nice. As a Luxury Collection property, it has one of my favorite books, detailing the unique artwork and design of each property - tailored to their location.

For dinner, we found a nearby Chinese restaurant called Imperial Lamian. It was pretty full when we got there, so we decided to get takeout and eat back at the hotel.

It’s hard to get a good shot of takeout food, but everything was really delicious. This was a great first day in Chicago and it was pretty chill while exploring the nearby areas.