Hi there, Sephyroth here. I’m taking a trip to Chicago soon to see a show featuring Rob Lowe, who one cannot help but just have a deep appreciation for. The only problem is that when I travel, I am a person who has little to no manner of researching things, so I wind up just figuring it out as I go, or letting others figure it out for me. For the most part, if I’m travelling with Snoskred and her Other Half, she’ll do the research and I’ll say yeah, sounds like a plan and carry on. I mean, how else does one wind up flying in a helicopter and holding a snake? ;)

This time, the only planning that she has done for me is to suggest the show that I am going to see, along with pointing out a bridge in Millennium Park because it was the bridge that was walked along in the Netflix show “Ozark”.

She was also instrumental in getting me to book my hotel a record 4 months! prior to my trip. Looking back, the prior record was 2 months when I was travelling to Hawaii and organized a hotel room near the airport since my flight was at 7AM. There was even one trip that I’ve taken where I booked my hotel at noon the same day that I left. That trip was nice, but kind of ended up being a bit of a mess, considering that my skill in this planning led me to drive over 1,000kms in a single day. That did at least net me the opportunity to get this close to Canada…close enough to take pictures, but not cross the border since it was before getting my Passport.

However! Hard as it is to believe, that isn’t my record, since a few years later (and this was planned!) I drove nearly 1,400kms in one day–and that was in November, when it gets dark at 5:00pm!

Needless to say, for me to actually have researched things and chosen things to do is quite the miraculous event. Again, booking a hotel 4 months prior to the trip? Crazy talk! Looking at attractions to visit a month prior? Insane! Choosing restaurants…at all? Now you’re just crazy dude…but I’ve done all of that! Wait…purchasing tickets to an event 1) 5 months in advance and 2) on the same day they go on sale…I got nothing here :)

So, this trip is going to be three days and two nights, and there are a few things that, in the time between when I purchased the tickets and the actual trip, I had learnt. Those things were –

1. The opening of a new IKEA store just 2 days before I leave; and
2. As a Pokémon Go player, an in-game event occurring on the same day as the show.

So, the one thing that I don’t want to do when going to Chicago is drive in the city. Even though I love driving…especially long distances…driving in a city of nearly 3 million people as part of a metropolitan area of almost 9 million is a bit daunting. At least in Atlanta, they decided to put shedloads of lanes in their freeways to compensate for the number of travellers on the road. Chicago? The big roads are on the outskirts of the city, and the main freeway in town is, at best, 4 lanes wide…usually 3 lanes.

Plus, there’s parking in the city – when I travelled down there for a day trip on a Thursday, I wound up paying $38 for parking in a parking ramp outside of the loop…but that was fine since Eataly was near to the garage, and my curiosity had been piqued about it. Plus the event that I went down there for was near the Tribune Tower – about a 10 block walk from there. It gave me an opportunity to check out parts of the city that I’d never seen before – such as the underground road network.

All of that led me to deciding to want a hotel out in the suburbs, and near to public transit…the L trains in particular. What does that mean? Staying out by O’Hare Airport, since it’s right on the Blue Line, and there are plenty of hotels out that way, all with a really good rate usually. Also, I’d done that in my trip about 9 years ago, and it worked out nicely – as well as netting myself a stack of dollar coins when I used a $20 note to pay for parking at the CTA’s lot :D

In searching the map, I discovered that one of the best rates available in that area wasn’t at one of the airports outside of the main airport area, but actually at the airport itself, and so booking for the Hilton O’Hare was set. One of the innumerate travel secrets that I’ve learnt over the years is that, if you’re certain about the hotel you want to stay at, book from that hotel directly – not only will you actually know you’ll get that hotel, you’ll be able to choose your room, and normally get the best price…not to mention the ability to earn traveller points through something like Hilton HHonors. As someone who loves airplanes and the like, I of course have chosen a runway-view room at the hotel so I can get some planespotting in as well as some rest during my stay.

The next thing was to start looking at attractions. In previous trips to Chicago, I’ve visited the Sears Willis Tower Skydeck twice – once before the ledge, and again after the ledge was created. What is the Ledge, you ask? It’s literally a porch on the 103rd floor of the building that lets you step over the city, but don’t worry. It’s fully enclosed in glass, but it can be a bit frightening (though I did step out on it…at night). I will note that the only problem about going up in the Sears Tower in the evening is that most of the shops, except for the one on Skydeck, natch, are closed, so you kind of miss out on some of the “touristy charm” if there is such a thing, but I was able to see a cutout of President Obama.

Plus, at this time, it was when Chicago was still in the running to get the 2016 Olympics…imagine holding the sailing on beautiful Lake Michigan? At least the support was huge a couple of months before learning that they would not get the Olympics, especially at what was just then freshly renamed Willis Tower.

As much as I love going to Chicago and visiting the Loop and downtown, I’ve never explored much outside of the main downtown core. The farthest out I’d been is out to Navy Pier and the Art Museum, so I thought…what about the John Hancock Center erm…uh, “875 North Michigan Avenue”…guess that naming rights deal ended…in February! It’s the second tallest building in the city of Chicago, and I’ve never been there before. At least there’s no question to its address now!

So, I look up the John Hancock Observation deck, to find that it’s now called 360 Chicago, and they now have this attraction much like the Ledge, but slightly different, in which you are actually cantilevered out over the street below; it’s called TILT, and billed as a thrill ride…so I think, well, why not? The other part of it is that after some digging I found that there is a Yoga class that goes on every Saturday Morning at 9AM, so again…why not? I’ve done Yoga a couple of times, and it’s quite enjoyable – and this time it would be with a whole group of people, not just in my basement in front of a computer monitor, bonus socializing!

That’s Saturday morning sorted; the next thing was to figure out where to go for the Pokemon Go events…so I joined a group that is focussed on downtown Chicago. I had assumed that they’d probably congregate at like Millennium or Grant Parks. Except they didn’t in the end. They chose the following locations –

– Lincoln Park Zoo – Not a bad idea, but quite a ways north, and not something I was looking to see
– Navy Pier – easy to find, and sort of easy to get from there to Millennium Park
– “The Glen” – which I have no real clue as to what it is, but I think it’s out toward Glenview…and I was going to be downtown.

Keeping in mind all of that I was doing, it was pretty easy to figure out which place to go to – Navy Pier. My plan is to go from Navy Pier, get checked in and pick up a piece of swag, and then head towards Grant Park and Millennium Park to walk around, followed by going over towards the Cadillac Palace Theatre for the show, picking up lunch and coffee along the way.

After the show, the plan is fairly straightforward – catch the L back to the Hotel and tuck in for a good night of sleep…then get up on Sunday Morning, and head back home, possibly stopping at IKEA again, and maybe a couple of other shops along the way.

As far as finding food, I decided that stopping at IKEA on the way down for breakfast would be a great idea, and an opportunity to check out the new store — seeing that I was that weirdo who actually went to the parking lot before it opened to get an idea of the surroundings. For lunch, I don’t have a good idea, but will probably just have some coffee or a Chai Latte from a restaurant, possibly going to Eataly if I get into town early enough, or try out an illy owned and operated cafe at the NBC Tower, but that’s not open very late, so may not be the best option.

For dinner, I was researching restaurants and came across a list on the Chicago Tribune’s website that is somewhat up to date (except for the Japanese restaurant they recommended closed last year…and the map that they used isn’t loading the Openstreetmap tiles). That list has a restaurant called Fat Rice which serves Macanese cuisine, or Chinese-Portuguese fusion from Macau(o).

The best part about Fat Rice is that it’s a short walk from the L train stop at Logan Square – just about 650m, or 10 minutes walking, depending on lights and such :)

On Saturday, the only meal I’ve planned for sure is dinner – at Luke’s Lobster City Hall. I figure that meandering from Navy Pier to Grant Park, I can snag something to eat while out and about, as well as get a coffee somewhere, probably finding a local cafe and trying to avoid Starbucks like the plague.

Then on Sunday, it was a drive home, and potentially making a second trip to IKEA to do a more extensive shop and get some Meatballs.

To make things easy, here’s an itinerary, of sorts –

Friday –
* Leave home as early as possible, 8 or 9 AM doesn’t sound out of the realm of possibility
* Make a quick stop to deliver a package that would be needed over the weekend
* Breakfast at IKEA, check out the new store
* Stop at the Outlets, get new shoes since the ones that I mainly use are over 2.5 years old now (and still in pretty good shape)
* Find lunch somewhere, and coffee
* Get to the hotel somewhat early, check in and head into the city
* Dinner – Fat Rice, a restaurant that serves a fusion of Chinese and Portuguese cuisine; a/k/a Macanese

Saturday –
* 9AM Yoga at 875 North Michigan
* TILT reservation at 10:30AM
* Pokemon from 1-4 at Navy Pier, then meandering over towards Grant Park
* Dinner at Luke’s Lobster City Hall
* 8:00 The Show that I set this trip up for in the first place

Sunday –
* Check out of the hotel
* Head home via some random route, but probably the Tollway

Goals? Have fun and don’t get robbed or murdered :)

Tune in Next Monday to see how this plan goes. :)

Similar Posts:

• The Chicago Trip, Part 1
• The Chicago Trip, Part 3
• The Chicago Trip, Part 2
• The Chicago Trip – Part 4
• Sephy Out of His Niche – My World In Pictures