Winter in the Windy City: 3 Days in Chicago

I’m writing this post very tired and only a little relaxed after my Chicago weekend away. I know some of you may be thinking, why on Earth would someone choose to vacation to Chicago in the middle of February? Fair point. To be quite honest I don’t know how clearly I was thinking when I decided to book the trip.

Yes it was cold. Freezing. WAY below freezing actually but we happened to luck out. It was actually colder in Toronto this past weekend than it was in Chicago. You might laugh when I say this but on Saturday it was -23C in Toronto and a balmy -16C in Chicago. Win! As a Canuck you learn to embrace the cold and work around it. That’s just what I intended to do. I didn’t let the winter weather ruin or affect my trip too much (except of course there were certain things we couldn’t do).

Where we stayed:

When we booked the trip, we booked it through Porter Escapes, a somewhat new subsidiary of Porter Airlines where you book your hotel at the same time as your flight. With our package we got a three night stay at W Chicago Lakeshore.

The hotel itself is gorgeous and really modern. Attached to the lobby is a nice bar (perfect for a nightcap) and restaurant. I’m not sure if it’s because we booked through Porter or it’s something the W Lakeshore does but we received $30 EACH a DAY to be used for breakfast. I thought it was too good to be true until I actually sat down that next morning to breakfast and was able to order a deliciously healthy smoothie, and full egg breakfast. Yum!

The rooms are edgy and really comfortable. However, it was just our luck that all of their one beds were taken. Seriously every time Ben and I go away we are booked into a room with two beds.

I have two quick notes about the W. The first is that wifi isn’t free unless you are sitting in the lobby. A four star hotel that does not offer free wifi these days baffles me but just beware. The second is that this location, while I’m sure beautiful in the summer, may not be the best fit for the winter.

What we did:

We covered quite a bit of ground during our three days but as mentioned before, because of the cold weather we didn’t get to experience everything the windy city has to offer (an excuse to go back right?).

Millennial Park:

This was probably my favourite part of the city. The park is beautifully laid out with quite a few amenities and things to do. Right near Cloud Gate they have a small ice skating rink where people can cruise around, surrounded by skyscrapers and famous landmarks. Of course my favourite thing about Millennial Park was Cloud Gate. Arguably the most famous icon of Chicago, it’s hard to visit when there are no crowds. Even on a cold (really cold) day the crowd was large, as everyone tried to take their picture inside the gigantic mirrored bean.

Buckingham Fountain:

Okay, I technically saw the fountain but honestly not really. It wasn’t running. I did get a really good idea of what it would look like in the middle of the summer, which I’m sure is gorgeous and refreshing, but it’s not the same. One thing that astounded me though was the amount of concrete and open space surrounding the fountain in the middle of Grant Park. I’m sure in the summer the space seems much smaller with hoards of people crowded around but in the middle of the winter, and completely empty, the space is intimidating.

The Signature Room:

When I was doing my research I came across a blog post (forgive me I forgot which one now), that encouraged its readers not to visit the Willis Tower. I found this odd until I read about the Signature room in 360 Chicago (formerly John Hancock Tower). I am SO glad I read that post. Going up to the Signature room and enjoying a few drinks was probably the highlight of my trip. The views are absolutely astounding and the drinks are good too. We really drew it out and stayed until sunset just to get some fantastic pictures.

Howl at the Moon:

On Saturday night we headed to the infamous Howl at the Moon bar downtown. It was about a 20 minute walk from our hotel and pretty centrally located. Although we debated it at first, I’m so glad we bought tickets to be seated at the rail. We truly had the best seats in the house. Arrive around 7 and you’ll experience the bar for what it is, fantastic entertainment and great music. As the night goes on though and more bachelorettes, birthday parties and other celebrations come in, the entertainment shifts a bit. Too many people think they’re superstars and get up on stage to dance which detracts from the real entertainers I found.

Field Museum:

I’m pretty picky on museums I go to. Often I find them overpriced for what they are. While it was really cool to see the famous Sue T-Rex, other than that the $40 we paid to get into the museum wasn’t necessarily well spent. It definitely was a good way to get out of the cold however and I did learn a few things and see some cool things but if it was a nice summer day it’s likely I would have skipped over the museum.

Navy Pier:

Again, something that would have been really cool in the summer. We did get some cool shots and it was really neat to see Lake Michigan frozen over like it was. The inside of Navy Pier was something interesting to see and we ate a quick lunch at Harry Caray’s, which apparently was a famous restaurant (there were walls and walls of celebrity visitors to prove it).

Chicago Tribune Building:

I hadn’t read about this anywhere but the Chicago Tribune building was definitely the coolest and most underrated building we saw. Not for the reasons you might think though. Apparently former owner of the Chicago Tribune sent a request to reporters from around the world to send stone fragments from famous landmarks worldwide. He took these fragments and incorporated them into the buildings structure. It’s really quite an interesting thing to walk around the building and see all of the stones.

Magnificent Mile:

A bit overrated. If you’ve been to one well-off shopping district you’ve quite frankly been to them all. Either way it’s something to do and see so why not right? The streets are usually very busy, as are the stores so if you’re looking to avoid crowds, maybe skip this place!

Other than that we did a lot of walking and general travelling. We did the subway loop above ground, walked through the financial district, walked all through all the parks and downtown area. We tried deep dish pizza (not sure what the fuss is about) and I even tried a Bloody Mary (sorry guys Cesar’s are better)!