I cannot begin to tell you how amazing this trip was. Ever since I visited Chicago back in 2013, (for a job interview) I fell in love with this city full of personality. This time, I fell even more in love with it. Having the opportunity to have my BIL and his wife to show us around, was the best!
They already know all the best cool spots and the best way to travel in between. Of course if you don’t have somebody to guide you, the city is still incredible. I will explain here what we did and a few tips that made our trip the absolute best.
Now, we made this trip just this past weekend (December), meaning it is already cold. We wanted to be there around Christmas time to check the decor. And we were also feeling brave and wanted to venture out in the cold for a bit. We are planning to go back during the summertime, and do all the summer activities. I will of course, share that scoop with you.
Now let’s get started with that guide, and you’ll be surprised how much we were able to do. And I am also going to talk about clothing in case you are wondering what to bring.
what’s the weather in chicago in december?
First, I feel like I need to say this, we were really lucky with the weather. We were expecting low temperatures, but not below freezing. We had anywhere from mid 40s to mid 30s and it was perfect. I won’t lie, it got really cold at times, but nothing that we weren’t expecting, that’s what we wanted anyways. And when I say we got lucky, I mean that it wasn’t windy the whole time. It was only a a few hours here and there, and when it wasn’t windy, it was actually enjoyable. We didn’t have much rain either, only the last day. It wasn’t very intense, and no snow at all. Everyone there told us we got lucky, so I’m guessing these temps aren’t common this late in the year.
what to wear in chicago in december?
Ok, for this one, I feel I can be more useful. I am a professional cold-at-all-times-during-winter person. And so, I can assure you these tips are very helpful and critical for maximum enjoyment of your trip. The trick is to avoid getting cold, because it takes a long time to warm up again. So with these few tips, hopefully your trip will be a success!
clothes
Don’t go overboard with the layers. My inner layers were a tank top, a sweater (not super thick) or a warm long sleeve on top. That’s it. As for the outer layer, I had a long puffer coat and it worked perfectly for me. My BIL didn’t recommend us taking wool coats, as they don’t cover you very well from the wind, which was bone chilling at times. So we stuck with our puffer coats the whole time.
So that’s it, basically three layers on top. You are walking around on the streets and then you step inside anywhere, and it is very warm. Like VERY warm, so you immediately want to take of your jacket. Its easier to just take your puffer coat off, instead of peeling off multiple layers. You’ll end up having to carry them around or keep them in your lap and it can get annoying. Also,there’s less things you have to worry about forgetting.
As for bottoms, I did alright with jeans, but I wore high stockings underneath. I think the stockings where crucial, as one day I didn’t wear them and my legs got really cold. I your feet get cold easily, I’d definitely recommend wearing an extra pair or some really thick socks.
For shoes, if you plan to walk a lot, which I recommend, bring sneakers or really comfortable booties or flats. For going out I wore booties to keep my feet warm.
accesories
As for accessories, you definitely need gloves and something to cover your head and specially your ears. You might be ok for a few minutes without anything on, but after a while you really start feeling it in your ears. My forehead itches when wearing a beanie or headband, but I just dealt with it. Maybe a chenille beanie would help with the itching. As for gloves, you need ones that won’t let the cold in at all, if possible with fleece inner lining. Knit ones will not do the trick. Trust me. I used ones similar to these.
Now for the good part…what to do in chicago in december!
I am telling you what we did day by day. We are very intense and did a whole lot of walking, but it was totally worth it. Two days we did about 12 mi/day, and two other days we biked about 3 mile/day plus walking. But if you are not a fan of walking you can easily get around by Uber or using the Metra. I will split the trip by day so you can get an idea of how much you can do in a day.
Day 1
We had reservations for brunch at The Allis, which is one of the most beautiful places I have been in. I wanted to stay there and live in a corner. You need a reservation to ensure you get a spot. And since we didn’t want risk waiting in line and wasting precious time, we made one. The place was mostly empty when we arrived but was pretty full when we left. The food was delicious, we got the Allis breakfast and the breakfast pizza. Drool worthy. To get here we took the Green Line from Roosevelt Station and got out on Morgan. We walked around 5 blocks to get there. There are lots of other cute restaurants and pretty shops on the way.
After that, we took the Green Line back but stopped at State/Lake to walk to see the Chicago Theatre. That’s the theatre with the famous Chicago sign, then walked to Macy’s to see the Christmas window displays. We also went in, it has something like 7 floors with a restaurant and a bar, so pretty big. I was most impressed by the architecture and the gorgeous mosaic ceiling at the center of the store.
Millenium park
From there we walked towards Millenium Park, which was two blocks east. We took pictures at the Christmas Tree and the Bean (always fun), and the Jay Pritzker Pavillion. There’s also a super cool garden right in front that I have loved since my first visit to Chicago.
Right in front of the park is the Chicago Athletic Association, which is a hotel with a beautiful lobby. It gives me Harry Potter-esque vibes. Behind the lobby there is a bar called the Game Room, with pool, bocce and foosball tables.
HINT: before going in the Game Room, there are some glass doors to your right. It was a speakeasy back in Prohibition time, now it is a bar called the Milk Bar. You need a reservation, and it only has 8 seats, so its a pretty intimate experience.
michigan ave
After a bathroom break at Chicago Athletic Assoc (or is it the 1 1/2 floor?) we walked north on Michigan Avenue. Very close is the DuSable Bridge where we stopped for more pics. It is an absolute gorgeous view from here and a must stop for pictures. Passing the bridge there is Wrigley Building which has a really photogenic overpass, so we stopped for pics again. On the next block there’s Michael Jordan’s Steakhouse. Michael Jordan is my hubs basketball hero.
I feel like I have to stop here because this is an already super long blog post. I don’t want to make it so overwhelming that you end up not knowing where to start. I’ll let you take it all in and next week I will share the rest!
