A Weekend Trip to Chicago in the Winter | www.goldhattedlover.com


Most people wouldn’t think to take a weekend trip to Chicago in the winter – I get that – but there is something magical about walking around the city when you’re all bundled up and popping in to restaurants and shops to warm up.  My husband and I took a weekend trip to Chicago a few years ago in December and had such a good time that this year I begged that we do it again.  In early January we layered up and ventured out for a weekend in Chi-town and had the absolute best time so I wanted to share what we did as well as my tips for what to wear to ensure that you have the best time too!




On our way into the city we stopped at the Museum of Science and Industry.  I still prefer the Exploratorium in San Francisco, but this was a cool interactive museum.  It would be really awesome if you have kids but even so, we enjoyed it!


Checked into our Airbnb around noon.  If you are heading into Chicago, I highly recommend this apartment!  The location is prime – right on Armitage Street in Lincoln Park and the guys who live there were really helpful and easy-going.
*Only thing to note is that it is directly next to a metro stop so you will hear each train that passes by pretty loudly.  I got used to it quickly though and they provide ear plugs for sleep if it still bothers you.


Walked to Restoration Hardware.  This is not just any old Restoration Hardware store.  This is a five story store with floors for each room of  the home, complete with a restaurant, wine bar, coffee shop, and rooftop. This place is especially great in the winter because there is so much to see here that you could easily spend a few hours hiding out from the cold.  I’ve heard great things about the restaurant so I desperately need to go back!


A Winter Weekend Trip to Chicago | www.goldhattedlover.com


Walked downtown and got in line for the Skydeck, which is the observation deck in the Willis Tower where you can walk out on a glass ledge 103 stories above downtown, but after 15 minutes waiting in line outside we were told that there was still a 3 hour wait once inside.  Not happening.


Walked over to the West Loop.  Explored there for a bit and scouted restaurants for dinner.


A Winter Weekend Trip to Chicago | www.goldhattedlover.com


Grabbed ice cream at Cone.  I’d heard of this place over the summer but never made it so we popped in and were so impressed with the samples we tried!  We shared two scoops: Cookie Monster (their most popular – made with Oreos and cookie dough) as well as the Key Lime Pie.


Dinner at Nando’s Peri Peri – super great restaurant if you are on a Paleo, Wheatbelly, or Gluten-Free diet because all they do is flame-broiled chicken, but they do it really well.


Grabbed a drink at Bar Siena – their variation of a Moscow Mule was delicious – and their indoor lit tree was really incredible!


A Winter Weekend Trip to Chicago | www.goldhattedlover.com





Early morning mass at St. Vincent’s right on the edge of the DePaul University campus.


Donuts and coffee at Glazed and Infused – right across the street from our Airbnb.  The maple bar with bacon was so good!


Checked out of our Airbnb.


Went back to Willis Tower and had much better luck getting to the Skydeck – I recommend going at a non-peak time like we did here on a Sunday morning.


A Winter Weekend Trip to Chicago | www.goldhattedlover.com


Lunch at Pierogi Heaven.  We both agreed that it was fun going somewhere different, but neither of us loved it so we wouldn’t recommend it.


Did a little shopping around the Michigan Avenue area.  We stopped in to Nordstrom – I finally got matched for this foundation! – Anthropologie – Matt made fun of me for smelling every. single. candle – and J.Crew.  I was still trying to find a late Christmas present for him since I forgot, whoops!


A Winter Weekend Trip to Chicago | www.goldhattedlover.com


Headed back to Lincoln Park and grabbed dinner at Butcher and the Burger.  It is a build your own burger place and we both agreed it was one of our favorite meals – highly recommend.  Make sure to get fries with the black truffle aioli!  Plus, the old man who runs the shop is the sweetest thing!




At last, with tired feet, full bellies, and contented hearts, we hopped in the car and headed back home.  Though we were just there for the two days, we were able to do and see so much!  It helps that we’ve been there a handful of times before so we were able to do more “normal” stuff and give it a go as if we lived there.  In the end, we were actually really sad that we decided not to live there next year because we both really love it and had the best time!


If you’re ever considering taking a trip to Chicago during the winter but are afraid about the weather, don’t be!  You’ll find that there are many less tourists so you’ll have the city more to yourself and you’ll find much better rates on hotels and flights.  As long as you dress properly, you will be just fine.  Below is what I wore that kept me perfectly toasty from morning to night…


A Winter Weekend Trip to Chicago | www.goldhattedlover.com


Main Layer: Jeans (I swear by coated denim – something about the coating doesn’t let the cold air in!), Knit Sweater, Puffer Vest
Outer Layer: Quilted Coat – Needs to be long enough to at least cover your backside
Shoes: LL Bean BootsSorels or Sperry Boots would also be great options, the main thing is that they have good traction and insulation and ideally are waterproof
Accessories: Warm Gloves, Scarf, and a beanie, earmuffs, or headband (my ears were pretty cold because I forgot those)


I know it sounds like a lot but if done properly, it won’t be too thick and you won’t feel like a marshmallow – and most importantly you will be warm.  As a note, a coat with a belt will really help slim you and keep you from feeling much larger than you are.  In fact, I felt pretty cute all weekend despite all the layers!



I hope that this recap and outfit advice has inspired you to plan a cold weather trip, whether to Chicago or elsewhere.  It is definitely a different experience than visiting a city in the summer, but I think it’s a really rewarding one.  These cold weekend trips to Chicago have been some of our favorite memories together – here’s to you making memories, too!


A Winter Weekend Trip to Chicago | www.goldhattedlover.com

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