If you haven’t been to Chicago during the Winter months, you’re missing out. While already a fabulous city, full of fun, food and more midwest spirit than Harry Caray could dream up, Winter takes Chicago from magnificent to magical. And magical beats magnificent. Obviously.
Just 90 miles away from our Midwest home base in Indiana, we venture over to the Windy City as often as we can. This is the second time we’ve done the whole Winter adventure and needless to say, it’s become a holiday HAVE-TO in our house.
But before I get into all that, let me first talk about the mechanics of visiting Chicago. Chicago used to intimidate me a little. I was not a huge fan of the parking situation, nor did I like cabs. Stinky and dirty, they just weren’t my thing. Enter, Uber. And my favorite parking lot.
We’ve recently discovered a parking lot that we love. (Is that a weird sentence, or what?) Yeah, we L.O.V.E. this parking 
lot. It’s centrally located to all the things we enjoy. It’s easy to get in and out of. And it’s one of the cheaper lots in Chicago. We park, walk to the nearby donut shop for a cup of coffee and a gluten-free blueberry donut then we Uber ourselves anywhere that’s not within walking distance. To say Uber has changed our Chicago-loving lives would be an understatement. It’s a great way to get around what is a busy city, which can be complicated to drive. Plus, you get to chat with fun locals. Usually. If you haven’t taken your first Uber yet, I suggest you download the app and give it a go ASAP. Or better yet, head to Chicago and try it out there.
Back to the fun stuff. Chicago is chock-full of Winter activities. An obvious one is the Christkindle Market. It’s a very realistic copy of the European Christmas Markets. Now that I’ve seen the actual markets in Germany and Austria, I can confidently say that the Chicago version is on-point. Handmade goods like ornaments, wooden toys, paper stars, and various crochet/knit items grace several booths. You’ll also find every kind of German-inspired food you can imagine. Spiced nuts, mulled wine, sausage and pretzels, just to name a few. It’s a great place to spend a couple hours snacking, shopping and… more snacking. (Poutine from the Döner booth… it’ll fry your tastebuds. In a good way.)
From there we make the short walk to the iconic Macy’s. If you have shopping to do, it’s 9 levels of shoppers paradise. But if you just want to check-out their famous Christmas Tree in the Walnut Room restaurant, be sure to make a reservation. Saturday afternoons the wait can be 2 hours + for a table. Even if you don’t want to shop or eat in the Walnut Room, I’d still say it’s worth a ride up the escalators to see the beautiful Christmas Decor, warm-up a bit from all the Winter fun and grab a hot chocolate from the Frango Mint booth.
Next-up is “the bean”. Or officially known as, Cloud Gate. An easy walk from Macy’s, this is usually on everyone’s list. The restaurant below turns into an ice skating rink which is FREE if you have your own skates. Or you can rent skates there as well. Beware the line for skate rental can be long on weekends and evenings. This place is one of my favorites to see at night. The 9500lb Christmas Tree, reflected amongst the buildings in the “bean” is stunning. Great photo-op or place to snuggle with your sweetie and people watch.
From here we really just like to walk up Michigan Ave and enjoy the lights, sights and sounds. You can really feel the hustle and bustle of the holidays when you visit Chicago in Winter. There are carolers and musicians playing Christmas songs all over the city, and lights everywhere you turn.
If you’re into lights, grab that Uber and head to Lincoln Park Zoo. The zoo is free and they deck the place from head to toe in lights for the holiday season. They sell snacks, beer/wine, hot chocolate and coffee. It’s a beautiful place to just meander through some lights. You can also get some incredible views of the Chicago skyline from the zoo. Several of the lights are handmade displays and things that are unique to the zoo. Of course, this is all out-doors. Bundle up.
That’s how we spend our typical Winter day in Chicago. It usually ends with a dinner of some type. There are literally thousands of places to eat in Chicago, so I won’t even attempt to direct you on that… Gibsons *cough* Gibsons. Okay, I could’t resist. After you’ve been there, you’ll understand. Gibson’s all the way. Reservations required though.
That’s a pretty full day of Winter fun in the Windy City. What is your favorite place to visit in Winter? Leave me a comment below. I love hearing about the places you guys like to go and things you enjoy doing.
If you’re seriously considering a trip to Chicago in Winter, here are a few hot tips:
- Find a parking lot/space you can leave your car all day. Then Uber or walk.
- Speaking of Uber… if you’re on a serious budget, try Uber rideshare. But if you’re feeling ritzy, Uber Black is our favorite. You get a professional driver in a big, nice vehicle. Once you go Uber black, you’ll never go back. Okay, sorry… bad joke. But seriously. You won’t.
- The Christmas market, ice skating and zoo lights are super-popular Winter activities in Chicago so they’re SO crowded on the weekends. If you can do this trip on a weekday, do it. You will enjoy these things so much more. Heads up, the Christmas market is wall to wall people on weekends. It’s doable… but only if you’re insane. Just sayin’.
- If you snag an Uber (yes!) or cab (icky) to the zoo lights, it’s best to be dropped off on the West side of the zoo, if your driver knows how to get there that way. Traffic is bad from the East and North sides. Be prepared to waste 10-20 minutes just sitting in that traffic… so close, but yet so far.
Happy Christmas!
Stacey
