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Chicago during the Holidays: A Ladies Weekend Out!

It’s the Holiday Season! This might be not Dutch enough, but German. Close enough to feel a little homesick….just a little!

And I think we have developed a new tradition here. A few years ago, our family went to Chicago in the beginning of December. Only because we love the Christmas decorations, the beautiful displays….. but best of all: we found a real German-look-a-like Christmas Market. Last year I went with a dear friend only, but THIS year it turned into “A Ladies Weekend Out!”

Chicago by night

By now you probably have noticed, we LOVE to go to Chicago. There are enough things to do for kids, but I recently discovered how fun Chicago is for a Ladies Weekend Out! But I bet there is more to discover….

When to go?

Last year my friend and I had this spontaneous, last minute idea to “work” in Chicago. And by “work” I meant work on our preparations for our “Winter Camp for Kids”.

“Lets go to Chicago and get into the Holiday Spirit. You know, strolling down Magnificent Mile, enjoying the lights and Christmas decorations, warm up with a nice cup of Chai Tea Latte.”  SOLD!

When I was younger, I watched “Friends” on television at home in the Netherlands. I thought it would be so much fun and cozy to sit in a coffee shop (no, not the kind they have in Amsterdam), you know like Starbucks or something like that. Listening to jazzy music, or, in this case to real American Christmas music, sipping my hot Chai Latte or Vanilla Latte, reading a book, study or work on my laptop.

Sorry, but I like the winter…not many people do, especially not where we live here in Iowa, but I love it!

I bet a summer Ladies Weekend Out would be fun too… an idea for another blog post, maybe?;)

Christmas decoration in Chicago

When we visit Chicago with the kids, it’s a whole different trip. It is quickly in and out of a Starbucks to go to the restroom, warm up a little bit and move on! Get a quick thing to eat….always what the kids like, not what we like. And I like to try out different kinds of foods and restaurants.

Also staying longer past the kids bed time doesn’t work on a family trip.

By myself, I could watch people (while sipping my hot Chai Latte or Vanilla Latte), enjoying some me-time. So, I was thrilled, my friend and I got to do it…in real life….in the middle of December! Did I mention we like Chai Latte or Vanilla Latte?

And off we went by train, packed with only a backpack. It was nice, stress-free without the kids, so we did it again this year! We just asked a few friends to join us!

Where to stay?

Last year my friend was renting an apartment in downtown Chicago, so that was easy! It was great! It felt like we were living in a big city, trying to be part of it. Using all kinds of transportation, enjoying the view during the day and at night!


This year we invited more friends and ended up with 4.

We also ended up taking a car instead of the train. The train is very nice, but also expensive if you travel with 4. Now we could share the fuel and toll costs and even switch off driving. It was less than half.

To get that feeling again of being part of a big city, I researched Airbnb apartments. We choose an hotel near the airport instead. And here is why:

  • Even though you can split the costs, most apartments have a nightly rate, tax and on top of that a cleaning fee, which can be really expensive. On Hotwire we got a great deal for an hotel near the airport with easy transportation to downtown.
  • Parking is expensive too. Instead of the train, we took a car this time. Parking at the hotel was free.
  • At the hotel we had free breakfast. If we had an Airbnb, we had to make breakfast ourselves or go out again. Don’t get me wrong: I love to cook and love to go out for breakfast, but I had to think about our budget too.
  • Okay, the distance to the things we wanted to visit, would have been a lot closer, but the subway and using Lyft was not bad at all. One Lyft driver gave us a tour where beautiful lights were on our way to the subway station and another lady talked all about her family, one daughter singing in church and the other one being a stand-up comedian! Hilarious!!!

At the hotel we had 1 room with 2 queen beds and again we shared the cost. From the hotel we took a Lyft ride to the subway station and then with the Blue Line to downtown.

We wanted to see the Christkindl Market which is located on Daley Plaza. It was very busy that day, because I think it was not that cold! We saw some incredible handmade crafts, we drank hot cider, hot cocoa or “Gluehwein” out of mugs you could keep and bring home for your collection (I have 2 already, heheh). We ate some delicious warm pretzels in all kinds of flavors from cinnamon till feta/spinach. There was Sauerkraut and “Bratwurst”, German chocolates, other candy and roasted nuts.

Every year the Christkindl Market is open from half of November until Christmas Day. Admission is always FREE. The exact days and opening hours and more information change every year, so check before you go!

What else to see in Chicago around the Holidays?

After this visit we were so overwhelmed and tired, we decided to go back to the hotel. We all agreed we could watch a movie before bedtime. BE AWARE!!! It is very easy to click the wrong button and you’re forced to watch a movie you actually don’t want to watch in the first place. For us it was a $22 Flatliners movie we had to watch, sigh!

The day after we got up on time to catch the free breakfast. It was busy in the breakfast room. If we only could get some good coffee. That was important;)

Off to downtown Chicago we went. We found the Chicago library first, which is an impressive building by itself. I’d love to go inside another time to look at the architecture. Instead we had a Chai Tea Latte (or coffee) across the street.

Chicago
Chicago’s Public Library
Chicago

We walked to Millennium Park where the Art museum is located. Fun Fact: Did you know that Route 66 starts right there? I did not know that! Now I do!

A lot of people were admiring “the Bean”. It was just too much to make a picture! Crazy busy!

It was very warm for the time of year. Still, I kept my jacket on, because we were in the “Windy City” after all. It was quite windy in certain parts of the city.

It was time to think about lunch: Chicago’s famous deep dish pizza! Of course! The restaurant was full, but we ordered ahead and we wanted to eat outside anyway. But where? There were no parks around. We found the Rainforest cafe a few blocks away from the restaurant. They had a few benches outside to sit on. We enjoyed watching people passing by who just bought a Christmas Tree. They were all so happy:)

Restaurants for kids in Chicago

Must try Foods in Chicago

It was time to embrace probably the busiest street in Chicago: Millennium or Magnificent Mile. Two ladies in our group were interested in a make-up supply store. My other friend and I had a lot of fun with a software program on a computer in the store where you could “try on” different kinds of make up. It also told you which brand to buy and how much it would cost. Of course we tried the most crazy colors….

What to do in Chicago

After another cup of tea, we decided to go to the movies. It’s not recommended to go to a theater close to Magnificent Mile, because you pay easily $18. We already bought a day pass for our subway, so we decided to go to the ShowPlace ICON more south of downtown. Here we enjoyed the movie “Ladybird” for $8.50, kicked back in lounge chairs and munched on some popcorn!

Chicago

On our way back to downtown Chicago we enjoyed the Christmas displays at Macy’s and a 55 feet Christmas tree. We were not very hungry by the time it was 6 PM, but we decided to eat some appetizers and have something to drink at “the Kitchen”.

The day was done! Back to the hotel.

Monday morning we had a slow morning and….we missed our free breakfast! On our way home in Schaumburg, we found a great breakfast place called “Wildberry cafe”.

The food was amazing, the staff was friendly and the food came very quickly! We shall return!

We talked already about next year!

Any other ideas what to do and where to stay with friends in Chicago?

I’ve heard about an 24/7 Spa in Chicago called King Spa and Sauna. Definitely need to check that one out!!!

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