Chicago in the winter

I will start off by saying, if you have followed me you know, I’m not a city person. I did however absolutely love Chicago in the Winter. It was a nice weather for the beginning of December, no snow, but of course, wind! Chicago is by far the prettiest city I have seen in a while when it comes to holiday season. Streets of tiny lights, the river set in red, green and white. Just an all around great place to bring the family for some holiday traditions and of course Christmas cheer.

Chicago never fails when it comes to the holiday season. Whether it’s dying the river green for Saint Patrick’s Day or the fireworks for the Forth Of July. Christmas was just as stunning.

So let’s get into what you can find around Chicago in the winter.

Getting here

You can fly into O’Hare International, drive or, like me, train it in. I took the train from Dearborn Michigan to Union Station downtown. I met up with my long time friend and future sailing partner Matt. Taking the train or flying into Chicago in the winter is your safest way.

Driving or renting a car is a good choice, however, here are some tips. Be prepared for busy highways. . The parking in downtown is not cheap and a lot of the hotels use the indoor parking so you may be out of luck finding anything.

If you stay downtown you will not need a car. Local transportation is easy to get around, and if you are lucky you will hop on the Christmas bus. Staying in “the loop” area you will get to all the hot spots within a 20 min walk (I walk slow).

Where to Stay

We chose to stay at The Palmer House in the loop district. This was not only a beautiful hotel but it really was the perfect location. We were near Millennium Park, only a 10 minute walk away.

I love history and this stunning place has all that and some. As you enter the main room you can see the amazing architecture and workmanship put into this luxury hotel. The halls to the rooms are lined with portraits of social elites and Hollywood’s greatest. The ball room is another spot we visited. I could just imagine the fabulous weddings that have taken place here.

We got a double queen size room and it was super spacious. The view, well it was of a brick wall so not that great. I found a great deal on Hotels.com and didn’t mind spending what is a lot for me. I spent less for two weeks accommodations in Thailand lol.

Here are some other places to check out.

Your best bet is to book 4-6 weeks in advance. I found the prices to be at least 25% lower if you did.

Under $200 per night

• Hilton Garden Inn – near the river and still a great central location to the must visit places
• Hampton Inn – close to the Hilton Garden
• Warwick Allerton – Along the Magnificent Mile – stunning during Christmas (I talk about this further down)

Historical Hotels

• The Drake Hotel – sitting at the beginning of the Magnificent Mile it is stunning and luxurious
• Staypineapple – I was looking at here to stay but it lost the toss up. A great area and reasonable price
• The Blackstone – updated to sleek and modern. I would put this, for Chicago downtown, as Moderate. It was about 100 more a night than Palmer House
• Chicago Athletic Association – A great hotel in the perfect location and a stunning fireplace to warm up in front of after walking around Chicago in the winter time.

Things to do around the city

Chicago in the winter is amazing, yes it is cold, but still so exciting to walk around. They go all out with decorating for the holiday season and it put me right in the spirit for Christmas. You will find so many things within walking distance from list of hotels I had mentioned before.

Walk The Magnificent Mile

One of the, if not the top, things to go in Chicago in the winter. The Magnificent Mile is lit!!! Located on Michigan Ave it spans .8 miles between the Chicago River and Oak Street. Literally one of the prettiest streets I have seen. Here is your trail to retail stores, amazing restaurants and culture. The first night we were in the city we got here by accident. I hadn’t planned to go here till the second night but so glad we did. Our first night the weather was amazing and the streets were filled with shoppers and light gazers. For our history buffs don’t forget to visit the historic water tower at E Chicago Ave and Michigan Ave. And if your lucky you might even come across a Christmas Carol.

Millennium Park

Take a stroll through Millennium Park and visit Cloud Gate aka the bean! This iconic structure is probably the most visited in Chicago. Come here in the summer and it will be packed! Visit Chicago in the winter mornings and you will have the place almost to yourself. Millennium Park is also considered to be the largest rooftop garden as it sits on a parking garage. It covers just over 24 acres and has a large variety of art scattered throughout. During the summer months you can see special events and all kinds of entertainment at the Harris Theater and for the winter months ice skating.

Don’t just stop at these places. Make your way around the park to see some of the fountains and botanical gardens. Now you may not have the stunning flower displays but the walk is great with a coffee in hand for sunrise.

Macy’s Display and Walnut Room

Now buying at Macy’s is not free lol, but you can take a visit and see the amazing display at no charge. Did I mention that it is windy in Chicago (winky face)? Well this is a great way to get out of the cold and put some warmth back in your hands. Macy’s displays on the outside are great but head on in for some Christmas cheer.

We had bumped into a family that visits here every year, a family tradition. We were on our way to The Walnut Room on the elevator. We asked them if we were going in the right direction and the agreed but gave us some advice. Don’t eat here! Now normally I don’t pay attention to what others say but we had just eaten and I couldn’t eat another thing. Have you ate here? Drop me a line and tell me what you think.

We did however still make our way to the first ever restaurant to ever open in a store. This stunning dining room features a beautiful Christmas tree. I love blue and silver and it was decorated very nicely. Even if your not hungry, may I suggest a hot chocolate. There were no tables available while we were there but I could have used a warm up.

Don’t stop there. Make your way around to all the cute displays they have around the department store. I counted 11 just in the short distance around. They definitely go all out for Christmas.

Riverfront and Navy Pier

A great place to bring the family and great out of the cold. You will need to show proof of double vaccine to get in if you are over the age of 12. If you are 5 years to 11 years you will need to show proof of one vaccine. For hours of operation and ticket info visit navypier.org

This is another popular place in the summer and is pack during peak times. In the winter it is not as packed and another place to take advantage of during the winter months.

The riverfront is spectacular. No matter which bridge you cross you will see the stunning light display. There are restaurants along the river that has cute little igloos for outdoor dining.

Christkindlmarket

Looking for something different? Maybe that Christmas gift for the, out of this world friend or family member? Make your way to Washington St, Daley Plaza, to the Christkindlmarket. Get yourself a comfy pair of shoes and dress for the weather. Getting into this spectacular place takes time and a lap around the block. It is worth every blister, even if you just come for the treats and beer!

Here you can find vendors from around the world selling their native work. Stunning tree ornaments, wood work and wool clothing. But lets be real, most are there for the craft beer and stuffed pretzels and they are both delicious.

Museum of science and Industry

This is a fun filled adventure for the whole family no matter what age. Head to the fairy castle and farm area for the kids. Take a trip back in time and walk through a U-505 submarine. A great piece of history now sits in Chicago. Check out some natural wonders of the world in live science and science storms. Watch the kids eyes light up to a tornado forming right in front of them.

However when you come here during the winter/holiday season you will get the opportunity to learn about the Christmas spirit around the world. As a world explorer and wanderer I really wanted to learn the ways we as humans in different area codes celebrated Santa.

There’s a tree from each country that celebrate. Each one decorated in traditional ways. Under each tree is a plaque. Here you will find the country, how they say Merry Christmas and a detailed description on their ways of celebrating. For anyone that loves to explore, this is a must stop.

Chicago Theatre

Now if you have time why not check out a show. We didn’t have time this weekend, but I’m sure we will be back. Another great place to check out as a family, or even a nice relaxing date night.

Don’t have time like us, well make sure you get the “iconic” photo. Plus you are right there for the stunning Macy’s trumpet display.

The Polar Express

I’m going to end winter in Chicago with my 2nd reason for wanting to go to Chicago. Yes Matt you were the main reason 🙂 The Polar Express is my favorite Christmas movie. The adventure, jumping on a train with a bunch of strangers and not knowing where you are going!! Yes this is every Backpacker out there.

On a serious note this was such a fantastic experience not only for us, but watching those kids light up during the songs. The beams of happiness when Santa came with our very own bell. The staff and conductor were truly wonderful and the music was amazing.

You have to buy your tickets early as they do sell out. If you want to avoid the rush of a hundred kids take the latest train.

Other places to check out

• The Art Institute
• 360 observation deck
• Wrigley Field
• Chicago Riverwalk
• Chicago Culture center
• Chicago water tower

Food

You can’t come to Chicago and not have a deep dish pizza. Now this is something I researched more. Although I loved it, I know there is that one spot that has the best. We stopped at Giordano’s. The staff were amazing and the food was fantastic. I wasn’t a big fan of the beer but Matt loved it! For me if the food is good and the service is great I consider it a great place.

Which brings me to the place to go to for breakfast. Wildberry. You had better come early and still prepare to stand in line. We went on a Monday and just made it in before the rush. This was by far the best service we encountered in all of Chicago. And the meal…….amazing!!!!!!! Matt had the omelete and pancakes and I went the the eggs and turkey bacon. You really can’t go wrong on mine but Matts was delicious.

There are so many places to dine in or if the day is nice enough get it to go and sit in a park.

I would say I love it because of the lights, music and cheer around the city. Would I go back, meh, maybe one day. I would like to visit in the summer. Maybe Matt and I will make it a stop on our sailing adventures.

Have you been here before? Tell me your favorite place to get deep dish and what makes it stand out from the others.

Final Note: Safety is important to me and I will always give warning when needed. Matt and I never had any troubles but just like any major city you are going to have crime. Stay on well lit streets at night. Don’t wonder anywhere alone. Chicago has it’s high crime but they are trying to make it better. Stay classy and not flashy.