Located on the southwestern shores of freshwater Lake Michigan, Chicago is the third-most populous city in the United States. But how does one survive all of the ins and outs of Chi-town during the winter? Don’t worry. As long as you do what the White T-Shirt Guy does then you’ll be set up for the ultimate winter experience in the windy city.
I made my way to Chicago starting with a flight from Raleigh/Durham International Airport (RDU) to O’ Hare International Airport (ORD) for $97. When I got there I quickly realized that public transportation even above Ubers was the best option for getting to my hotel and traveling between excursions. Why? Because like any big city, the traffic is horrendous. For my subscribers who aren’t familiar with the specifics on the way public transportation operates in Chicago, let me give you a quick run-down. There are numerous buses and trains called the “L” that are located in nearly every corner of the city. On the metro, a single ride is $2.25 per ride and a bus ride is $2. The Chicago Transit Authority (CTA) also use transit cards, which can be loaded with any amount from $2, or as high as $100. Both Ventra tickets and transit cards are available from vending machines located at all train stations. There are also visitor passes that will allow you to have unlimited rides for a specific amount of days. 1-day: $10, 3-day: $20, 7-day: $28. I bought the 3-day pass because I knew that most of my activities would be done in various parts of the city. Had the weather been nicer I definitely would have planned to walk more, but being in Chicago during the winter is like being in the North Pole. There’s nothing but snow, often up to 10 inches depending on the month.
After taking the train to the “Grand” stop on the red line, I walked right up the street to check into the newly renovated studio suite at the Chicago Marriott Downtown Magnificent Mile hotel. Other than the fact that this hotel is absolutely stunning and modern, I liked that it’s in the heart of the city. Everything from restaurants to clubs and shopping is located relatively close to the hotel. Because I stayed in Magnificent Mile, one of the hot spots for shopping in Chicago, I spent a lot of the first night sight-seeing in the area and making my way between 900 Michigan Shops and the Water Tower Place before finally ending up at Giordano’s. It was inevitable that I’d have to stop somewhere to try Chicago’s famous deep-dish pizza. It was convenient that the restaurant had a system where you can pre-order your pizza while you wait for a table to ensure that there’s less of a wait overall. I’ll admit that even if I had to wait for hours, it would’ve been worth it for that world-famous artisan deep dish pizza.
On the second day, I woke up bright and early to walk right up the street to the Starbucks Reserve Roastery. I’ll admit that I’ve never been a huge coffee fan, but considering that this is the World’s largest Starbucks, I wanted to see what all the hype was about. Before I could even see the entrance, there was a long line wrapping around the building. Luckily, the line went at a reasonable pace. When I finally stepped inside, my jaw dropped. The building was around 35,000 square feet with 4 full floors (one of them being a coffee-infused cocktail bar floor) and a rooftop on the 5th floor. The architectural design of the building has a futuristic look, accented with earthy colored walls and furniture and golden cylinders in the middle of the store.
I ordered one of their handcrafted pastries made with European-style butter and Italian fillings with a small hot chocolate. Later on in the day, I took the train further downtown to stop by Christkindlmarket, Chicago’s annual Christmas market held in Daley Plaza. Chicago’s Christkindlmarket is about as close to a festive German Christmas market as you’ll find in the United States. There were lots of vendors and tiny shops selling Christmas ornaments, cold-weather clothing, and German food like bratwurst and sauerkraut. I got a cup of hot spiced apple cider, bratwurst, and German potato pancakes from Traditional German Food, LLC. The best part of all is that it’s so crowded that the natural warmth generating from everyone practically being a shoulder to shoulder almost made me forget how cold it was outside.
On the last two days of my trip, I mostly focused on going to events and areas of the city where I could take pictures of festive scenery and commonly known Chicagoan landmarks. Everyone who’s ever been to Chicago knows that no matter how many times you’re there, you have to take a picture in front of Cloud Gate (a.k.a. “The Bean”). Much to my pleasant surprise, there were exhibitionists like Chicago Children’s Choir and the Wicker Park Choral Singers there performing a series of winter concerts and sing-alongs. There were a lot of people surrounding the area and I overhead quite a few people talking about the Zoolights at the Lincoln Park Zoo so I made sure to take the train up there later that night to see it. They had such an awesome set up with assorted Christmas-themed lights. There were multiple light shows, a light maze, gift shops, beer booths, outdoor rides, an indoor section with live music, and ice sculpture shavings! The whole entire zoo amplified the spirit of the season up to the point where it genuinely looked like a Winter Wonderland.
Chicago is a beautiful city with lots to offer. The weather there was extreme, but it was worth it. My time there was filled with good food and fun experiences. Now I understand why so many people live there.
Full price breakdown: Round Trip airline ticket from RDU to ORD- $97 Stay at Chicago Marriott Downtown Magnificent Mile- $760 3- Day CTA pass- $20 Giordanos- $22.75 Starbucks Reserve Roastery- $15 Christkindl market- $14 Room service at hotel- $25 Room service at hotel- $30 Food at Lincoln Park Zoolights- $10
Total price: $993.75
In closing, it cost the White T-Shirt Guy $993.75 to spend four days in Chicago and so can you.
10 inches of snow in a month 🤔
Hi Lisa, that would depend on the month but yes.
We ate at RPM Steakhouse when we visited Chicago. Food was delicious.
Welp have been close but not quit in Chicago but u made the trip sound so amazing so I know I gotta try this one out!!!