Chicago is second to no city, especially at Christmas time. Our family recently spent two nights in the Windy City, doing all things Christmas. It was a jam-packed couple of days filled with twinkling lights, warm beverages and frosty activities and experiences we won’t soon forget. Here’s how we spent our time:
Chicago is about a nine-hour drive (with stops) from our house. We left very early in the morning and arrived at our Michigan Avenue hotel by mid-afternoon. Chicago is always busy, so we chose to do most of our sightseeing on a Monday hoping we’d have to navigate smaller crowds and fewer headaches.
Day 1
Zoo Lights at Lincoln Park Zoo
Upon arriving in the city, we got checked into our hotel and then geared up for after dark adventures. Our first stop was Lincoln Park Zoo to see the Zoo Lights. Parking in the area is horrific so we took an Uber and used Apple Maps to avoid clogged streets and chose to be dropped off two blocks from the zoo’s main entrance. Zoo Lights is free and runs on weekends from Thanksgiving to New Years. We visited on a Sunday evening in early December and it was busy but manageable.
We spent about two hours at Zoo Lights before taking an Uber to Millennium Park. Our plan was to go ice skating at the Maggie Daley Skating Ribbon. When we arrived at about 7:00pm there was an approximately two hour wait for skate rental. We opted instead to see the city’s Christmas Tree at the park and move skating to our itinerary for the next day.
Millennium Park Christmas tree
Chicago recently moved the city’s Christmas tree from Daley Plaza to Millennium Park to provide a more central location. The 55 foot blue spruce dazzled against the city’s iconic skyline. Since it was a beautiful night with temperatures in the mid-forties we decided to walk from Millennium Park to Water Tower Place. The beautifully light streets and Christmas displays were a perfect addition to our nighttime stroll. At Water Tower place we climbed aboard a horse and carriage to enjoy more of the city’s ambiance set to the sounds of our horse Fiona’s hooves clip-clopping down the street.
Michigan Avenue and Water Tower Place
Day 2
On the second day of our trip our youngest son came down with a slight fever. We spent the morning in our hotel room, lounging and waiting for the Tylenol to work its magic. By mid-morning he had perked back up so we took another Uber to Nay Pier for Winter Wonderfest. I highly suggest checking Groupon for discounted tickets. Winter Wonderfest includes 170,000 square feet of inflatables, rides and other attractions as well as an indoor skating rink. Our boys are nine and seven years-old and for them the highlights were the Cliff Hanger ride and the indoor sledding hill.
Winter Wonderfest
Winter Wonderfest also offers concessions like hot dogs and cotton candy. We ate at one of the Navy Pier dining options prior to entering Wonderfest. In total, we spent just over three hours enjoying Wonderfest’s rides and slides. We were there on a Monday, so there was no waiting in line. Perfect. On our way out of Navy Pier we stopped at a candy store for a little afternoon pick-me-up as we made our way to the Maggie Daley Skating Ribbon. Try number two.
Maggie Daley Skate Ribbon
We were very pleased when we arrived at the ribbon that there was no wait for skate rental. In fact, there were only about 15 other people skating. We were very much looking forward to skating at Maggie Daley because it’s a ribbon instead of a rink. Skaters meander along a path about twice the length of one lap around a traditional rink.
We spent about an hour and a half at the ribbon, including a short break for a cup of hot chocolate, we then made our way to State Street to see the Christmas windows at Macy’s and have dinner at the Walnut Room.
Macy’s and the Walnut Room
The window displays have been a Macy’s tradition since 1967. This year’s window’s are themed “Believe in the Wonder” and they span the entire length of the building on State Street. The displays chronicle the journey of Santa on his magical ride on Christmas Eve. Inside, on the 7th Floor, we enjoyed the iconic Christmas Buffet at the Walnut Room. The center of the wood clad room features a 45 foot tall tree covered in 6,000 lights and 2,000 ornaments. We enjoyed signature cocktails and their famous chicken pot pie, prime rib and an 8 foot long dessert table. There were plenty of choices on the kids’ buffet as well so everyone left feeling full and happy. Reservations at the Walnut Room are scarce and nearly impossible to get. We walked up just before 5:00pm on a Monday and were seated immediately.
Polar Express at Union Station
The last stop on our jam packed day was to Union Station for a round trip ride to the North Pole on the Polar Express. Since we had been out and about all day, traipsing across town, we did not pack pajamas for the train ride. Many passengers did sport jammies (usually matching) and looked adorable. The Polar Express is more of a theatrical performance than a scenic train ride. The train itself goes back and forth at a slower speed through the train yard. The window’s of the train cars are covered in a festive film and rider’s attention is drawn to the performance happening at the center of each car.
Before boarding the train, riders check-in at Union Station’s Great Hall. Union Station was built in 1925 and is the third busiest station in the country. The station’s Great Hall was beautifully decorated for the season and included a replica train that was perfect for pictures. From the start of the Polar Express experience we were immersed in the sights and sounds of the Polar Express film.
All Aboard the Polar Express
Once we had our train tickets, the conductor called “All Aboard!” and we were led to our train car called the Aurora Borealis. We purchased tickets two months in advance for a Monday evening ride so we could be seated in the front row of our car and close to the performance. Before riders ever board the train, the performance has begun with characters lining the tracks waving and greeting passengers.
Once aboard, our tickets were punched with a special message and the train moved forward. Characters sang and danced as the story of the Polar Express unfolded. Dancing chefs served hot chocolate and cookies as we journeyed to the North Pole where Santa boarded the train and handed out the first gift of Christmas.
The Bell Rings for all who Believe
With our Christmas bells’ in hand, we returned to Union Station as our hour long Polar Express experience concluded. The train ride was a great way to end our time in Chicago. The next day was spent traveling back to Minnesota and recapping all our wonderful experiences. At separate points in the trip, both our boys shared thoughts of how magical the city was at Christmas time. Our youngest even declared he’s moving to Chicago when he gets big. We are allowed to visit.
Our Chicago Christmas trip was not the first time we’d been to the city. You can read more about our Windy City Adventure with the boys here.
Happy Adventuring, Rochelle