Having just returned from a quick weekend trip to Chicago with my 10-year-old son, my only thought is: why haven’t we done this before? We had an amazing time exploring the city and soaking up the holiday atmosphere!
A Weekend Getaway to Chicago – From Anywhere
We left Santa Barbara on a Saturday morning, escaping the smoke and fires that have dominated life in Southern California for weeks, and were in Chicago by 2:30pm. A 45-minute taxi ride later, we checked into an Elf Decorated Suite at the Swissôtel Chicago. So cool! We walked in to find our two connecting rooms completely decorated for the holidays. There were two Christmas trees, wreaths, festive pillows, and even a mini-reindeer – but not a real one, luckily. It’s a great setup for families of 5 or 6, with a master bedroom in the suite side and two double beds in the room next door. But we didn’t hang out in the room for long. Because Chicago! We left to explore and start our weekend.
Stop One: Christkindlmarket
I love European Christmas markets, but by the time we’re out of school in December, the Christmas markets are wrapping up. So we’ve never taken the kids over. Chicago’s got it covered though. The Christkindlmarket in Daley Plaza runs from mid-November to Christmas Eve every year (exact dates/times are here) and is authentic – right down to the sausages everywhere. Well that’s also a Chicago thing. But it’s a perfect match! It gets crowded, but we had fun and it immediately got us into the big city holiday spirit. It was only a 15-minute walk from the hotel to Christkindlmarket.
Stop Two: Macy’s
Only a few minutes from Christkindlmarket is State Street and Macy’s – with a full city block of holiday-themed windows. So fun seeing all of the impressive windows and the kids who were drawn to them. This year’s theme is Reasons to Believe, and the displays will be up until January 7th.
Stop Three: Frontera Grill
My son is a foodie, and he’s wanted to eat at Rick Bayless’ Frontera Grill for years. So we made a reservation for 8:30pm Saturday night – easy for us since we were still on California time. Dinner was excellent! One highlight: the queso fundido with pumpkin seeds, bacon and poblano peppers. And my son loved the chipotle-glazed ribs.
Stop Four: Ice Skating
The Elf Decorated Room package at Swissôtel comes with VIP skating vouchers at Maggie Daley Park. We could even see the skating ribbon from our window. So Sunday morning, after an excellent breakfast at the hotel, we walked five minutes over to the park, skipped the line (thank you Swissôtel), rented skates and hit the ice. My son hadn’t skated in a year and it took him a a couple loops to become confident again, but after that it was a blast. We skated for roughly an hour and a half.
Stop Five: Santa!
After skating we returned to our 41st-floor suite, dropped off our coats, and then walked down the hallway to the Santa Suite. So cool! Every year the Swissôtel turns their Presidential Suite into a Santa Suite. It’s filled with trees, the table is set, and Santa is waiting. An utterly impressive setup. Guests can visit the suite from December 1 through Christmas Day.
Stop Six: Hamilton
It was at this point, after returning from our visit with Santa, that I looked into what was taking place in Chicago. I had forgotten about Hamilton! There was a 2pm show and, miraculously, there were fifth-row tickets available for $216 each. I had paid $600 or so for a mediocre seat in New York, and tickets in LA were going for over $700, so this was a great price. I bought the tickets and we walked over to the CIBC Theatre.
My son LOVED it! Worth every penny. Ten is a great age. I’d probably take kids as young as nine. Any younger and the story may go over their heads? If you want to see the show, definitely look into Chicago. Given our success getting last-minute tickets, it seems like a great alternative to New York and London, and even to the touring productions.
Stop Seven: The Bean
So we technically walked by the Bean (aka Cloud Gate) on the way to Hamilton, and stopped for a couple of quick photos, but we spent more time there after the musical. It’s become the iconic symbol of Chicago, so you have to go at least once!
Stop Eight: The Museum of Science and Industry
Monday morning, after breakfast at the hotel, we took a taxi over to the Museum of Science and Industry. We went to see the annual display of Christmas trees from around the world, but also experienced the flight simulator and walked through a lot of the interactive exhibits. It’s a very impressive museum. Be sure to purchase a Gravitron when you go! You place an order (for $5) and then watch the toy being machine-assembled in front of you. It was my son’s favorite activity there.
What We Didn’t Do
We didn’t buy anything all weekend that we didn’t eat. But some of the best shopping in the world is on the Magnificent Mile, just a few minutes’ walk from the hotel.
Dinner at Frontera Grill was roughly $100. Hamilton was $216 per ticket, plus Ticketmaster fees. The taxi from O’Hare Airport to the hotel was $57, and it was $53 back to the airport. Taxis were $21.50 each way between the hotel and the Museum of Science and Industry. Otherwise we walked everywhere.
We were guests of Swissôtel Chicago. Elf Decorated Rooms start at $250. Prices differ based on room availability (Santa’s elves can only decorate so many rooms at a time) and how close you book your stay to Christmas. Elf-Decorated Rooms/Suites are available through December 31st. The milk and cookies delivery is an add-on special.
Have you spent a holiday-themed weekend in Chicago? What did we miss?