A few years ago, I had the most fun December Saturday EVER. I’ve told several friends about this, and today, I’m letting you in on this delightful way to get in the Christmas spirit β take a day trip to Chicago! Grab some friends; this will long live as a favorite memory.
Imagine this: For less than $120 roundtrip, you could spend the day in Chicago, bundled up and walking Michigan Avenue β all decked out for Christmas, eating a fancy lunch, going to the famous Christkindlmarket, an authentic German outdoor Christmas market, and wrapping up with an early evening cocktail before you go. You could even catch a 2 p.m. Broadway show if you’d like.
Here’s how to make it work!
Your One-Day Itinerary: Nashville to Chicago
I’ve compiled this suggested itinerary for a magical December Saturday in Chicago.
SB Note: Don’t dress in your yoga or athleticwear. Some of the places I’ve suggested for meals have a dress code. You can still be comfy and dressed nicely! Do check the dress codes just to make sure.Β
Take a United Airlines flight on Saturday, December 7, or December 14, which leaves at 8 a.m. and arrives at 9:53 a.m. There are plenty of flights to Chicago, but this one leaves at just the right time, and it is super cheap. If you’d like to leave earlier, United has a 6 a.m. flight as well. Personally, I wouldn’t want to leave any later than 8 a.m. as you won’t have enough time to enjoy your one-day trip.
And here’s the flight you need to book back, leaving at 7:45 p.m. and arriving back in Nashville at 9:27 p.m.
Now, you need to decide if you’d rather catch a cab, Uber or Lyft, or take public transportation. As it’s a weekend, I suggest a taxi or rideshare. It’s more expensive, but there is not as much traffic on the weekend as during the week, so it should save you about 20 minutes versus the L-train. If you want to save money, the L is only about $5, which is pretty sweet.
If you decide to change this itinerary up to work for kids, well … young kids might like the adventure of the train. But, by the end of the day, you may have some bags from shopping and be more comfortable in a cab or rideshare on the way back. Either way, it’s time to start your Chicago adventure!
CHRISTKINDLMARKET CHICAGO
Experience an authentic German-style Christkindlmarket by heading to this outdoor Christmas Market, which opens at 11 a.m. (The taxi from O’hare to the market is about 25 minutes). Stroll through here for 45 minutes. Order some glΓΌhwein (warm spiced wine) in the yearly keepsake mug or some hot cider, hot chocolate, or a warm chai latte.
Consider a beautiful wooden Christmas ornament or a traditional German Christmas pyramid, which uses candle heat to spin the wooden carousel.
LUNCH
Head to lunch for a noon reservation. Here are three suggestions to consider for a reservation:
Option #1: Shaw’s Crab House is a 13-minute walk from the Christkindlmarket. While I dearly miss their huge buffet β it may have been the best seafood buffet in all of America before Covid destroyed it βΒ you can order off the menu. There are a variety of raw bar options and a large selection of sushi and other fish options, including one amazing lobster roll. There is also a delicious cheeseburger and petit filet on the menu for non-seafood people. If you like a noon cocktail, the bloody mary is highly suggested!
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Option #2: The Dearborn is just a one-minute walk from Christkindlmarket and opens at 10 a.m. So, you could start here for an early brunch and then hit the Christmas market. You know how those Chicago flights typically get in early … But, it’s great for lunch as well. It’s also cozy, with a beautifully decorated tree to greet you.
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Option #3: The Cherry Circle Room at the Chicago Athletic Association Hotel is a lovely place to celebrate your day in Chicago, and it is just a nine-minute walk from the Christkindlmarket. This historic restaurant, with its rich wood paneling and leather booths, feels like stepping into the city’s elegant past. It’s completely cozy and offset by elegant seasonal decor, creating a festive lunch spot. The beautiful, soaring windows overlook Michigan Avenue as well.
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FOR NEXT YEAR: I highly recommend The Walnut Room at Macy’s for 2025. You’ll need to make your reservation in September 2025, the day it opens, as it books up super fast! The Walnut Room at Macy’s is just a five-minute walk from the Christkindlmarket. During the holidays, there’s no place quite like it. This is THE iconic place to go.
Since 1905, Chicagoans have gathered at this Macy’s landmark to dine beneath the soaring Great Tree, a towering spectacle draped in thousands of lights and ornaments. Yes, the 3,000-pound decorated tree hangs from the ceiling! This is also the very first restaurant ever to be opened in a department store.
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AFTERNOON ACTIVITY
Choice #1: If you are in Chicago on December 7-8, 2024, walk or catch a taxi to the beautiful Cadillac Palace Theatre for the 2 p.m. showing of Broadway’s & Juliet (this show is two hours and 40 minutes long, including intermission). If you are there on December 14 or 15, consider The Hip Hop Nutcracker.
Choice #2: Spend a few hours shopping on the famous Magnificent Mile (North Michigan Avenue). The stores, hotels, and street will be completely decked out for Christmas. If it’s super cold, just go into more stores β problem solved!
EARLY EVENING COCKTAILS OR ICE SKATING
When the show is over, or you are finished shopping, enjoy the lights, as it’s dark in Chicago by this point. In December, sunsets are around 4:20 p.m. This means it’s time to head to one of the following for an early evening snack and cocktail before going to the airport. Consider ice skating in an outdoor rink if you’d rather skip the cocktail.
Option #1: Cindy’s Rooftop is a beautiful place atop the Chicago Athletic Association Hotel β the same place where the Cherry Circle Room is located (one of my lunch suggestions).
Pro tip: Reservations open 15 days in advance and fill up quickly, so once you’ve picked your date, mark your calendar for 15 days before. AND you’ll need to order a meal, per the rules, to have a reservation, so grab an early dinner. The view is stunning. There are multiple bars in this hotel, including Milk Room, a microbar that seats just eight people. Perhaps you can snag a 5 p.m. reservation this early on? The lobby bar, called the Drawing Room, is also a great place for a drink and small bites.
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Option #2: The Peninsula Hotel’s lobby bar occupies a dramatic two-story space in one of Chicago’s most luxurious hotels, and it’s always stunning during the holidays. Location-wise, it’s perfectly situated at Michigan and Superior, making it an easy stop before heading back to O’Hare. Pro-tip: Their club sandwich is iconic if you’re having a light dinner.
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Option #3: Volume 39, located in the Kimpton Gray Hotel, is just a five-minute walk from the Cadillac Palace Theatre. This sophisticated lounge feels like a private library, with leather chairs and vintage decanters, and is known for perfectly executed classics and tableside martini service.
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6 p.m. β Now, it’s time to head to the airport!
While I like to be at an airport two hours early, you won’t have luggage to check (unless you really went crazy shopping). You should be okay leaving promptly at 6 p.m. for O’Hare for your 7:45 p.m. flight. You’ll be home by 9:30 p.m.!
Take photos and encourage others to plan a happy December day where your one goal is to hang with friends all day long and do something new!
I’ll also put together another Chicago day trip article for warmer weather β it’s just such a fun thing to do, and there are SO many more things to do in Chicago.
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Looking for fun new places to eat in Nashville? Check out our “New Restaurants in Nashville” article, which is updated monthly.
