I knew when I moved to California that trips home to the Midwest would be few and far between. But as a romantic and sentimental and homesick kid at heart, I couldn’t bear the thought of a Christmas without snow. So at the last minute, I booked a three day trip to Chicago to spend time with family and friends for the holidays!
How to spend Christmas in Chicago for 72 hours:
Afternoon: Land at Chicago O’Hare Airport and check in to a fabulous Airbnb in Old Town. We chose Old Town for its access to boutique shopping, cozy bars and quick walk to downtown. It is located just north of the city sidewalks, busy sidewalks, dressed in holiday style, with a slower pace and a more homey feel than downtown on Michigan Avenue.
Evening: Enjoy some seasonal cocktails and a few appetizers on the rooftop of Hotel Lincoln at the J. Parker, which looks out over icy Lake Michigan. Then, dinner at Maple & Ash or perhaps pick up some tacos at Velvet Taco.
Late Evening: See city streetlights, even stoplights, blink a bright red and green on Michigan Ave downtown - admire the Water Tower and the Hancock building -perhaps another glass of wine at The Purple Pig? (Probably.)
Morning: Being a former resident of the city, I like to indulge in nostalgia by visiting the neighborhood of my first apartment: Lakeview. A lot has changed here since the Cubs have started winning and the interest in renovating the stadium seems to have extended to the whole area. Now we are likely to meet smile after smile as we go ice skating next to the stadium (while enjoying some delicious coffee from Emerald City). After working up an appetite from all the skating we will likely get brunch at Southport Grocery down the street. As we head back to Old Town to walk around we will likely smell spices and buy oils at two of my favorite local spots.
Afternoon: We plan to meander our way back north to dinner in my other old neighborhood, Rogers Park. The first stop will be to snag some-Christmas goodies at my favorite card shop, Foursided. Then, stock up on Chicago-made bath, body, and kitchen items at Rogers Park Provisions. Finally we will have dinner at Heartland Cafe. I want to pretend I will venture out on their menu - but who am I kidding - I’ll have the Barnyard Burger just like I always do. In the evening, we plan to see a Second City show. Before the show begins, we are excited to explore their expanded training center and snag a selfie next to a giant wall of Tina Fey’s face. (Make sure to buy your tickets early - they sell out months in advance!)
Morning: We plan to grab some hot cocoa at Cocoa + Co. after we check out of our Airbnb. Then hear the snow crunch as we venture on a Food Tour in Old Town. Each place gives you a sampling of the best of what they offer and you get a little walking tour of Chicago on the way. If we are still hungry, or maybe if we just want a mimosa, we can grab a drink and a bite at Kanela Breakfast Club.
Afternoon: As our short but sweet Chicago vacation comes to a close, we head back to the airport and remember it’s 80 degrees on the West Coast!
Italicized phrases are all sourced from the Christmas song: "Silver Bells"