Chicago at Christmas

There is no time like Christmas in Chicago, where you can’t help but feel the magic of the holiday season. The city is full of bustling excitement and seasonal celebrations, from The Magnificent Mile to Millennium Park. If you’re traveling with kids, Christmas in Chicago is a one of a kind experience for Home Alone movie fans and an authentic holiday market experience at Christkindlmarket Chicago.

It was windy, it was cold, and even sleeted while we were there, but that hasn’t stopped us from planning our next visit at Christmas time.

“Eventually, I think Chicago will be the most beautiful great city left in the world.”

Frank Lloyd Wright

Chicago is a city of architecture. Skyscrapers, historic streets, museums and luxury stores overlook Michigan Avenue, the city’s main strip, and the holiday sites are endless. We planned our trip around a few key must dos: The Art Institute of Chicago, the new Harry Potter Magic at Play experience, the Christkindlmarket, the Home Alone house, and of course, food.

Chicago does not disappoint when it comes to culinary delights. I dream of the deep dish pizza I had at Giordando’s, the eggnog chocolates from Fanny May, and the fabulous breakfast we had at Wildberry Pancakes & Cafe.

A major highlight of this trip for me was the Christmas Market at Daley Plaza, It’s one of the top Christmas Markets in the Country. The german food, the handmade artisan goods, it was everything I hoped it would be. The walk to it from our hotel to the market was nothing short of fabulous. We walked right through the bustling Broadway district, and had to make a stop at Macy’s. A note – at no point of our trip did we feel unsafe. We logged around 20,000 steps each day and covered a good portion of this area.

See you next time, Chicago!

3-Day Itinerary with 2 Kids

Day	To	From	Mode	Departure Time	Arrival Time	Trip Notes
1 Thurs	Chicago Midway (MDW)	BWI	Southwest Airlines	9:15PM	10:20PM	MDW is a less busy option than ORD. A bonus is that there are plenty of Southwest flights from BWI to MDW
	Hyatt Regency 151 E Wacker Dr, Chicago	MDW	Rental car	11:00PM	11:30PM	Fabulous hotel in the heart of downtown and steps to the Riverwalk. Would 100% stay here again. Tip – Hyatt’s parking is $79 per night. There are cheaper options at self parking decks close by at $40 per night.
2 Fri	Hyatt Regency breakfast	Our room	Walk		8:00AM	It was cold and raining so we opted to stay at the hotel for breakfast. The buffet was wonderful!
	Michigan Ave shops	Our hotel	Walk	9:00AM	11:00AM	It was here that my youngest daughter discovered her love of Ulta. There are so many great shops and beautiful buildings to look at just steps from our hotel.
	Millennium Park	Our hotel	Walk	12:00PM	12:15PM	Do not miss! Can you even say that you’ve been to Chicago without making a stop at the Bean?
	The Art Institute of Chicago 111 South Michigan Ave Chicago	Millennium Park	Walk	12:30PM	12:45PM	Do not miss!
	Giordano’s 130 E Randolph St, Chicago	The Art Institute	Walk	3:30PM	3:15PM	Do not miss!
	Harry Potter Magic at Play Water Tower 835 Michigan Ave, Chicago	Giordano’s	Walk	6:00PM	6:30PM	I was less than impressed. If you have kids under the age of 6, this is a good stop. Otherwise, I’d skip it.
3 Sat	Stan’s Donuts at Millennium Park 181 N Michigan Ave, Chicago	Our hotel	Walk	9:00AM	9:10AM	Do not miss the eggnog donuts in December!
	Navy Pier	Stan’s Donuts	Walk	10:00AM	10:45AM	Do not miss! Chicago’s waterfront destination is a little bit of a hike from the Hyatt Regency but Chicago is such a walkable city that we didn’t mind at all.
	Riverwalk	Navy Pier	Walk			The 1.25-mile long path to the Riverwalk was surprisingly pleasant and I felt safe walking with my family.
	U Dawg U 300 N Happ Rd, Northfield, IL	Riverwalk/Our Hote	Rental car	11:00AM	11:30AM	We were looking for highly rated spot to get Chicago-style hotdogs and try a pizza puff – it did not disappoint.
	Home Alone house 671 Lincoln Ave, Winnetka, IL	U Dawg U	Rental car	11:40AM	11:50AM	Do not miss if you are a Home Alone fan. The suburban town of Winnetka is charming and the area is easy to get to from the city.
	The original Billy Goat’s Tavern Lower 430 North, Michigan Ave, Chicago	Our Hotel	Walk	5:00PM	5:10PM	I don’t think I’d go just for the food again, but this subterranean location is a cool spot to stop at in American sports history.
	Macy’s 111 N. State St, Chicago, IL	Billy Goat’s	Walk	6:00PM		Macy’s at Christmas time – it felt like a NYC with all the hustle and bustle. Toys ‘R Us has a large presence here so my kids enjoyed being a kid again.
	Christkindl Market, Daley Plaza	Macy’s	Walk			Do not miss! My favorite part of the whole trip. It’s admission free, and one of the few authentic German Christmas markets in the world!
4 Sun	Breakfast at Wildberry Pancakes & Cafe	Our hotel	Walk	7:00AM	7:10AM	Do not miss! There is a reason that you have to get up early to get a table here because there’s usually a line outside of the door – it’s just that good.
	MDW Airport to head home	Our hotel	Rental car	9:00AM	9:30AM	No issues with Southwest Airlines and found this route to be a good option for flying in and out of Chicago.