If you’re looking for a different way to experience Chicago, I have the BEST ITINERARY for you. Downtown gets all the attention, so I hope this inspires you to branch out this holiday season!
It doesn’t matter if you’re single, have kids, visiting or even live in the city – you will LOVE IT!
Hotel Zachary recently invited Sean, Penelope and I to experience their hotel and surrounding area for the weekend. We went for a fun time and left with a new family tradition.
Since they put together an epic guide planned to the nines, I wanted to share it with you.
But first, a little bit about the area!
The New Wrigleyville
Ever since the Cubs won the World Series, this area has just boomed. So if you haven’t been here in awhile, its SO NICE. The neighborhood is bustling about with families and busy restaurants. Several of the hottest local restaurants have set up camp here too {Smoke Daddy’s, Big Star and Jeni’s to name a few!}. We were blown away by the festive decor. Gallagher Way Winterland offers ice skating and the Christkindle market this time of year! My brother-in-law and his fiancé live just a block away and love it here too.
Why Hotel Zachary
Everything is at your finger tips when you stay at Hotel Zachary! It’s truly the only hotel of it’s kind in the area. This luxury hotel has top notch service and so much to offer. I mean…check out their Glamping on the terrace! Oh, and did you know it’s dog friendly? Larry visited but stayed with his uncles so he could get attention around the clock!
We spent the entire weekend in a one block radius and did SO MUCH. If you have a baby it doesn’t get any better than this! We bounced around and did all the things. Then when Penelope got fussy or needed a nap, we just popped back into our room. Effortless.
Our beautiful room had a million dollar view of Wrigley Field, the ice skating rink and Chriskindle Market! Penelope was on cloud nine exploring the room and taking it all in.
Now that you know a little more about Wrigleyville and Hotel Zachary, here’s our exact itinerary so you can do it too!
3 Day Winter Itinerary Wrigleyville
How To Use This Itinerary: Keep in mind the times we chose were accommodating for Penelope. So use your best judgement here! Take bits and pieces and fill in the rest with your own ideas. Or copy it exactly for a stress free weekend. It’s planned to the T!
Day 1
- Friday
- 2 p.m. – Check in to Hotel Zachary {normal check in is at 4 PM but we asked for an early check in}
- 4 p.m. – Appetizer and Drink in the Lobby {this area is bump’in 24/7 and has the best atmosphere. Penelope joined us and very kid friendly!}
- 5:30 p.m. – Dinner at Smoke Daddy BBQ {the BEST food and perfect for Penelope!}
- 7 p.m. – Cocktails at Mordecai {my brother-in-law raves about the cocktails here. Sean confirmed they’re top notch. ‘Dad’ got to go out while ‘mom’ put Penelope to bed ;)}
Day 2
- Saturday
- 10 a.m. – Breakfast at The Bar at Hotel Zachary {get the mushroom omelette and their coffee is top notch}
- 11:30 a.m. – Ice skating on The Rink {sooooo fun!}
- 12:30 p.m. – Shopping Christkindlmarket {get a spiked apple cider or hot chocolate in a boot shaped mug and cross off some Christmas shopping from your list}
- 1 p.m. – Pizza at Lucky Dorr {fun fact: my nephew dog, Carl, is the ambassador here! It’s dog friendly and has a great beer selection! Larry and Carl met us here too.}
- 2 p.m. – Bloody Mary at Smoke Daddy {because they are to DIE for!}
- 3 p.m. – Back to the Hotel {a little rest and relaxation. Penelope took her nap.}
- 5 p.m. – Dinner {we did dinner at my Brother-in-law’s because Penelope had quite the day. But any of the restaurants in the area are amazing!}
- 6 p.m. – Bed Time {Penelope went to bed (we put her pack-n-play in the bathroom) while Sean & I enjoyed a movie in bed. Tip: If you are in the same boat, grab a glass of wine from the bar and bring it up to your room!}
Day 3
- Sunday
- 10:45 a.m. – Check out of Hotel Zachary
- 11 a.m. – Teddy Bear Tea at Hotel Zachary {The cutest thing you’ve ever seen! Enjoy tea, hot chocolate, bit sized sandwiches and desserts. Penelope and I got dressed up and we ate alllll the food!}
This is truly THE BEST LITTLE HOLIDAY WEEKEND! Use this as a fun date idea, a genius way to get the kids outdoors or even a new way to spend quality time with friends. Enjoy and let me know if you have any questions!
Click to book your room today!
A huge thanks to Hotel Zachary for hosting us! They provided us with a complimentary stay and comped our meals but opinions are 100% my own!
