How To Enjoy Chicago Without Risking Frostbite

After a long summer, the cold weather the city is known for is here. But that doesn’t mean you should enjoy your time any less!


Many of us didn’t see this coming. After all, it was a warmer than usual fall. Then, snow. A lot of it. Not to mention the below freezing temperatures you can anticipate for weeks to come.

Even those who have lived here for quite some time weren’t prepared to hibernate quite yet. This week, we’re seeing temperatures in the teens and a “feels like: in the single digits. Go for a stroll outside? No thank you. Continue reading “How To Enjoy Chicago Without Risking Frostbite”

A Q&A With Jetpack

In today’s guest post, the founder of Jetpack shares what he loves about Chicago & what he always forgets when traveling.

Deep Dish Note: We’re grateful to have Jeff, the founder of Jetpack, sharing with us on the blog today. He took some time to answer some of our questions about traveling in Chicago and how Jetpack is helping Airbnb guests everywhere.
Continue reading “A Q&A With Jetpack”

5 Jolly Holiday Events That Will Get You In The Christmas Sprit

The holidays are here! It’s best time to explore the city and feel the Christmas cheer. So save the date for these festive events!

While the weather may say differently, the holidays are just around the corner. If you can believe it, Thanksgiving is next week!

When people ask me when Chicago is at its best, I always enthusiastically say “Christmas!” That’s typically met with a few strange looks. However, it’s such a great time to be in the city! Continue reading “5 Jolly Holiday Events That Will Get You In The Christmas Sprit”

Set Sail With The CAF Architecture Boat Tour

If weather permits, the architecture boat tour is one of the best ways to explore the city. Here’s a few reasons why

Cruising with the Chicago Architecture Foundation down Chicago River is an opportunity that should not be missed. If you’re new to the city or have lived here for years, you’re sure to see the city in a new way.

I have a confession. I have lived in and around the Chicago area for a very large part of my life, give of take a few years. I had always heard the Chicago Architecture Foundation boat tour was “the best thing you can do In Chicago” (my husband’s words) but it wasn’t until recently that I actually decided to go. Continue reading “Set Sail With The CAF Architecture Boat Tour”

Why You Need To Attend Open House Chicago This Year

Have you ever been curious as to what the stories are behind some of Chicago’s famous buildings? Now’s your chance to see them.

Have you ever wondered what Chicago looks like from above? What about that building you’ve passed a bunch of times, but have never been in. Now is your chance to get a look at over 200 buildings throughout the city…for free.

Continue reading “Why You Need To Attend Open House Chicago This Year”

A Q&A With Ballet 5:8

Pick an evening and I can probably direct you to a show you should see. That being said, here’s a recommendation for you.

From the latest musicals (read: Hamilton) to comedy shows and dance, Chicago is a city full of the arts. Pick an evening and I can probably direct you to a show you should see. That being said, here’s a recommendation for you.

One of the best parts about living in the city is the vast amount of events I have to choose from. Thankfully, my husband and I have friends who do a lot of awesome things that we get to see, and share with others! Continue reading “A Q&A With Ballet 5:8”