A Winter Guide to Chicago

Written by Megan Biddix
Photography by Brooke Van Groningen

Moving to Chicago was an easy decision for us and we’ve loved it more and more in the three years that we’ve lived here. One of the things that we didn’t realize until living here is how different each neighborhood is, making them so enjoyable to explore.

I work as an event coordinator, so it’s not only my job to keep up with all of the hot, new things to do in the city, but is also a joy for my personal life. When Brooke asked me to put together a winter guide to Chicago my first reaction was “of course, I’d love to!” but the more I considered it the harder it seemed because there is truly so much this city has to offer.

Here’s just a glimpse of my favorite Chicago winter-inspired activities, experiences, and good eats.

Good Eats

Whisk | West Town

A Ron Swanson-inspired bacon enthusiast's dream, offering breakfast, lunch, and dinner – but you must come for the brunch. Be prepared to wait for up to two hours and BYOB, but the variety of savory and sweet breakfast selections are just too decadent to miss!

Bro Bagel | Bucktown

This tiny storefront is the best cure to the winter blues boasting the best, freshest bagels in town! Stop in to grab-and-go, or, wait for one of the four spots at the counter. Open only for breakfast and lunch with unbeatable prices! We like to grab our everything bagel breakfast sandwiches to go and take them to our favorite coffee shop, Ipsento, to sit and enjoy them with a latte in hand.

Ramen | West Loop, Fulton Market

It’s hard to choose between the many ramen options in the city, but here are two favorites. High Five is a hidden, intimate space serving, as most would agree, “the best ramen in the city.” Opening at 5pm, the line begins forming two hours prior just to put your name in since the space only accommodates around 20 people. If you can’t handle the 2-3hr wait, head on over to Ramen-San. Ramen-San is a neighborhood noodle joint that slings hot broth, ice-cold beer, and ‘90s hip-hop music.


Damn Fine Coffee | Logan Square

My favorite oatmilk vanilla latte in the city and conveniently located only four blocks from our home. The natural light and hanging plants make this fresh space so homey. Get there early for a selection of locally made pastries.


Sprout Home | West Town

The cutest plant shop with large varieties of types and sizes, as well as locally made artisan pots. You’ll forget all about the freezing temperatures outside when you’re inside this house-plant oasis. Put your name in at Whisk and walk over and pick out a new plant while you wait!

Garfield Park Conservatory | Garfield Park

One of the two conservatories in the city with free entry and wifi – you can stay for hours exploring and relaxing. The desert room is a personal favorite with its neutral colors and warm climate.



Sporting Event

To leave the drab outdoor weather behind, enjoy watching the Bulls or Blackhawks at the United Center and engage in the thrilling and lively atmosphere of a local sports game. We had the best time and it didn’t hurt the Bulls pulled out the W!


Honorable Mentions

Good Eats: Lula Café, Beatrix, Bongo Room, Parlor Pizza, Daisey’s, Three Arts Café

Activities: Penguin Foot Pottery, Ace Bounce, Bad Ax Throwing, Scratch Goods, Le Labo Perfume

Experiences: Second City, Magic Lounge, Chicago Architectural Boat Tour

Stay: Ace Hotel, Marine Layer Loft, or the Biddix’s Air BnB.


Megan Biddix

Megan resides in Chicago, IL with her husband Chris and goldendoodle, Millie. She is an event planner who loves coffee, barre and exploring new cities in her free time. Follow her on Instagram.