Chicago Day Trip: What to See & Do In Downtown Oak Park

This little suburb, which lies just outside Chicago’s western border, is one of my favorite places to spend an afternoon when I’m feeling overwhelmed by the city. It’s easy enough to get to via driving or the CTA (take the green line to the end) and, despite its close proximity to Chicago, a day spent in Oak Park browsing the little shops and admiring the beautiful, old Victorian homes can feel like a mini getaway. The pace is slower, and the downtown district has a distinctly small town charm while still offering plenty to see and do. 

Day Trip to Oak Park, IL // List Maker Picture Taker
Lake Theater has been showing movies sine 1936.

This past weekend, Eric and I ventured here on something of a whim. I’ve been feeling rather homesick lately for Vermont and my family there, and needed a little escape. We headed to Oak Park and were pleasantly surprised to find the season in full swing with Home for the Holidays, a free, old-fashioned Christmas event.
Day Trip to Oak Park, IL // List Maker Picture Taker
A mini getaway in Oak Park, IL. Christmas in full swing with Home for the Holidays.

It was fun to watch the excitement from all the little ones as they enjoyed the carolers and horse-drawn sleigh rides down Marion Street.

A mini getaway in Oak Park, IL. Christmas in full swing with Home for the Holidays.

A mini getaway in Oak Park, IL. Christmas in full swing with Home for the Holidays.


Shopping
We ducked in and out of the many little shops to browse and defrost our toes. There are a number of larger chain stores, including one of my favorites, Paper Source.
A mini getaway in Oak Park, IL. Christmas in full swing with Home for the Holidays. A mini getaway in Oak Park, IL. Christmas in full swing with Home for the Holidays.
But there are also quite a few locally owned shops that shouldn’t be missed, including these:

Scratch & Sniff
While technically a pet store where you can find all everything from dog treats to bow tie collars, this store actually has some fun, quirky gifts for everyone.
Oak Park Shopping // List Maker Picture Taker

Update Interiors
If you’re like me and you have Apartment Therapy bookmarked in your internet browser, Update Interiors is definitely a store for you. They have everything from beautiful place settings and candles, to funky holiday decorations.
Shopping in Oak Park, IL - Update Interiors

Shopping in Oak Park, IL - Update Interiors
Some coal for the stocking. We strongly considered getting a lump of this stuff for a few people on our list.
Shopping in Oak Park, IL - Update Interiors
How cute are these little felt snowmen?

Sugar Fixe
This cute little cafe bakery is a great place to satisfy your sweet tooth. They have a pastry case full of treats to eat, as well as lots of pretty packaged goodies to take with you.
Shopping in Oak Park, IL - Sugar Fixe // List Maker Picture Taker


To See
Oak Park was once the home of two very famous artists: writer Ernest Hemingway and architect Frank Lloyd Wright. The more you explore, the more evident the distinct imprint these two men left on this little midwestern community becomes.

Frank Lloyd Wright Oak Park, IL // List Maker Picture Taker Frank Lloyd Wright Oak Park, IL // List Maker Picture Taker

Frank Lloyd Wright Oak Park, IL // List Maker Picture Taker
I loved the ornaments decorating the front yard of this beautiful Wright home. So festive!

Wright was commissioned to create quite a few homes here, and his trademark ‘Prairie Style’ stands out among the many old Victorian mansions in the historic district.How pretty are these holiday decorations?
Frank Lloyd Wright Oak Park, IL // List Maker Picture TakerFrank Lloyd Wright Oak Park, IL // List Maker Picture Taker

Frank Lloyd Wright Oak Park, IL // List Maker Picture Taker
Clearly not one of Wright’s works, but I’ve decided I would like to live here nonetheless. Thank you.

There are daily tours of the Frank Lloyd Wright Home and Workshop, though Eric and I opted just to walk around the area and explore for ourselves. While I admire his work, I think I’d much prefer a beautiful victorian with a wrap around porch.
Wright House and Workshop

Hemingway House
Eventually, we made our way to the nearby childhood home of Ernest Hemingway. Restored to its original glory, this beautiful house is now a museum with tours given daily. Hemingway House in Oak Park IL // List Maker Picture Taker

Even if you aren’t familiar with Hemingway’s work, the tour itself is so interesting, if only because you get to glimpse what life was like at the turn of the century. Admission is very reasonable, and gains you access to not only the house, but the museum up the street for that same day, as well as any other day within the next year.
Hemingway Birthplace//Day Trip to Oak Park Illinois//List Maker Picture Taker
Our guide, Michelle, has been working at the site for over eight years and had some very interesting stories to share about the house itself and its infamous occupants.

Hemingway Birthplace//Day Trip in Oak Park Illinois//List Maker Picture Taker
Despite the fact that Ernest’s father was a well known and respected doctor in the area, his mother, Grace, was actually the breadwinner of the family. Once an aspiring opera singer, she made over $1,000 a week giving music lessons. I’m not completely sure what that is in today’s dollars, but I have a feeling she’d still have some bragging rights.
Hemingway Birthplace//Day Trip in Oak Park Illinois//List Maker Picture Taker
According to our guide, this is most likely the table around which Ernest developed his love of storytelling, as his grandfather would share stories with the children and encourage them to make up their own.

 

Hemingway Birthplace//Oak Park Illinois//List Maker Picture Taker
There was a skeleton in the attic the children named Susie Bones-a-part. This isn’t her head, but an interesting bit of trivia nonetheless.

 

If you find yourself needing a break from the hustle and bustle of the city, definitely hop over to Oak Park and look around.
Fellow Chicagoans, where do you go when you need a day away?

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3 thoughts on “Chicago Day Trip: What to See & Do In Downtown Oak Park

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