Clouds over Chicago? Cute. We have plans.

A rainy day does not have to become a sweatpants-and-delivery day.

Chicago is ridiculously good at bad weather. The city is packed with tiny boutiques, sprawling bookstores, contemporary galleries, cozy bars, vintage photo booths, art studios and neighborhood shops where you can disappear for an hour without realizing it.

So instead of waiting for the weather to clear, build the day around it.

Here's our Chicago Brella Day Crawl on Google Maps

Pick a neighborhood. Save three or four indoor stops. Put on an outfit that deserves to leave the house. Grab your Brella. Then use those little rainy walks between a bookstore, gallery, perfume studio and photo booth as part of the adventure.

Because getting caught in the rain is significantly more fun when your umbrella is cute.

What are the best things to do in Chicago on a rainy day?

Our formula:

Find something → make something → see something → eat something → take a ridiculous photo → pop your Brella open → move on to the next place.

Chicago makes this especially easy because so many of its best shopping and cultural experiences live inside distinct, walkable neighborhoods. Wicker Park/Bucktown combines boutiques, vintage, bookstores, records and art, while Andersonville is packed with independently owned shops. West Loop and River North give you excellent gallery-hopping options.

Start in Wicker Park if you want a little bit of everything

Wicker Park is probably our favorite Chicago rainy-day neighborhood.

Start at a vintage photo booth. Get lost inside Myopic Books. Look at things you absolutely do not need at Neighborly. Dig through vintage jewelry. Make a custom perfume or charm bracelet. Buy a record based entirely on the album cover.

Then step back outside.

Brella up.

Walk three blocks through the rain to the next stop.

The little walks are not the annoying part of the itinerary. They’re the connective tissue.

Chicago’s Wicker Park/Bucktown corridor is known for its concentration of vintage shops, boutiques, bookstores, record shops, cafés and art spaces, making it particularly easy to build this kind of stop-and-go rainy-day itinerary.

Make something

Rain is an extremely good excuse to become a person who has hobbies.

Make pottery at Penguin Foot.

Blend your own fragrance at Aroma Labs or Lovely Intentions.

Take a cooking class at The Chopping Block.

Make jewelry or ceramics at Lillstreet.

Paint something questionable at Color Cocktail Factory.

The bar for success is low. You made a thing. We’re proud of you.

Find a store where browsing is the entire activity

Some stores are errands.

Other stores are destinations.

We want the second kind.

The ones filled with ceramics, stationery, vintage glassware, strange kitchen tools, candles, books, art and objects that make you pick them up and say:

“Wait. Why do I kind of need this?”

Try P.O.S.H. in River North for European-style tabletop and home finds, Neighborly for modern indie-made goods, Andersonville Galleria for a multi-level local-maker treasure hunt, or Mary Mary for shelves and tables packed with gifts and home pieces.

Our official Brella Day rainy-day shopping rule:

Touch everything and buy three things you didn’t need.

Go gallery hopping without turning it into homework

You do not need an art history degree.

Walk in.

Look around.

Choose your favorite.

Make a sweeping statement like “I actually think this is about capitalism.”

Leave.

Chicago has excellent gallery clusters in River North and the West Loop, while Kavi Gupta, Rhona Hoffman and many smaller spaces make it easy to build a free or relatively inexpensive art-heavy afternoon.

Our favorite game: everyone chooses the artwork they’d buy if money suddenly became completely fictional.

Take the photobooth picture

No discussion.

Rainy-day hair + four friends crammed into one booth + slightly chaotic analog lighting is significantly better than a perfectly posed phone photo.

Wicker Park’s Strip Club Photobooth Studio is built entirely around vintage analog and retro-style booths, while Rainbo Club has its own longstanding booth inside the neighborhood bar.

Keep the strip in your wallet until it becomes inexplicably sentimental.

Spend a rainy afternoon in Andersonville

If your favorite activity is looking at little things, Andersonville is your neighborhood.

Browse local makers at Andersonville Galleria. Pick up a book at Women & Children First. Look at clothes and accessories at Milk Handmade. Find a Chicago-themed object that doesn't scream “airport gift shop.”

Clark Street is particularly good for slowly moving between independently owned stores while keeping your outdoor stretches short.

Translation: excellent Brella territory.

Do something stupid with your friends

This is crucial.

A perfect rainy-day itinerary cannot be 100% tasteful.

Take distorted photos at the Museum of Illusions.

Play pool at the Chicago Athletic Association Game Room.

Make an aggressively bad ceramic object.

Buy each other ugly vintage sunglasses.

Choose perfume for one another.

Go into a gallery and decide which painting represents everyone's dating life.

The rain gives you permission to be unserious.

Let the weather make the city prettier

This is the part we really care about.

The entire Brella Day philosophy is not about hiding indoors until the weather goes away.

It's about having enough great places to duck into that you actually enjoy moving through the city while it rains.

Chicago gets glossy when it rains.

Streetlights reflect off the pavement. Storefronts glow. Umbrellas come out. Everything feels slightly more cinematic.

So use your Brella between stops.

Take the rainy mirror selfie.

Take the umbrella group shot.

Walk the extra block because the street looks pretty.

Your umbrella is not ruining the outfit.

It is the outfit.

The Best Chicago Neighborhoods for a Rainy Day

Wicker Park + Bucktown

Best for vintage, photo booths, bookstores, fragrance, cool boutiques and records.

Logan Square

Best for indie books, pottery, local makers, stationery and creative activities.

West Loop + Fulton Market

Best for custom fragrance, contemporary art, upscale shopping, food and spa stops.

Andersonville

Best for browsing, independent boutiques, home goods, books and gifts.

River North

Best for galleries, beautiful interiors, homeware, museums and slightly fancier rainy-day energy.

Lincoln Square + Ravenswood

Best for cooking, ceramics, art classes and a cozy neighborhood movie.

10 Questions People Ask About Rainy Days in Chicago

1. What are the best things to do in Chicago when it rains?

Try gallery hopping, vintage shopping, browsing bookstores, taking a pottery or cooking class, making your own perfume, visiting a photo booth, exploring independent shops or spending the afternoon at a spa.

2. What are fun indoor activities in Chicago?

Chicago has indoor art museums, contemporary galleries, bookstores, cooking schools, ceramics studios, craft workshops, photo booths, game rooms, spas and independent shopping districts.

3. What can adults do in Chicago on a rainy day?

Build a neighborhood crawl around art, cocktails, shopping and food. Wicker Park, West Loop, River North and Andersonville are especially good areas for stringing multiple indoor stops together.

4. What are good rainy-day date ideas in Chicago?

Make a custom fragrance, take a pottery class, visit a gallery, cook together, use a vintage photo booth, play games over cocktails or book a bathhouse experience.

5. Where should I shop in Chicago when it rains?

Wicker Park and Andersonville are particularly good for independent boutiques and gifts, while River North works well for elevated home and design shopping.

6. Are there free things to do in Chicago when it rains?

Yes. The Chicago Cultural Center offers free exhibitions and programming, and commercial art galleries generally allow visitors to browse exhibitions without museum-style admission.

7. Is Wicker Park good on a rainy day?

Very. Its dense mix of vintage stores, bookstores, record shops, cafés, boutiques and art spaces makes it easy to move between indoor stops without crossing the entire city.

8. What should I do with friends in Chicago when it rains?

Take photo booth pictures, make pottery, choose books for one another, build custom perfumes, play games, gallery hop or set a budget and buy each other completely unnecessary gifts.

9. What are unique indoor things to do in Chicago?

Try a vintage photobooth studio, fragrance blending, ceramics, the Chicago Athletic Association Game Room, independent artist markets or a thermal-bath experience.

10. Should I cancel my Chicago plans because of rain?

No.

Adjust the itinerary.

Pick one neighborhood with several indoor destinations, grab your Brella, and let the rainy walks between stops become part of the day.

A Better Forecast

We can't make it stop raining.

We can make you kind of happy that it did.

Save the Brella Day Rainy Day Guide to Chicago, choose a neighborhood, grab a friend and take your umbrella somewhere good.

Make something.

Find something.

Take the photo.

Buy the ridiculous little object.

And when it’s time for the next stop?

Open your Brella and go.