Casey’s Favorite Spots in Chicago

Skyline of the city of chicago

Bridget & I have lived near Chicago our entire lives. I say “near” because we grew up in a southwestern suburb that is about 45 minutes outside of the city, so it isn’t technically considered Chicago. But, we still consider ourselves Chicagoans.

The Chicago river with water taxis and boats

Finn and I have lived in the city of Chicago for 5 years now and absolutely love calling this place home. Chicago is such a cool place because it’s so big and there is so much going on all the time. Winter isn’t the best (obviously…), but when it’s nice out this place is truly magical!

Casey walking in the wicker park area of Chicago

Jeans // Sweater // Bag // Shoes // Sunglasses // Watch

We’ve chatted about our city on the blog before…like in our tourists’ guide to The Windy City, our Christmas guide, and even our most Instagrammable Chicago spots post.

The Bean and Millenium park a favorite spot in Chicago

I thought it would be cool to share some of my favorite spots for food and drink in Chicago. I’m certainly not an expert, but I have lots of places in our neighborhood that I’d recommend, as well as some other non-touristy spots to hit up.

So if you’re visiting Chicago soon, here are my favorite restaurants, coffee shops, and happy hours in the city! Hopefully, these help you plan your trip and you can hit up some of my favorites (and if you need more tips on how to get around, activities to do, etc…check out this blog post).

Casey’s Favorite Spots in Chicago

Casey shares her favorite spots in Chicago for food, drink, and coffee

Neighborhood Eats

Division street in Ukrainian village is a favorite spot in the City of Chicago
The mural on Parlor Pizza in Wicker Park

So let’s start with the area I know the best…my neighborhood! Finn and I technically live in the “Ukrainian Village” neighborhood of Chicago. This is west of the downtown and is an awesome spot. We’re about a block from Wicker Park and just north of that is Bucktown. So we frequent these areas all the time. Plus, my mom, sister, and brother all live in these neighborhoods too, so we seem to go out around here the most often. 

  • Parlor: A good spot for drinks and yummy thin-crust pizza. They have a huge outdoor patio in the summertime. We like spending long afternoons here with friends with some cocktails. There is also a location in the West Loop, but the one on Division street is so close to our house.
  • Yuzu: By far our favorite sushi spot. It’s BYOB so it makes for an inexpensive date night out, plus their prices are already pretty good. Or we’ll pick up and eat our sushi at home for a quick and easy weekday dinner.
  • West Town Bakery: An awesome diner (pretty amazing when you’re a tad hungover) with good breakfast and lunch food, but don’t miss their bakery! Their cake balls are heaven…
  • Roots: This is a good family-friendly restaurant in our neighborhood and we’ll head there when we have kids in the group. Good pizzas and salads. Mimosas and Coffee at the Winchester are a great way to start your Saturday morning
  • Janik’s Cafe: Another brunch spot that we adore. Can you tell that I have a thing for brunch? I love a fluffy veggie omelet! Janik’s has a huge menu with all kinds of delicious choices.
  • Smoke Daddy’s: I’m not a huge meat eater, but this is an awesome BBQ joint. Plus, the atmosphere can’t be beat.Brunch food at the Winchester in Ukrainian Village

I certainly have more favorite restaurants in our neighborhood, but these are just the ones we visit regularly. I’m sure I’m missing some good ones on this list, there are just too many amazing spots around here!

Favorite Coffee Shops

Casey explores the Wicker Park neighborhood of Chicago

Jeans // Sweater // Bag // Shoes // Sunglasses // Watch

Give me a hot vanilla latte with almond milk and I am one happy girl! Now that I’m working from home, I’ll take one day a week and spend a few hours at a coffee shop to get out of the house. Here are some that I can walk to and love in my neighborhood…

Scone and vanilla latte from Scone City in Wicker Park
  • Scone City: I visit Scone City the most often because it’s closeby, has the cutest interior, and their scones are to die for! Get there early before they sell out (especially on the weekends). They have both sweet and savory scones and it’s always hard choosing which one to get. Plus, their coffee is delish.  I spend a lot of time working away in this cute cafe. The hot chocolate from The Wormhole Coffee shop is so delicious
  • The Wormhole Coffee: You step into this place and you feel like you’re transported back in time to the 80’s. It’s the coolest interior with items from Star Wars, Back to the Future, and Ghostbusters. Plus, they serve some yummy beverages. Finn and I have popped in here on a cold day for their hot chocolate and it can’t be beaten!Alliance Bakery on Division Street in Wicker Park has delicious treats and cakes
  • Alliance Bakery: While they do serve coffee, Alliance Bakery is well-known for their custom cakes! In fact, our wedding cake was actually from Alliance Bakery. Definitely pop into this cute spot if you’re ever walking on Division Street for a sweet treat, or at least check out their awesome window display of over-the-top cakes!
  • Fairgrounds Coffee: This is more of a walk for me, so I don’t visit Fairgrounds as often as I’d like. But this spot is amazing! The interior is stunning, the coffee is delicious, and I always want to order one of everything on their food menu. A good spot to come for breakfast or lunch.
  • Caffe Streets: This is the closest coffee shop to our house and it’s a good one. I like to bring my laptop and get some work done here every so often. They don’t have almond milk, so I can’t order my usual, but their lattes are still really good!

Favorite Happy Hour Spots

A glass of prosecco at Navy Pier on a boat ride in Chicago
The rose all day sign at The Hampton Social in chicago is a great photo spot

You guys know I love a good cocktail (bring on the champs!), and I love meeting Finn or my girlfriends for a drink. This list ventures outside of my neighborhood, because I’m often meeting friends for happy hour after work in other parts of the city. 

  • Hampton Social: You’ve probably seen Hampton Social’s “Rose All Day” sign on Instagram because it really is a great photo op! This place is perfect for a girls’ night out…with a big list of rose and wine. During the week they have half off bottles of rose and pizzas, so I’ve had many a happy hour here with friends!Beatnik chicago is a delicious spot for a cocktail or a yummy moroccan themed meal
  • Beatnik: This is a new spot and I’m officially obsessed. First of all, it’s walking distance to our place, so you really can’t beat that. And holy smokes, the interior is to die for. It’s got Moroccan vibes with layered rugs, huge chandeliers, and jewel-toned pillows everywhere. The food and drinks are even better than the interior design! While I don’t know if they have any happy hour specials, they have a really creative cocktail menu.
  • Sparrow: I’ve only been to this spot once with a friend and I need to visit again! This Gold Coast spot is unassuming on the outside, but when you walk in you’re transported to Cuba in the 1930’s. Very sophisticated with a large rum-cocktail menu. Their wines are 1/2 off during happy hour, so it’s a good place to get the prosecco flowing! Casey and Michael Finn's 1st anniversary photo session
  • RM Champagne: Finn and I actually took our 1st-year-anniversary photos at this spot, which seems fitting for a gal who loves her champs! This West Loop restaurant is a great place for a quick drink after work or an evening of dinner. Try to go in the summer when their entire patio is open. A cocktail on the rooftop of Cindy's overlooking Millenium Park in Chicago
  • Cindy’s Rooftop: This is the bar at the top of the Chicago Athletic Association overlooking Millenium Park. If you want good views of The Bean with yummy drinks, this spot is for you! But note that it can get pretty packed, especially on a summer day.

  • The London House: The outdoor bar on top of the London House hotel is a bit pricey but we would definitely recommend stopping up there to check out the stunning views of the Chicago river and Michigan Ave. when you’re in town. If you go early enough, the staff is more than happy to let you go out on the gorgeous patio and take pics without ordering any drinks. But grabbing a cocktail, relaxing on their trendy outdoor patio and taking in these views is pretty amazing too.
    The 3 arts club cafe in Restoration Hardware is a favorite spot in Chicago
  • 3 Arts Club Cafe: This cafe is located inside the Restoration Hardware store and if you’re an interiors addict…it can’t be missed! The store is 5 levels, with the cafe on the first floor. This place does get crowded, so I’ll often grab a glass of wine & walk around the store with friends while waiting for a table. Be sure to order the burrata to share…it’s incredible. Drinking coffee while wandering the neighborhoods of Chicago
  • Summertime in Chicago can't be beat. Here are some of our favorite spots in Chicago for food and drink

    Is anyone else super hungry and thirsty all of the sudden? I want to eat and drink all the things after this post. I will be the first to admit, that I certainly don’t know all of the “cool spots” in the city of Chicago. But these are some of my tried and true favorites, and they’re ones we go to over and over again!

    We show you our favorite spots in chicago for food, coffee, and happy hours!

    Hopefully, my list of favorite spots in Chicago will help you as you plan your next trip here to the Windy City! And locals, help me out, what good restaurants/bars/coffee shops am I missing? Tell us in the comments below.


    The Year of Casey

    Hey there!

    I’m Casey Finn, the voice behind The DIY Playbook. I’m a Chicago gal teaching you how to design, DIY, and maintain your home…by yourself! Learn more about me right here.