Cafes with Dog Friendly Windows in Logan Square & Wicker Park

Walking our dog is a fun little treat for our dogs… but we deserve a little treat on our walks too! And while it is nice to have a dog friendly place to sit and eat or drink, sometimes we’re looking for ways to keep our adventures moving. Walking and exploring new areas is a great way to meet both our needs and our dogs’ needs. So let’s explore a couple locations here in Chicago, specifically in the Wicker Park and Logan Square areas!
Ordering Outdoors with a Dog Friendly Cafe Window
For this list, we’re going to focus on where we can order outdoors, without needing to tether our dog or leave them inside to get a quick fix of coffee or a snack.
While you’re working on training your dog to be comfortably tethered, they may need some more time before they’re ready for the coffee order test (and you may need some additional time to train yourself how to not be craning your head to check on your dog every three seconds while ordering a coffee to go). So finding cafes with outdoor ordering capabilities is a happy medium as we wind down the summer months, and take advantage of every possible millisecond we can spend outside.
Logan Square & Wicker Park Dog Friendly Cafe Window Reviews
Logan Collective (Armitage Ave & N Whipple St)
Logan Square
Training Difficulty Level: ★★☆☆☆
Review: Relatively new coffee shop, but with such an easy front window. It gets bonus points for being so close to the extra greenery up and down N Humboldt Blvd, not to mention being only a couple blocks south of Palmer Square. You can take busier traffic routes or go up Whipple pretty leisurely to visit the park.
Red June Cafe (Leavitt St & W. McClean Ave)
Wicker Park
Training Difficulty Level: ★★★☆☆
Review: At times can be a little dog-heavy and kid-heavy because there is a school right across the street. But if you have time to go by in the off hours, it can be a calm field trip for new sights and smells for your dog.
Necessary & Sufficient Coffee (Wrightwood x Monticello)
Logan Square
Training Difficulty Level: ★★★☆☆
Review: Not a far walk from Kosciuszko Park just west of Logan Square. Outside of the park, the sidewalks are spacious with trees and grass aplenty, which is a more calm and quiet alternative to Kos park itself during busy hours. Keep in mind that there is an elementary school around the corner, but outside of drop-off and pick-up times, it’s a good area to let our dogs explore with drink or pastry in hand.
Four Letter Word
Logan Square
Training Difficulty Level: ★★★★☆
Review: Just north of Logan Square by a couple blocks, the location is convenient for a leisurely walk down Logan Boulevards’ grassy area, or a busier stop at the Logan Square Park. It also has a cute doggy window! Their pastries are very much worth a mention as a human treat, and have some unique options that have me coming back to try them all. Heads up, the area just north of Four Letter Word is very dog heavy at peak walking times, so plan accordingly!

Honorable Mentions
Cult Classic Coffee (W Palmer Square & N Kedzie Blvd)
Humboldt Park/Logan Square
Training Difficulty Level: ★★☆☆☆
Review: While only available on Sundays from 9 AM - 2 PM, this mobile cart is set up in a perfect place for walks, training, or chilling around Palmer Square. While the Farmers Market is happening to the north, Palmer Square won’t be nearly as busy. You can venture to the Farmer’s Market if you and your dog are up to it, or explore around the neighborhood, to gauge how much challenge you’d like to encounter on your walk with your dog.
Collectivo Coffee
Wicker Park and Logan Square
Difficulty Level: Varied
Review: Collectivo has a really good online ordering option, so if you want the briefest time of leaving your dog tethered outside, they are a valid honorable mention. Both cafe locations can be rather busy, but for my dogs’ experience, I prefer the Logan Square location (Milwaukee x N. Washtenaw Ave) for its larger common outdoor common area and wider sidewalks. In the winter they even have some heated parts to the outdoor area.
Miko’s Italian Ice (N Sacramento Blvd. x W Lyndale St.)
Logan Square
Difficulty Level: ★★★★★
Review: I love their Italian Ice, but so do a lot of people. The sidewalk where the ordering window is can be rather tight, so I only recommend their Logan Square location if you’re feeling exceptionally confident in yourself and your dog. Hanging out to have your Italian Ice is easy, since you’re only a couple blocks north of Palmer Square. If you’re looking for a less congested option, their location further north (Kimball x W. Warner Ave, all the way up in Irving Park) is a more spacious and a slightly quieter residential area to try out.
Enjoy Your Little Treat(s)!
Everyone will have different degrees of what constitutes a difficult walking environment for them and their dog. As you start to explore the city with your dog, it won’t hurt to have your own way of recording what dog friendly locations were your favorites to check out, or your least favorite. Ultimately it’s a great excuse for both you and your dog to get a chance to explore the world.
Did we miss any of your favorite dog friendly cafe locations? Feel free to share your favorite spots to order outdoors in Chicago with your dog, whether in the Logan Square, Wicker Park, Humboldt Park, or elsewhere!
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Venus and Mars K9 provides in-home private dog training and group class for basic obedience, puppy socialization, trick training, dog sport foundations, leash reactivity training, and other canine behavior problems. We travel most frequently to neighborhoods such as Humboldt Park, Hermosa, Logan Square, Avondale, West Town, South Loop, Downtown Chicago, Ukrainian Village, Bucktown, Wicker Park, East Garfield Park, Fulton Market, North Center, Lincoln Park, Lakeview, Roscoe Village, Irving Park, Portage Park, Oak Park, River Forest, Forest Park, Pilsen, and Bridgeport.





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