Fun things to do in Wicker Park in a day!


The neighbourhood of Wicker Park is one of my ultimate hangout places in Chicago. And with so many fun things to do in Wicker Park, you best start early if you want to see everything, .

Top things to see, do and eat in Wicker Park

A background

If you’re completely unfamiliar with Chicago, here’s some quick facts you should know about Wicker Park.

  • Wicker Park’s in the West Town community area of Chicago, which is northwest of the Loop.
  • It’s easily accessible from Downtown, with 2 train stations (Damen and Division) within walking distance.

Around 40 years ago, Wicker Park was a less than desirable neighbourhood to live in. Affordable housing, close proximity to the Loop and gentrification changed Wicker Park into the area it is today.

Many Chicagoans consider Wicker Park to be the ‘hipster’ area of the city though I didn’t see it. I did see, however, the many interesting buildings, independent coffee shops and plenty opportunities for shopping.

Luxury experience in Vienna - Burggarten



Places to visit in Wicker Park — The Robey

If you’re visiting Wicker Park by metro, take the blue line train to Damen. Upon exiting the station, turn left, and you’ll see a very busy intersection. This is basically where you can decide to go straight to Bucktown or right into the main street of Wicker Park.

At the corner of W North Ave is The Robey. It was originally built in 1929 to provide office space. This Art Décor building has been home to a hotel and café since November 2016.

Café Robey is open to the public, as is the lounge on the second floor. It was here that I started my day with an iced latte and views of the outside world below. The rooftop pool opened in 2017, adding another feature to this attractive abode.

The Robey, 2018 W North Ave, Chicago, IL 60647, USA

Luxury experience in Vienna - Vienna State Opera
Luxury experience in Vienna - Vienna State Opera

“It was here that I started my day with an iced latte and views of the outside world below.”


Luxury experience in Vienna - Burggarten
Luxury experience in Vienna - Burggarten
Luxury experience in Vienna - Burggarten

1 day in Wicker Park – shopping on North Milwaukee Avenue

If you love shopping of any form, North Milwaukee Avenue will probably be your first stop. This street’s literally across from The Robey Hotel and has a lot going on. That said, make sure to wear good shoes, and save your appetite!

Related post – Chicago Food Planet tours

North Milwaukee Avenue has a nice mix of shops, but with notably more independent stores (something I love). Commercial names include Urban Outfitters, Levis and Steve Madden, but the independent stores are far more interesting.

There are tons of places to shop for vintage/secondhand clothing. To name a few, these include US #1 Vintage Clothing, Store B, Buffalo Exchange, Vintage Underground, Ragstock and Crossroad Trading Co. 

For fans of Boho chic (you’ll understand this if you like it!), you’ll love stores like Fab’rik, Emma, Pitaya and Free People. Belmont Army and Mildblend Supply Co. specialise in utility chic such as army surplus and Doctor Martins. For lovers of modern urbanwear, head to, Una Mae’s and Transit Tees.  

Men’s clothing stores in Wicker Park

There are some great shops for men too, ranging from t-shirts to more upscale designs. Iridium Clothing Brand has more unique urbanwear, while Saint Alfred offers more designer pieces. Guys should also be happy with the Chicago-inspired t-shirts on sale at Transit Tees and Rapha Chicago. 

Shoe shopping in Wicker Park

From sky-high heels to the more practical, North Milwaukee Avenue has styles to suit every budget.

I particularly like Steve Madden, but those with more adventurous tastes may enjoy the selection at John Fluevog Shoes. Some of the shops mentioned above also sell shoes, so you may just find yourself a hidden treasure.

Miscellaneous shops in Wicker Park

North Milwaukee Avenue also has a range of other stores ranging from selling furniture to record shops. Reckless Records isn’t just great for browsing, the shop front’s also great to photograph. Another unique shop in the area is Myopic Books. More than just a book haven, this store also has an interesting shop front.

Wicker Park restaurants

There are so many great restaurants around Wicker Park, and rather than list them all, I’ll mention my favourites.

For tacos bursting with epic flavour, I highly recommend visiting Antique Taco. They’re pricier than those you’d find in a Mexican taqueria, but still very good. For a modern take on Japanese tapas like snacks, visit Oiistar. The pork belly buns are to die for, and it’s really easy to eat more than 2!

Kanela Breakfast Club serves up all your favourite American breakfast food stuffs. You can also dine al-fresco (weather pending) on their dog-friendly patio.

There’s only one place to go for ice cream in Wicker Park, and it’s at Jeni’s Splendid Ice Creams. They make their own waffles in the store, and the ice cream flavors are so heavenly, it leaves you thinking about returning the next day. I tried the salted peanut butter flecks and roasted strawberry. If that’s not all, you can also try before you buy! Now that’s one way to keep the customers coming back.

Coffee shops in Wicker Park

Again, Wicker Park has so many good places to choose from, that I’ll just list my favorites.

For a seriously delicious and different coffee served on tap, you need to visit La Colombe Coffee Roasters. It’s a fast-growing chain, but don’t let that put you off. The Draft Latte is so good and its chilled frothy full-bodied coffee is served in a takeaway tumbler. 

Another must-visit coffee shop is The Wormhole. Nostalgia in a coffee shop its decor pays homage to 1980s movie memorabilia.

Luxury experience in Vienna - Kunsthistorisches Museum

“The pork belly buns are to die for, and really easy to eat more than 2!”


Expect Pacman style fonts on the menu board and very good coffee in this local favorite hangout.

The final noteworthy coffee shop is Filter Café. I’ll hold my hands up to this one and admit that it’s a little bit hipster! Rugged and slightly ripped vintage sofas line the cafe, with complimentary WiFi and of course, good coffee. 

Wicker Park bars

From day to night, there’s a seamless transition to a buzzing nightlife in Wicker Park. The area’s synonymous for its plentiful and lively bars.

Start with a beer or drink of choice at the Publican Anker. It’s right at the top of North Milwaukee Avenue, and a popular choice for many locals and visitors too.

Get your arcade on at the Emporium Arcade Bar Chicago. Here, you can play all your favorite childhood arcade games such as Double Dragon and Baywatch (!), as well as grab a beer with friends. The bar also has over 60 whiskeys to choose from — so book that taxi in advance.

For something a little more on the intimate side, Davenport’s Piano Cabaret fits the bill. Enjoy some live music or join in the fun at one of their karaoke events that takes place every Friday night.

In the instance you prefer to walk home after a night’s drinking, The Robey is nearby and a great hotel in Wicker Park.

Have you been to Wicker Park when in Chicago? What activities did you enjoy when you were there? Leave me a comment below, I’d love to hear from you.

Disclosure: This post may contain affiliate links, which means I may receive a commission if you click a link and purchase something that I’ve recommended. Thank you for your support.

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Fun things to do in Wicker Park in a day! 1
Fun things to do in Wicker Park in a day! 2
Fun things to do in Wicker Park in a day! 3
Lisa R sitting in a wicker chair

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