Explore the area
Whether you arrive by train (stop is Damen) or by taxi, the neighbourhood of Wicker Park is a short distance from downtown. Wicker Park, and nearby Bucktown and Logan Square, are all places where you can shop, eat, and observe local Chicago life.
Have breakfast or coffee at The Robey
Start your time at this Art Deco looking hotel in Wicker Park. The Robey used to be an office, before it was transformed into a hotel. It has a restaurant, cafe, and rooftop pool. Cafe Robey on the ground floor, and the lounge on the second floor is open to all. I particularly enjoyed having a latte in the lounge and watching the world go by outside the window.
There are a ton of great shops to buy, or browse, if you're more of a window shopper. Fans of independent and vintage clothing will love this area, as there are so many around Wicker Park and Bucktown. Popular shops for stocking up on vintage garments include US #1 Vintage Clothing, Store B, and Clothing Exchange.
If you prefer to know your brand names, there are many well-known stores in this area, such as Levis and Urban Outfitters.
Get some ice cream!
The best, and I did the research (!), place in Wicker Park for ice cream is Jeni's Splendid Ice Creams. I'm no expert, but I can only tell you that this place is amazing. I went 2 times over 2 days, which tells you a lot! The ingredients are all top quality, and they even make the waffles to accompany the ice cream in store. Flavours range from the classic, like roasted strawberry, to the more adventurous like salted peanut butter. Trust me, go, go twice, it's that good!
Eat some delicious Japanese buns
Oiistar is one of those places where everything looks good, it's so hard to choose what to order! As well as specialising in traditional Japanese dishes like ramen, for me, the best thing to order are the steamed buns with choice of filling. I loved the pork belly buns, and finished in a record of 3 minutes!
Walk the 606
The 606 is one of the newest features in Wicker Park. Essentially, it's a high line, that kind of resembles the one in New York CIty, but with less features (yet) on either side. It's 2.7 miles in length, and is a recreational trail which is perfect for walking, running, taking the dog and general exploring. Naturally, it's also free!
Step back in time at the Wormhole
When I say there are plenty of coffee shops to choose from in Wicker Park, I'm not exaggerating. However, if you want to go somewhere retro, and with a real nostalgic feeling, head to The Wormhole.
There's a big Delorean (car Back to the Future) hanging from the ceiling, and the menu board has references to films from the past. Best thing of course is the coffee. It's very good, and a memorable cup in Wicker Park.