Back in the day (when everything was much better?) our flight schedules looked so much different. There were less flights so the layovers were longer. Sometimes you could even be stationed somewhere and fly back and forth to certain destinations. Today there are so many flights per day that the layovers could be as short as 24 hours. And within those 24 hours you’d like to do some sight seeing, have dinner oh and, sleep! The other day when I was busy making my weekly schedule, I stumbled upon a six day (!) Chicago trip. I think I’ve just been to Chicago maybe once or twice and that was about a hundred years ago. So I really wanted this special trip. Despite my high request counter* I had a good chance of getting the flight. And I did get it, so started to plan my trip. After San Francisco I always considered Chicago to be the headquarters of anything hipster. And anyone who has ever read my blog, knows I’m always on that quest. Want to know what I found in Chicago? Let’s goo!
Arrivée! Before heading over to the cool areas I took a stroll around downtown first. One of the things Chicago is famous for is the iconic elevated train tracks running through the city. Because of the shape it forms, the area is also called the Loop. Inside the Loop you’ll find The Windy City’s financial district. When I’m in New York I like to pretend I’m a local and I do know my way around perfectly. In Chicago however, my radar was totally off. And there are far less train stations around. To get to the closest station I had to walk about 25 minutes, so have your Uber driver on speed dial.
Old meets new. Downtown has a perfect mix of Old Chicago and new high rises.
Ain’t no party like a backdrop party! If I didn’t get a colorful backdrop picture for Instagram, the trip wasn’t complete. Chicago has plenty of amazing backdrops like this flamingo wall. It might look like a swimwear shop but this is actually the side of the Flamingo rum club. It’s located on 601 N. Wells Street.
The elevated train tracks and Chicago sky line also make a nice backdrop.
Good morning! Time to tick off the first hipster area on my list. I took the blue line of the L train to Wicker Park. This is where I would find all the cool stuff. And I struck gold when I entered the first vintage boutique. I spotted some amazing vintage pieces from Chanel, Givenchy, Dries van Noten and Missoni. If you are looking for some awesome designer vintage or interior decoration, Store B Vintage is the place to ‘be’.
Logo mania! This just in, a pair of vintage (and made populair again by influencers) Fendi pants. Store B Vintage, 1472 N Milwaukee Ave.
Every trendy area needs a trendy bookstore. At Volumes book café you can not only buy books but also enjoy a coffee in the stores front cafe.
What I always do..just not silently?. Also available at the store knick knacks and other stationary at Volumes book cafe, 1474 Milwaukee ave.
Are you a vintage jewelry hoarder? Than you can’t afford to miss this place. Vintage Underground has an amazing collection of jewelry next to their big assortment of vintage clothing. Take your time, you’ll be here for a while. Vintage Underground, 1507 N Milwaukee Ave.
Foood! Just a short walk away from Wicker park you’ll find another nice street, called Division. Not as many shops as Milwaukee avenue but more bars and restaurants. The evening before I had some incredible vegetarian food at Mana cafe (sadly they recently closed?). For lunch I went to Milk & Honey cafe. This deli like and affordable cafe serves some mean avocado toast and breakfast can be ordered until 2:30pm, love that.
Another day another dollar! Time to discover another part of town. When I stepped out of the train at Logan Square I thought, ‘ok, where on earth did I end up?’. It looked kinda rough and not trendy at all. Or maybe that was the whole idea? ?
Because the weather was kinda crappy I decided to take a break first. I spotted this very nice looking coffee bar, Intelligentsia shortly after arriving. You can get all kinds of delicious coffee blends and personal fave, turmeric tea. There are a few locations in Chicago, this one is on 2642 North Milwaukee Ave.
You have cat ladies but I am definitely a plant lady (yes I talk to my plants) So when I passed this place I just had to enter. At Fleur they sell beautiful plants, bouquets as well as home decor.
Oh and if you frequently use the hashtag ‘I have this thing with tiles’ on Instagram, at Fleur the tiles are #goals. Just across the street from Intelligentsia on 2651 N Milwaukee Ave.
These popsicles do not only brighten up you feed, they are also very tasty! I had a hard time choosing so I still have to try the mango lassi, pineapple punch and red cherry. At Pretty cool ice cream you’d have to deal with an occasional kiddie temper tantrum but the popsicle are so worth it, 2353 N California Ave.
I think Chicago is pretty cool ?.
- Bucktown just around the corner at Wicker park for Diptyque, Aesop, Lulu Lemon and Scotch & Soda, 1639 N Damen Ave.
- Damen forget Dunkin’, you haven’t been in Chicago if you didn’t get a donut at Stan’s Donuts, 1560 N Damen Ave.
- Logan Square for the die hard fans there’s a GAP outlet on 2778 N Milwaukee Ave
*request counter: each time you request a flight you will get a point on your counter. The higher the counter there smaller the chance of you getting the flight. If a colleague with a lower request counter will request the same flight, he or she will get the flight.