My friend Abby invited me to join her on a recent trip to Chicago for an event put on by Wolverine. She wooed me with promises of a free pair of boots but, truth be told, I’d have gone just for the chance to wander Chicago with someone who appreciates my need for finding adorable coffee shops and the best food a city has to offer.

We got a hotel room at the Godfrey downtown, which conveniently was where the Wolverine event was taking place. Our room was super swanky and the location was perfect. Once checked in, we dropped off our bags and checked out the Popular Pays app to see if we could find some nearby free coffee/eats. If you’re not familiar with the Popular Pays app and live in a big city or plan to visit one soon definitely download the app and check it out. It’s brilliant. Basically they give you free coffee, donuts, lunch, even hotel stays in exchange for basically promising to post photos of said food/drink etc. For someone who enjoys posting photos of pretty coffee even when it’s not free, this app is a no-brainer for me. I could eat and drink my way free through an entire weekend.

Our first stop was a short walk to Cafe Integral.

The offers available through Popular Pays are basically dependent on your instagram following so at this first stop, I could get a free latte but Abby was able to get a free latte AND a “tasty toast” because she had over 1.5k Instagram followers. She’s super popular and stuff. : ) Lucky for me she’s also a good sharer and let me try a bit of her tasty toast, which was indeed “tasty”. She went with the Smoked Whitefish Tartine topped with frisee, caper berries and preserved lemon. Not even sure what half of that is but I’d happily pay for it the next time I’m in town.

Here’s how the Popular Pays app works (basically)…

step 1 – choose from the local “gigs” available wherever you’re at…from what I gather the app started in Chicago and has expanded to cities like New York and DC but for the most part it’s only available in large cities for now.

step 2 – click on the “swap” button for the deal you’d like to use.

step 3 – hand the phone to the barista/cashier and they swipe to swap (photo for food).

step 4 – take a photo of your pretty coffee/food and post to Instagram using the hashtags copied from the app.

Step 5  – drink the pretty coffee/eat the tasty food. : )

Genius right?!

We made one more Popular Pays stop for a free doughssant at West Town Bakery. Then it was back to the Godfrey to get ready for the Wolverine rooftop blogger event.

The event was a bit surreal for me as a rather newbie blogger (kinda – I actually started blogging before most people had any idea what a blog was but for the most part I’ve spent the last 5 years or more helping clients blog and ignoring my own)…but these were super stylish bloggers and social media darlings like Abby and Shelley.

We got gift bags with Wolverine merch and a nice leather care kit for our new boots. We ate (and took photos of) mini hamburgers. As you can see below, Shelley is totally my people. Not ashamed to place her mini hamburger on a swanky leather couch to get the perfect shot.

I may regret my decision to go with the riding boots (non-runner with runner’s calves) but the pretty ones on the right should be on their way to me just in time for fall back in Michigan. It’s a $600 pair of boots so you better believe I’ll be googling “exercises to slim your calves” if they don’t fit. 😀

Shelley got us reservations for 9:00 that evening at Bar Siena – the hottest new restaurant in Chicago.

With limited time, and a lunch date with Shelley, we went straight from C.C. Ferns to the next coffee shop on our list. This little road trip is the stuff dreams are made of, right?! Well, for me anyway. Give me pretty coffee in charming coffee shops to visit all day long. Add in friends who totally get it and let me take photos of their pretty coffee before they drink it and it’s basically my version of heaven. : )

Our next stop was Heritage Bicycles. And yes, it’s a coffee shop. Cool, right?

This place was so fun. They somehow flawlessly pulled off a combination custom bike shop *slash* charming coffee shop. If you go, get the lavendar latte. I passed on coffee since we’d just had some at CC Ferns but Abby tried the lavendar latte and LOVED it.

After getting our name on the waiting list for lunch we wandered to a couple shops nearby. Such a cute area. I’m a huge fan of the little areas just outside of downtown Chicago. Didn’t miss wandering Michigan Avenue even a little bit.

Lunch was at Southport Grocery & Cafe. Very cool atmosphere. Another fun combination space with the small grocery section right in the middle of the cafe. Unfortunately they had just started some new “home-delivery” system and maybe underestimated how many people would love to have their food delivered directly to their home. The service was beyond slow and the food was cold by the time we got it. We ended up eating for free (although the popular pays method of eating free is a much more enjoyable experience). I could definitely see it’s potential and totally get that there will be bumps when a restaurant tries a new method of delivery. Given the number of options in the area I wouldn’t likely go back, but I could definitely see it’s charm and trust that on a normal day their food (and service) is likely amazing. Me…I’m just happy to be eating at a cute little cafe with people who “get me” when it comes to taking a bunch of photos of our food. : )

After lunch we made a quick stop at Sweet Mandy B’s for cupcakes and snapped a few photos for a future Stitch Fix post (coming soon). I left Chicago loving it even more than I already did. And with a growing list of places to check out the next time I visit. So thankful for this #adventureinabbyland and for the chance to meet the very talented @chicagoismyboyfriend. Until next time Chicago. I will definitely be back. <3