What to do when you have a flight credit about to expire? See where that dollar amount gets you and go! We had somehow never been to Chicago, and the flight price and times were just right. Steve was NOT interested in seeing Chicago, and worried it would be cold and blehhh in September, but it turned out to be nicer weather than D.C.! Our weekend timed perfectly with Hurricane Florence, so we escaped the rain and 100% humidity in D.C. and arrived to 70s/80s with virtually no sticky air in Chicago.
We both agreed we really liked Chicago. Like NYC, but cleaner and greener. I’m sure our opinions would change in the winter, but hey, we survived life in upstate NY…it can’t be THAT bad, right?
WHERE TO STAY:
We stayed in an AirBnb in Lincoln Park. It was pricey, but in a nice neighborhood within walking distance of the park and beach. It was a little walk to the subway, but there were also buses running nearby.
WHERE TO EAT:
The most important part of travel is obviously the food, which Chicago has no shortage of. Let’s start with caffeine, shall we?
Hero Coffee: Multiple locations, but this one was just the cutest. There’s no inside space here, but the little alley way seating area was a perfect respite from the warm temps and sunshine. It was also Instagrammable paradise for the fashion bloggers who kept coming in to snap pics casually sipping their drinks with the twinkle lights in the background.
Left Coast Juice: WHY do we not have more of this in D.C.? I love South Block, but wish we had something like this, too. Healthy eats, smoothies, and coffee. They have multiple locations, and we ended up visiting 2 of them.
It can be hard to find a savory breakfast when you don’t do gluten or eggs, but this hit the spot!
This mural, on the backside of the restaurant, is just one of the Kind Way murals found across the U.S. Check them out, what a happy series!
On our walk to Left Coast, we encountered a Bill’s bar. I didn’t catch the name, but I understand that Bill’s fans need a place to drown their sorrows in every city.
Ipsento 606: This coffee shop is located right off the 606 park trail. We enjoyed the green space adjacent to the coffee shop to soak up a little more sunshine.
Paradise Park: This place was so fun! It is half inside, half outside with a kitschy retro trailer park theme, if that is a thing? They have gluten free pizza and cheap champagne. A win in my book!
Bad Hunter: Described as a “veg forward” restaurant. Pretty interior, probably should have opted to sit inside because no shade patio was not forgiving.
Real Good Juice Co.: Apparently they have since changed their name to Real Good Stuff. Maybe they have more food now? Either way, this gluten free avocado toast was delicious. I was a bit envious of the real deal bread; it was so thick and luxurious looking.
Goddess and Grocer: Prepared foods, salad bar, and small grocery selection. Multiple locations and another concept called Goddess and The Baker, too.
Three Arts Cafe at Restoration Hardware: We walked in to see it, but there was a long wait. Look how beautiful it is, though!
WHAT TO DO:
We stopped through the Green City Market in Lincoln Park and it was huge! And pumpkins had arrived!
The 606: This is similar to the High Line in NYC. If I were a biker, this is where I would go! It’s also a great running trail.
There are beaches! The beach is accessible via an underground tunnel, so you don’t have to cross the busy street above. There’s a paved pedestrian road right next to the beach with plenty of bikers and runners. I saw a few runners post-workout jump into the lake to refresh. What a great reward after a sweaty workout!
We stopped through a fall festival at Fulton Market District, which was lined with a bunch of restaurants.
Lincoln Park: The lily pad garden in the park was specifically recommended to us, and it was well worth a visit. What a serene little pocket of the park.
Millenium Park: Go be touristy and see Cloud Gate, aka The Bean. The park has a whole series of gardens and a little waterway. A number of people were cooling their feet off in the water, but I’m not sure how clean it was…
Street art: Go wander the streets and you’ll discover some fun art along the way!
Although we didn’t get around to it, I hear the architectural boat tours are worthwhile as well.
TRANSPORTATION:
We walked almost everywhere. About 11 miles on Saturday to be exact. I didn’t realize how big the city was until weThe subway was great getting mostly North-South. We Ubered across the city East-West direction. The bus system is supposed to be easy to navigate as well. There are Divvy bikes if you want to cruise around on 2 wheels.
Below is a map of everything listed above, and then some.
Do you have any tips for Chicago? I can’t wait to find a reason to go back!
Let me tell you a little story. I have been wanting a ‘real’ camera for years now, but didn’t feel like I could justify the cost. Last year, I decided if I hit my big first quarter sales goal, I’d reward myself. Well, our team didn’t hit that number. So, I continued to hold off. This year, I got a big promotion and decided I finally deserved a camera to record our travels. My photographer friend (hey Joy!) was helping me learn how to use it and analyzing photos to improve for the future. She convinced me to get a fancy schmancy lens to effectively capture our memories in Greece, and it took me a few months to pony up the money for that. I got it just in time for our trip, and figured I’d learn on the fly! I couldn’t have asked for better subject matter to practice with.
But you know what? At the end of the day, life is good. We have our health (minus having mono, but whatevs), our animals (they thankfully didn’t escape during the burglary), and the ability to have these global experiences. I am so grateful for all of this, and having some photos lost is nothing in the grand scheme of things. I still love living in the city, but gosh darn it, this is why we can’t have nice things. Remind me to tell you about our neighbor’s poop revenge package some other time.
WHERE TO STAY:
The iconic blue domed churches, seen in pretty much every picture of Santorini, were right behind our place. Tourists were lined up at all hours trying to snap an unobstructed photo. I opted for the postcard, since my attempts did not do it justice.
Dimitris Ammoudi Taverna: This was recommended to us as some of the freshest seafood right on the water.
Once we arrived, we saw more adventurous people cliff jumping, but I was happy spectating. I’ve never been much of a thrill-seeker, and after observing an eventful cliff jumping incident in Jamaica, I will never ever do it. Thanks, Dana for scaring me out of that for life!
Below is a map of all my Greece recommendations. Zoom to Santorini to see everything!
Summer vacation 2018- spolier alert: nothing crazy happened. No food poisoning, no rabid dogs, no missed flights or lost wallets. So tame! Except for the sunset cruise…more on that some other time. Let’s start with the most unique spot on our trip, Naxos. This Greek island is very rugged, and not overly touristy.
The correct path led us through the very small, sleepy village with a rapidly rising elevation. We followed the signs toward 
The views were spectacular. As far as the eye could see, there was nothing. Just rolling hills and white rocks dotting the landscape.
I think we could have gone inside the ruins, but I heard some jingling as we approached. I was concerned there were some mountain dwellers living there who would not be pleased with us crossing the brick wall.
Turns out they were security goats. Or at least goats wearing bells. I don’t know what happens when you make a goat angry, but wasn’t about to find out!
After checking out the castle from a distance, we trekked on through the small villages en route to Halki.
I found some photogenic cats along the way.
Oddly, we were the only people on the trail for 90% of the time. I questioned my sense of direction again, but we continued on the path, hoping I hadn’t led us astray. The signs were less than helpful; it was all Greek to me. (I was waiting for an excuse to use that one).
The sights along the way included all sorts of berries, grapevines, flowers, and bees. And shotgun shells. It all seemed safe and serene except for that last detail…
Once we approached Halki, there was a sign for a Byzantine-era church. After hiking all morning, what was another short walk? 
After the church discovery, we headed into the village of Halki for a little break and food.
Up first: coffee! 
After resting, hydrating, and caffeinating, onward to lunch! I had read great reviews on 
The chicken came right off the spit, paired with the freshest tomatoes. Maybe it was the appetite we worked up from hiking, but it was some of the best food I’ve had. All the meals we had in Greece were simple, but so fresh and flavorful. I’m still not sick of Greek salads after coming back and making one almost daily!
At this point, we decided to weigh our transportation options. We could try to find a taxi back to our hotel, or we could navigate 
Our hotel also had great food. I could not get enough of their Greek yogurt for breakfast!
The grounds were filled with plants, palm trees, and cats.
Cats seems to gravitate to us, no matter where we are. Of course, the mangiest-looking hotel cat wanted love. He snuck into our bungalow and then jumped onto my lap. Well, at least I am immune to rabies!
Here is a map of all the suggestions I have for Greece. Just zoom in to see Naxos pins. Stay tuned for