Last weekend Josh had the privilege of being the best man in our good friend’s wedding.
They have a really precious and sweet love story.  Including us crashing their first date.
Which is clearly how they ended up together.

But really.  They’re made for each other.

Since we knew the wedding would be only a few hours from Chicago, we decided to plan a little getaway after the festivities.

And by plan we had a place to stay, train tickets, and a river tour booked.
The rest was whatever our spontaneous hearts desired.
Josh would also like to add that he planned on visiting Intelligentsia Coffee.
(Which we did.  Three times.)

We travelled by train which was new (and a bit outside of our “get in the car and go” comfort zone.) for us but we enjoyed every minute of it.  I loved sinking into the communal aspect of public transportation.  On our first train ride we sat behind two women in their fifties who had just been introduced as they took their seats but chatted like old friends (complimenting their attempts to “Go grey!” and sharing their love/hate relationship with Facebook) and two men just released from prison, en route to see their families. It was fascinating. I’ve felt this feeling one other time in my life and it’s really hard to explain.  Maybe I’m overanalyzing it? When the rich, middle-class, and poor are gathered together on a level playing field (i.e. Amtrak coach class, church gathering room) and can talk and relate and laugh as natural as can be. It’s beautiful.


On our first Chicago “L” train experience, while getting off at our stop, a man looked at us, smiled, and said, “Don’t worry, be happy.” He must have seen the (obvious) flustered looks on our faces while glancing down at our Google Maps and then up again at each other to confirm that this was in face the right stop, our luggage pulling our arms down as we shuffled to exit.  Maybe he was crazy and just says that to everyone.  Maybe he felt sorry for us.  But for whatever reason it stuck with me.  Don’t worry about messing everything up.  Just enjoy it.  And we did.  Soon we were tapping those Ventra cards like pros.

A few details:

Favorite Moment: Biking around the Uptown neighborhood and around the lake with Josh.

Moment I Wanted to Cry:  When no pie places were open on Memorial Day.  I had one prospective place and we took a one-way train to get there, got lost walking there.  And it was closed.  We ubered back.

My sister was a huge help in planning a few details for our trip. They’ve been there a few times and pointed us in the right direction for many things.  Plus, she’s a travel goddess.

We tried Airbnb for the first time and loved it.  Our place was quite a ways outside the downtown “loop” but we enjoyed biking and strolling the beautiful neighborhood and lakeshore and finding some local spots that were a bit less crowded.


Antique Taco – Hands down our favorite.  Unique but not too weird.  We sat outside and watched the trains roll by. We both had the sweet and spicy chicken tacos and I sipped an agua fresca.  It was delicious.

Wildberry –  Good. But a bit disappointing?  This was on the top of a lot of brunch lists downtown but was a little “meh” to me.

Shake Shack – We had to.  The fries were worth the hype.  The plain hot dog was delicious.  They served fruity lemonade.  Win. Win. Win.

Thai Aroma – We wandered in here while walking through our neighborhood.  We didn’t even consult Yelp.  We just walked in. So adventurous.


Intelligentsia Coffee – Like I said, we found ourselves here three times in two days.  Josh loved trying different brews while I enjoyed their pastries, grapefruit soda, and exceptionally good decaf lattes.


Divvy Bikes –  Take them everywhere. Josh used the CityMapper App to locate the pick up and return stalls.

Architecture River Cruise – I loved this. A good way to get a feel for the layout of the city and learn about the famous buildings that make up the Chicago skyline.

Millennium Park –  It was beautiful but packed when we went on Memorial Day.  Still, you have to. Plus, your husband will be thrilled as you point out all the buildings in the background that you learned about from your architecture tour.

Milwaukee Avenue Stroll – We walked down the busy street and popped into the shops along the way.


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