In Love with the Windy City: My Girls’ Trip to Chicago (Part 2)

Read Part 1 here!

Our game plan for Thursday was to use Divvy to see as much of the southeast part of the city as we could.  Our first destination was Michaela’s only itinerary request: Skydeck Chicago at Willis Tower.

The Skydeck is a pretty touristy stop, but it was really cool — and the glass ledge was unexpectedly heart-stopping.


By the time we descended from Willis Tower, we were ready for lunch, so we hit up a Chicago classic: Giordano’s pizza. I’m gluten-free but I threw caution to the wind for the opportunity to try true Chicago-style pizza for the first time. It was pretty good, but I’d have to say I prefer New York style. We ate at the 223 W Jackson Blvd location just up the block from Willis Tower, but you can find Giordano’s locations all around the city.

Our next stop ended up being kind of a funny failure. As we headed to our next Divvy dock to pick up another bike, we saw a Chicago Public Library bus.

“Hey!” I suggested. “We should go check out the library! I bet it’s pretty awesome!”

“Um, yes,” Michaela — a fellow book lover — responded.

So, we put “Chicago Public Library” into Google maps and away we pedaled.

Word to the wise: When you put “Chicago Public Library” into Google maps, you will indeed end up at a library. But it will be the one in Chinatown. No one will speak English and you will be far away from everything.


There was a pretty awesome mural at the Chinatown branch, and we used their bathroom and picked up new bikes, so it wasn’t all bad. The ride was actually quite nice, too — the streets were quieter and there were dedicated bike lanes in many areas. I was a little apprehensive as we pedaled south, on the alert for anything that looked like the Chicago crime ghettoes constantly showing up on the news, but as far as I could tell, we didn’t end up anywhere sketchy.

That little detour completed, we did some research and found out that the library we really wanted to see was the Harold Washington Library Center. If you’re looking for it, it’s at 400 S State Street, which is not in Chinatown 😉

Harold Washington Library Center
Photo from

The building is totally awesome, and you have to go to the 9th floor and check out the Winter Garden. It is amazing, and I can only imagine how wonderful it is to have a beautiful green place like that to go during cold Chicago winters.

The only thing I love in a city more than pizza and books is lots of green spaces — and again, Chicago didn’t disappoint. Our next stop was the parks: Grant ParkMillennium Park, and Buckingham Fountain. Tragically, my phone was totally dead at this point, so no pictures, but the weather was perfect and the parks green and expansive.

At this point we hit our first Divvy snag: we wanted to pick up new bikes after visiting the fountain, but all the nearby docks were empty. At one point we found a dock with two bikes, but one had an error message and couldn’t be undocked. Womp womp. We had planned to head north up the Lakefront Trail to check out the beach, but without bikes we realized we’d probably have to make our way back in the dark. Instead we decided to return to our hotel rooms, clean up, and figure out what we wanted to do next.

I’m not a beer-drinker, but I get pretty excited about gin — so when I found a distillery a couple miles from our hotel, we decided it would be the perfect way to top off our evening. Back on the bikes we hopped, pedaling about a mile and a half to Randolph Street and the CH Distillery.

CH Distillery | Our Streamlined Life

The ambiance was really cool — behind the bar was a huge window looking into the distillery! — and the drinks were seriously awesome. I had a classic gin & tonic, to give their gin a true test run, and it was terrific. I also tried the Baby Sharks, made with strawberry, cucumber, and red pepper — perfect. We chose to Uber home instead of biking in the dark, much to the amusement of our driver: “Ya’ll coulda walked!

Friday we were joined in the city by our sister Bridget, who made the drive from Peoria with her boys to visit us. In the spirit of a 7-year-old-boy-friendly adventure, we spent more time in the park, had pizza and ice cream for lunch, then opted for a boat tour. We did the Shoreline Sightseeing Classic Lake Tour leaving from Navy Pier, and we all had a blast.

Chicago Skyline from Lake Michigan | Our Streamlined Life

Sadly, once our boat docked it was time to head back to the airport. As we drove I was already scheming ways to get Ryan to come with me to Chicago. Stay tuned for my list of things I wish we’d had time to do in Chicago … and all the reasons I loved it so much!

That’s everything we did, saw, and ate during our three day girls’ trip to Chicago! Have you been to Chicago? How would you rank it?

For more ideas on things to do in Chicago, check out our Chicago Pinterest board.

In Love with the Windy City Part 2 | Our Streamlined Life

I'm the oldest of 12 crazy kids and two pretty awesome parents. My love of travel developed during my early years traveling the globe as an Air Force brat. I'm a runner, a writer, and a reader, and I love cooking up good food and cozying up our camper.

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