I'd been asking Jacob to go to Chicago for years, but he was never interested. When my birthday rolled around and he wasn't sure what to get me, I suggested tickets to my most anticipated musical, Hamilton. I thought maybe he'd get me the tickets and I could have a quick weekend in the windy city with a friend. But he surprised me and said he actually wanted to go! So we booked a red eye and spent three days exploring a new place together, which is my favorite thing to do.

We landed in Chicago early Monday morning. We caught the L into the city, got an early check in at our hotel, and walked down to the river for an architectural cruise of the Chicago River and Lake Michigan. We got a little history and a lot of great views.

Afterwards, we went up Willis Tower to the Skydeck where we got even more amazing views of the city and had fun messing around on The Ledge at 1353 feet. We'd done something similar at CN Tower in Toronto (which was a little higher, at 1465 feet), but it was a totally different feeling being out in those boxes, rather than just standing on a glass floor. Creepy! Jacob jumped around, but when it was my turn, I sat on the floor, cringed for a picture and got out of there without looking down. I wouldn't say I was terrified, but I was definitely not comfortable.

We had a late lunch/early dinner at Pizzeria Uno, which claims to be the oldest deep dish in Chicago (1943), then headed north to The Second City. Neither of us have ever seen improv before! So many comedy greats (Tina Fey, Steve Carell, John Candy, Key & Peele, Amy Poehler, Stephen Colbert, Catherine O'Hara, Bill Murray, etc.) came from that place so who knows if we saw someone who may make it big someday. We had a really good time and laughed nonstop.

We were exhausted and jet lagged and went to bed right after the show so we could gear up for day two. We grabbed breakfast near the hotel and hopped on a trolley tour to see more of the city. We learned even more history and enjoyed the landscape from the top deck on a warm day. We got off to explore Millenium Park, Grant Park, and the Navy Pier.

We ate lunch at Shake Shack then went back to the hotel to nap and get ready for Hamilton! (Check out my review here.) I was on post-show high and it was such a warm, clear night, we decided to walk back to the hotel when it ended.

We kicked off day three with a huge breakfast at Hash House A Go Go, spent some time at Oak Street Beach, and took the L up to Wrigleyville. We took a tour of the field then ate more deep dish at Giordano's. We walked Magnificent Mile, picked up some souvenirs, and took the L back to the airport.

As usual, it was a whirlwind of a trip, but so much fun. Jacob and I love spending time together and Chicago was really pretty with friendly people, and we never felt unsafe. I'd love to bring the kids back some day to check out all the museums (Nolan freaked when we told him about this trip because he knows SUE (the largest, best-preserved, and most complete T. rex) lives in The Field Museum.) Even Jacob, who was so reluctant to go in the first place, loved it, said he could even see himself living there, and can't wait to go back for some hockey.


SMD @ lifeaccordingtosteph said...

Perfect trip! I'm glad you got to see Hamilton.

I loved the Architecture Boat Tour and Second City!

Misty said...

I went years ago and spent about 3 days. I got to see a lot while I was there. I'd really love to go back though. There's still so much I didn't see. It's truly a great city!

lil desiqua said...

A whirlwind trip in the windy city sounds like so much fun! Last time I was there was for a conference in the dead of winter so I didn't get to do much sightseeing. I didn't even get to see the Bean! That pic of you at Willis Tower is so cool! I think I would've been freaking out too though! You guys saw so much in such a short time- sounds like an awesome little getaway!

Jo said...

Man, I need a trip over to come visit you!!