2023 Chicago Adventure

Although I’m not a huge fan of big cities, there are a few cities that have always piqued my interest and Chicago is one of them. Visiting Chicago was a bucket list item….I say “was” because it has recently been checked off that prestigious list of places I still want to see and things I want to do. This was achieved during the week of July 26-31 on a fun girl’s trip with friends who were going to visit a family member who lives there – my friend Cathy’s granddaughter, Catherine – and they let me tag along. We traveled from far and wide to gather there…..well, “far and wide” may be a stretch — Cathy, her daughter, Tara, and I traveled from Albion via Buffalo airport and Cathy’s sister, Linda, traveled from Long Island via LaGuardia in NYC. We all met up in Chicago Midway Airport where Catherine greeted us and our adventure began!

Catherine was the absolute hostess-extraordinaire!!! I like to joke that she expertly herded us through the city like a group of cattle…..but, that makes it sound unpleasant and it truly wasn’t. She ensured we saw everything we wanted to see, did everything we wanted to do, and got there on time in the best way possible. She was amazing! Our trip would have been a very different experience without her….we can’t thank her enough!

We used various modes of transportation to get around the city — the public bus system, ubers, and the Big Bus Hop-On-Hop-Off buses. We had considered taking the elevated train around the loop for that experience, but we ended up not working it in, but, that’s OK!

Our first views of the Chicago skyline from the plane as we approached Chicago Midway

We rented a condo through Airbnb. It was a perfect location – about a block from Wrigley Field in the neighborhood called Wrigleyville and just a few blocks from Catherine’s apartment. It was clean and comfortable with a cute layout — a long, narrow building typical of cities in a lovely and quiet tree lined neighborhood. That said, it was an older building in need of some TLC and repairs…..minor inconveniences, but noticeable. Here are some pics of the condo and the surrounding neighborhood:

Our building

The neighborhood

There were three bedrooms – one had a queen bed, one had a double and a twin, and one had two twins. I took the one with two twins – pictured above.

We were all tired our first night. Catherine visited with us at the condo where we ordered pizza and watched TV, read, set up our public transportation passes, and chatted about the plans for the trip. I claimed that fur covered lounge for reading a couple of evenings…..nice!!!

I took a walk outside to get some photos after dinner….there was a club on the corner up from the condo that Catherine said was a popular spot for Instagram Influencers. So, I had to get a selfie at “Lost Never Found” and some other shots of the area around the condo:

All the stuff at the corner of the block our condo was on:

After a good night’s sleep, the sightseeing began. We booked 48 hour Big Bus hop-on-hop-off tickets, so Thursday and Friday were devoted to things we could see/do from the Big Bus.

The gang in the neighborhood by the condo before heading out on our first day of the Big Bus and the next two are all of us at various stops along the way.

The first day, we rode the bus around the loop sitting on the upper deck to see the sites in all their glory. What a spectacular city — most of my photos that first day were looking UP…..WOW!!!

Views from the top of the bus:

I LOVED how these two shots came out – the first shows the sun rays reflecting off the building top and the second shows the low clouds hovering around the tops of a group of buildings! 🙂

Some of the sculptures we saw:

Above is “The Chicago Picasso” – it actually doesn’t have a name, but that’s what it has come to be known as. It was installed in 1967 at the Daley Plaza. Picasso was offered $100,000 for the commissioned piece, but he refused the fee stating that he wanted it to be his gift to the city of Chicago. There was quite a bit of controversy about it, but it has become an iconic piece for the city.

Some views of the Chicago River and Lake Michigan from the bus:

Lunch on Thursday was at the Dearborn – a very nice restaurant downtown. Three of us had the “Fish and Chips that Beat Bobby Flay”…..they were good, but not what I would think could beat something Bobby Flay made – I expected something a bit more “special”! Two had sandwiches they said were good. We also had the “Everything Parker House Rolls” as an appetizer – they were very good!

The gang at lunch – The Dearborn

The plan on Thursday evening was to do an Architectural River Cruise, but we were all exhausted and hot, so we decided to change the tickets to Saturday afternoon, instead. We headed back to the condo and decided on just snacks and unwinding that evening…..Catherine and Tara jumped in the lake…..I was sooooo jealous!!!

Here are some of the cool sites we saw when he “hopped off” a few times on Friday:

Our first stop was lunch at Portillo’s – it boasted “All Chicago Style Food”. I had the Chicago Hot Dog – hot dog, mustard, celery salt, onions, relish, tomato, and a Kosher pickle, on a steamed poppy seed bun! (Also comes with sport peppers which I left off) – it was really good!!! The food the others got was “meh”, but it was a fun stop.

Everywhere we went, the plants were full, stunning, and so healthy — even lots of impatiens right out in the hot sun and thriving — amazing!!!

The inside had a nice atmosphere – the room we sat in had lots of photos of celebrations of the end of prohibition!

One of the stops I wanted to be sure to do was the sign noting the start of the historic Route 66! I had a bucket list item to drive the entire length of Route 66 in the year I was 66 – this year! But…..I discovered just how long that drive would be and decided that at my age, it might not be the best idea…hahaha! So, I am settling for getting my photo by any signs for the historic route whenever I find one. I have them in Arizona and New Mexico from previous years. So far, this one is the only one taken when I was actually 66 years old! Hhhmmm….

We killed some time waiting for the next bus at a Starbucks — my very first time ever in a Starbucks! I don’t drink coffee, so never saw the benefit of going to one. But, I discovered they have non-coffee drinks and this frozen strawberry-acai lemonade was PERFECT on the super hot day we were having! And it was sooooooo good!!!!

At one of our stops…don’t remember which one….I saw this bull and got my photo with it….no particular reason – I just liked it and the market was being quite “bullish” the week we were there, so…..photo op!

Isn’t he a handsome bull??? LOL

We were on the bus and saw a Barbie Photo Shoot…..not sure why she was there, but it looked like she was on her way to a promotion thing and the photographers were shooting her inside her Barbie car and then standing with Ken….wish I could have gotten off and taken some photos…..it warmed my heart to see her stop to allow a little girl’s daddy to take her photo with her!

The big thing we did on Friday was Navy Pier! I rode the Centennial Wheel – the huge ferris wheel! I really wanted to do this cause I regretted not doing the one in Seattle and I’m getting too old for regrets and “I’ll do it next times”! It was fun — I’m glad I did it…..and, it wasn’t as scary as I thought it’d be – the seats were in fully enclosed baskets that stayed very stable and were air conditioned. But, the views were spectacular and I enjoyed it! I treated myself to an ice cream after……the rest of the group shopped and explored inside Navy Pier while I was out in the extreme heat being adventurous…..not sure who had the better experience! hahaha

Navy Pier itself was a bit of a disappointment for me — oh, don’t get me wrong – it was very nice – lots of shops and food choices and it was air conditioned (a HUGE advantage on a day when the temps were in the high 90s and heat index of 110!!!). But, I guess I was expecting a pier more like others I’ve seen – Santa Monica Pier in California, The Steel Pier in Atlantic City, NJ, and others…..this was fully enclosed (except for the rides) and just “different”. I think if my expectations weren’t so strong, I would have thought it was amazing! So, let’s go with that — it was AMAZING!!!

Some other sites from Friday on the Big Bus:

First up is the castle-like structures of the old water tower and pumping station on Michigan Ave in downtown Chicago – built in 1869 and survived the Great Chicago Fire of 1871. Very cool!!!

We also saw a huge fountain in Grant Park….we couldn’t get close enough when we hopped off to check it out – too far to walk, so this photo was taken from the bus – I actually think I was able to get a better photo from this distance/angle!!!

Friday evening we had planned to go up Willis Tower (formerly Sear’s Tower) to look out over the city at sunset, but they were predicting sever thunderstorms and high winds, so we changed out tickets to Saturday night and went back to the condo. We had dinner at Bernie’s Tap and Grill on the corner of the block our condo was on. I had the three mini burgers appetizer – which was more of a full meal than an appetizer and very good!!! With the exception of the mac and cheese bites, I think everyone else liked their meals, as well.

Saturday we packed the day with LOTS of cool stuff – including the two things we rescheduled from earlier plans (the River Cruise and Willis Tower)…..we started out with a tour of Wrigley Field – WOW!!!

That was AWESOME!!! I loved everything we did and it was all special for different reasons, but I do think the Wrigley Field Tour was a highlight for me! There is just something about being in a ball park – even if I’m not there for a game (I was disappointed that the Cubs were away while we were there). It was a thrill — especially in the visitors club house when the tour guide talked about all the greats that had stood right where we were…it was quite emotional! We got to sit in the stands, go up to the press box, into the visitor’s club house and dugout (we couldn’t go in the cubs dugout because there was a summer camp going on and they were using it) and onto the sidelines of the field.

AND…..we got up close and personal with the famous IVY WALL!!!

We were told to please not touch it — apparently, it is still the ORIGINAL ivy planted in 1937 that has been lovingly cared for and preserved all these years!!!

When we left Wrigley Field, we shopped at the gift shop and then headed out for lunch. We considered going to a cool spot near there called “The Stretch” that is based on the movie “Ferris Bueller’s Day Off”, but there was a “Mustache Crawl” going on with HUNDREDS of young people pub hopping for the event.

So, we decided to get an uber away from that area and went to a diner called “Hutch” that Catherine had been wanting to try for brunch. It was a good choice!

After brunch, we went back downtown to catch the Architectural River Cruise — that was amazing!!! An hour and a half boat ride learning all about the architectural history of Chicago while cruising down the Chicago River! What’s not to love???

BTW – this is my favorite photo of the trip….

While looking at the following photos, notice how totally DIFFERENT each of the buildings are…we were struck by the fact that this is definitely NOT a cookie cutter city — even residential neighborhoods didn’t have any buildings that looked the same! STUNNING!!! You will also see shots of the Chicago River Walk along the way.

After the River Cruise, we headed to “The Bean” – one of Chicago’s most popular attractions. The sculpture, officially named “Cloud Gate” is in Millennium Park and was dedicated in 2006 and is best known by it’s nickname: “The Bean”. We couldn’t leave Chicago without seeing it!

It was really cool to see up close and made for some iconic “Chicago” photos for us!

We had dinner there at a little Mexican vendor – we all had tacos of some variety:

We ended the evening at Wilis Tower – formerly known as Sears Tower!

The black building is Willis Tower.

Willis Tower is the twelfth-tallest building in the world; it is the third tallest building in the North America and the Western Hemisphere, standing 1,450 feet and 110 stories tall. Willis Tower is home to the highest public viewing area in the United States.

The Ledge: Step outside what’s not only the tallest building in Chicago but the third-tallest building in the Western Hemisphere! The viewing tower offers spectacular views spanning up to four states, but there’s also The Ledge, a glass balcony extending four feet outside Willis Tower’s 103rd floor.

I stood on the glass ledge 103 floors up at the Willis Tower – had to force myself to step out on it….but so glad I did!!!

I can’t tell you how intimidating it was to step out onto this glass floor…..but, I did it!!! (remember what I said earlier about being too old for regrets???)

Views from the top of the tower at sunset — the city is gorgeous from up there!!!

When we left the tower and were waiting for our uber back to the condo, we saw these carts that were available for rides around the area. We didn’t take them, but they made for a cool photo!

On Sunday we rested….LOL!!! Catherine had a soccer game in the morning, so we met up for lunch and went to fabulous super trendy upscale food court called Time Out Market in the Fulton Market!!!

This was my absolutely favorite of all the places we ate!!! I’m so glad we fit it in our crammed schedule!

I chose an amazing ramen bowl at Bill Kim Ramen Bar and followed it up with a key lime tart! Sooooo good – we all got different stuff from different “kitchens” and we all really enjoyed our meals! Catherine’s roommate, Sam joined us.

Then, we spent the rest of the day hanging out at Catherine’s apartment with Catherine and her roommate, Sam. They have a GREAT place! I loved all the exposed brick and the whole layout and feel of the building. And, there is a wonderful outdoor space where we grilled out and ate dinner. We even had cake and ice cream and sang Happy Birthday to Cathy, who’s birthday was just a couple days before we started our adventure!

And….I’ll end this post with this photo — it sums things up, nicely! Catherine snuck this photo of the three of us when we all fell asleep at her apartment waiting to grill out dinner! It shows just how FULL our visit was! When she shared the photo with me, it cracked me up! Definitely wins the prize for the funniest photo of the trip!

It was a fantastic trip……great memories with dear friends…..it was a bit rough on a couple of us, but we made it through and had a fabulous time!

I lied — I’m not having the sleeping ladies be my parting photo — I’ll now leave you with the morning sunrise over Lake Michigan!!! And…that’s all for this adventure!