Chicago

 10/3/2024

We left the house at 3:00, stopped to pick Beckett up at school, swung by to get Norah and headed to the airport for our 6 PM flight to Chicago-midway.

The airport lounge had a two hour wait, so we grabbed Panera for dinner and hung out at the gate. We flew Southwest because we were able to use points and ended up only spending like $32 for all four of our flights AND hotel. This was the first time we haven’t had to fly with car seats since we’re not renting a car and planning on just taking the train and buses. 

The kids did great on the plane, the lady behind us and her family made friends with the kids, one of them was a former first grade teacher, and loved asking Beckett questions and even wrote him a sweet note to take home. We got their flight passports stamped, the attendant was shocked what frequent flyers they are. 

We had checked two suitcases and a stroller and brought the other stroller through the airport with us. Beckett doesn’t usually go in a stroller anymore, but we knew we’d be walking miles every day, so we purposely brought two strollers that were of adequate height to push for multiple days, non stop. Unfortunately, our stroller that we checked, didn’t make it to Chicago… they didn’t automatically offer Mike one so I went back in to ask if they had any we could borrow. She said “sure! But…they’re super basic umbrella strollers” she wasn’t joking, we had to bend down to push it. Not ideal, but the kids were exhausted and we had 2 suitcases, 4 backpacks and a diaper bag so carrying one of them wasn’t an option… they gave us the option to pick ours back up tomorrow to exchange for a $200 travel voucher or they’d deliver it to our hotel. We were 40 mins away so we opted for them to come to us. 

Well we headed to the train station and realized the elevator was broken…so we had to get all of our luggage AND the strollers and the kids down a good amount of stairs!  What a warm welcome, Chicago! lol

We got on the orange train towards the Loop and got off at the Washington/Wabash stop. The hotel was only a block or so away. The kids were a bit wired and wanted to hop around on the train.. We got to our hotel around 9:15 and Norah was exhausted. She saw the pnp and went right to it saying “night night! Night night” (put me to bed NOW!). She was up at 4am crying and didn’t go back to bed…so that was fun, thankfully Beckett slept right through it- even though we are all in one room. 

We stayed at The Chicago Athletic Association hotel, which is perfectly situated on Michigan Avenue at the heart of downtown Chicago. We are right across the street from Millennium Park and can see Lake Michigan.

Once Beckett was up, we slowly got ready for the day and stopped at Goddess and the Bakery for breakfast. We bought tickets to the Color Factory, but it didn’t open until 10, so we had quite some time to kill. We walked around the city and stumbled upon the public library. We went to the children’s library and read a couple of books about Rosh Hashanah since it was actually the start of the Jewish new year that day. The kids played and colored for a little while before we headed to Willis Tower. The color factory was actually a lot of fun, we tried different candies and had a blast, taking photos in each of the different colored rooms. At the end, you slide into a ball pit, which was really neat! We met my old friends from Japan, Jennelle and Gene, for lunch at Umai. It was only appropriate that we had sushi! I think it had been about 11 years since I had seen them last.  We picked up right where we left off and had such a fun time catching up. Unfortunately, Jennelle had to head back to work, but Gene walked with us a bit as we headed towards Shedd Aquarium. We said goodbye to him and walked with us through Grant Park. We had a great time at the aquarium, the kids had never been to one before. Mike loved the beluga whales the most. I think Norah and I liked the dolphins and Beckett the otters and penguins…and maybe the sharks. We got to see a dolphin show and then headed back to our hotel. It was about a mile and a half walk and we stopped at Clarence F. Buckingham Memorial fountain for a couple of pics. Beckett said he wasn’t feeling well and napped the whole way back. He had a bit of a fever and a sore throat, so we decided just to pick up some soup and dinner and eat in the room. We opted for Italian,  from Pisano. I had a chicken Parm sandwich, Mike had spaghetti. Beckett had tortellini in a chicken broth soup and Norah had a bit of everything. Early to bed for all.

Everyone slept great, thank goodness! Friday morning we got up and just grabbed breakfast to go and went across the street to see the Bean, there weren’t many people there so we got a great family photo. Our stroller got in late the night before, so we picked that up on our way out. We hopped on a bus and took it to the Navy pier . We had 10 AM tickets to the children’s museum. We played for a couple of hours and then grabbed Chicago style hotdogs at Americas Dog and Burger. We walked to the end of the pier for an incredible view of the city. When we left the children’s museum, Norah hopped in the stroller and immediately fell asleep. She woke up when we were finishing lunch and enjoyed the walk outside next to the water- she thought the wind was funny. We picked up our traditional Christmas ornament of the city as a souvenir and a sticker for the scrapbook and walked to the magnificent mile. (which eventually disappeared-must have fallen out of the stroller...thankfully my good friend Jen went to the same place the following month and replaced it for me <3)

We walked to the Chicago water tower, which survived the Great Chicago Fire of 1871, although the area around it burnt to the ground. We went into Bloomingdale’s and Mike entertained the kids while I did a bit of shopping! I was super excited to find a $280 dress marked down to $26! The kids were exhausted and losing their minds, so we decided to walk back and find dinner on the way. We stumbled upon a Giordano’s and ordered a deep dish pizza for me and Mike, spaghetti Alfredo for Beckett and a regular small cheese pizza for Norah – and they ended up switching. That was my first time having deep dish pizza and it was delicious! We got there around 4:30, it’s a good thing we did because it took about an hour to cook the pizza. We walked the mile back to the hotel,  stopped to grab some popcorn at Garrett’s. Everyone showered/took baths and relaxed in bed.

Norah had us all up by 5:30 once again, we grabbed coffee in the hotel, muffins for the kids and got ready for the day. We went back to the Goddess for breakfast, then headed to the playground in millennium Park. Bex had been asking to go up in a lighthouse the last couple of days, so he really enjoyed the fact that he got to go into a play lighthouse at the park . They had a super cool bridge and lots of fun slides for the kids to waste some time on. The flowers around Chicago are arranged beautifully, even big bunches of cabbage arranged into flowers. We hopped on the bus and headed to the Lincoln Park zoo

“Hey big fella!” was Beckett's greeting to some of the animals 

“Bye bye 'amil'!” was Norah's salutations to the all the animals

We all had a really fun time at the zoo, we saw so many animals! A beaver even played with us!!

We got home and changed and went up to the rooftop bar at our hotel called Cindy’s. We weren’t sure if kids were allowed and doubted there were any reservations available but glad we went up! They put us on a cancellation list, we grabbed a drink from the bar and went outside to check out the view. The kids sat down and played for a bit while we enjoyed our drinks, just as we were saying that we likely won’t get seated here and we should probably have a back up plan, they text us to say our table was ready! We were a bit unsure as we had the only children in the place, but they had a highchair and offered a couple kid options so we decided to stay. We split a chilled king, crab and lobster dish as well as a whole fried Bronzino. Beckett devoured a full hamburger and Norah snacked on all of ours.

By the time we left, there was another family with kids ! It was gorgeous up there, I’m glad we stayed and experienced it. The rooftop above us was all windows! 

It was getting late, but Beckett asked to go see the bean again, so we went to Amarino for some gelato to eat on the way. It was so good!! we got some fun, family pictures and headed back to pack and go to sleep. 

The kids did great traveling home, there was a baby behind us that Norah really enjoyed playing with.