Trip Report – Summer Grand Tour: The Windy City

Wednesday 21st June 2017

After collecting our luggage and making out way out of the station we headed to the street & the lick up points for ride share. We requested a ride and moments later we were being picked up. Off to the hotel we went.

Due to peak hour it took a while to get up to the hotel from Union Station but it was fine. We were dropped off in the driveway for our hotel, The Waldorf Astoria Chicago. The hotel was one of my work benefits so we had used it for 2 of our three nights. Check in was a breeze & within a few minutes we were on our way up to our suite. We had been upgraded to a Waldorf Suite on the top floor. The room was amazing, so much space. The view though was blocked by other buildings bit we could see glimpses of the lake.

After checking out the room and waiting a few minutes for our bags we got ourselves settled & then headed out to dinner. We decided to have some pizza the first night, so I let Heidi decide. She went with Giordanos which was only a short walk from the hotel. Sadly when we got there it was a 45 minute wait for tables & then it’s another 45-60 minutes for pizza. We waited it out and it was well worth the wait.

After waddling back to the hotel we crashed for the evening as it was getting late by that stage.

Thursday 22nd June 2017

After waking up & heading outside for a long morning walk along the lake, I had to meet a hotel rep in the morning so we took it easy to begin with. I headed down to Dunkin for some breakfast, Heidi had leftover pizza.

After getting to check out the hotel, including some amazing rooms like the Presidential Suite, we headed out for the day. We hopped the Red Line down to Millennium Park & checked out the sights. We took photos with The Bean & then worked our way down to the Buckingham Fountain. More walking as we made our way back through the city to Portillos for lunch.

Portillos is famous for its hot dogs & Italian beef. Since my allergy precludes me from eating Italian beef, I’ll stick to the hot dog. We got there & the waits were not to bad. We were smart & got a table first. I had forgotten how wierd the Chicago hot dog really is. It has so much stuff on it, you would think someone was drunk when they invented it. Still tastes good though. I surprised Heidi with a slice of their famous lemon cake which you can only get on rare occasions, luckily one of them was the day we visited. Heidi enjoyed her first try of a Chicago hot dog so that was good.

After lunch we went back out into the humidity & 90F weather. We walked back down to the river slowly before our 4pm cruise along the Chicago River. Time for the architecture cruise. I had done it when I first came & loved it. So much history & learning a lot about different styles of buildings. I thought Heidi might like it. Of course the minute we get on board the open top boat it begins to rain.

The cruise was great & I learned a few new things. Heidi did too after a while, to begin with it was a but too much information for her. But by the end of it we had both enjoyed it. After the cruise we walked along the riverfront for a bit, grabbed some dinner & hopped a train back to the hotel. We finished off a long day of walking by relaxing on the couch eating sandwiches from Hannah Bretzels, a flashy kind of subway that offered Pretzel Bread rolls. They were delicious!

Friday 23rd June 2017

Woke up at a normal time today & hit the hotels gym for a bit. After returning to the room & cleaning up it was time to pack up our stuff. We decided to leave our bags at the hotel & head out. We would come back later on & grab our stuff before heading to the other hotel.

We had breakfast at the Dunkin Donuts near us & then headed off to explore North of the river today. Started off with the water tower and then off along the waterfront to Lincoln Park. Heidi wanted to explore the park so off we went. She had earlier told me she didn’t want to see the zoo but the moment we got there she all of a sudden wanted to see the zoo. Sadly no time 😉

We took a long walk through the Lincoln Park neighborhood on our way to lunch. While not from Chicago, we wanted to give a sushi burrito a try. We found one at was once called Sumo Restaurant (since changed name) & it was delicious. I had the Angry Salmon & boy was it spicy,covered in cheeto dust too. After lunch Heidi & I walked back to the Red Line to jump a train over to the Magnificent Mile, for a donut, before returning to the hotel.

After collecting our bags & ordering a ride share, this is when things went awry. The driver that had been sent to us by the rideshare decided not to use the hotel driveway but instead park on the street out of view of us waiting on the driveway. The car looked run down & he had music blaring. Those two I can forgive, but the way he drove us to our other hotel was the killer. He ignored the directions on the app, he ran several red lights & stop signs too. A 35 minute rode took almost an hour. By the time I got to the hotel I was hot under the collar, literally too as it was stinking hot in that car.

We checked into our other hotel, the Sleep Inn Midway airport. A one night stay by the airport for our 6am flight the next day was all that needed. The room was booked as a name your own price on priceline & I got a relatively good deal. Although the hotel was basic it was pretty nice. We did get the typical priceline treatment of an accessible room. Not much in the way of options for food around the hotel but what they did have was a Lou Malnati’s close by. We choose to compare pizzas.

After an amazing dinner of deep dish we waddled back to the hotel to crash till the Weee hours of the morning.

Current Location: Country Inn & Suites Ontario Mills

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