Good Morning Chicago
The sounds of a big city – honking, sirens, construction. Those are the sounds I awoke to around 6:30am on my second day in Chicago. While the time seems very early, at least to me, the time zone was one hour to my advantage! The roads had been quiet in the middle of the night, for the most part, but the day starts early in a big city. Also, the beds must have been quite comfy because I had slept great!
The Tremont Hotel provides tickets to receive a continental breakfast for $5 at the attached Ditka’s restaurant. However, I was not very impressed with the small selection and lack of variety – pastries, cereal, fruit, juice, milk, coffee.
Heading Out on the Town
In my attempt to pack lightly and take a carry on suitcase only, I only had one pair of ballet style flats for walking. Day 1 proved that was not a good idea for daily walking so I borrowed my sister’s, slightly small for my feet, tennis shoes before heading out to Michigan Avenue.
My first pit stop was at one of the many ATMs lining the street (thankfully). When you travel you should take money, as in cash, at least it’s generally a good idea. Helpful tip for ya!
The Magnificent Mile, Millenium Park, & Grant Park
I walked the length of the Magnificent Mile to Millenium Park and Grant Park. Along the way I admired the historic Chicago Water Tower and the many blooming spring flowers.
Once to the parks, I checked out a couple of the quintessential Chicago sites – The Bean (Cloud Gate) and Buckingham Fountain where I also found many other tourists.
The parks have beautiful landscaping and structures to check out so I meandered around seeing what I could see before checking out the Chicago Library and heading back up the Magnificent Mile.
On the way back, I crossed what I deemed the “scary bridge” over the Chicago River. The bridge has small gaps, well large gaps to me, that I’m sure have something to do with the bridge expanding and contracting in various weather conditions.
I also saw what I thought was the Sears Tower (sorry, the Willis Tower) but later learned is actually Trump Tower.
Along the sidewalk, I observed a street performer and a non-street performer but could’ve fooled me with what he was wearing since he looked straight out of a movie to me.
Lunch @ Big Bowl
Back in the area of the John Hancock building, my sister texted me a couple of recommendations for lunch. I walked northwest to Big Bowl and was super impressed by their delicious panang chicken curry and I’m not usually a fan of curry. Afterwards, I wandered down Rush Street checking out the shops and restaurants.
Contemplating Chicago
Eventually returning to the hotel, after walking for 3+ hours and around 5 miles, I decided it was time for a rest. I enjoyed the view of the John Hancock Building from our hotel room and contemplated Chicago. It’s known as the windy city but during this visit it was not overly so. The people in general seemed friendly (saw nods and received hello greetings) and helpful (saw someone stop to pick up a rag, dropped by a cleaning man, that was getting blown away by the wind).
Back Out on the Town
Before my sister was finished for the day, I headed back out to do some shopping. Mother’s Day was right around the corner and even though I was traveling I must remember holidays and loved ones! I also went back to get the high heel shoes I could not resist at Filene’s Basement from the previous day.
With my sister done at her conference, we headed back out and retraced some of my steps earlier in the day. It was fun walking down Michigan Avenue with my sister’s perspective and knowledge as a frequent business traveler to Chicago. We made it all the way to The Bean and had fun taking more reflection photos, including doing things like handstands!
On the walk back, my knowledgeable sister pointed out the Chicago Tribune Building and the many historically significant stone embedded all around the base of the structure. I had not noticed this earlier in the day – very cool!
Seeking Shelter
About this time is when the sky decided to open up and it began pouring rain. Of course, we were not prepared for this, so we found the nearest awning hanging over the sidewalk to take shelter. It was rather amusing to watch the busy sidewalks vacate as people scrambled into taxis, buildings, or under overhangs.
My sister produced a tiny travel umbrella from her bag for us to share. Not being certain when and if the rain would be stopping anytime soon, we headed out attempting to walk as one person with an undersized umbrella. We made our way to Heaven on Seven for a New Orleans style dinner.
With soaking wet pant bottoms and arms, soup was high on our food list. We started with turtle soup (not sure I agree with eating turtles but it was pretty good) and potato parmesan soup (delicious). For dinner my sister selected fried green tomatoes with crabmeat and I chose the sampler dinner. While very good, I concluded it was not really my thing but that’s a completely personal preference and you never know unless you try!
Walking the Streets of Chicago & Cinco de Mayo
By the time dinner was finished, the rain had stopped. We headed out into the evening and just enjoyed chatting and walking around the city. Being on main streets that were busy and not alone, we never felt unsafe.
For most of the day, I had forgotten it was Cinco de Mayo but soon remembered when we walked past Blue Agave. This Mexican restaurant was very busy so we decided to stop in. We circled the bar, tried to find a place to sit or a waiter and had no luck with either. Chatted with a couple people but ultimately decided to leave due to the crowd and noise (hard to communicate when even shouts can’t be heard). But, it was definitely a place to be for Cinco de Mayo!
Packing Up
After walking close to 10 miles that day, I decided I was rather tired and needed to pack for my early flight the next morning. Packing is so difficult when you’re really tired and I wasn’t really getting anything accomplished. Finally, I took a shower to wake myself up enough to finish packing.
My sister called the front desk for me to find out about getting a taxi around 4:30am (just ask at the front desk when I was ready) and to get a wakeup call. I wanted to take a shuttle (unavailable that early) or even the train (not near enough to the hotel for me to feel comfortable walking around alone so early in the morning) but a taxi it would be even if it was more expensive since it was faster and safer.
So Long Chicago
Four hours of sleep later, I was awake and preparing to leave for my 6:00am flight. I got to the front desk just after 4:30am and the gentleman there was kind enough to go out into the middle of Chestnut Street and flag down a taxi up on Michigan Avenue. Apparently the taxi drivers drive the main road looking down the side streets, without actually driving down them, for hotels needing taxis.
This is when my tipping etiquette begins to fail me. Pretty sure I was supposed to tip the front desk gentleman for helping me out but I didn’t because I wasn’t sure what to do. When in doubt, tip for services?!?
With no traffic at the early hour in the morning, the ride to the Midway Airport was only 15 minutes but cost about $30. Being one of the first flights of the day and arriving with just over an hour before my departure time, I was in good shape even though the airport was definitely showing signs of already being busy.
Chicago was fun but it was time to go on to the next adventure!




The parks in Chicago are truly a highlight of the Windy City. I remember spending hours just wandering around Millennium park people watching. I can’t wait to come back to Chicago again soon.
I can’t wait to get back either. I feel like there was so much more I did not have time to see and more people to watch too.