Saturday, 23 June 2018

Chicago in 48 hours (Part 1)

I usually don't celebrate my birthdays, but in the year 2017 I had a unique and a memorable way of celebrating my birthday - I had it last for 34 hours. You might be wondering how it is possible? I kept moving towards the west to gain hours. I'm illustrating the entire cycle below.

Aug 4 - 00:00 IST - Entering Chennai International Airport's security check
Aug 4 - 03:30 IST - Boarding Qatar Airways flight to Doha
Aug 4 - 03:30 to 08:30 IST - Flight journey
Aug 4 - 06:00 GMT+3 (which is 08:30 IST - see, I've gained 2.5 hours) - Arrival at Doha
Aug 4 - 07:10 GMT+3 - Boarding Qatar Airways flight to Chicago
Aug 4 - 07:10 to 23:00 GMT+3 - Flight journey
Aug 4 - 15:00 CDT (which is 23:00 in Doha's time - see, I've gained 8 hours) - Arrival at Chicago

So, when I arrived at Chicago, it was 3 PM local time, and the time in India was the next day (Aug 5) 1.30 am IST, which means, from the minute I entered the airport and to the minute I landed in Chicago, I've gained 10.5 hours, which means I extended my birthday by another 10.5 hours.

Alright, enough about my birthday. In this article, I am going to cover what I did when I was in Chicago for 48 hours. The article will be divided into two parts. I'll be summarizing the cost involved for the trip at the end of part 2.

In the month of August 2017, I was on a B1 (Business) trip to the United States. Visiting Chicago was more of an extended layover as I had to travel to this small town called "La Crosse" in Wisconsin. La Crosse is 5 hours train ride / 1-hour flight from Chicago. Since I had a plan to land in Chicago on a Friday, I didn't want to get to La Crosse immediately and spend the next two days sitting idle at the Hotel (trust me, there isn't much to do around La Crosse as I don't know how to drive a car). So I spoke with my office management and they agreed to have the stay arranged for me at Chicago for two nights (Fri and Sat), but they said I have to cover the other expenses on my own (food, sightseeing, etc). It sounded like a pretty good deal to me and I agreed to it.

Expenses covered by office management for those two days - 
  • Hotel stay in Chicago
  • Train / Flight to La Crosse from Chicago 
  • Transportation (claim) to Train station / Airport before the departure

Expenses covered by me for those two days - 
  • Sightseeing
  • Breakfast / Lunch / Dinner
  • Shopping
  • Transportation (other than the one covered by the management)

Since the trip was finalized at the last minute, I didn't have any sort of plan handy. From the day the air tickets were reserved, I had just three days to come up with a solid plan to cover "Chicago in 48 hours". 

The planning phase initially involved sorting out the mode of travel from Chicago to La Crosse. I had two options - either to take a train or to fly. Flying to La Crosse seemed costly as the round trip cost around 20000 INR (approximately 294 USD) per person. Since the trip involved two persons, the cost would account to almost 600 USD just for traveling from Chicago to La Crosse. I had to choose the only alternative - to take Amtrak - which was exciting to me because I've never taken an Amtrak before. I logged into the Amtrak official website and noticed that the coach cost 99$ per person and it would account to 198$ for two. To my surprise, the first class, which is called 'Superliner Roomette', costed just 220$ for two. This seemed pretty much a kick-ass deal to me. After confirming about the claim from the management, I went ahead and booked the ticket on my own. 

Boarding pass of Amtrak Empire Builder to La Crosse from Chicago

As the travel plan from Chicago to La Crosse was sorted out, I then moved on to make sightseeing plans for August 5th and August 6th. As the outbound train from Chicago was at 2.15 pm on the 6th, I couldn't dump much for that day, so I decided to create a tight schedule for the 5th.

Day 1 - Aug 5, 2017

10:00 am - Chicago Crime and Mob Tour

This marked the first tour of the day - Chicago Crime and Mob tour. Chicago is well known for its criminals like John Dillinger, Al Capone, Frank Nitti, etc., and this tour seemed to be a perfect choice in order to get to know the city completely. The tour lasted for 1.5 hours and almost all of the criminals' history were covered.

The second, third, fourth pictures shown below is the location where John Dillinger's death trap was set and the fifth picture is where John Dillinger was shot to death. The sixth picture is where Al Capone used to reside.

11:30 am - Chicago hop-on-hop-off tour by Big Bus

Opting for the hop-on-hop-off is the best thing one could do when visiting a place like Chicago. There are buses plying for every 10-15 minutes and the commute from one point to other seemed easy with this option. By taking the Big Bus, I was able to get to get a glimpse of the entire city just by riding the complete circuit. In the end, I spent a couple of hours at Alden's planetarium clicking pictures of the beautiful Chicago skyline. 

5.15 pm - Lake Michigan and Chicago River Architecture Cruise by Speedboat

I initially booked for the 4.15 pm slot but re-scheduled it later to 5.15 pm to witness the sunset as we cruise on the Chicago River. I then decided to opt for the night tour at 7 pm to enjoy the dazzling skyscrapers in night lights. But what I didn't expect was the sunset happened at 8 pm, which was a big 'LOL' moment I had that day. The 5.15 pm tour was delayed slightly. The tour commenced at 5.30 pm and lasted till 6.45 pm. It was by far the best cruise I had taken till date.


I was provided with a private room at "Freehand Hostel". The location of the hostel was great - the Navy Pier was just 20 minutes walking distance and all the eateries were within 5 minutes of walking distance, including an Indian restaurant. The hostel was pretty cool and very economical. Since it was a weekend, a private room cost 120$ per night, which was, in fact, cheaper compared to other hotels in the downtown. The private room given to me was compact and cozy. The room was at the 13th floor and bore some excellent views of the skyscrapers from the window.


Food hasn't been a problem for me. I decided to stick to McDonald's for breakfast and lunch, and there was an Indian restaurant named "Indian Garden" where I had Chicken Tikka and Egg Biriyani for dinner (yes, on both the nights - Fri and Sat). The Biriyani served by them was freaking delicious. It costed 20$ and it can be easily shared by two persons - quantity = quality! For breakfast, on day one I had my first streak burger at McDonald's and on day two, I had the complimentary breakfast served at the hostel. Breakfast, Lunch, and Dinner together cost me approximately 70$ for both the days.

Here are some additional pics captured on Day 1.

Continued in Part 2


  1. Awesome!! It's nice to see you enjoyed your visit to Chicago, my friend! Nice writing and excellent pictures!!

    1. Thank you brother! Wish I could've visited North Carolina as well :)


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