eastern USA backpacking holidayChicago is probably the most exciting city east of the Rockies. Having now visited New York, Boston, Miami, Houston, Austin and a number of other US cities I don’t understand why Chicago is not higher up on the list. It has some amazing parks, a huge botanical garden, a great public transport network and great restaurants and hotels. It is also far less crowded than New York and nowhere near as expensive.

This was my second trip to Chicago (out of three) and I decided to stay for one night only. Problem is, for some reason I forgot to book a place! I looked at various hostels when I was planning my trip but someone must have distracted me and I never booked any. This sort of dawned on me about halway up to Chicago and back then I didn’t have mobile internet so I just had to wait until I arrived in Chicago.

Read the first part of this series about my low cost Eastern USA backpacking holiday 

In the end I decided to go back to the same hostel where I stayed in March. To my shock and horror they told me they were full! I was there with all my stuff and I didn’t have a booking – I was kind of upset!

Chicago Low Cost Backpacking Holiday

The hostel staff did not want to help at all as it was nearly 11PM and the receptionists were cashing up to go home. I was super disappointed as I had such nice memories from my first visit. In the end I went downstairs, checked my bags into the locker room and walked around town looking for a place to stay. That weekend was very close to Memorial Weekend and everything was so expensive – I even contemplated sleeping at the airport.

Chicago Bean DowntownInstead I sneaked into the hostel lounge and slept there on the coach in their TV room! It was the HI Chicago Hostel on East Congress Parkway. The hostel has an amazing atmosphere and I really wanted to stay there again, but obviously I never booked the night.  The room where I stayed in March had 12 bunk beds and three huge windows. The ceiling had massive beams and every now and then the train on the loop rattled past. It totally felt like I arrived in “Big City USA”!

Sneaking Out

I was hoping to stay there for a second time which in the end sort of came true. Since I slept there before I knew where the lounge was and I just walked past the receptionist when I entered. By then they changed shifts so nobody recognised me.

It worked out pretty well, I even made a friend with one of the residents. There was also free internet in the lounge on a free computer so I couldn’t complain. It was well past midnight by then so I passed out on the sofa and didn’t wake until 6AM. Shift change tends to be around 7AM so as soon as it started to be light outside I grabbed my rucksack and headed out into Chicago!

If you enjoyed this post and want to read a similar story, scroll down to see the related posts section. You might also want to watch some of my other videos on Youtube.

Leave a Reply

Your email address will not be published.