$220 all expenses paid Chicago vacation.. How?

October 9th 2015

It all started with an email. Well, actually, the dream started while I was on bedrest, following my third surgery fighting cancer.. I was writing my bucket list, and the first thing I wanted to do was meet my nephew in person… the second thing was see the WORLD!!!  I painted a picture I found online of Chicago.. and the dream was born..


Southwest Airlines had a special going on and was kind enough to let me know about it. Usually I never open spam email, and in fact I have changed my email address to start over on the masses of spam email I would get in a day, and have to fish thru to retrieve personal emails… and yes.. I still use email. It’s my preferred method of contact with my therapist. It respects boundaries, isn’t time sensitive, but keeps the communication open. Since I am traveling, it is hard to maintain my therapy, but it has been a vital part of my recovery, and it feels safer the more doors I have open where I can be open, honest, and real about where I am at. It is too easy to get caught up in the adventures, and before I know it, none of my basic skills to manage my mental illness are in place, and I am once again spiraling out of control, heading for depressed and suicidal fast! Which reminds me, I should see her while I am in town.. I love how that works. BRB
ok email sent!

Soo.. cost breakdown.. Southwest Airlines email.. so I click on my departure airport; New Orleans, and view the flights. A list populates and I scroll down the results to find the cheapest flight, and where it is going. “Midway Intl. Chicago $83 one way”

well, I know that Chicago is a major city, and I can only imagine how cheap the flights to various places out of there might be. I have many friends in the windy city, and I’ve really never visited Chicago on my own, as a tourist with a camera, and just let myself go wherever the wind blows. I’ve always (all 2 times) been there with an alternate reason, and a time constraint. So I go to my “what do I need to survive if I go to Chicago” list. Shelter, food, a way home. Next step, I load my AirBnb app, switch to a traveler (from a host.. for those who don’t know, after I discovered AirBnb I listed rooms for rent in my house so that others could travel for as little as possible, therefore promoting and inspiring more people to travel) “Where am I going?” Chicago! I type in the info, drop my $ range to $0-$30 and look at what comes back. Scroll, scroll, scroll.. $20 a night, a bunkbed in what looks like a hostel type of environment (hostel as in a place to sleep, not hostile) I check the calendar and it has 2 nights available when I get there.. booked. Flight… booked. Holy shit I’m going to Chicago! $79 for the flight, $20 to sleep, shower, change, charge my phone and camera, and the ability to eat for next to nothing… I am in!

I remember an article I read about finding cheaper flights after a flight is booked, and two days later I check out cheaper times to travel to Chicago, if there are any? Sure enough there’s a flight for $44!

I log on, change my flight and receive a credit of $35. I price tickets from Chicago to NY, and find a flight for $59.. I use the credit and pay the remaining $24… I guess I need to start planning for NY TOO!

At the airport, I am packed into one backpack that weighs about 60lbs. Three outfits, camping cooking equipment, camera, journal, chargers, and toiletries. Two bottles of water, couscous (just in case) and a determined mind to do this!

First lesson… bottled water can not go through the security check if it is more than 3 oz, so there went my waters! I paid the $3 at Subway for a new bottle once I was on the other side. I have to drink all of the time. When I get dehydrated, my body panics and panic escalates quickly into an attack where I am unable to function to just get a drink.

Once at Midway, I pay $3 for a train ticket into the city. I have no idea what I want to do first, but time is ticking, so the city it is. Besides, that’s where I need to be to take the pink train to the general area of where I am staying. I later realize that if I had done more research on the metro payment system, I could’ve saved that $3 and just bought the weekly unlimited travel card for $28 (there is a $5 fee for a new card, but by filling out a form on their website, it is refunded… yes I am that frugal! $8 in savings is groceries, cereal and milk, or almost half a nights stay at another hostel, which means a whole new perfect day I can add to my travels. Trading time for savings gives me more time before I ever have to actually go to work. (Which has now been 10 months since I actually clocked into a job anywhere)

This blog is taking forever to write! I feel my concentration slipping, but I want to get it done because I have been wanting to write it, knowing that so many of you want to know.. so yea day one.. I find a list of things to do in Chicago for free, and I start doing them. $12 in groceries when I get to the airbnb. (Thank you Harrison!)

Unexpected expenses included filling prescriptions – $12 and I lost my transit card, so I had to pay another $28 for a weekly travel pass. I did treat myself to a nice formal dinner, and ate at cheaper dine in places a lot more than I anticipated. It is exhausting walking all over a city and seeing everything, not to mention I had pneumonia and didn’t know it, so it’s not surprising I didn’t have the energy to be conservative about food, and preparing my own meals. I also paid $21 for the 360 observation deck. It’s $19 for one visit, and was $21 for two visits within 48 hours. As a photographer, who doesn’t want a night and a day time experience?
After the two nights at Harrison’s place, I found another airbnb to keep me for a night at $35 – a little more than I’d like to spend, but it was a private room, and tho I attempted to find another traveler thru the nomad facebook groups, and various other travel friends groups I interact with, it was short notice, and I had the room to myself, which given I didn’t know I had pneumonia, was probably for the best. Over the counter meds and cough drops, thermometer etc $25 Two days in bed at a friends house (free lodging and amazing company, Thank you Annette!) An amazing free raindrop technique using Young Living oils, and I was up and running for another couple of days! Lincoln Park Zoo, skyline pictures, a free guided walking tour, and before I knew it, it was time to fly to NYC!
Total expenses for a week in Chicago, flight, lodging, food, attractions, and medicine = $220!
Stay tuned for an even cheaper week to and in NYC!!!