What he's saying is, there are a decent amount of minimum wage jobs in the city, and plenty of cheap housing. $800 can get you into something comfortable and clean and safe, SOMEWHERE in this city. Plus right now Chicago has really strong job growth so you're lucking out a little bit in that department.

The CTA is $2 each way with a Ventra card. Do you have a car? Do you REALLY need it? If you're going to Uber or do deliveries, figure that out ASAP.

Get the jump on a job ASAP. Shit I saw Dominos advertising positions on top of their pizzas because they couldn't hire enough people. Last I saw, they were offering $500 hiring bonuses but I'm not sure about that anymore.

But you're absolutely right. I think getting on your feet will be easier in the city, given the cheap nature of the CTA.

You might even be able to get a decent amount of that money just by driving for Uber/Lyft etc. Also check out tasker or the other "on demand" apps.

Also, Amazon is always looking for delivery drivers and I hear their scheduling is VERY flexible in that you basically sign into the app and start working.

https://goo.gl/maps/mxREMCbhoHVdCZ3K7

https://www.indeed.com/cmp/Amazon-Flex/reviews?fcountry=US&floc=Chicago%2C+IL

Also, you're married, so once the both of you solve shelter, food, and water. The next thing you'll need to take care of is both your stress levels. Don't forget to keep dating your wife. Here is a ton of free stuff to do in the city you can both do to save money on dates after you're on your feet. I highly suggest Chicago Symphony Orchestra concerts free in Millennium Park. Free dance lessons in Grant Park through Summer Dance. Free Thursdays from 5pm to 8pm at the Art Institute. Bike rides along the lake front.

Maslow's Heirarchy of needs. Work upwards. Do what you need to do.

Cheapest groceries tend to be from Aldi FYI.

Check out Wag and Rover. Both have apps where you can make money walking dogs. Wag accidentally sent someone's W2 to my address. I wasn't paying attention when I opened it but the person made like $4k that year walking dogs.

There's delivery for GrubHub/Fooda/all that shit don't forget.

Also, don't ever be too proud to walk around to various companies in the area and explain that you have a wife and are looking for any job to get you a cheap place to live. There is NOTHING shameful about your situation. You're trying to take care of yourself and your wife, IMO that is something to be proud of. People in Chicago want to help. Maybe they won't have a job for you, but know someone who knows someone. Check meat packing companies, or maybe check the chocolate factory in the west loop. I don't know what kind of skills you have so I'm being very generic here.

Tons of hotels here too, they might be looking for cleaning staff?

If you have any clothing you're not using or any household items you're not using. Check out what their eBay value is. You can also check out plenty of thrift stores and try your hand at reselling cheap local items online.

Check the free section of craigslist and try to sell some of it on eBay and the other online selling apps. That VCR some dude is giving away? Might be selling for $25 online. As someone who has been on eBay since 1999, my total sales amount is up to like $60k. I've made a ton of money flipping items over the years. But be careful because you can lose money if you're not mindful.

For example. This hacksaw is in Edgewater. Try to double up your time. If you're driving around for Uber/Lyft and end up on the north side. Temporarily sign out of the app and go pick this item up. It'd sell for about $10-$15 in profit on eBay. If you pick up a ton of little items to eBay while cruising around for Uber you can kill two birds with one stone and double the amount you're making per hour. Aim for little things nearby. Ship cheaply but always with a tracking number.

Another example is this blender pitcher. It sold for $29 shipped.

Long term, after all of this. You need to start thinking stability. What skillset do you have. Are you good with computers at all? Are you good at learning how to learn? That's a huge skill. If you can follow some basic Youtube tutorials and learn some programming. You could have yourself a pretty lucrative career. Maybe start out with bash and write some basic stuff to get a feel for things and move on to other languages.

Other skills, once you get on your feet. The City Colleges of Chicago have some really great associates degrees. Nursing for example is actually VERY good at CCC because you get your nursing degree for PENNIES on the dollar. You or your wife could take 2-3 years, get certified to be a nurse. There are still hospitals around here that hire nurses with an associates. That's easily $50-60k/year.

If both you and your wife became certified nurses, bam, you just became a 6 figure household for the price of CCC tuition.

Check city jobs too. Garbage workers make bank. Water plant might be hiring. CTA might need bus drivers. City hall might need a security guard. City jobs come with health insurance.

Sorry for the word dump. Good luck man.