<prompt> Human: Edit: Awesome stuff here guys, really appreciate the outpouring of advice and suggestions. Even the shitty ones. I will get a receipt for everything. I promise. Okay? Oh and I am in the process of getting clarificiation and details from my bosses, and I feel much better doing so after getting the basic info from you all. Chicago sounds awesome. Im gonna improv some ketchup on a hotdog on top of a shiny Bean thing, after I deep dish the shit out of something something Wrigleys field. Cant wait. Thanks again for all the helpI know I should be asking my bosses, but Im just trying not to come off as too inexperienced. But I have a ton of stupid questions, so I have come to reddit for answers. BackgroundHourly Employee, Pittsburgh area. Company offered to fly me to Chicago. Questions:1- Do I get Paid? Do I get paid for travel time?2- They are making flight arrangements, but I guess the hotel arrangements are up to me. Whats a reasonable price to pay per night? Should I book in advance?3- Do I take taxis? Ive never rode in a taxi. Do I Uber? 4- They said they can either provide me with an advance or I could pay for things like hotels, food, taxis on a credit card and then submit an expense report for reimbursement. Is one better than the other?5- What do I do in a strange city at night by myself? I am not a social person, but I refuse to stay in a hotel room the whole time.  <response>: Chicago native Born, Raised, and Still Here. Yes, from the city. Not the suburbs. here. Im also a consultant who has been on several travel projects so I consider myself experienced in this area. Some of the following will be repeating what others have said. Some will have a Chicago spin on it.1. Do I get Paid? - You better be. Most training is considered to be on work time. Particularly during the hours that youre actually being trained. Make sure youre getting paid. Do I get paid for travel time? - This one is up to your company. As a consultant we dont bill our clients for travel time so effectively we are not paid for time spent traveling. This is more a question for your company. I wouldnt expect anything, but you might get lucky and get Yes for an answer. Every company is different.2. Whats a reasonable price to pay per night? - It depends on where your training is. Youll likely be asked to book a hotel in the most convenient location. In Chicago Id expect anywhere between 100 and 150night. It really depends on the area. But you should check with your manager or whomever is in charge of paying the bill for your training and find out what they expect. Should I book in advance? - Yes. Definitely. Book as soon as you know how much youre able to spend and where youre expected to stay. Prices only go up as rooms are booked so book ASAP. Many hotels have a cancellation policy as long as youre outside of a week before your travel time.3. Taxis or Uber? - Again depends on the company. If you work at a large company then they really wont care - its up to you. If you work at a smaller company then they are likely more cost conscious. Taxis and Ubers will be factored into the cost of getting you to Chicago and tofrom training, so I doubt it will make much of a difference monetarily. It depends on which one youd prefer. If youve never taken a taxi before here are a few tips: Stand on the curb of street corner that is pointing in the direction you need to go, raise your hand in the air, and look at every taxi that approaches. One will stop for you.4. Credit Card of Advance? - I pay for everything on my credit card because I get points or cash back. Your company should have a policy on receipts and expense reports. At my firm we are expected to show a receipt for any purchase over 25. Spend 24.99? No receipt. I take a picture of my receipt The receipt that isnt itemized with my cell phone and I toss the receipts away. When Im back home Ill email these receipts to myself and attach them to my expense report. If your company expects physical receipts then make sure you store them all somewhere Likely your wallet or a pouch in your bagsuitcase. Make sure you know your daily spending limit. My daily allowance per client was between 60 and 75 to be spent on food only. Your company may differ. If you cannot pay off your credit card then take the advance. The worst possible mistake you could make is charge too much to your credit card and not be able to pay it off. You will end up being charged 15 on your entire monthly credit card statement. Not fun.5. What to do? - This depends on where you are in the city. If youre in the loop then things slow way down around 78PM. I suggest walking along the lake - there is a well-lit walkrunbike path that spans our entire lakefront. Its beautiful and usually well-populated. You can go to Navy Pier and - depending on the day - see the fireworks display there The restaurants and stores in Navy Pier are a ripoff so dont go there to shop. Several neighborhoods have a great night scene - good restaurants, awesome bars. Make sure you try at least one Chicago Hot Dog. I know this sounds cliche and you dont need to love it, but you can say you tried it. If you can avoid it, dont eat at any chains. Youve probably seen 1,000 chipotles, Taco Bells, Starbucks, etc. Try something new. Try something you wont find in Pittsburgh. Post on rchicago a few nights early and see if anyone wants to hang outshow you around or if there are any events ongoing. Most Chicagoans hate the touristy stuff but Im sure if you ask nicely there will be someone interested in giving you a tour. Im sure Ive left out a lot of options. Feel free to bounce any ideas off me and Id be glad to tell you if theyre worth your time.Good luck! 