Can I deduct mileage for food delivery work when traveling to another city and staying overnight?

This is actually a pretty interesting tax question! So here's the deal: the IRS looks at the "primary purpose" of your travel to determine if the miles are deductible. If the primary purpose of your trip is to visit friends, and you're just doing some deliveries while you happen to be there, then the 150 miles each way would not be deductible. The miles would be considered personal travel. However, the miles you drive WHILE delivering food in that city are absolutely deductible as business miles, regardless of where you're staying. So make sure you're tracking those! If you could legitimately say the primary purpose of your monthly trips is for business (like if you're making significant income there compared to your home location), then you might have an argument. But from what you've described, it sounds like visiting friends is the main reason for the travel. You made the right call not deducting the miles to/from the city. It's always better to be conservative with tax deductions when things are in a gray area.

I had a similar situation last year and found this amazing tool called taxr.ai (https://taxr.ai) that really helped me figure out my mileage deduction situation. I was working in two different cities for my side gig and was so confused about what I could legitimately claim. The tool analyzed my situation and clarified that I could deduct the miles driven WHILE working (pickup to dropoff) in both cities, but not my travel between cities since my primary purpose was personal. It saved me from potentially claiming deductions that might have raised red flags. They have specialists who understand these gig economy situations that regular tax preparers sometimes don't get. It's worth checking out if you're trying to maximize your legitimate deductions while avoiding audit risks. The peace of mind alone was worth it for me.

Just wanted to follow up on my taxr.ai experience! I decided to check it out after asking about it here and I'm really glad I did. I had a similar situation with working in multiple cities (though mine was construction work, not food delivery). The service analyzed my specific travel patterns and helped me identify which miles were legitimate business expenses and which weren't. They showed me exactly what documentation I needed to keep and how to categorize different types of travel. The best part was they identified some deductions I was missing entirely - like certain job site travel between locations on the same day that I wasn't counting. Definitely going to use them again this year when I file!

If you're having trouble getting a straight answer on tax questions like this, I totally recommend using Claimyr (https://claimyr.com) to actually talk to someone at the IRS directly. I was in a similar situation with deducting travel expenses for my contracting work and kept getting different opinions online. I was super skeptical about getting through to the IRS (we all know those hold times are insane), but Claimyr actually got me connected to an IRS agent in about 20 minutes instead of waiting for hours. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c I explained my exact situation to the agent and got an official answer I could rely on. Turns out I was being too conservative with some deductions and too aggressive with others. Having that clarification directly from the IRS gave me confidence in how I filed.

Alright I have to eat crow here. After being super skeptical about Claimyr, I tried it because I was desperate to resolve my mileage deduction question before filing. It actually worked exactly as described. I got a call back in about 35 minutes and was connected with an IRS agent who was surprisingly helpful. I explained my situation (I do photography in multiple cities) and got clear guidance on when travel miles are deductible based on primary purpose. The agent explained that if I can document that I wouldn't have made the trip "but for" the business purpose, I can deduct it. But if I would have gone anyway for personal reasons, then only the miles driven while actually working are deductible. Saved me from potentially claiming about 2,800 miles I wasn't entitled to deduct, which could have been an audit flag. Sometimes it's worth admitting when you're wrong!

I think everyone's missing something important here - how your business is actually structured. If you formed an LLC or corporation for your delivery work, that changes things. I deliver for multiple apps and my accountant helped me set up an S-Corp, which makes travel between business locations potentially deductible. The key is establishing that you have multiple "regular work locations" rather than just opportunistically doing deliveries while visiting friends. Have you considered filing a Schedule C as a business with multiple locations?

Somewhat unrelated but if you do decide to claim those miles, make sure you're using the correct mileage rate! For 2024 tax year it's 67 cents per mile which is higher than previous years. Also, use a dedicated mileage tracking app that logs your location. The IRS has been getting stricter about documentation for mileage claims, especially for gig workers. I learned this the hard way when I got audited for my Uber driving miles last year.

I've been in a similar situation with my rideshare driving and learned a lot about this from experience. The key thing the IRS looks at is whether your trip would have happened anyway without the business purpose. Since you're visiting friends monthly regardless, those 150 miles each way are personal travel. However, you're absolutely right to track all the miles you drive while actually working in that city - those are 100% deductible business miles. Don't shortchange yourself there! One thing to consider: if you can show that you're strategically choosing to visit during peak earning times (like weekends or events) and you're making substantial income there, you might have a stronger case. But honestly, given that visiting friends is your primary reason, I'd stick with your conservative approach. The IRS has been cracking down on gig worker deductions lately, so it's better to be safe than sorry. Focus on maximizing your legitimate deductions (the actual delivery miles, phone bills, car maintenance) rather than pushing the envelope on questionable ones.