The hardest part of planning a hip hop based tour, is securing venues.
You will be executing Part 1 and Part 2 of BUILDING CONSENSUS simultaneously.
College towns are the way to go. Especially if you can book your show for a Thursday night in these towns (most college kids have Friday off, or a late class, if that.) So a lot of venues have that night for a "college night" anyway. In your bigger cities, if you can link up with a great act, you want a weekday, Tues or Wed depending.
Try not to book on Sundays, unless that is all the venue will give you. If you cannot give the venue a strong lineup with artists they may be familiar with (which is why you looked up the shows for each artist) They WILL most certainly not give you a weekend. Plus, most of these venue owners have a problem with hip hop, and "the kind of crowd it brings" So not having it on a Friday or Saturday night, helps you to put them at ease about it.
Let's face it, (now I'm going to go there) Hip Hop gets a bad rep from people who say they are serious about performing, but invite people who are looking for trouble, or they themselves are troublesome, ie; smoking weed in the venue, fighting, not buying drinks at the bar, bringing their own drinks to the bar, not tipping, etc... You have to be very careful that you don't give yourself a bad name by not respecting a venue, which is why they have reservations about booking hip hop acts in the first place.
It is this reason mainly that I created this blog, as a hip hop artist, you have too many tangibles that could hold you back from being successful at touring. And unless we identify these intangibles, we can't make moves. The more you understand, the better you can plan.
So, I go to a place online called IndieOnTheMove it is free to sign up with and you can compile your "following" list for venues you want to work with. When you use a filter like "hip hop" to search for venues, the ones that show up don't quite "as-a-matter-of-fact" accept hip hop submissions, and there are some of course who want nothing to do with hip hop or rap. Metal is another one of those red-headed stepchildren that gets no respect. (Shout-out to the ginger kids)
Look for venues that are currently booked with hip hop acts and contact them. You need to make sure your spelling is pristine and that you should always communicate as a "representative" of the act. Don't say, "I'm a rapper, and I want to book a show", talk a bit about the date you have in mind (it should be so far away (monthS), the venue will most times have it open; Unless they are a national touring spot. Then who knows?)
Venues don't really care about your submission, they would rather meet you so whenever you find their booking email, send them your press-kit, wait 1 week, and then give them a call. Be nice and professional, they might not even had a chance to look at your press-kit, and if you behave as though they slighted you, they will show you what that slight really could be. You see, most venues usually have a SIN (Service Industry Night) and this is where venues offer drink or food specials to employees of other venues, just so you know, they talk and if you have made an impossibly irreversible impression, you can bet this is where, "you'll never work in this town again!" Can be true to the bone.
I got my first job by calling and showing up to the place EVERY SINGLE DAY FOR A WEEK, I'm not kidding you. They weren't even hiring, but I showed my earnestness and commitment to the objective; they appreciated that and hired me within that week. I loved that job. So don't be afraid to call, the absolute worst thing they can say to you is they "don't want no nigger music here!"
That is an obvious worst thing, but even if that's what they want to say, they won't say it like that. So, "no" will be the worst (usually) that you will hear. Because of this, you need to compile a list of every venue willing to work in hip hop, that's all. Some cities have more than others, your job is to make one of those venue commit to a date. If they'll listen, tell them your plan, which should include a roster or lineup, your touring dates, your promotional plan, etc... Most venue owners just want a professional act. They, like you and I, are tired of live music acts from all genres who plan poorly and suck. But then they blame the venue for not doing more.