Ask Fan Landers: What Can I Do To Make My Album A Success?
You want to be consistent, not pushy. A simple two-line email inviting them to any bigger show you are playing about a week before the show is ideal. You do not need to invite them to every show. Things that can help develop a rapport: tell them if there is another awesome band on the bill, or that you agreed/disagreed (respectfully) with their review of a new record, respond to one of their tweets--just something that isn't like MY BAND MY BAND OMG PLEASE LET ME TELL YOU ABOUT MY BAND, all desperation robot style. You are paving the way in advance so that you have a direct route to them once it is time to drop the album.
If you would like to hire a publicist/radio/marketing for your album promotion, three to six months out is the time to start shopping for them. Ask bands you know, bookers, folks at small labels for recommendations, find out whom they usually hire (or if they do). If the new album is a departure from your existing material, having demos of two or three songs will be useful in this process, if you do not have the entire album already in the bag.
Network with other bands with more touring experience and see if you can't find folks who want to do weekends. One of the great things about Chicago is the Midwestern college town circuit. Play some shows with bands that aren't an exact fit with your indie rock pop sound. Make yourself known to other scenes, other fanbases.
Your website is pretty solid, utilitarian. Like that Downtown Chicago in glowing reggae colors graphic. Make sure you have a few songs that are downloadable, a press photo that is downloadable (both high and web resolution) with the band members ID'd left to right, and a bio that is actually about your band. The amount of bios I get from bands where there is no useful information--the names of members, where they are from, who produced the album, what they might sound like, how many records they've made previously, how long they have been together--is staggering. If there is anything special about the album or the song that one might not instantly derive from listening--a concept, theme, inspiration, it is useful to mention that as well. Make sure your online shiz serves you well and is functional and all connected.
Since you are investing a lot of effort and (probably) money into your band at this point, make sure you have all your insurance ducks in a row. Everyone in the band should have renters insurance; having gear stolen can jeopardize your existences as a band (see also: fellow Chicagoans Nude Sunrise, currently trying to raise funds after being robbed of all their gear). Renters insurance is, like, $8-12 a month if you tack it on to an auto policy. Go visit your insurance agent and make sure you have a policy that covers your van being broken in to, and make sure the policy accurately reflects what it would take to replace all your gear. Ask all the annoying what if questions you can think of. Document your gear: take photos, get serial numbers, and any documentation on it. Make a couple copies of all that business and each of you stash one in a safe place.
All that stuff is the unsexy end of the hustle, so make sure to throw in something fun. Start a tumblog, screen some shirts, start a band zine, make a mixtape for your fans, come up with a contest that happens at your shows, play a birthday party, do an elaborately staged publicity photo or, perhaps, nurse a rivalry with another band. Everyone loves a good beef.
Good luck with your album and have a safe tour.