Since it is seeming less and less likely that I'll be able to get a cancelation to a hotel with a skybridge....

Are there hotels that have regular shuttles to/from ICC? Since the hotel I'm booked at will most likely have the 'airport' tax/pricing associated to it, Trips back/forth could equate to $200+ a day. Doable but I'd rather use that money for a closer hotel or plan with the convenience of a shuttle.

PS: if anyone has a skybridge hotel reservation they want me to take over so they don't get the cancelation fees, feel free to ping me! I can afford a pricey room but don't want to support the resellers asking $700-900 per night or the BNB folks asking for $1000 per night.  

Not that I know of. There is a bus that goes from the airport to the convention center (although it doesn't run late at night), and I assume a number of airport hotels have shuttles to the airport, but I don't think any outlier hotels have shuttles that go anywhere downtown.  If you think it will cost you $200/day to travel back and forth, have you considered renting a car and a downtown parking spot?

They tried shuttles in, if I remember correctly, 2014 and 2015, but there were too many problems with them (one of which was, unless you had a hotel near the beginning of a shuttle's route, they tended to fill up before they got to your hotel.

@del_grande  a little of column A a little of Column B, right? 

Renting a car is about $115 per day (cheapest on Enterprise) and then you have traffic, parking($20-75 per day), & gas. From what I hear parking is a PITA as well.

Uber price estimator shows $60 one way WITHOUT an event going on... so $200 a day is a guestimation at best. 

I assume you're near the airport, so my guess is, the #8 bus that goes to/from the airport is your best "cheap" option. However, I can't guarantee that every hotel has a shuttle to/from the airport.

It seems like my current options are:
1.  Get really lucky and get a cancelation and everything is great.
2.  Keep my current reservation but basically pay the same amount as the skybridge folks due to transportation and have less time. 
3.  Keep my current reservation, not pay $200 per day and have even less time at the con and reduce my schedule.  

It's killing me too because I HAVE a good budget for this trip. But unless you want to pay $5-20k for the hotel alone you're out of luck(...f@#$ forced scarcity and reselling mechanics...) 

To illustrate the point, I can see two resellers:

• one reselling a Crown Plaza Downtown room (without tax) $271 per night for $784 per night (resold around $4600 total) 
  
• one reselling an Omni room (without tax) $277 per night for $1084 per night (resold around $6000 total)
  

Non-Gencon arranged rooms:  TBF, I would probably pull the trigger on the Hotel Indy if it had 2 Queen beds. 

• Le Meridian - $725 per night (without tax)
  
• Hotel Indy - $576 per night (without tax)
  

Not being super-familiar with the Uber pricing model, is a regular taxi likely to be cheaper than surge-price Uber?

just found an AIRBNB for $390 per night under a mile from ICC and thinking about pulling the trigger....

If they're a superhost, I personally believe your should. 

If they're not, I won't recommend that you avoid it, but I think a superhost would be more conscientious of not cancelling reservations just to relist for more money. That's the problem some Gen Con goers have suffered: Cancelled reservations so that owners can relist for more. So that one would be your call. 

Really, both ways are your call, but the advice I've seen is to go with superhosts when possible. If that doesn't apply to this one, I don't know what to say. I don't even know what I'd do in your shoes. 

It’s not going to cost $200 to Uber/Lyft back and forth. I’ve done so ever since my first GenCon in 2018, and I’d estimate it’s about $60/round trip each day.

OMG, if dingodefalco's going to buy you $140 worth of steak, take the deal!!

Hehe, yeah. I've paid some prices in Chicago before! And I think Seattle's even more expensive than that. 

I was also about to say there's nothing that pricey in Indy... but then I double checked. Turns out Hyde Park Steakhouse (downtown, just past Buca Di Beppo's and Giordano's) has "Steak Andretti", a 40 ounce (zomg) tomahawk ribeye for $120. 

I can't even finish a 20oz. I'd be unconscious before I got halfway through a 40! 

So anyway, yeah, I guess it's not that hard to blow $140 on steak after everything is said and done. Even in Indy. 

You going to be hungry by Gen Con mpagnotta310? :D 

On one hand, yes, there’s surge pricing. But on the other, there is absolutely no shortage of available Ubers/Lyfts. In fact, most Lyft/Uber drivers know about GenCon and are working extended hours because not only do they do good business, but GenCon attendees also have reputations for being generous tippers. I don’t know how you got that figure, but from past experience, it’s wildly off. The most I paid for a Lyft last year was $36, and that one was with surge pricing. Expecting to need $200/day is not a good estimate.

And if you’re going to buy me $140 worth of steak, I do have a reservation at St Elmo Steakhouse on Friday night…

$36 per ride sounds about right from my experience too. You can generally avoid surges by waiting 10-15 minutes, walking a block or two, or switching apps. 

• Caveat: The steak is null, if I end up getting a hotel closer to the con. Currently I'm at one of the hotels with the words Airport in them. For privacy, I'm not saying which. If I'm stuck, the game is afoot.
  
• I will take screenshots of the e-receipts but will blur my name & account numbers... I suspect at that point you'll get the idea of where I'm staying.
  
• We'll check the totals for trip & tip to and from the con for 2 people for both Thursday and Friday. I'll calculate the average of the total for each day.
  
  
  
  • If the amount is closer to your prediction($60 per day) I'll buy you the steak of your choice at St.Elmos on Saturday.
    
  • If the amount is closer to my prediction($200 per day) I'll buy you a drink. 
    
  
  
• Caveat: I can't tip more than 20% but I can get to pick the service & car.
  
• Caveat: If you can't show up while I'm at St.Elmos, this will all just be for fun. I'm not changing my schedule to buy you a steak/drink.