Note, in shipping bikes it is cheaper to ship to a business then a residential address. If your company has an office in Chicago that might work or maybe someone might be able to offer theirs as a shipping ground. Each airline has different policy's regarding fees for bikes..for example Sun Country is $40 each way whereas NWA is $80. Yes, it makes no sense.
Would love to make this and see some of my old friends in Chi-town...let me check the schedule and flight miles.