DH and I are currently in the planning process for a trip to Chicago too but we're going for a Cubs game
We're also flying into Midway and will be staying on the Magnificent Mile near Navy Pier and plan to take the CTA "L" everywhere. Unfortunately I don't have any recommendations for hotel deals as we are using hotel points for a free room for the duration of our visit.
We've already ordered CTA Ventra 7-day passes online so that we don't have to deal with them when we arrive. They have a $5 charge for the card and can get it credited back to the card but it's a process to get it back in order to pay for the multi-day pass with those funds. Too much trouble! If you order them online in advance you don't have to pay the $5 fee plus it's free shipping! They have 1 ($10), 3 ($20), and 7 ($28) day passes.
https://www.ventrachicago.com
We've scoped out all of the touristy things we want to do and decided the buy a Chicago CityPass as this will provide the greatest savings for what we want to do.
I've looked everywhere online for discounts for this but there aren't any and even the website mentions how it's already a huge savings that they don't offer any additional discounts for them. I found discounted pricing for the Chicago CityPass through "Tickets At Work" which has a discount website which my employer is an affiliate and saved $13 on each adult pass (we paid $85 each vs. list price of $98 each). There are other passes out there too - Go Chicago and the Chicago Explorer Pass, but be careful if you get the Explorer Pass as I've read online that this pass doesn't allow for skipping lines/fast pass at sites.
We've also done loads of research on restaurants we want to try and have already made reservations for seatings even though our trip is many weeks out. And, although they have lots of great stores for shopping, DH and I have decided not to plan to shop there since their sales tax went up to 10.25% in January and there is no tax exemption for clothing.
We are so excited as we plan our upcoming trip!! Glad to see this thread and I'll also be following to get more tips!