You can technically fly into either O'Hare or Midway. However, O'Hare will be closer to whatever accommodations you will make on the northside of the city as well as D.O.C Wine Bar, so we recommend O'Hare.
There is metered street parking available along Clark and the surrounding area. D.O.C Wine Bar offers $6 validated parking just south of the wine bar after 5PM.
Cocktail party attire is fine. Not too stuffy. Dress comfortably, but if you want to class it up, we're all about it. The Grooms will be in suits.
There are tons of things for you to do! You can wander around the various neighborhoods and just loosely explore the city or visit some of the larger tourist attractions here. There is the Willis (Sears) Tower, with their Sky Deck and great views of the entire city and the John Hancock Tower with excellent views as well with their signature tilt out viewing. The "Bean" is a great place to grab some photos downtown in Millennium & Grant Park (as well as walking over to see Buckingham Fountain). Wrigley Field is worth checking out as are many of the bars in the surrounding Wrigleyville area. As far as deep dish pizza goes, some of the best options are Pizzeria Uno and Pequods. There are also tons of museums if you're interested, with the most famous probably being the Art Institute of Chicago in downtown Chicago. If you have any other questions about what to do just let us know!