Flight
Out of the two main Chicago airports (O'Hare and Midway), ORD is closer to to the Northern suburbs and only about a half hour to forty minutes from Winnetka.
Hotel
We have a small room block (Youngbrandt Skibinski Wedding Block) at this hotel and will likely be staying there ourselves. Only 12 minute drive (or uber) from the Community House Winnetka.
Hotel
Youngbrandt Wedding Block
Hotel
While we do not have a block here (hotels are definitely pricier in the area), Evanston is a great place to stay since you have access to the Metra line that will take you directly up to Winnetka if you didn't want to worry about driving. There's also plenty to do in the area and you have access to Lake Michigan. If looking to book here I would pay attention to whether the hotel has free parking or not (if needed).
Hotel
Skokie has a handful of reasonably priced hotels near Old Orchard Mall. Plenty to do and only 15 minutes from the venue.
Train
If you are staying in Evanston there is a Metra Stop on Davis Street that will take you up to Winnetka. The train ride is about 12 minutes and from the Winnetka Station it is a 6 minute walk to the venue. There's a train shortly after 3 and one closer to 4 (check the website for times and tickets). If opting for the earlier train, there are plenty of shops and restaurants downtown Winnetka within walking distance from the venue. Guest access to the venue begins at 4 pm (you will not be able to arrive earlier than that). The Metra is also an option if you are wanting to stay downtown. The train ride from the city is about 40 minutes. This line runs to the Ogilvie Transportation Center Near the West Loop. As with any public transportation, plan ahead to be aware of potential delays.