re: chicago in july

If you want to save a ton on hotels, you can stay in the suburbs, take the train into town, and then take it back out to the suburbs. It would obviously be a bit annoying, but if saving money is the #1 priority, it's not a huge hassle.

If you were to do that and you wanted something super cheap, you could book the Red Roof Inn in Northbrook for around 60 bucks a night. You're a 20 minute walk or cheap uber/cab ride away from the Lake Cook train station. Round trip train tickets are like 12 bucks each and the ride is 40-60 minutes each way depending on time of day. The hotel is in an upscale suburban area.

When my parents have out of town guests stay with them, they take the train in to the city to spend the day and don't find it to be a huge inconvenience.

I mean, if you want the best experience possible, staying downtown would obviously be preferable, but you can save a few hundred bucks with what I suggested above. Sort of a crazy idea, just throwing it out there in case.