Originally Posted by sard

Just got back from my trip, brief recap:
1. We ended up staying at the Homewood Suites on 40 E Grand. Good location, nice staff, I liked it. The staff for the food/kitchen/breakfast was very very nice and helpful - thumbs up!

2. First trip for a family event and first trip with kids.
2a. Multiple family dinners, so that cuts into the sight seeing time
2b. Totally was not prepared for traveling with kids. You don't realize how much time is spent on things while at home - for example breakfast. We spent over an hour each day at the hotel trying to get the kids to eat their breakfast. By the time breakfast was done and the kids were cleaned up - its after 10am!!
So on Friday after breakfast, we walked to Navy Pier - by the time we got there (15-20 minute walk) - both kids were asleep! So we turned around and walked back to the hotel and bought lunch. (family dinner that night)

3. Picked up the rental car on Saturday morning - the Hertz location ran out of cars so I had to wait about 20 minutes for one to show up.
Took donnde's suggestion and did a one way to Union Station that night
3a. Union Station's after hours location is very hard to find. I circled the area for over 30 minutes trying to find it, finally asked a police officer who told me where it was. The Hertz address is: 225 S Canal - but the garage is on the perpendicular block!
3b. The location/staff gets a thumbs down from me. I called Sunday morning to check on the return status (called 10 times before someone picked up the phone) was told they have a lot of cars to return so they will get to it sometime "today or tomorrow". Finally called again 5 minutes before closing and was told the same thing. Called Monday and was put on hold for 15 minutes before I hung up. Finally called customer service who told me the contract was closed out. BUT I NEVER received a receipt from them (no email receipt) - horrible customer service

4. Sunday we took the kids to the Childrens Museum at Navy Pier - they enjoyed it. Then family dinner again.

5. Monday - Millennium park, the kids enjoyed Maggie Daly park - then we went back to the hotel for their nap and then family dinner

So did not get much sight seeing done due to family meals and the kids nap schedule and their eating times.

Thank you all for the helpful suggestions