During a week in July, my husband and I hosted his family for vacation. Spread between three houses (including ours), were 19 family members, ages 6–70 years old. With a small backyard and a basement only a teenager would love, we had to get out and about in the city.
To help inspire anyone who's in a position to play host this fall and beyond, I'm sharing what we did and how it went — both the "goal" and the "reality."
Chinatown on a (sweltering) Tuesday ⭐⭐
Goal: Drive to Chinatown, take a water taxi to downtown and back, shop, eat, drive home.
Reality: The water taxi was only running on weekends over the summer. Bummer #1.
Parking was easy in the Chinatown North Parking Lot (2001 S. Wentworth Ave.). After parking, we met inside the beautiful, air-conditioned library (2100 S Wentworth Ave.). So far so good.
We ate lunch at Triple Crown Restaurant (2217 S. Wentworth). Amazingly, they sat all 19 of us right away, at two big tables right next to each other. The dim sum was delicious but it was a severely hot day and the A/C couldn’t keep up. I sweated through lunch.
[Related: Chicago date-night ideas that go beyond dinner and drinks]
After lunch we tried to stay together, but as a big group on a narrow sidewalk trying to make a decision about where to go next, this was not fun. Eventually we all made it to the plaza together and that was much better. Bubble tea, shopping, finding some shade…everything was OK again. Except for the fact that when we got to the parking lot, we realized that we had neglected to get our parking tickets stamped at the restaurant, and had to pay full price for parking. Sigh.
Downtown on a Wednesday ⭐⭐⭐
Goal: Take the El downtown, go to the Skydeck Ledge in the Willis Tower, then to Millennium Park and Maggie Daley Park. Eat lunch along the way.
Reality: We purchased tickets to the Ledge ahead of time and took the train to Willis Tower. There was no wait to get into the elevator. So far, so good.
The winding line that we stood in to actually walk out onto the Ledge was long, but moved quickly. We were a group of 20 and they allowed 14 of us on the ledge at once. Pictures turned out great!
Back down at street level, half of our group went home. The rest of us (ages 6-70) ate lunch outside at Willis Tower and then walked to the Crown Fountains at Millennium Park. Everyone had a good day.
Climb Zone on a Thursday ⭐⭐⭐⭐
Goal: Let the kids burn some energy while (some of) the adults do other things.
Reality: We had eight kids in our group, ages 7–16. They all climbed and played video games, bumper cars, and laser tag. We ate pizza, chicken strips, and salad. Parking was tight in the lot (2500 W Bradley Pl.), but we had the inside almost all to ourselves. Easy and fun.
[Related: Chicago venues that cater to kids with special needs]
Miko’s Italian Ice on a Sunday ⭐⭐⭐⭐⭐
Goal: Walk to Miko’s (4125 N. Kimball Ave.), eat Italian ice, be happy.
Reality: Exactly as planned!