Where to meet in Chicago
- the West Loop
- Wicker Park
- Lincoln Park
- the Gold Coast
How the day runs
Chicago is friendlier and less formal than New York, and dresses that way, though the better downtown rooms still expect smart. Dinner is between seven and nine. The city loves its food without fuss, and a day here pairs well with the lakefront, a museum and a long meal.
Getting around
The L runs around the clock on two lines and late on the rest, and the downtown grid is easy to walk. The lakefront trail stretches for miles and is one of the finest urban walks in America.
When Chicago is busiest
May to October is the good season, when the city lives outdoors — festivals, the lake, rooftops. Winter is hard, with a wind off the lake, so from December plans move indoors. Thanksgiving and Christmas bring families home and fill up first.

Questions about Chicago
Is the lakefront worth putting in the plan?
From spring to autumn, absolutely. The trail runs the length of the city, and a walk there before lunch or dinner is an easy way to start the day.
Can she come home with me for the holidays?
Yes, as one full day. Give us the date and where the family lives, agree arrival, the meal and the end of the day in writing, and meet somewhere public first.
Does winter make the day harder?
Cold enough to plan around but not to stop anything. Build the day around indoor places — theatre, music, museums and restaurants carry the season.
Good to know before you book in Chicago
Availability
Available by private request
Response
We reply within 20 minutes, 9am–9pm daily.
Meeting style
Public places first: cafes, restaurants, museums, parks and markets
Strictly platonic, and written down
Every rental is one day, planned with you and agreed in writing before you meet. Nothing romantic or physical is part of it, and either of you can end the day.

Days people rent for in Chicago
Every rental in Chicago is one full day, planned with you, with the boundaries written down before anyone meets.
Plan your day in Chicago
Tell us the date in Chicago and what the day is for. We will tell you privately who is available, and nothing is booked until you say yes.
We reply within 20 minutes, 9am–9pm daily.
