Chicago is a city built for going out -- bars on every corner, a restaurant scene that competes with anywhere, a lakefront that fills the second it is warm enough.
And it is under snow for a good part of the year.
Those two facts together make it one of the better American markets for paid company, because the need swings hard in both directions and never disappears.
Roavi is not a tour company and you are not a guide. People pay for your time and your company -- dinner, a concert, an afternoon walking somewhere, someone to talk to. That is a real trade with a long history: platforms built on exactly this have operated across the United States for well over a decade.
Summer: nobody wants to do it alone
From roughly May to September the whole city is outside. Beaches, patios, street festivals almost every weekend, the lakefront path, baseball. All of it is visibly, obviously group-shaped, and doing any of it by yourself is conspicuous in a way that eating alone in a restaurant is not.
Winter: the opposite problem
January to March, Chicago is dark and very cold and the weekend is long. This is when people who have not built a circle notice it most sharply. Bookings go quieter, warmer and longer -- a two-hour dinner, a bar with a fire, a museum afternoon, a coffee that runs on.
A lot of people in this city are from somewhere warmer and are having their second winter.
Who books
Transplants from across the Midwest and beyond. A very large graduate and professional student population. Corporate relocations. People who moved neighbourhoods after a breakup and lost their local life with it.
The neighbourhood rule
Chicago socialises by neighbourhood and people genuinely do not cross the city on a Tuesday. Pilsen, Logan Square, Hyde Park, Andersonville, Bridgeport -- these operate almost as separate towns.
Which makes one line on your profile unusually important: where you are, and how far you will actually go. It is the difference between a booking and a polite decline.
Rates
$30-55 an hour. Chicago's cost of going out is reasonable by big-city standards, so bookings run longer here than on either coast -- a four-hour evening is more common than a rushed two.
Starting
Photo, a few sentences, your rate, and your neighbourhood. Free to publish.
"Renting a friend" in Chicago
That is the phrase most people type, and it comes from RentAFriend, which has run this exact model in the United States since the late 2000s. Fifteen years of a company being paid to introduce people who want company, without a regulator ever taking an interest -- which is the clearest answer there is to anyone wondering whether this is a real thing to do.
It is the same idea here. The differences are money: RentAFriend charges you a listing fee before anyone has booked you, and Roavi does not charge you anything, take a commission, or touch the payment. We wrote the two up side by side in RentAFriend vs Roavi.
Searched in February more than in July, for reasons anyone who has spent a winter here will recognise.
Frequently Asked Questions
How much can you earn?
$30-55 an hour. Chicago is a large, well-paid city with a comparatively reasonable cost of going out, so bookings tend to be longer than in New York or San Francisco.Do I need a licence?
No. Illinois does not regulate being paid for your company, and neither does the city.When is it busiest?
Two peaks, for opposite reasons. Summer, when the whole city is outside and nobody wants to do it alone, and January through March, when the weather makes an empty weekend genuinely hard.Does the neighbourhood thing matter?
A lot. Chicago socialises by neighbourhood and people rarely cross the city for an evening. Say where you actually are and where you will travel to -- it is the most practical line on your profile.