Four people laughing at a dinner table in a red velvet booth

Singles and dating events in Chicago

Meet other singles in Chicago. Singles dinners, Tuesdays at 7:00 pm. Everyone at the table booked a singles event, and we keep a balance of men and women.

Next date

Tue, Nov 17, 7:00 pm

then Tue, Nov 24, 7:00 pm

Upcoming singles events in Chicago

The next dates in Chicago. Pick one, create your account, and book it in the app. In October, 79 people took part in singles events in Chicago, 29 of them at their first Timeleft event.

Find your group

All times are Chicago time.

Where singles events happen in Chicago

We pick the places and book the tables.

The app shows you the address before each event.

Marina City’s twin towers above the Chicago River

Some of the places we book in Chicago

AmericanGoogle rating4.5(2,039 reviews)
The Smith
Clark and Kinzie, River North
27 Timeleft dinners
Global comfort foodGoogle rating4.9(138 reviews)
Ila’s
Hubbard Street, River North
27 Timeleft dinners
Restaurant and coffeehouseGoogle rating4.5(5,243 reviews)
Beatrix River North
North Clark Street
21 Timeleft dinners
Modern AmericanGoogle rating4.7(487 reviews)
The Evie
Magnificent Mile
15 Timeleft dinners
DinnerGoogle rating4.5(962 reviews)
Bar Mar by José Andrés
10 Timeleft dinners
DinnerGoogle rating4.7(250 reviews)
Vela Bar y Cocina
8 Timeleft dinners

A singles night in Chicago, step by step

Three people laughing at a restaurant table under a paper lantern

When you book

Pick a singles event

Choose a singles dinner, or a singles coffee where your city runs one. Booking closes 13 hours before, or at midnight the night before if that would fall between midnight and 8:00 am.
Before the dinner

We put the table together

Everyone at the table booked a singles event. We keep a balance of men and women and group people by age band, then book the restaurant.
7:00 pm The start

In person first

You get a sense of someone across a table, from how they laugh to what they order, before any private messages. No one-to-one date to get through, just a table of people to talk to.
Afterward

If you like someone

The group chat stays open, and in the app you can stay connected with anyone from the table. What happens next is up to the two of you.

Safety

Is it safe?

Singles events are at public venues we've vetted, and nobody can message you one to one before you meet. If you report someone, you're never placed with them again.

99%

Over 99% of Timeleft experiences happen without any safety incident, according to the safety framework we published in June 2026.

Read our safety guidelines

Two women laughing together at a Timeleft dinner table by a big window

What members say

Signed up in March 2024 to meet more people. It is 2026 and I have indeed met more people - including my fiancé. And the 50 or so time lefters who we invited to our wedding.

Akethy

Timeleft member · App Store review
I moved to London last year and within a few weeks I decided to try Timeleft and I met some really interesting people, and ironically one of them became my partner and we are now planning our future together. It was my intention to make new friends, so this was an unexpected bonus. Thank you, Timeleft!

J4y8

Timeleft member · App Store review
I was at a birthday dinner and asked a girl how she met my friend. She said at a Timeleft dinner! I had never heard of the app, but I decided to give it a go. I have been to two dinners so far and plan to go to more…

Anna B.

Trustpilot review

Questions from singles

When are singles events in Chicago?

Singles dinners, Tuesdays at 7:00 pm. Booking closes 13 hours before each one, or at midnight the night before if that would fall between midnight and 8:00 am. The dates above are the next ones you can still book.

Where in Chicago do singles events happen?

The next ones are in River North. We book the restaurant, and the app shows you where to go before the evening.

How is this different from speed dating in Chicago?

We don't run speed dating, where you get a few minutes with each person. Here you share a whole dinner with a small table of singles, so a conversation has time to go somewhere. Afterward you can stay connected in the app with anyone you got along with.

Who will be at the table?

Other singles who booked the same event. We group people by age band and keep a balance of men and women.

In the last three months, most people at singles events in Chicago were in their 30s and early 40s, and about half were women.

Can I go on my own?

Yes. You book on your own and we put the table together, so you don't need to bring anyone.

What does it cost?

You need a Timeleft membership to book, and the app shows its price in your country before you pay anything.

As many events as you like, singles events included. Dinners, coffee, and whatever else runs in your city, all on one membership.

Your own food and drinks. You order what you like and pay the venue yourself.

Have more questions?

Visit our Help Center