Make a Reservation

Wednesdays just got a little more interesting 👀 Let Timeleft’s personality algorithm match you with five strangers for an unforgettable dinner.


Dinner with Strangers 😅

Experience a unique dining event at Kama - Wicker Park with Timeleft. Get matched with strangers for lively dinners every Wednesday.

Group Dinner

✅ Before you go
• Dinners are every Wednesday in big cities all over the WORLD! 

💪 Pro tips
• Some restaurants might not be able to split the bill 6 ways, so bring cash to pay for dinner!
• Go in with an open mind and don’t over think it! My biggest tip is just to be curious + ask questions ❤️
• I felt safe the entire time but just a reminder to always keep track of your belongings/drink and before you head to the restaurant, tell a trusted friend what you’re doing + where you’re going!

Book a dinner with Timeleft 📍

I'm about to have dinner with five strangers so…

I can't remember the last time I made a friend

who wasn't from work or school, if ever??

I filled out their personality quiz and the day before they

sent a few hints about who would be at my table,

they sent the location of the restaurant,

But the Timeleft algorithm worked its magic because our

table hit it off immediately and the restaurant was fire.

I met such cool people and we had lots of spirited conversations,

but the app does have a game to break the ice if needed.

I kept forgetting to film because I was having so

much fun and didn't want to be on my phone.

After dinner, we wanted to keep the good vibes going

So luckily they do this thing called “The Last Drink,”

 the name of a bar within walking distance

where you can chill and meet up with more people who use the app.

This was the best Wednesday night I've had in a long time.

So next time someone tells me not to talk to strangers,

I'm gonna tell them to book a dinner with Timeleft.

Here's your plan for vibing, working remotely, enjoying drinks, sandwiches, and weekend DJ sets. Watch the video 👇

Enjoy the vibes and atmosphere of Drink Happy Thoughts where you can work remotely or catch up with friends while enjoying cute drinks and delicious food like sandwiches and empanadas. 

Drink Happy Thoughts 🙂

Drink Happy Thoughts in Chicago is a bright, lively coffee shop perfect for remote work or meeting friends. Enjoy unique drinks, tasty snacks, and a fun weekend DJ vibe.

Coffee & Cafe Vibes

💪 Pro tips
• If you order a large of their Honey Honey iced latte, it comes in a bear shaped cup you can keep. 🧸

Drink Happy Thoughts

Drink Happy Thoughts in Humboldt Park is a great

coffee shop to work from during the week.

and the music will have you vibing out while getting your work done.

You will not want to miss out on this breakfast classic.

Not to mention if you want to come back over the weekends,

Make plans to stop into Drink Happy Thoughts

in Humboldt Park or their location in Uptown.

Here's your plan for rooftop drinks and enjoying the best burger in Chicago. Watch the video 👇

Rooftop drinks + best burger in Chicago?!!

Best Views 🏙️+ Best Burger 🍔

Sip drinks at Kennedy Rooftop for stunning city views and $10 happy hour specials—no reservation needed, just head to the 7th floor!

Rooftop Drinks

✅ Before you go
- Don’t need to be a hotel guest to drink at the rooftop! Just go up to the 7th floor. 

💪 Pro tips
- Happy hour runs Monday- Friday 4-6pm 

1. Drink at the Kennedy Rooftop 🍷🍸🍹🥂

Enjoy the famous Mott Burger—available only before 7pm—plus inventive drinks and delicious starters at this cozy Asian fusion spot.

Burger Dinner

✅ Before you go
You can make a reservation here: https://www.mottstreetchicago.com

💪 Pro tips
- The Mott Burger is only available before 7pm!! 

2.  Dinner at Mott St. 🍔

This is the plan for the best views and the best burger,

my boyfriend and I went to the Kennedy rooftop at the Hyatt Place Hotel.

You just have to go up to the rooftop on floor 7.

We didn't even need a reservation for a Friday night.

Then we headed over a 6-minute walk to Mott Street.

I had heard about the burger here so many times,

They also have some more Asian fusion foods if you're in the mood for that as well.

so I would make sure to get a reservation.

We started with the Brussels sprouts cause we had heard really good things.

Then we ordered another drink that were a little bit funky,

this burger was gigantic and absolutely delicious.

we had to end with this Snicker-inspired sweet treat.

Here's your plan for grabbing coffee, exploring murals, visiting art events, and maybe creating art yourself. Watch the video 👇

Ravenswood is a great neighborhood to visit if you want to try a new coffee shop and admire local art. 

Coffee & Art Walk in Ravenswood

Bad Coffee is a hidden spot in North Center, Chicago, perfect for grabbing a unique coffee, admiring murals, and enjoying a creative, off-the-beaten-path vibe.

Coffee Drinking

✅ Before you go
• The coffee shop is located “off the beaten path”, so be sure to look out for the Jazz mural and Bad Coffee sign to stop in.
💪 Pro tips
• There’s also a speakeasy hidden in this coffee shop 👀 Find them on Instagram @badcoffeechi to know where. 

Bad Coffee

Explore rotating markets, art galleries, workshops, and interactive art installations at Artifact Events in Chicago's Lake View neighborhood.

Art Fair & Gallery

✅ Before you go
• Visit the venue’s website at https://www.artifacteventschicago.com/public-events to know what upcoming creative events are coming to the space! 

Artifact Events

Ravenswood is just the neighborhood to grab coffee and go for an art walk.

Once you see this mural and find this sign,

Bad Coffee is tucked in an alleyway and known for its murals and atmosphere.

take about a five-minute walk down to artifact events.

Here you'll see the other art fair was in town,

but this event space is known for its rotating markets,

you'll have the opportunity to purchase light bites or drinks,

participate in art workshops or art installations,

or even make an art purchase for yourself.

If you're looking to tap into your artistic side,

a trip to Ravenswood is the perfect opportunity.

Here's your plan for working and relaxing at Collectivo Coffee with tasty drinks and cozy seating. Watch the video 👇

Work from this cafe with a delicious menu and indoor/ outdoor seating. They even have a fireplace in the winter! 

Cafe Reset: Collectivo Edition

Work, relax, and sip unique seasonal drinks at Colectivo Coffee in Wicker Park. Enjoy ample indoor/outdoor seating and a cozy fireplace during winter.

Coffee & Cafe

✅ Before you go
-There are many Collectivo locations in Chicago! This is the Wicker Park location 

💪 Pro tips
- Check out their seasonal menu here: https://colectivo.com/pages/wicker-park 

Collectivo Coffee ☕️🍵🧋🫖

I love an innovative and seasonal drink menu,

and I'm pretty sure Collectivo Coffee has one of the most unique.

which is perfect because they have a gigantic location here.

They have a ton of seating on the 1st floor,

and then the staircase up to the 2nd floor.

I grabbed a table upstairs so I can enjoy my lemon loaf and latte.

they have these large garage doors that actually

the doors will be open and it's a perfect place