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


Here's your plan for a fun dinner with five strangers, followed by drinks nearby. Enjoy

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 singing karaoke and enjoying $5 happy hour drinks at Brando's Speakeasy. Watch the video 👇

Happy hour deals, strong drinks, and a night of singing your heart out—Brando’s in the Loop is the perfect spot for karaoke lovers and anyone looking for a lively night downtown. 🎤🍸

Karaoke + Happy Hour 🎤🍻

Sing karaoke and enjoy $5 cocktails, wine, and flatbreads at Brando's Speakeasy—a lively Loop spot perfect for date night or after-work fun.

Karaoke & Happy Hour

✅ Before you go
• Make a reservation to snag a table here: https://brandoschicago.com/loop/about/

💪 Pro tips
• Happy Hour runs daily from 5-7pm! This is what’s included for $5: 
Caramelized onion flatbread 
Thai Peanut Flatbread
Old Fashioned
Espresso Martini
Moscow Mule
High Noon
Paloma
Modelo
Lagunitas IPA
House Wines

Happy Hour + Karaoke

I think I found my new favorite happy hour in the loop.

Come along on date night while my boyfriend and I went to Brando's Speakeasy.

then we went to the bar to grab their happy hour drinks.

It's every day of the week from 5:00 to 7 p.m. and they have $5 drinks.

My boyfriend got a beer and I got a Moscow mule.

we decided to explore the bar a little bit more.

there was this quieter area that was perfect for conversations,

and cheers to our new favorite happy hour deal.

Here's your plan for grabbing fresh açaí bowls and smoothies at Playa Bowls before a lake day. Watch the video 👇

Check out recently opened Playa Bowls in Lakeview East for a yummy bowl, smoothie, and more on your way to the lake!

Best Açaí Bowls for sunny days

Stop by Playa Bowls in East Lakeview for fresh, delicious açaí bowls and smoothies—perfect for grabbing on your way to a sunny lake day in Chicago.

Açaí Bowls & Smoothies

Mon - Fri: 7am - 9pm, Sat - Sun: 8am - 9pm

Quick info ℹ️ 🕑

Customize your bowl at Playa Bowls with açaí, pitaya, or mango bases and delicious toppings—perfect for a healthy treat in East Lakeview.

Açaí Bowls

✅ My Reccos
• Pura Vida Açaí bowl, Nutella Açaí bowl, Goji Pitaya Bowl, Power Açaí bowl

Browse by base 🥣
• Açaí: The acai berry is renown for its vast range of energy-boosting, cell-healing, immune-stimulating properties. This jewel is what got this whole party started!
• Pitaya: This vivid fruit is a tropical orb of phytonutrient-packed, metabolism-stimulating, digestive-aiding, body-detoxifying gold.
• Mango: Alphonso Mango is sourced from India. Vitamins A, C, K are present in Alphonso mangoes, as are minerals like Magnesium, Manganese, Phosphorus making them a very healthy fruit.
• Also included options are coconut, green, banana, and oatmeal. 

What do I order? 🍓🍍🍌🫐

Lakeview East just got the ultimate sunny day vibes.

and more are basically made for these last few warm days.

and they're perfect lake day fuel while the weather's still on our good side.

So grab Playa Bowls on your way to the lake

to relax and take advantage of these warmer days.

Here's your plan for drinks, live music, and dinner with amazing Chicago River views. Watch the video 👇

If you’re looking for the perfect mix of amazing food, cocktails, and unbeatable vibes on the river, River Roast is a must. The menu is packed with flavorful dishes that are perfect for sharing, and the drinks pair beautifully with the views. What stood out most for me was the ambiance, lively yet relaxed and a patio right on the Chicago River. It’s the kind of spot that makes any meal feel like a special occasion.

Dinner at River Roast 🍷✨

Enjoy dinner, cocktails, and riverside views at River Roast in Chicago. Perfect for happy hour, live music, or a night out with friends.

Dinner and Drinks

✅ Before you go
• Grab a reservation here! https://www.opentable.com/river-roast

💪 Pro tips
• Happy Hour runs Monday- Friday 4:00-6:00. I recommend getting the $9 featured cocktail! 🍹 
• Live music happens on Thursdays from 5:00-7:00pm! 🎤🎵
• They also do weekend brunch Saturdays and Sundays 11:00am- 3:00 pm! 🍳🥞🧇

Dinner and Drinks at River Roast 🍔🍴🍷

and views of the Chicago River is the perfect way to spend a Chicago night.

which is located right on the Chicago River,

headed downstairs where we first listened to live music,

and then headed out to our seats on the patio.

4 to 6 p.m. and we took advantage and got a glass of sangria for only $9.

I think our favorite was this pork belly,

I loved all the thoughtful details the restaurant put into their presentation,

I highly recommend what you see on the left here,

which are the golden goblets that were crisped to perfection.

Here's us cheering with our peach martinis,

which were probably our favorite of the whole evening.

We stuck around during and after sunset to

get these beautiful nighttime views of the city.

I highly recommend checking out River Roast either for

Here's your plan for visiting Pilsen's newest coffee shop, enjoying coffee and avocado toast. Watch the video 👇

Newest coffee shop in Pilsen! 

Visit Café Carranza, a new spot in Pilsen to enjoy coffee, avocado toast, and study. Located half a block from the CTA Pink Line, paid parking only.

Coffee & Cafe Visit

✅ Before you go
• if traveling by train it is a half a block away from the CTA pink line

💪 Pro tips
• if driving there is only paid parking 

What to know before you go 

Let's go try a new coffee place in Pilsen.

come with me to Pilsen's newest coffee shop,

They opened a month ago and I saw a lot of new customers coming.

I took some time here and I did some homework and reflected.

I wish the bread was a little bit more toasty,

They just started out and can't wait to see where they go from here.