An Uber Sweetest Day

Engagement Chicago

Help Uber!

When we received this tweet from big Uber fan Josh Puckett, we were quick to say we’d try to help, not knowing what he had planned.  It turns out Josh was looking for some Uber assistance in proposing to his girlfriend.  Here’s how the night played out…

“I wanted to surprise her at a secret location and knew I had to arrive in style, so Uber was clearly the right choice. I used the iPhone app to secure a ride, and we picked Kayleigh up at her apartment. She was stunned that we were going to ride around in a Lincoln Navigator with a ‘chauffeur’, and was beaming. Girma, the driver, was awesome and played along perfectly. We drove to Adler Planetarium at sunset, and I led her to a table I had set up, with rose petals, candles, and an iPad photo slideshow of our relationship. The gig was immediately up, but she loved every minute of it and said yes when I proposed! We then took Uber back to Merlot on Maple to finish off the evening with a nice romantic dinner. Uber provided perfect transportation for one of the most special events in my life, and I couldn’t be happier with their service!” – Josh

Engagement Chicago

Josh kinda nailed it in the Scenery Department 🙂

We love being part of the Chicago community, but knowing we’re making a positive impact is the most exciting part!  So in honor of Josh, and Chicago love, lets celebrate Sweetest Day together! Yes, the (made up) holiday where we celebrate those who we truly care about.  It’s a day to spend time with loved ones (even though you spend every other day of the year with them). Ok, so it’s not Valentine’s Day, but hey what’s wrong with another excuse to go out and enjoy yourself? At Uber, we’re always down for that.

Uber Love

Lisa Frame & Ryan Lange Loving their first Uber

We wanted to give some suggestions to Chicago Uberverse on where to spend Saturday night, and presumably arrive in style. So we thought, let’s reach out to some loyal users and find out their favorite date spots in Chicago.  The feedback was great, and as a BONUS, our friends at HBLOOM are randomly dropping flowers in Ubers Saturday night (Oct 15th), so lucky ladies will get what they adore most, some appreciation!

Now for some reviews…


One of my favorite date night restaurants is Via Carducci in Lincoln Park. My boyfriend and I have gone there every Valentine’s Day for the past 5 years. The atmosphere is authentic Italian and cozy and the food matches this perfectly.  We always order the Emiliana pizza with portabella mushrooms, sun-dried tomatoes, fresh mozzarella and goat cheese and we usually end the night with a limoncello and espresso :). Via Carducci, Lincoln Park & Bucktown


Towards the northern edge of Lakeview (Corner of Addison and Broadway) and just enough away from the general demeanor of Wrigleyville, Angelina Ristorante has quickly become a favorite for my girlfriend and I. With the choice of indoor and outdoor dining, Angelina uses low lighting, strategically placed candles and an extremely engaged and friendly wait staff to create a very comfortable, intimate and inviting atmosphere. Their meals are savory and authentic (Italian) served in generous portions which are quite economical – certainly more so than other restaurants of lesser charm and expertise around the city. Angelina Ristorante affords you the opportunity to enjoy the company of your date and the quality of your meal. Angelina Ristorante, Lakeview

Ruxbin Exterior


My favorite date location is Ruxbin — it is unlike anything you have experienced. They do not take reservations and the space is small, so you may need to drop by the Chip Inn around the corner for a cocktail to kill some time. It is BYOB, the decor is insane, the walls are covered with album covers and charred music sheet paper. You definitely must take a look at their bathroom!The food is unique, fresh, and an explosion of flavors from local vendors. Great place for a romantic date without breaking the bank, and did I mention BYOB? Ruxbin, West Town


My fav date spot in Chicago is Piccolo Sogno in the West Loop.  I took my boyfriend there for his 24th birthday and got the burrata hand-stuffed mozzarella with prosciutto, the gnocchi, and the 16 oz. ribeye.  The food was amazing but the decoration and style inside the restaurant absolutely won me over.  My boyfriend was also extremely pleased with the food, and coming from an italian that means a lot! 🙂 Piccolo Sogno, West Loop


If I’m in the mood for sushi there is no better place than Sunda.  Not only is it on one of my favorite streets in Chicago (Hubbard), but is also the best spot to wow a female on a first date.  The hand rolls in soy paper are very unique, especially followed with Uncle Paul’s Roasted Chicken and some delicious cocktails…its like I’m in Japan (even though I’ve never been there I imagine the food to be similar).   I’m not Japanese but I know Asian cuisine and I look no farther than Sunda when it comes to the best meal and best atmosphere in the city. SUNDA, River North

So take out your lady, or your man, or whatever loved one you want this Saturday night.  Most importantly, do it in an Uber, cause they only know you really care when you say those wonderful words, “Our Driver is waiting outside“.  We want to continue doing posts like this.  Let us know some of your own life cases for how you’re using Uber, and who knows, it might be the feature of our next blog. Enjoy the weekend!

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