Thank you! Your submission has been received!
Oops! Something went wrong while submitting the form.

Discover your city, together

Wing sends you on an adventure to restaurants, bars, and experiences you'll love in Chicago and New York City.
Receive an itinerary.
All you have to do is show up.
Learn more ↓
Just 5 minutes
to get started!

Receive personally curated itineraries for your dates

How it works

Share your date preferences
by filling out a quick questionnaire about your preferences—interests, dietary restrictions, and more.
Choose a day
and theme to guide your Planner, so we can tailor the best experience for your first date or fifth-year anniversary.
Receive your custom itinerary
a week in advance or as a surprise, complete with logistically-optimized activity bookings and tailored restaurant reservations.
Start your subscription

Simple pricing

Wing charges $25 each month for unlimited date night planning, plus 13.5% of each of your date's total cost.
Unlimited Dates
Single Date

Single Date

We'll plan unlimited date nights for you and your partner each month within your designated budget

  • - Single Date
    - Fully-Customized Itinerary
    - Event Bookings
    - Restaurant Reservations
    - 100% Happiness Guarantee

$ 75 per date


We'll plan unlimited date nights for you and your partner each month within your designated budget

  • ✅ Unlimited Dates
  • ✅ Exclusive Experiences*
  • ✅ On-Call Concierge
  • ✅ Fully-Customized Itinerary
  • ✅ Event Bookings
  • ✅ Restaurant Reservations
  • ✅ 100% Happiness Guarantee
    $ 25 / month + 13.5% concierge fee
    * Pre-paid dinners, chef experiences, gifts, and more!

    “Wing allows us to commit to our date night”

    “We've been able to explore Chicago without the hassle of planning every time we want to go out. Wing is as simple as sharing our preferences and our planner, Susie, comes up with ideas and books everything! We've been sent to Shakespearean improv, axe throwing, and even trusted them to surprise us for our anniversary date.”
    - Samantha & Jonathan

    See one of their dates

    Want to chat with a local guide?

    How do I guide the date planning?

    For each date, you'll share specific date preferences, beginning with your themes. Your themes are used to guide your Planner.


































    Is Wing right for my relationship?
    Wing is a done-for-you date subscription service. We plan custom date nights for busy couples.

    It’s the chance to introduce yourself to a new activity in your city, go on a romantic date to celebrate your anniversary, or just get out of the dinner-as-a-date routine. Our date experts are here to support your relationship.

    Wing handles all of the bookings, reservations, and unique touches for your dates.

    How does it work?
    Once you start your subscription, you'll receive a date night preferences survey so we can learn more about you and your partner's interests.

    Any time you're looking to go on a date—whether that's twice a week or once a month—you'll fill out a quick questionnaire to let us know what you're in the mood for.

    Our planners handle all of the bookings, reservations, and unique touches.
    What's a typical date like?
    With Wing, there is no typical date!

    Each date is catered to your relationship and interests. For a more casual date, you could be headed on a scavenger hunt.

    For your fifth anniversary expect us to plan you a memorable, luxurious experience like the one below.

    See a sample date night
    How does your pricing and the 13.5% concierge fee work?
    We charge $25 each month for access to our platform and 13.5% of the actual cost of your date.

    Each time you would like to go on a date, we ask for your budget.

    Let's say you want to spend $250 for your date next weekend. We'll authorize your card for $250 through Stripe.

    Your Planner will work within your budget to purchase tickets, pre-pay for your dinner, or purchase any other custom gifts. Let's say the entire cost of your date is $230.

    If so, $20 will be refunded to you instantly. We only charge our 13.5% fee on the actual cost of the date, $230, so an additional charge of $31.05 will be charged.
    What if I can't make the date?
    If it is less than 7 days until your date, we'll work with the vendors to provide a fair resolution but we cannot guarantee a full refund of any bookings made.

    If you can't make the date, let us know within 24 hours of scheduling your date and we'll reverse the authorization charge and allow you to reschedule.
    What is your 100% Happiness Guarantee?
    If for any reason you're unhappy with the date we planned for you, we'll refund your entire month's subscription fee and give you a full month free, with 0% concierge fees.

    That's how much we believe in the quality of our service and your customer's experience.