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Date night,
planned by locals

From searching to booking, Wing's local planners build personalized date nights for busy couples in Chicago.
Receive an itinerary.
All you have to do is show up.
Learn more ↓
Just 5 minutes
to get started!

Remove the burden of planning a stellar date night

How it works

Share your date preferences
by filling out a quick questionnaire about yourself—date night interests, things to avoid, and more.
Schedule your date
and select from options to guide your Planner, so we can tailor the best experience for your your date
Receive your personalized itinerary
a week in advance or as a surprise, complete with schedule-optimized activity bookings and tailored restaurant reservations.
Share your preferences


Wing charges $25 each month, plus 10% 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
  • ✅ Event & Restaurant Reservations
  • ✅ Fully-Customized Itinerary
  • ✅ Exclusive Experiences*
  • ✅ On-Call Concierge
  • ✅ COVID-19 Precautions
  • ✅ 100% Happiness Guarantee
    $ 25 / month + 10% concierge fee
    * Pre-paid dinners, chef experiences, gifts, and more!

    “Wing enables us to commit to our date night”

    “Since John and I work full-time jobs, it's difficult to find the time to plan our date nights. Working with Wing's local planners allows us to spend more time on our relationship and go on more exciting adventures together. We've been sent to Shakespearean improv, axe throwing, and even an exclusive experience for our anniversary”
    - Samantha & John

    See one of their dates

    Want to chat with a local planner?

    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.

































    What is Wing?

    Wing is a date night concierge for busy couples. Our planners learn about your relationship through a short questionnaire and text with you to plan your date nights.

    Wing's itineraries are built from scratch by a local.

    They can include special additions such as: pre-paid restaurant experiences, exclusive tickets, gifts, and other unique touches.

    What is a typical date like?

    Each date is tailored to your relationship, interests, and budget. We can accommodate both in-home and out-of-home experiences.

    Some examples include:
    - Pre-paid restaurant reservations, experience, or an in-home chef
    - Theatre, shows, and intimate concerts
    - Unique hidden gems in the city

    See a sample date
    What is your cancellation policy?

    We'll work with the businesses to provide a fair resolution but we cannot guarantee a full refund of any bookings that were made.

    If you can't make the date, let us know within 24 hours of scheduling and you can reschedule or cancel.

    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.

    How does pricing work?

    We charge $25 each month for access to our date night planners.

    Each time you would like to go on a date, we ask for your budget, and charge 15% of the actual cost of your date.

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

    Your Date Night 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 $200.

    In that case, $20 will be refunded to you instantly. We only charge the 15% fee on the actual cost of the date, $200, so $30 would be kept by Wing to cover the concierge fee.

    What is your 100% Happiness Guarantee?

    If for any reason you're unhappy with the date we planned for you, Wing will refund your subscription fee and provide a complimentary month with 0% concierge fees.

    We believe in the quality of our service and want to ensure it exceeds your expectations