A different way to explore a new city.

Note: I am in the process of making a few more changes to my site. Apologies for the weird links and photos! Hopefully I can get them fixed soon. Thanks for bearing with me!

My friend Ginger and I are headed to Chicago at the end of May for a quick weekend trip (total cost: $5 with points and miles). We’re really looking forward to exploring the city, and we have plans to bike, boat, walk, and (thrift) shop till we (almost) drop. We’re also super excited to try a bunch of the restaurants you recommended (thanks again for all the great tips)!

So our weekend was already packed with promising discoveries, but as I was thinking about it, I had a fantastic idea: what if we booked a few Chicago “dates” from HowAboutWe?

HowAboutWe is a dating and relationships company that creates and sells discounted dates in a handful of cities around the country. I love their site and use it all the time in San Francisco: the dates are usually very original and also very budget-friendly. Josh and I recently went on an epic date that cost a grand total of $35 – we lingered in the late-afternoon sun at a tiny neighborhood bakery, enjoying fresh-baked cookies and coffee; we savored piping hot bowls of ramen in Japantown as the San Francisco fog rolled in around us; we sat at the bar of a packed BBQ joint in the Mission as we drank Miller High Lifes and chowed down on mac and cheese; and we ended the evening with a late-night flight of premium scotches at a bar downtown. ALL FOR $35.

So I was interested to see what Chicago held in store.

To be able to see Chicago dates, I logged into my HowAboutWe account and changed my zip code from San Francisco to Chicago. Then I was able to browse and select a few that looked fun. While HowAboutWe is marketed to couples in a relationship, they certainly don’t mind if you decide to take a friend on a date instead of your partner. They also don’t mind where you decide to enjoy the date – the world is your oyster! Of course in reality you are limited to New York, Chicago, Los Angeles, San Francisco, and Seattle…but my point is that you don’t have to live in a city in order to go on a date there.

The first date I chose was a “Custom Sundae Making” extravaganza. This was a freebie, because members get one free date per month.

Next, I decided to book a “Custom Fragrance Making” date. This seems perfect for our girlfriend getaway weekend, don’t you think? Total cost: $50 with HowAboutWe (regularly $120). You could also get this date for FREE if you sign up with a friend’s referral link, because new members get a credit of $50 to use towards their first date.

I love trying new things like this while I am traveling. I think that doing different local activities is such a great way to really explore a new city – you get to meet people, see new neighborhoods, and have new experiences all at the same time. These two dates are definitely going to hit all those notes!

There were a lot more dates in the HowAboutWe datebook that looked intriguing, interesting, or appealing (Couples DJ Lesson? Cocktail Class at the Violet Room? Learn to make salsa from the guys at The Salsa Truck?), but I decided to start with sundaes and fragrance. Good combo.

And for for future trips, I’m going to remember to use this “travel tool” (my HowAboutWe membership) again.

How about you? What kinds of things do you like to do when you visit a new city?

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Note that I do get a referral credit if you use the links above. As always, I really appreciate and thank you for your support!