4 Chicago-Centric Ways to Give "the Gift of Experience" this Holiday

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As the holiday approaches, we’re all faced with the same question: “What do I get *insert name here* for Christmas?”

Some people are hard to shop for, especially those who tell you, “I don’t need anything this year. Don’t get me anything.” 

But you want to show your loved one just how much they mean to you, and giving them a special gift is a wonderful way to do that this holiday season. 

On the flip side, you also don’t want to buy them a sweater that they’ll return two days later.

Instead of getting them an impersonal present that they may never use, give them the gift of a truly Chicago-centric experience.

Why Gift an Experience?

Some people prefer to avoid accumulating “stuff” or clutter and don’t see a purpose for knick-knacks or function-free gifts. Others are just plain hard to shop for— they may have a very unique style or taste, and you can never seem to find something they actually like.

You’ll commonly hear the anti-gifter say, “I don’t need a present. I just want to spend time with you this holiday.” That’s because this type of person doesn’t get excited about a physical present, and would rather spend quality time with their loved ones.

By wrapping a thoughtful gift card or handwritten “experience pass” in a box under the tree, your special someone will still have a present to open while still getting what they asked for: the opportunity to make new memories with you.

Here are four experiential gifts to knock those hard-to-shop-fors off your holiday list:

1. A Tour of Downtown

Chicago features 40 blocks of fun right in the heart of the Business District. Those who take the pedestrian walking system pathway — coined the Pedway — can enjoy five miles worth of landmarks, theaters, unique shops, and more.  

If your gift-receiver likes sightseeing, they’ll get a real thrill weaving through underground tunnels and overhead bridges. You can even do a little research on some places you think they’d like and treat them to a drink at a hip bar or dessert at a nice restaurant. Weather permitting, take them to Millennium Park for a surprise picnic. 

Who knows—you may even stumble upon a gift in a shop you can get them after all. 

Get as creative as you’d like with this awesome list of 67 places to stop on the Pedway.

2. Dinner at Alinea (or Another Posh Restaurant)

Gift your loved one a treat-’em-to-dinner experience coupon instead of a gift card to a restaurant. This ensures they’ll dine with you, instead of taking their card to eat with another. 

One excellent place to indulge in Chicago is Alinea, as their high-priced platters are certainly a sophisticated treat (one that your loved one might not otherwise splurge on). 

Alinea has been named the Best Restaurant in America four times, and it’s one of only 13 restaurants in the U.S. to earn three Michelin stars. While the restaurant has been open since 2005, they recently went through an extensive remodel this past year, making it an exciting experience for even those who dined there before. Book your elegant feast here.

If this fine dining experience isn’t the right fit, Chicago has hundreds of other nice restaurants  where you can treat your loved ones this holiday. Check out Chicago’s Eater’s Guide.

3. A Trip to the Museum

Is the person you’re shopping for a history buff or big-time learner? Make their experiential gift an educational tour of an interesting local attraction.

Whether it’s the Art Institute of Chicago, the Museum of Science and Industry or the Adler Planetarium, our city is packed with some remarkable institutions. Many have hands-on interactive displays and one-of-a-kind marvels to stimulate your brain  for hours upon hours. 

Take your recipient to one museum that you think would really spark their interest, or make a day out of it and create an agenda to hit your top three choices. Here are 10 of Chicago's best museums to choose.

4. Skydiving

Skydiving is the perfect thrill-seeker experience. While December is generally too cold to skydive around Chicago, it’s a terrific month to get a gift certificate for a tandem freefall for the spring! 

While you won’t be able to skydive strapped to your buddy, you can ride up on the plane together and watch as they take the plunge with a trained instructor. Best of all, if you book this experience at our dropzone, you can treat your guest to dinner and drinks at Flight Deck Bar & Grill after your jump. 

As an added perk, gift certificates at Chicagoland Skydiving are good for up to five years and refundable without 30 days of purchase if needed. Grab your freefall experience here.

Is Skydiving Really the Right Gift?

You might be sold on the idea of gifting a skydiving certificate, but what if your recipient gets nervous? 

Download our Tandem Skydiving Guide and email it to them after they unwrap your certificate. This helpful booklet explains everything you need to know about skydiving safety to get your loved one just as excited about this unique holiday present as you are to gift it. 



Douglas Smith is CEO/President, and Guest Relations Associate at Chicagoland Skydiving Center. He has owned and operated the business since 2000. He has been skydiving since 1994, and in addition to leading the CSC Team, is currently an instructor, videographer and pilot for CSC.