Manny and I are all about keeping things simple during the holidays, so we stick to exchanging little gifts. But our true love is venturing out and exploring our awesome city of Chicago together! That’s actually how I got started with this account! We’re always up for a new adventure in the city, so we usually snag tickets or reservations for a memorable date night. 

Here’s my wish list of Chicago experiences for 2023, perfect for adults who crave some excitement and fun! (Psst, Manny, take note!) 

I’ve divided these up by indoor and outdoor date ideas, gifts for foodies, and my favorite spa experiences. If you’re searching for kids’ experience gift ideas, check out my other post here!

Plan a Chicago Holiday Date 

My ideal downtown winter day-to-night date looks a little like this: yummy coffee and a snack, a fun activity like ice-skating or seeing the trees along Michigan Avenue, a nice dinner, maybe a cocktail, and then enjoying holiday lights on the way home. 

There are a ton of things to do, but below are a few ideas to help you plan your perfect holiday date!

Outdoor Dates

• The Ice Skating Ribbon at Maggie Daley Park.  Reserve tickets online for your session and rent skates for $16-22. Reservation dates are released two weeks in advance of the session date. You could totally pair this with a reservation at the Lodge at the Fairmont Chicago! (See below.)
• Stroll by the Macy’s State Street window displays and/or dine in the Walnut Room. Reservations are already full, but you can always try and walk-in or get on the waiting list. 
• Browse the Christkindlmarket and have fun on Wrigley Field at Winterland at Gallagher Way. 
• Visit the Jack Frost pop-up in their new West Loop location! The ice bumper cars are now included in all the packages.
• Go curling at the Gwen or Stone’s Throw at The Emily Hotel!

Indoor Dates

• Have dinner at the iconic pre-show Italian restaurant Petterino’s, and then see Hamilton at the James M. Nederlander Theatre! This would be such a great night! Folks can use the code SHARE23 to save up to 40% on main floor seats! This offer expires on December 11 at 7:30 PM!
• The Lodge at the Fairmont Chicago offers a cozy experience with hand-crafted cocktails, fondues, s’mores, and live entertainment on select days. Choose from three packages ranging from $100-140. 
• Topgolf Swing Suite 900 is an indoor golf simulator space with a curated menu from Aster Hall Chicago featuring Small Cheval, Chicago Char-Dogs, and Pretty Cool Ice Cream.
• Disney100: The Exhibition is a perfect date activity since it’s not great for little kids. (Lots of informational posters, etc!) It takes you along the journey of Disney for the past 100 years from the start of Mickey Mouse, Disney World and all the movies! 
• If you haven’t experienced a Candlelight Concert by Fever, you’re missing out! They have a few tickets remaining for their holiday shows, but new performances are continuously added!
• Plan a Boozy Bar Crawl in Wrigleyville! There are FIFTEEN holiday pop-ups this year! Start at How Lost Never Found Stole Christmas, stop by Santa Baby (Bamboo Club), Elf’d Up (Stretch Chicago), and eventually make your way to 8 Crazy Nights (Graystone Tavern)!
• See a show like The Magic Parlor, a one-of-a-kind experience. It’s a bit of magic, some drinks, mind-reading, and just a full show! It’s a bit of a splurge, but I think it is worth it! The Second City’s iconic improv institution never disappoints! They’ve got tons of different holiday sketch shows like “Cuffing Season’s Greetings” and “The Good, The Bad, and The Ugly Sweater.” You could also visit a Speakeasy at one of Chicago’s oldest bars, The Drifter! They have cabaret shows, magic, and live music! It’s downstairs from The Green Room, a big Al Capone hangout back in the day.

For the Foodies

• Make a reservation for a special Holiday Afternoon Tea! I was just invited to The LondonHouse tea, and it was so beautiful and delicious! Check out our whole list here!
• The caviar cones with caviar and potato chips at Bar Mar are definitely a foodie’s dream!
• Give a gift card to a cooking class at Tutore Italian Cooking School. I have heard nothing but amazing things about these classes! Your favorite foodie can choose between classes like Gnocchi 101, Italian Christmas Cookies, or Pasta 101.
• Chicago Food Tours – I love their neighborhood restaurant tours like Chinatown, West Loop, and Pilsen. Each tour ranges from about $75-99 per person and includes food, drinks, and a behind-the-scenes look into the Chicago foodie scene.
• Lettuce Entertain You Gift Cards are a no-brainer since they have a restaurant for every taste. Some of my favorite restaurants are RPM Seafood, Aba, Cafe Ba-Ba-Reeba!, Ema, and Summer House Santa Monica.
• Brewery tour – These Barrel Run Brewery tours are so fun! They stop at different breweries, and tickets include tastings and transportation! Bonus! They are also on Groupon right now!
• Create your own Malt Row beer crawl – I did this with Manny for a day date in Ravenswood, and it was so much fun! You can check out the website and plan your day ahead of time. There are so many breweries to choose from. I think it’s one of the most unique holiday experience gifts in this guide!
• Bettie’s Chicago class – Bettie’s Chicago is a 1950s diner-themed event space and baking school in the River North. The newish space offers baking classes and events! Fun date idea!

Spa Day

• Aire – the ultimate luxury spa! Great for couples or alone!
• JW Marriott Spa recently invited me to check out their facilities, and it was incredible. I had a great massage and enjoyed all the amenities: gym, heated pool, jacuzzi, steam room, and more. I ended the day upstairs at The Florentine for lunch! The focaccia were made in-house, and the meatballs were great.
• Langham Spa is the ultimate relaxation destination. Spa guests have access to all the amenities like the indoor pool, hot tub, steam room, and salt stone saunas.
• Now Massage has six city locations! Their massages are excellent AND affordable. They have a deal on gift cards right now, too!
• Face Foundrie – treat a busy mom in your life! Love this facial bar, with many services below $100! Use code TheChicagoGoodLife for $10 off first-time services!
• Legendary Lash & Nail – I just started going recently and am obsessed! They use a Gel Overlay to help your natural nails grow. A gift card would be so nice, and I’m working on a discount for you!
• Kohler Spa in Lincoln Park – A two-floor Kohler spa in Lincoln Park with some of the best amenities to use before/after your service! The pool, hot tub, steam, lounging area, etc., are really nice!
• Piva Beer Spa – Such a great gift option for him or any beer lovers! Available on Groupon for single or couples!

And that concludes this epic list of holiday experience gifts! I hope you find something perfect for your loved ones or yourself. Be sure to check out all my holiday content here!

Cheers!

Christine