Chicago Holiday Experience Gifts for Adults This Year

November 4, 2022

Manny and I usually only exchange very small gifts over the holidays, but we really love exploring our city together. It’s actually how this account got started initially! We just love getting out and trying new things in the city So, we usually get ourselves tickets or reservations and make a date or two of it! Here’s what on my 2022 Chicago experiences wish list for adults. (Hint, hint, Manny!) If you need kids experience gift ideas, see this post for my ideas for kid experience gifts!

Plan a Chicago Holiday Date Downtown (Loop/Gold Coast/River North Area)

Chicago experience gifts are the best! Here is a huge list of ideas.
Union Station has such a pretty tree every year!

My ideal downtown winter day-to-night date looks a little like this: yummy coffee & 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. It’s nice just to walk up and down to see all the decor!

There’s a ton of things to do, but below are holiday specific things to help you plan your perfect holiday date downtown:

Walnut Room Tree

Curling at The Gwen makes a great gift!
Curling and rooftop bar at The Gwen
Ice skating makes such a nice date for the holidays!
Day Date Downtown (a full holiday experience gift day!)
Outdoor Experiences
  • Go Ice Skating at Maggie Daley Park or McCormick Tribune Ice Rink. Both of these have free admission, but you need to reserve tickets online for your session and rent skates when you get there for $16-20. Both rinks’ reservation dates are released 2 weeks in advance of the session date but they do fill up that quickly ahead of time.
  • See Macy’s State Street window displays and/or dine in the Walnut Room. Reservations are going fast, but you might be able to snag a weekday spot, or get on the waiting list. (both indoor and outdoor!)
  • Browse the OG Christkindlmarket at Daley Plaza. Did you see their annual mugs this year? So cute! I would go early to avoid waiting in long lines! If you want to avoid the long lines, the Christkindlmarket at Gallagher Way is usually less crowded- just further north from downtown.
  • Stroll and shop your way down Michigan Avenue to see the Wrigley Building Christmas tree. Be sure to stop by the Fanny May flagship store right across the bridge to pick up their new Chicago collection chocolates– they make such a great gift idea for out-of-towners!
  • Go curling at the Gwen!
Indoor Experiences
  • While you are on Michigan Avenue, LaBriola on Michigan Avenue (right across from the Wrigley Building) has an amazing happy hour deal starting with $3 glasses of wine. Plus their pizza is actually very underrated in my opinion, it’s really good!
  • Check out the Waldorf Astoria tree (then go to Butch McGuire’s…see below) or even the one at the 900 building (then go upstairs to their Library bar for a drink…it’s kind of hidden!)
  • Visit a Holiday Pop-Up bar like Butch McGuires in Gold Coast areas (It’s like the OG of holiday bars), Happy’s at the Chicago Athletic Hotel (SO CUTE!), Fairmont Lodge hotel lobby is really cute, or London House igloos. If you want to warm up and experience some luxury, for Four Seasons or Langham have stunning holiday decor in their hotels and offer tea time!

Waldorf Astoria Tree

Butch mcguires for the holidays!
Butch McGuires is my fav during the holiday days!

See a Show

  • The Magic Parlor – Take your partner to a one-of-a-kind experience at The Magic Parlor. It’s a bit of magic, some drinks, mind reading, and just a full show! It’s definitely a bit of a splurge, but I think it is totally worth it! They also have cash back right now on Groupon!
  • Luminaire by Cabaret ZaZou – I’ve heard great things! It’s a sexy, funny, and magical evening. Groupon is offering discounted tickets!
  • Copa at Carnivale – This stunning dinner and a show combo happens on select dates only, so check their event schedule. Tickets to the show are separate from your dinner tab, but it’s such a worth-it add-on!
  • 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, which was a big Al Capone hangout back in the day 🙂

Take a Class

OffBeat Mural Art Walk on Groupon makes a unique holiday gift!

Offbeat Street Art Mural Tour

Brooklyn Boulders is a great gift experience for those that like to move and be active!
Climbing class at Brooklyn Boulders

There are so many different workshops and classes in the Chicagoland area on any given day. If you’re looking for a holiday experience gift for someone who loves to keep learning new things, check these out!

  • Aura Candle Bar – I want to do this with friends! You can make your own scent, it’s BYO and located on Southport with lots of restaurants/places to grab food afterwards. It looks fun!
  • Not so much a class, but the Offbeat Art Street Mural Walk is really unique! It’s 1.5 hours of walking through Bucktown and Logan Square learning about the street art. I recently did it and it’s cool! Follow up with a lunch a Cafe Robey or drinks at Big Star! See the pic above! They are currently on Groupon!
  • Brooklyn Boulders – I took a climbing class here and it’s SO fun! It looks like a lot of work, but would make a great holiday experience gift for those athletic friends in your life!
  • The Second City – The Second City offers so many cool classes like improv, writing, stand-up and public speaking, production, physical comedy, and more!
  • Rebuilding Exchange – Rebuilding Exchange hosts workshops for the DIY enthusiast! They have different series based on Home Improvement (how to rewire a light fixture, prepping or painting your home, etc.), Woodworking (tool basics, make your own serving tray), and Creative Reuse (mosaic art, make a lamp out of anything!) This would be so fun to do with a partner, friend, or parent!
  • Old Town School of Folk Music – This Lincoln Square mainstay has so many great classes (in-person and virtual options) like Paul McCartney Bass Style, Brazilian Dance, Guitar 101, and Songwriting Fundamentals.

For the Foodies

Malt Row makes a great experience gift for all the beer lovers!

Cultivate- Forbidden Root apart of Malt Row

  • Chicago Food Tours – I love all their different 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.
  • Frontier – Manny has done this with friends and it’s a cool group dining experience. You start with an animal of your choice, then pick all the sides from there. This would be good if you and your friends wanted to do something different and not exchange your typical gifts this year!
  • Lettuce Entertain You Gift Cards
  • Brewery tour – These Barrel Run Brewery tours are so fun! They stop at different breweries, includes the tastings and transportation! Bonus! They are also on Groupon right now!
  • Create your own Malt Row beer crawl – I just 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 on this guide!
  • Bettie’s Chicago class – Bettie’s Chicago is a 1950’s diner-themed event space and baking school in the River North. The newish space offers baking classes and events! Fun date idea!

Spa Day

Face Foundrie has 2 locations- Bucktown and West Loop

Kohler Spa in Lincoln


Legendary Nails gift card would be a nice gift!


Aire Baths
  • Aire – the ultimate luxury spa! Great for couples or alone!
  • 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!
  • Heavenly Massage – I’ve had a massage here a few times! They have a few locations and one in Gold Coast. It’s maybe not as luxurious as hotels but it’s always a good massage for under $100! Plus they are on Groupon!
  • Legendary Lash & Nail – just started going recently and I’m 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! Pool, hot tub, steam, lounging area, etc. it’s really nice!
  • LH Spa – Another great luxurious spa option at the London House hotel spa! Also on Groupon with single or couples massage options!
  • Piva Beer Spa – Such a great gift option for him or any beer lovers! Available on Groupon for single or couples!

For the Ladies

Langham is beautiful during the holidays!
  • Afternoon Tea at Langham – if you are looking for a luxurious tea time to experience with your friends or even a mommy/daughter date, this would be perfect!
  • Nock Nock to host a party without having your clean your house – we did this for my family meet up and it was a perfect space. These are spaces to rent in peoples homes like patios, backyards, kitchens, yoga studios, etc. Use code GOODLIFE for $25 off your first booking!
  • Solo hotel stay/momcation – I have stayed at the Waldorf Astoria by myself and it was amazing! If you are looking for something in the Chicagoland area, the Hyatt Lodge Oak Brook was amazing when I stayed there.
  • Van Gogh Immersive – this is another great activity for couples, friends, or mother-daughter days.
  • Urban Stems subscription – I just think it would be so special to have beautiful bouquets delivered every couple of weeks!

For the Gentlemen

  • Shop 900 Golf Suite – an indoor golf simulator space with restaurant on Michigan Avenue.
  • Piva Beer Spa – Such a great gift option for him or any beer lovers! Available on Groupon for single or couples!
  • Windy City Smokeout tickets – This is THE BBQ event of the year. And yes, I know it’s a half a year away, but tickets go fast and the 2023 lineup is so good!
  • Tickets to a concert – Muse, Depeche Mode, and Blink-182 are on the schedule at the United Center.
  • Nock Nock (night out with the guys, recording session) See above!
  • Museum of Science and Industry membership for your science guy

And that concludes this epic list of holiday experience gifts! I hope you find something perfect for your loved ones or even for yourself!


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