PICKLEBALL LEAGUE & COURT RENTALS
January 28, 2026 at 4:00 pm
Our storied spaces are a spirited, inclusive hub of culture, dining, and architecture—beloved by both locals and travelers. Recognized in the inaugural MICHELIN Guide Keys, which celebrate the world’s most authentic and distinctive travel experiences, we have grown from our iconic past as an exclusive members-only club into a landmark gathering place for all, infusing every detail of our hospitality with passion and care. Join us in one of our celebrated social spaces—whether at Cindy’s on the rooftop, or over the famed food and drink creations of Boka Restaurant Group at Midōsuji, Game Room, or the Drawing Room.
No matter what type of meeting space you require, the Chicago Athletic Association’s iconic and adaptable spaces are ideal for achieving great things. Our halls have a legacy of making history, and are ready to help you make your own.
Chicago Restaurant Week is here! Join us for lunch at @drawingroomchi and @cindysrooftop—two iconic spots, one delicious reason to plan your next midday escape.
See their websites to see CRW menus and hours.
#ChicagoRestaurantWeek
Jan 23
When it’s too cold to leave the covers, let @shakeshack come to you. We’re the only hotel in the world offering Shake Shack room service—so you might as well take full advantage.
Jan 20
Your winter wellness playground all under one roof✨
Jan 13
A season to settle in✨
Where winter days are meant for lingering—by the fire, between the pages of a book, over a perfectly poured cocktail, or cozied up in our beloved robes with room service.
Jan 2
Wishing you a bright, happy, and safe New Year ✨ Thank you for being part of our family and story in 2025!
Jan 1
Start the New Year with intention ✨
Join us this January for a lineup of workshops and experiences designed to support both mind and body. From movement and mindfulness to music and connection, these events are here to help you step into 2026 feeling grounded, inspired, and energized.
Jan 11th | 9:30–10:30 AM - Winter Warm-Up Stretch Class with @stretchlabwestloop
Jan 18th | 1–2 PM - New Moon Sound Bath with @lightbylindsay
Jan 23rd | 7:30–10 PM - Immerse yourself in an intimate @sofarchicago live music experience
Jan 25th | 2–4 PM - Workshop: Intentional Dating in 2026 with @theyentepages
Plus, starting January 5th through April, we’re hosting Pickleball League play and Court Rentals in partnership with @chisportsocial now open for sign-ups on property!
Tap the “Upcoming Events” highlight in our profile to explore everything we have planned this month.
Dec 30
From our family to yours, wishing you all a happy holiday✨
Dec 25
Step inside the Drawing Room and stay awhile. Warm light, intimate seating, and a bar built for lingering—this is where winter nights are best spent. Come for the cocktails, stay for the cozy.
Dec 19
Still searching for the perfect holiday gift? 🎁 We put together a curated guide to help you find something unique for everyone on your list this year. Just tap our Gift Guide story highlight to start shopping items like our Champion of Robes, our signature scent candle, branded rocks glasses, and so much more.
Dec 14
POV: You’ve just checked into Chicago Athletic Association—and now you’re off to chase all the holiday cheer just steps away. ✨🎄
Dec 8
December is here and we’ve packed the month with festive things to do🎄✨ From a holiday light running tour to vibrant night markets and local shopping, there’s something for everyone this season.🎁
Dec 7 | 3–7 PM – On The Market
Produced by @theyentepages & @baqyardbabes
Dec 9 | 6:30–9 PM – Holiday Lights Running Tour
Led by @allison_b_yates
Dec 12 & 13 | 5–10 PM – SAUCED: Night Market
@saucedmarket
Dec 21 | 10:30 AM–12 PM – Fitness Class: Roller Dance with roller-skating guru @inspiredbyfavor
And all month long through January 16th, we’ve got Happy’s Holiday Pop-Up Bar!
Tap the “Upcoming Events” highlight in our profile to see what else we have in store this month.
Dec 5
Make your stay a little extra merry this season🎄✨
From our Holiday Hot Chocolate Kit—complete with house-made cocoa mix, truffles, and the option to add our keepsake CAA mug—to adding a little extra glow with a 2-foot pre-lit tree adorned with classic red ornaments, or enjoying Cookies & Milk for Santa (because everyone deserves a visit from Santa), our festive amenities bring the magic of the season right to your room. ✨🎄
Links in bio to book!
Dec 3
Give a little, get a little extra this season. ✨
For every $100 in gift cards you purchase to Cindy’s, Game Room, or the Drawing Room, you’ll receive a $25 digital bonus card—our holiday treat. Link in bio!
Nov 28
It’s the most wonderful — and sauciest — time of the year. ✨
SAUCED is back at the Chicago Athletic Association on December 12 & 13 from 5–10pm, filling our halls with 40+ local makers, artists, and tastemakers.
Free and open to all ages. Full vendor lineup at saucedmarket.com.
Nov 26
Cyber Week = the perfect time to treat yourself (or someone you love) 🎁
Whether you’re planning a cozy Winter getaway or dreaming of Chicago in Spring, book by December 11th and save up to 30% off as a World of Hyatt member on stays from November 20, 2025–April 30, 2026.
Not a member? You’ll still save up to 25% starting November 20 — or join now to get the full offer. Terms apply.
Link in bio to book.
Nov 24
We’re so honored to be nominated for @travelandleisure Best Awards and would be so grateful for your vote. If Chicago Athletic Association has been a special part of your travels, please consider voting us.
Your vote means so much to our team—thank you for being part of our story♥️Link in bio to vote!
Nov 21
🎄 Happy’s is back for its farewell holiday season!
Join us in the Tank from December 4–January 16 for one last round of cozy cocktails, comfort food, and all the nostalgic décor that feels straight out of grandma’s basement. Expect your favorite Happy’s meals, signature drinks, weekly programming, surprise moments, and plenty of holiday cheer as we toast to the end of an era.❤️💚
We’ll be celebrating Wednesday–Thursday from 4–11pm, Friday–Saturday from 3–11pm, and on select Sundays (details to come!). Please note: Happy’s is 21+.
Come drink, be merry, and help us make this final season one to remember. ✨
Nov 13
A cozy, snowy morning spent in Drawing Room✨
Nov 10
Game on in @gameroomchi 🏆 Games are complimentary and first-come, first-served – choose from skee-ball, billiards, shuffleboard, chess and checkers tables.
Nov 5
Our event lineup for November is here! From art installations to live music, vintage markets to roller dance, see what we have planned.
Nov 7 | 6-9PM — Experience Rupture: A Solo Exhibition by @jennyvyas
Nov 2 | 2–5PM — Dance it out with @chicagomehfil + choreographer Harini Nilakantan
Nov 2 | 7–11PM — Live music featuring the sounds of @parkingbandus , @hallogalloinc , @goodflyingbirds , @mod__lang
Nov 16 | 10AM–4PM — @pickwickvintage Market
Nov 17 | 10:30AM-12PM — Roller Dance Class with @inspiredbyfavor
These are just a few of the events we have planned. Tap the “Upcoming Events” highlight in our profile to see the full calendar!
Oct 29
Live your best life with @ShakeShack room service 🍔 It’s true: we’re the only hotel in the world offering it (alongside traditional in-room dining options to suit whatever you’re craving).
Oct 27
The @drawingroomchi is more than a lobby — it’s a gathering place for locals and travelers alike with cozy corners made for conversation. It’s a modern ode to the hotel’s storied social past.
Oct 16
Lean into cozy season and awaken your senses. Join us for an intimate candle-making and perfumery workshop with @hydeandparkco on Thursday, October 23 from 7–8PM. Discover the art of scent and craft your own bespoke candle. 🔗 Link in bio!
Oct 13
We’re incredibly honored to once again be recognized in the MICHELIN Guide Key 🗝️ listing for 2025, celebrating the world’s most authentic and exceptional travel experiences.
This continued acknowledgment is a testament to our unwavering commitment to delivering unparalleled stays — where design, service, personality, and hospitality come together seamlessly.
Congratulations to the other remarkable hotels earning their keys this year, and a heartfelt thank you to our devoted team, whose passion and dedication make this recognition possible. ❤️
Oct 9
Chicago does it again 🏆 Named Best Big City in the U.S. for the ninth year in a row by @cntraveler.
We’re endlessly proud to call this city home — and even prouder to welcome travelers who make it their favorite, too.♥️
🎥: @jersey_drone
Oct 8
Rally your ghouls and lace up for our Night of the Skating Dead! Our haunted roller rink takes over the vintage gym Friday, October 17. Expect eerie throwback films on the big screen, costumes encouraged, killer beats from DJs @djallthewaykay and @oprah_gucci , and a night where the ghouls rule the rink.👻
Link in bio!
Oct 6
Art that inspires at every turn 🎨✨ Explore the stunning pieces throughout Chicago Athletic Association.
Sep 29
Autumn hues fill our guest rooms, where sporty accents are a nod to our storied athletic past.
Sep 25
Soaking up the last of these summer nights at Cindy’s ✨ But don’t worry—the outdoor terrace is open year-round.
Sep 23
A timeless tradition: a good book, a crackling fire, and the historic charm of our Drawing Room. No better spot to spend #NationalReadABookDay 📚✨
Sep 6
