Best Things to Do in Chicago

Dining

Timothy O’Toole’s: Where Sports and Festive Fun Collide

Situated in the bustling heart of Streeterville, Timothy O’Toole’s stands as a true haven for sports enthusiasts. Established in 1992 by Humberto Martinez Jr. and Sara McKinnon-Martinez, this family-owned sports bar proudly claims its place as the oldest establishment in the ever-evolving Streeterville bar scene. A Sports Fan’s Dream Timothy O’Toole’s is a sports fan’s… Read more »

Blog

Unwind in Style: Your Ultimate Holiday Staycation at The Robey

Discover the perfect holiday escape right in the heart of Chicago with a staycation at The Robey, where history and modern luxury meet in the Windy City. Nestled in the vibrant neighborhoods of Wicker Park and Bucktown, The Robey invites you to experience the magic of a holiday staycation like no other. The Robey: Your… Read more »

Culture

Holiday Magic at Museum of Illusions Chicago

Welcome to Museum of Illusions Chicago a unique edutainment destination that transports you into the mesmerizing world of illusions! This one-of-a-kind museum offers a wide range of classic illusions, mind-bending exhibits, and interactive installations that will challenge your perception and ignite your imagination. This holiday season, Museum of Illusions Chicago invites you to experience mind-boggling illusions that… Read more »

Shopping

Illinois Unwrapped: Unique Gifts, Decor, and Delights

The Illinois Made program celebrates local businesses whose creativity and distinctly Illinoisan essence infuse every handcrafted item.

Things To Do

9 Holiday Pop-Ups You Can’t Miss

Embark on a festive journey across Chicago, exploring these unique holiday pop-ups that promise Christmas cheer, delightful cocktails, and immersive experiences for everyone. Tinseltown Chicago at Welcome Back Lounge Dive into Christmas bliss at Tinseltown Chicago! This dedicated Christmas Bar by the Viral Group offers themed sessions with Santa’s elves, festive tunes, winter warmer drinks,… Read more »

Joyce Fong

Chef Concierge, Chicago Athletic Association

Holidays wouldn’t be the same without a hot cup of cocoa or holiday music in the air. Each Friday in December, until December 15, join in the voices at the Millennium Park Holiday Sing-Along at 6pm. You will be led in song by a different local choral group each week for a fun and heartwarming occasion.

Others to Try:

Hot chocolate at the Nutella Café ...
More hot chocolate at XOXO ...
... and more at Intelligentsia (it is not on their menu but just ask!)

Sharyne Tu

Concierge, Macy's

December is filled to the brim with fun and exciting happenings across the city for all ages. In addition to the popular holiday events downtown, check out the neighborhood festivities including Zoolights at Lincoln Park Zoo, Gallagher Way at Wrigley Field, drive thru light show at Guaranteed Rate Field, Christmas Around the World at MSI, and so much more! December is filled to the brim with fun and exciting happenings across the city for all ages. In addition to the popular holiday events downtown, check out the neighborhood festivities including Zoolights at Lincoln Park Zoo, Gallagher Way at Wrigley Field, drive thru light show at Guaranteed Rate Field, Christmas Around the World at MSI, and so much more!

Others to Try:

CTA's Holiday Trains and Buses
Millennium Park Sing-a-Longs
Navy Pier's Light Up the Lake and Saturday Fireworks

Philippe Gills

Chef Concierge, Langham

Bring a bit of Ukrainian culture into your holiday gift giving at the Cultural Showcase Pop-Up at 410 North Michigan Avenue! Clothing, home goods, Ukrainian arts, and of course sweet treats!

Twas The Night Before gets an ultra-creative – and athletically masterful treatment from the one and only Cirque Du Soleil.

For one night only the incomparable Chicago Human Rhythm Project celebrates their 35^th Anniversary with an all-new Holiday Rhythms tapping into the spirit of the season – literally! At legendary Jazz Showcase – open since 1947!