Night of 1,000 Jack-o'-Lanterns
Sun, Dec 20 · 6:30 PM
Glencoe
Christmas Break in Chicago.
The best christmas break in Chicago, chosen one at a time. Ask me for something more specific.
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Browse Chicago neighborhood by neighborhood, get ideas just for you, or ask me anything.
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127 activities · Page 1 / 3
A few to start with
Jack's Pumpkin Pop-Up
Sun, Dec 20 · 5:00 PM
West Town
Black Lagoon
Sun, Dec 20 · 5:00 PM
Lincoln Park
Vivir la Tierra : Acquisitions from the Permanent Collection 2010–2026
Sun, Dec 20 · 10:00 AM
Lower West Side
Carillon Tower Tours
Tue, Dec 22 · 11:30 AM
Hyde Park
Bluefin Tuna Experience
Wed, Dec 23 · 5:30 PM
Chicago Loop • $$$$
All activities
Sun, Dec 20 · 6:30 PM
Night of 1,000 Jack-o'-Lanterns
Chicago Botanic Garden · Glencoe
Sun, Dec 20 · 6:15 PM
SOS Party
May I Have This Dance · Norwood Park
Sun, Dec 20 · 10:00 PM
Sundown Sundaze
PRYSM Chicago · Goose Island
Sun, Dec 20 · 7:00 PM
Neo Soul Sundays: Convo & Candles
Above Average DIY Candle Studio · North Park
Sun, Dec 20 · 7:00 PM
Chicago Alliance of Film Festival
Chicago Cultural Center · Chicago Loop
Mon, Dec 21 · 7:00 PM
Music Bingo
Marz Community Brewing Company · McKinley Park
Mon, Dec 21 · 7:00 PM
Music Bingo
Dark Matter Coffee - The Mothership · West Town
$
Mon, Dec 21 · 4:00 PM
ROOF Happy Hour
ROOF on theWit · Chicago Loop
Sun, Dec 20 · 10:00 AM
Great Ideas of Humanity: One of a Series
Chicago Cultural Center · Chicago Loop
Sun, Dec 20 · 9:00 AM
Field Museum of Natural History Chicago Tour with Tickets
Field Museum Store · Near South Side
Sun, Dec 20 · 10:00 AM
Chicago Cultural Center Exhibition Exploration Tours
Chicago Cultural Center · Chicago Loop
Mon, Dec 21 · 11:00 AM
Ageless Grace® Brain and Body Fitness
Evanston Public Library · Evanston
Sun, Dec 20 · 5:00 PM
The Performance Bar
Chicago Magic Lounge · Ravenswood
Sun, Dec 20 · 11:00 AM
Lincoln Park Secrets: Private Enchanted Pedicab History Tour
William Shakespeare Monument · Lincoln Park
Mon, Dec 21 · 3:30 PM
Happy Hour
Lil' Ba-Ba-Reeba! · River North
$$
Mon, Dec 21 · 6:30 AM
D.A.S.H. Program – Aqua Workouts
FFC Oak Park · Oak Park
Sun, Dec 20 · 9:30 AM
Dinos!
Brookfield Zoo Chicago · Brookfield
Mon, Dec 21 · 9:00 PM
Monday Pro Blues Jam
Fuller's Pub · Irving Park
$$
Sun, Dec 20 · 9:00 AM
Pokémon Fossil Museum
Field Museum · Near South Side
Sun, Dec 20 · 10:00 AM
Creative Rebellion
Chicago Cultural Center · Chicago Loop
Sun, Dec 20 · 5:00 PM
Jack's Pumpkin Pop-Up
Jack's Pumpkin Pop-up · West Town
Sun, Dec 20 · 10:00 AM
Welcome Center
Chicago Cultural Center · Chicago Loop
Sun, Dec 20 · 12:00 PM
Explore the Evolution of Late Night TV
Museum of Broadcast Communications · West Loop
Sun, Dec 20 · 6:00 AM
Private Photography Session with Local Photographer in Chicago
Chicago · Chicago
Sun, Dec 20 · 5:00 PM
Black Lagoon
The Parlour at The Albion · Lincoln Park
Sun, Dec 20 · 10:00 AM
Exhibition Exploration Tours
Chicago Cultural Center · Chicago Loop
Mon, Dec 21 · 8:00 PM
Swing Night
Fizz Swing Dance · North Center
Tue, Dec 22 · 3:00 PM
Messy Makers
Roseland East 115th Street Health Hub · Roseland
Tue, Dec 22 · 8:00 PM
Tuesday Night Trivia
The Globe Pub · North Center
$$
Tue, Dec 22 · 4:00 PM
Hummus Hour
Beity - West Loop · Fulton Market District
$$$$
Tue, Dec 22 · 7:00 PM
Weekly Trivia Tuesdays
Punch Bowl Social · Fulton Market District
$$
Tue, Dec 22 · 7:00 PM
Cantina Night
Dark Matter Coffee - The Mothership · West Town
$
Tue, Dec 22 · 10:00 AM
Exhibition Exploration Tour (for student groups)
Chicago Cultural Center · Chicago Loop
Tue, Dec 22 · 8:00 PM
Trivia Night at Cleo's
Cleos Bar and Grill · West Town
$$
Sun, Dec 20 · 10:00 AM
Vivir la Tierra : Acquisitions from the Permanent Collection 2010–2026
National Museum of Mexican Art · Lower West Side
Tue, Dec 22 · 6:00 PM
Relax Attack Jazz Series
The Whistler · Logan Square
$$
Tue, Dec 22 · 11:30 AM
Carillon Tower Tours
Rockefeller Memorial Chapel · Hyde Park
Wed, Dec 23 · 8:00 PM
Pete's Dueling Piano Bar Wednesday Night Show
Pete's Dueling Piano Bar · Rosemont
Wed, Dec 23 · 6:00 PM
Open Mic Night
Ed & Joe's Restaurant & Pizzeria · Tinley Park
$$
Wed, Dec 23 · 7:00 PM
Trivia Night
Hillgrove Tap · Tinley Park
$$
Sun, Dec 20 · 11:00 AM
Happy Hour & Daily Specials
Tin Roof · Lake View East
$$
Wed, Dec 23 · 7:00 PM
Trivia on Marz
Dark Matter Coffee - The Mothership · West Town
$
Wed, Dec 23 · 6:00 PM
Tropical Wednesdays
Vintage Bar · Little Italy
$$
Wed, Dec 23 · 5:30 PM
Bluefin Tuna Experience
Miru · Chicago Loop
$$$$
Sun, Dec 20 · 10:30 AM
90 minute Chicago's Chinatown History and Culture Tour
2189 S Wentworth Ave · Armour Square
Wed, Dec 23 · 9:00 AM
Illinois Free Wednesday
Field Museum · Near South Side
Thu, Dec 24 · 1:15 PM
Public Group Tours
Chicago Cultural Center · Chicago Loop
Thu, Dec 24 · 12:00 PM
Turning Point Behavioral Health Care Center: Mobile Living Room
Evanston Public Library · Evanston
Thu, Dec 24 · 1:15 PM
Public Group Tours: Chicago Cultural Center Building Tours
Chicago Cultural Center · Chicago Loop
Thu, Dec 24 · 8:00 PM
Alan Gresik's Swing Orchestra
The Green Mill · Uptown
$$
Thu, Dec 24 · 12:00 PM
Thursday Bingo
Durbin's of Harmony Square Tinley Park · Tinley Park
$$
Thu, Dec 24 · 3:30 PM
Teen Grab and Go Kits
Scottsdale · Scottsdale
Thu, Dec 24 · 7:00 PM
Trivia Night
Ed & Joe's Restaurant & Pizzeria · Tinley Park
$$
Thu, Dec 24 · 1:15 PM
Private Group Tours: Chicago Cultural Center Building Tours
Chicago Cultural Center · Chicago Loop
Thu, Dec 24 · 12:00 PM
Renal Grand Rounds - Opeyemi Olabisi
Simpson & Kimberly Querrey Biomedical Center · Streeterville
Fri, Dec 25 · 9:00 PM
Friday Night House Party
Meeting House Tavern · Uptown
$
Fri, Dec 25 · 8:00 PM
FREE LIVE COMEDY - 2 Marks and a Mic Open Mic
Bizzy Bees · Forest Park
$
Fri, Dec 25 · 8:00 PM
Chicago Speed Dating (Ages 24-32)
The Fun Singles Chicago Speed Dating & Singles Events · Fulton Market District
Fri, Dec 25 · 9:00 PM
Latin Friday Nights
LV Club · Logan Square
$$$
Fri, Dec 25 · 8:00 PM
Fall/Winter Friday Nights at the Dearborn Observatory
Dearborn Observatory · Evanston
Christmas Break in other cities
Frequently asked questions
How are these christmas break in Chicago chosen?
I go through what's actually on nearby and keep only the ones worth the trip. Nobody pays to be on this list.
Is this list up to date?
Yes. If it's on the list, it's still on.
How do I find something that suits me?
Open the map and tell me what you're after — a good terrace, somewhere that works with kids, something on tonight. I'll answer and narrow it down with you.
Do I need an account?
No, everything here is browsable without one. An account is how I learn your taste, your people and your saves, so what I show you keeps getting closer to what you'd actually go to. You can also have ideas sent to you by email or message if you want them.
Is it free?
Yes, completely.