Events

Everything You Must Do in Chicago This Holiday Season

Updated On 12/12/2017 at 04:11PM EST Updated On 12/12/2017 at 04:11PM EST
Ice skating the McCormick Tribune Ice Rink
Ice skating at the McCormick Tribune Ice Rink | Miune/Shutterstock.com
November
christmas tree lighting
Christmas Tree Lighting | Alph Tran/Shutterstock
November
Wednesday - Saturday
Nov 15-Dec 30
Up Comedy Club
Laugh at the insanity that is the holiday season at this always-on annual yuckfest. These comedians will skewer tradition, current events, and the general madness that is apparently now just called life on this Earth.
Cost: $31-$41
Friday
Nov 17
Millennium Park
Join the cast members from the Goodman Theatre’s A Christmas Carol, country band Temecula Road, the Oakdale Christian Academy Choir, and Santa and Mrs. Claus for this annual tree lighting ceremony of a massive 62-foot Norway spruce. The action starts at 6pm, but if you miss it, the tree will be up until Saturday, January 6, 2018.
Cost: Free
Friday - Sunday
Nov 17-Dec 31
Daley Plaza & The Park at Wrigley
It may not be the coolest thing in the world, but a Chicago Christmas season spent without paying at least one visit to this popular German-styled outdoor holiday market in Daley Plaza is not a Chicago Christmas season. The market also pops up at The Park at Wrigley this year for the first time, from November 24 through December 31.
Cost: Free
Thursday - Saturday
Nov 17-Jan 13
MCL Chicago
We'll say it: Screw The Nutcracker. The real holiday musical is this Christmas-themed BYOB Die Hard parody whose shit you’re never getting too old for.
Cost: $20-$25
Friday
Nov 17
Millennium Park & The Park at Wrigley
Ice skating the McCormick Tribune Ice Rink over the holiday season is as essential to Chicago Christmas as a Red Ryder BB Gun under the tree, with caroling at the Bean and additional ice at the Maggie Daley Park Skating Ribbon. An 8,000-square-foot rink will also be laid down this year at The Park at Wrigley for the first time, available from November 24 through February 25, 2018.
Cost: Free at Millennium Park; $5 at Wrigley for ages 13 and up
Friday - Sunday
Nov 18-19
Pioneer Court
Watch the official lighting of more than one million lights on 250 trees along the Mag Mile with a tree-lighting parade down Michigan Avenue from Oak Street to Wacker Drive. (If you can't make it in person there will also be a one-hour, nationally televised broadcast.)
Cost: Free
Wednesday
Nov 23
Lincoln Park
Race along the lakefront for charity with pre- and post-race tailgates and free beer from Lagunitas plus turkey bowling, football, bag toss, and prizes for best-dressed “Thanksgiving inspired” group... whatever the hell that means.
Cost: $15-$40
Thursday
Nov 23
State between Congress & Randolph
A giant inflatable turkey, high school marching bands, Ferris Bueller-style floats, performances of 'Twas the Night Before Christmas, a Mongolian strongman, and Medieval Times knights duels? All on hand at the Thanksgiving Day Parade, taking place from 8 to 11am.
Cost: Free to attend, but $60 for VIP
Friday
Nov 24
Starts at John Hancock Center
See the city the Vince Vaughn-approved way (via double-decker bus) at this classic holiday trolley tour hitting Christkindl Market, ZooLights, and Michigan Avenue. You'll also get a free holiday cupcake from Sprinkles out of it.
Cost: $29
Friday - Sunday
Nov 24-Jan 7
Lincoln Park Zoo
This local Christmas tradition involves a massive display of twinkling Christmas lights, live ice carving, kid’s games, and -- of course -- spiced wine and beer at the zoo. Special events include the BrewLights craft beer fest on December 7, but it's fun all season long.
Cost: Free to enter; prices for special events vary
Friday
Nov 24
Various locations
Instead of battling a crowd of lunatics at Walmart for a discounted toaster, spend Black Friday doing your Christmas shopping at local independent record stores for deals and special releases from the likes of Paul McCartney, Fleet Foxes, The Decemberists, and any other artists that strike your fancy.
Cost: No cover
Friday
Nov 24
Mrs. Murphy & Sons
Decompress from a long day of holiday shopping with... more holiday shopping. And booze, of course, plus 30 booths of handmade goods at one of the finest Irish bars in the city.
Cost: Browsing is free
December
Renegade Craft Fair
Renegade Craft Fair | Renegade Craft Fair
December
Saturday
Dec 2
Downtown
Join another raucous crew of boozed-up holiday revelers in partially stained Santa suits as they crawl the downtown bar circuit and freak out plenty of confused tourists along the way for the 12th year running. The bars will be announced soon, so get ready.
Cost: Free
Saturday
Dec 2
Martyrs'
Party in a local music venue alongside St. Nick’s evil alter ego Krampus with a holiday art market, German-styled street food including Paulina Meat Market sausage, live bands, and a boisterous costumed parade down Lincoln Avenue.
Cost: Free
Saturday - Sunday
Dec 2-3
Bridgeport Art Center
Only the coolest people shop for cool stuff in this cool 'hood at this cool event featuring cool handmade goods from more than 250 cool indie makers. There will also be delicious eats from cool food trucks like Yum Dum and cool tunes from Lumpen Radio and Reckless Records.
Cost: Free
Saturday
Dec 9
Boards at DuSable Harbor
Kris Kingle meets the P. Diddy lifestyle at this mistletoe-ensconced party on Lake Michigan aboard a three-level yacht with live DJ, dancing, massive skyline views, and after-party at a River North bar that's still to be announced.
Cost: $20-$30
Saturday
Dec 9
FatPour Tap Works
Strap on your ugliest Christmas attire and raise funds for charity with a silent auction, raffle, and Ketel One/Bulleit-hosted bar from 7-8pm. The donations go to the Never Had A Bad Day Foundation and will hopefully help raise your confidence in your outfit of choice.
Cost: $10
Saturday
Dec 9
Various Wrigleyville locations
It wouldn’t be Christmas without this hedonistic (and slightly sadistic) costumed crawl of 12 Wrigleyville bars (very unofficially the world’s largest bar crawl), starting at 10am with beer-filled bowls of cereal and ending whenever you've had your fill.
Cost: $35
Saturday - Sunday
Dec 9-24
Music Box
With lyrics to Christmas carols projected on screen for group sing-alongs followed by a double feature of White Christmas and It’s a Wonderful Life, if you don’t get in the Christmas spirit after this, you may not have a pulse. This will run for just over two weeks, but definitely book in advance.
Cost: Single features are $15 and double features are $24, but both are cheaper if you book in advance
Friday
Dec 15
The Hideout
This Chicago native will host an intimate evening of music accompanied with My Brightest Diamond. The show's proceeds will go to benefit scholarships for the local music charity Foundations of Music.
Cost: $100-$200
Friday
Dec 15
Lagunitas Brewing Company
If you're a fan of classics like Elf, Home Alone, and Lagunitas beer, look no further than this movie series hosted by the brewery. Your ticket is good for a screening, a complimentary beer, and complimentary popcorn. Don't be late.
Cost: $20 per screening
Saturday
Dec 16
River North bars
In case you needed yet another excuse to party and dress in holiday attire, there’s this crawl of River North bars with drink specials, pre-party at Public House, and after-party at Moe’s Cantina. This is a true Santa crawl, and free gifts will be doled out too.
Cost: $10; Santa costumes not included
Friday
Dec 22
Pilgrim Congregational Church
Chicago's multicultural, LGBT-friendly Pilgrim Congressional Church will host a night of Christmas music led by artistic director Marsha Holmes. Fun fact: Pilgrim Congressional Church is also known for its donut ministry.
Cost: $11
Saturday
Dec 23
J9 Winebar
If you wine fans out there want to squeeze one more pre-Christmas celebration before the family festivities kick off, this Christmas in Vienna tasting event should slake your thirst. Running through a variety of Austrian wines doesn't sound like a bad Saturday at all.
Cost: $25
Sunday
Dec 31
The Drake Hotel
New Year’s Eve in Chicago means massive parties in fancy hotels, like this long-running annual monster sprawling out across five ballrooms of entertainment with thousands of guests and enough booze to get a small army plenty drunk. It may set you back a bit, but if you want something legitimately huge, with drinks and appetizers included, it's worth it.
Cost: Tickets start at $149