(This arti­cle may or may not con­tain affil­i­ate links. What does that mean?)

The hol­i­days are always my favorite time of year.  The mun­dane becomes the mag­i­cal.  And nowhere is that trans­for­ma­tion more evi­dent than in the city of Chica­go.  The steel and con­crete land­scape sud­den­ly becomes awash in green­ery, twin­kling lights, and rib­bons and glit­ter.  Though the oth­er 10 months of the year can be stark and mod­u­lar, for these two months dur­ing the hol­i­days, it’s com­plete­ly enchanting.

Chica­go goes all out for its hol­i­day fes­tiv­i­ties.  And we’re tal­ly­ing up our favorite, can’t miss, things to do with kids and fam­i­lies on your hol­i­day trip to the Windy City, Chicago. 



Zoo Lights @ Lincoln Park Zoo


seal with Christmas lights

This seal’s got the best seat in the house. Pho­to cour­tesy of the Lin­coln Park Zoo.


Even dur­ing stan­dard, non-hol­i­day times, the Lin­coln Park Zoo is an awe­some expe­ri­ence.  There are very few zoos in the world that are locat­ed right in the heart of a boom­ing metrop­o­lis and offer free admis­sion on top of that.  As locals, it con­tin­ues to be one of our favorite things to do as a fam­i­ly and with out-of-town guests.  And the Lin­coln Park Zoo Lights is one of our favorite hol­i­day tra­di­tions as a family.

Though per­haps small­er than most zoos, the Lin­coln Park Zoo still boasts a wide and exot­ic assort­ment of exhibits, with every­thing from zebras to goril­las just chill­ing in their urban habi­tats.  Their zoo lights dis­play is absolute­ly beau­ti­ful with the Chica­go sky­line serv­ing as a back­drop.  Tons of illu­mi­nat­ed dis­plays light up the zoo’s inte­ri­or, includ­ing a giant light tun­nel, an under-the-sea adven­ture, and a path of can­dy canes. 

There are also pho­to oppor­tu­ni­ties with San­ta, sea­son­al refresh­ments, and plen­ty of edu­ca­tion­al stops along the way to learn more about the zoo’s year-long residents.

For fam­i­lies with small kids, the Lin­coln Park Zoo Lights is a must-do and always gets rave reviews.


The Christmas Tree Lighting and Magnificent Mile Lights Festival


christmas tree chicago

Chicago’s Christ­mas Tree. Pho­to cour­tesy of Time­out Chicago.


While it’s no Rock­e­feller Christ­mas Tree, the Christ­mas Tree in Mil­len­ni­um Park in down­town Chica­go is equal­ly as beau­ti­ful — and with its own fire­works show to boot!  Tra­di­tion­al­ly tak­ing place the week­end before Thanks­giv­ing, the fes­tiv­i­ties also include the Mag­nif­i­cent Mile Lights Fes­ti­val and parade.  In recent years, the parade has become the third largest in the coun­try, with mil­lions of peo­ple show­ing up to watch the spec­ta­cle that begins at the top of Michi­gan Avenue by Oak Street Beach and slow­ly makes its way down to Wack­er Dri­ve beneath the glow of mil­lions of twin­kling hol­i­day lights.

The parade always includes notable appear­ances by Mick­ey and Min­nie Mouse, Ker­mit and Miss Pig­gy, and the big man him­self, tak­ing a brief trip away from the North Pole to enjoy the event with Mrs. Claus.

It’s a fun event that kicks off the hol­i­day sea­son and gets every­one excit­ed for the weeks to come. 



Ice Skating at Maggie Daley Park and Millennium Park


Want to get your skate on?  Down­town Chica­go has not one, but two ice skat­ing rinks in Mil­len­ni­um park that are open to the public. 

The tra­di­tion­al McCormick Tri­bune Ice Rink in Mil­len­ni­um Park is a peren­ni­al favorite among locals and tourists alike.  Skate in the shad­ow of the famous Cloudgate (or Bean as it’s lov­ing­ly nick­named) and the down­town sky­line.  Admis­sion is free if you bring your own skates. Rental skates are also avail­able.  Once you’ve skat­ed your­self hun­gry, you can pop into the Park Grill locat­ed right next to the rink for a meal or swing by the Park Café for a snack or hot beverage.

The oth­er rink is new­er and just as unique an expe­ri­ence.  The Mag­gie Daley Ice Skat­ing Rib­bon is a thick stretch of ice rink that lit­er­al­ly rib­bons around and through Mag­gie Daley Park, allow­ing you to tour the entire park while you skate.  Just a block or two from the McCormick Tri­bune Ice Rink, you could eas­i­ly try your hand at both and pick your favorite.  Both rinks are kid friend­ly and great for the whole family. 



The Nutcracker at the Joffrey Ballet


A few years ago, for my birth­day (which hap­pens to fall dur­ing the hol­i­days), my hus­band got us tick­ets to see the Nut­crack­er per­formed by the Jof­frey Bal­let com­pa­ny.  We’re the­ater buffs who are known for scop­ing out the best on and off Broad­way shows, but the Nut­crack­er by the Jof­frey Bal­let was one of the most amaz­ing per­for­mances I have ever seen.

The Nut­crack­er in gen­er­al is a spec­tac­u­lar show.  The score by Tchaikovsky is leg­endary and some of the most renowned hol­i­day music out there.  And the sto­ry itself is so mag­i­cal and full of won­der.  But what I was par­tic­u­lar­ly tak­en with was how the Jof­frey told the sto­ry.  Every bal­let com­pa­ny tells it dif­fer­ent­ly and puts their own per­for­ma­tive spin on it.  But the entire show, from the set to the cos­tumes, was noth­ing short of mesmerizing.

You sim­ply haven’t seen the Nut­crack­er until you’ve seen it per­formed by the Joffrey. 





Christkindlmarket at Daley Plaza


holiday ornaments christmas market chicago

Our favorite is the hand­made orna­ment house.



The Christkindl­mar­ket is far and away one of my favorite hol­i­day activ­i­ties to do in Chica­go, sec­ond only to going to the Christ­mas tree lot by Big Star Tacos in Wick­er Park to pick out our tree.  Inspired by the Ger­man Christ­mas mar­kets of Europe, Chicago’s Christkindl­mar­ket is the largest in the US, attract­ing over a mil­lion vis­i­tors every year. 

For some­one who loves to trav­el, the mar­ket is like get­ting a small taste of Europe at home.  The mar­ket is set up in the heart of the Loop in Daley Plaza.  There are a pletho­ra of arti­sans and crafters who set up shop at the mar­ket, sell­ing beau­ti­ful hand­made Christ­mas orna­ments, nativ­i­ty scenes, dolls and wood­en toys, and a vari­ety of oth­er treasures. 

Also on hand are food ven­dors, spe­cial­iz­ing in all the Euro­pean favorites, includ­ing schnitzel, hot pret­zels, hot cocoa, and my very favorite gluh­wein, which is a mulled wine that is often found in Switzer­land, Ger­many, and Austria. 

It’s become a tra­di­tion for our fam­i­ly to vis­it the mar­ket every year and pick out a new orna­ment or two for our tree (last year’s orna­ment was one that looked like our dog, Ruby) and enjoy some clas­sic Ger­man treats, includ­ing cocoa and gluh­wein (for my hus­band and I) served in the annu­al keep­sake mugs that we’ve tak­en to col­lect­ing and dis­play on our man­tel at Christmas.


dog and dog ornament

There’s a resem­blance there, right?


This year, in 2020, the mar­ket has gone vir­tu­al, which means any­one can find beau­ti­ful hand­craft­ed gifts and orna­ments with­out even leav­ing the com­fort of your home.  But I’m already count­ing down the days to next year and return­ing to the mar­ket in person. 


Don’t miss “Less­er Known Chica­go Restau­rants for Foodies” 



Window shop on Michigan Avenue


I’m a bit of a Scrooge when it comes to hol­i­day shop­ping.  I avoid­ed the mall like the plague even before we had a lit­er­al one on our hands.  Going to a store to shop for the hol­i­days gives me flash­backs to that movie Jin­gle All the Way with Arnold Schwarzeneg­ger, par­tic­u­lar­ly the scene where he’s strug­gling to make it out of the ball pit.



jingle all the way ball pit arnold schwarzenegger

Can we just admire the nineties hol­i­day sweaters?



But some­times it’s nice to hol­i­day shop for the expe­ri­ence instead of for the neces­si­ty, perus­ing the win­dows not because you’re look­ing for any­thing in par­tic­u­lar but just because you enjoy the dec­o­ra­tions and displays. 

Michi­gan Avenue is arguably one of the best places to do this, with over an entire mag­nif­i­cent mile of glit­ter­ing store­fronts decked out for the sea­son.  Nev­er a city to skimp on street dec­o­ra­tion, even in the sum­mer, Chica­go def­i­nite­ly does­n’t dis­ap­point in the win­ter, with all sorts of fes­tive dis­plays lin­ing the side­walks.  We high­ly rec­om­mend set­ting aside an after­noon for just walk­ing the avenue, maybe stop­ping by the new four-floor Star­buck­’s Roast­ery for sus­te­nance and hail­ing a horse drawn car­riage ride up by Water­tow­er if you get tired. 

It’s com­plete­ly free and sure to get you and your fam­i­ly in the hol­i­day spirit.



Winter Wonderfest at Navy Pier


Every year from ear­ly Decem­ber through the mid­dle of Jan­u­ary, the ever pop­u­lar Navy Pier trans­forms into a mag­i­cal win­ter won­der­land as part of the Win­ter Won­der­fest at Navy Pier event.  And the great part is, the major­i­ty of the expe­ri­ence is indoors (so you don’t have to deal with those bru­tal Chica­go win­ters you’ve heard so much about).  Tons of dec­o­rat­ed trees, count­less strands of twin­kle lights, and all sorts of fes­tive dec­o­ra­tions make the nor­mal­ly gener­ic look­ing Navy Pier seem almost as spir­it­ed as the North Pole.  Almost. 

With every­thing from car­ni­val rides and an indoor ice skat­ing rink, inflat­able bounce hous­es and rock-climb­ing walls, it’s the per­fect spot for kids of all ages to get into the hol­i­day spir­it.  And when it comes to the clas­sic hol­i­day activ­i­ties, Win­ter Won­der­fest checks all the box­es. You can get your pic­ture tak­en with San­ta, enjoy steam­ing mugs of cocoa, and lis­ten to groups of car­ol­ers as they make their way through the fest.

It’s a mem­o­rable expe­ri­ence that’s not to be missed!


Don’t miss “A Local’s Guide to the 11 Best Fam­i­ly Friend­ly Things to Do in Chicago”



When You Go


Chica­go is a great long week­end trip from L.A., with direct flights offered by all the major air­lines.  If you’re look­ing to go all out on your adven­ture, we rec­om­mend the Wal­dorf Asto­ria in Chicago’s Gold Coast dis­trict (and we also rec­om­mend treat­ing your­self to a mas­sage at their fab­u­lous spa if you have the time).  For a bud­get-friend­ly option that’s also cen­tral­ly locat­ed and easy for get­ting around, you can’t go wrong with the Hamp­ton Inn — Chica­go Down­town loca­tion.  It’s right on the riv­er and just off of Michi­gan Avenue.  Look­ing for a unique hotel expe­ri­ence?  Check out the Chica­go Ath­let­ic Asso­ci­a­tion Hotel housed in the refur­bished for­mer head­quar­ters of the Chica­go Ath­let­ic Asso­ci­a­tion, right across from the Bean.

If you’re look­ing for a week­end des­ti­na­tion that’s sure to get you in the hol­i­day spir­it, Chica­go can’t be beat!  Please note that due to chang­ing COVID con­di­tions in Chica­go, some of these events might be vir­tu­al only in 2020.  Please refer to event web­sites for up to date infor­ma­tion on the sta­tus of these events.


Mor­gan is a brand design­er and writer who splits her time between man­ag­ing her cre­ative stu­dio, Atlas + Anchor, and writ­ing about her life­long love affair with trav­el. A wan­der­lus­ter at heart, she’s a big pro­po­nent of explor­ing the roads less trav­eled because they often lead to amaz­ing views, mem­o­rable sto­ries, and the most unas­sum­ing but life-chang­ing restau­rants. Orig­i­nal­ly from Ohio, Mor­gan now lives in the heart of Chica­go with her fam­i­ly and is quite pos­si­bly the only per­son with­in city lim­its who hates deep dish pizza. 


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A family friendly, best of things to do with kids for the holidays in Chicago. Chicago is the place to be to celebrate all of the best of the holiday activities, things to to do with kids during the holidays in Chicago.

A family friendly, best of things to do with kids for the holidays in Chicago. Chicago is the place to be to celebrate all of the best of the holiday activities, things to to do with kids during the holidays in Chicago.