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

 

 

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

 

 

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

 

 

 

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.

 

 

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.

 

 

 

 

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.

 

 

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