The Lonely Planet guide to the holiday season in Chicago

From extravagant rooftop bars and ice rinks to citywide festivals and hot tub boats, Chicago turns into a full-scale holiday playground come November. Yes, it’s chilly (okay, okay – it’s freezing), but this city knows how to make winter magical, with steaming mugs of cocoa and mulled wine, lights and trees in every direction and 70-some neighborhoods that each celebrate the season their own way.

Whether you want to avoid the biggest crowds and kitschy tourist traps or dive straight into the chaos, there’s a lot to know to make the most of Chicago during the holidays. Here are our best tips to celebrate like a local.

The best Chicago neighborhoods during the holidays

The Loop, Magnificent Mile and Gold Coast are Chicago’s postcard-perfect holiday districts, packed with elaborately decorated storefronts, big-name shopping and hotels that go all out. Add the iconic tree and ice skating in Millennium Park, the Chicago Christkindlmarket and classic holiday shows in the Theater District, and it’s easy to see why this is the first stop for most visitors — and why it’s often shoulder-to-shoulder from Thanksgiving through New Year’s.

If you want full holiday overload, Wrigleyville is the city’s most spirited hub thanks to its concentration of Christmas pop-up bars and Winterland at Gallagher Way. Just outside the Chicago Cubs’ stadium, you’ll find an ice skating rink, outdoor holiday movies and a smaller Christkindlmarket outpost. Fair warning: it’s (mostly) kid-friendly during the day, but gets fairly rowdy after dark. 

Prefer neighborhood charm over crowds? Lincoln Square’s twinkling lights, indie shops and cozy restaurants give the area a Hallmark movie feel (in fact, the 2024 film Christmas in Chicago actually shot here). Farther north, Andersonville leans into its Swedish roots with choral processions, a free neighborhood trolley with Santa and treats, and nearly every bar, bakery and boutique along Clark Street joining in.

For a more eclectic, hyperlocal feel, wander the adjacent neighborhoods of Wicker Park, Bucktown and Logan Square. All three walkable areas string up lights, host pop-up markets and events, and turn shops and bars into themed destinations. 

Chicago’s best holiday markets

A solid stateside alternative to classic European holiday markets, Christkindlmarket draws shoppers – lots of them – with its striped-roof stalls, collectible souvenir mugs and the smells of mulled wine and apple strudel. The downtown location near Millennium Park is the biggest and most atmospheric (the others are in Wrigleyville and Aurora), but it also gets uncomfortably crowded. Go right at opening or mid-afternoon on a weekday. 

Randolph Street Holiday Market brings two weekends of antiques and vintage finds, while the One of a Kind Holiday Show features solely handmade items, from jewelry to art and furniture. 

The best holiday pop-ups in Chicago

Chicago takes holiday pop-ups to another level – these are full-scale themed takeovers with floor-to-ceiling decor, custom cocktails and live DJs. The number of pop-ups across the city grows every year, but Wrigleyville remains the epicenter, with dozens lining Clark Street and the “big three”: Christmas Club, Santa Baby and Frosty’s all becoming multi-room, multi-floor party zones. 

Beyond Wrigleyville, you’ll find rooftop igloos, sprawling winter villages and movie-inspired pop-ups that feel more like immersive sets than seasonal decorations. This list is hardly exhaustive, but here’s a start.

• Jack Frost at Fulton Market: A sprawling, family-friendly outdoor winter village with an ice rink, bumper cars, axe throwing, a Christmas tree trail, and over one million lights.

• Winterland at Gallagher Way: Home to Christkindlmarket Wrigleyville, ice skating, wreath classes, Santa’s workshop, a holiday train and weekly neighborhood nights.

• Rudolph’s Rooftop at LondonHouse Chicago: A Rudolph-themed pop-up on the hotel’s 22nd-floor tri-level terrace with skyline views and chic, reservable igloos.

• Château Carbide Winter Garden at the Pendry: Cozy, alpine-style rooftop lodge with bookable private chalets, winter cocktails and small bites with sweeping city views.

• Elf’d Up: Buddy the Elf fans, this one’s all you. The themed bar serves free cookies, candy-covered cocktails, and movie-inspired dishes like Buddy’s Breakfast Pasta.

• 8 Crazy Nights: A Hanukkah Bar: This blue-and-white Hanukkah takeover serves latkes, matzo ball soup, boozy jelly donuts and cocktails like the Gelt Martini and Hebrew Cold Brew.

• The Christmas Inn: Holidays on Hubbard: Another River North hotspot, this three-story pop-up hosts dinner parties, mixology classes, holiday trivia, movies and bingo nights.

• A Very Dandy Holiday Pop-Up at The Dandy Crown: A low-key neighborhood affair with free activities like trivia, an ugly sweater night, a comedy show and hot crockpot cocktails.

The best places to see holiday lights

Brookfield Zoo’s Holiday Magic has been lighting up the suburbs for over 40 years with 3.5 million LEDs, larger-than-life animal sculptures, and glowing tunnels. Meet Santa on select nights or warm up in a private heated igloo, available by reservation. 

Lightscape at the Chicago Botanic Garden’s 1.3-mile trail winds through immersive, artist-designed installations. Highlights include a choir of “singing” trees and the return of the Instagram-famous Winter Cathedral archway. Family nights feature pizza wreaths and s’mores, while 21+ evenings add festive cocktails and mocktails.

Another zoo option, ZooLights at Lincoln Park Zoo transforms the zoo into a winter wonderland with three million lights, a light tunnel and live ice carvers. Ride the Ferris wheel or warm up with cocoa and s’mores by a fire pit. Get free admission on Mondays with registration; tickets are released one week in advance.

Beyond the major attractions, several Chicagoland neighborhoods go all out with lights. In the Far Northwest Side suburbs of Sauganash, Edgebrook and Lincolnwood, entire blocks compete for the best display. Historic Riverside, located west of the city, glows with elegant displays lining its winding, gas-lantern-lit streets. Farther south, Orland Park and Tinley Park shine with standout homes like the TP Christmas House, while Larsen’s Light Show at Goebbert’s Farm in Pingree Grove – about an hour from downtown – offers one of the largest synchronized drive-through displays in the country.

Downtown, Chicago’s official Christmas tree towers over Millennium Park, and its popular ice skating rink and ribbon, the glittering skyline framing the scene. The Nov. 21 lighting ceremony and fireworks kick off the season, but the tree remains lit through early January. A few blocks down Washington, the German-style Christkindlmarket adds extra holiday spirit.

Pro tip: The towering railroad-themed tree inside Union Station’s Great Hall offers a quieter alternative to the Millennium Park tree. 

Where to stay for holiday flair

Chicago’s grand hotels go big for the season, especially the Four Seasons, the Waldorf Astoria and The Ritz-Carlton, all known for towering lobby trees, elaborate decor and festive traditions like holiday teas, caroling and visits from Santa. 

The Peninsula is one of the most popular picks downtown, thanks to its fourth-floor outdoor Sky Rink, plus themed room packages. The Gwen leans into vintage glam and adds a rooftop curling rink, while The Westin Michigan Avenue offers packages tied to the Festival of Lights parade and Mag Mile holiday shopping.

Just north of the city in Evanston, the Graduate Evanston offers a replica Home Alone Room. Bonus: the actual McAllister house from the movie is in nearby Winnetka. 

Things to do on a rainy (or snowy) day

Winter weather doesn’t slow Chicago down; it just moves the fun indoors. The city’s museums and aquariums are world-class, from the Field Museum and the Art Institute of Chicago to playful options like the Museum of Illusions and the Museum of Ice Cream. Don’t miss the Museum of Science & Industry’s Christmas Around the World and Holidays of Light, filling its rotunda with over 50 culturally decorated trees.

Dress up and book a holiday high tea, a Windy City tradition. The Peninsula, The Langham, The Drake, Four Seasons and LondonHouse all make a whole afternoon of it. Sports fans can catch a Bulls or Blackhawks game, while theater lovers can head to the Loop for a holiday musical. 

Bad weather also provides the perfect excuse to complete your gift list with a shopping spree. Indoor malls like Water Tower Place and Time Out Market keep you out of the elements, and you could spend a few hours in Macy’s on State Street (the former Marshall Field’s), especially if you also score a reservation in The Walnut Room.

What’s the weather like in Chicago during the holidays?

The average high in November hovers around 50°F, dropping into the upper 30s by December – but you’re just as likely to see sunshine as you are snow and freezing temps. On Dec. 10, 2021, the high hit 60°F; the high on the same day in 2023 was 36°F. The aptly-named Windy City’s infamous heavy snow and bone-chilling cold typically arrive after New Year’s, but pack for the full weather spectrum.

What to pack

Layers are non-negotiable – you’ll be in and out of shops, museums, trains and windy streets, so you need pieces you can easily add and shed. A packable puffer coat that covers your rear end is a game-changer, blocking the wind and keeping you warm without bulk.

Bring a hat, scarf, gloves and at least one thermal base layer in case of extra-cold days. For footwear, riding boots or insulated ankle boots strike the best balance of comfort, warmth and style. You don’t need snow boots unless a winter storm comes through, but you do need shoes you can walk miles in.

Even in winter, Chicago is a walking and transit city, so prioritize comfort over fashion. Wind is the real enemy, not snow, so fabrics that block it (down, wool, fleece-lined leggings) will serve you far better than jeans and chunky sweaters alone. And if you plan to hit any pop-up bars, pack an ugly Christmas sweater, reindeer antlers or other kitschy holiday accessories. 

How expensive is Chicago at Christmas?

Like most major cities, prices in Chicago climb in December, especially for hotels. You can splurge on a festive stay downtown, but you’ll save a significant amount by booking outside the city core. Look for neighborhoods along CTA lines for an easy, inexpensive commute. Speaking of CTA, look out for the Holiday Train!

The good news: many of Chicago’s best holiday activities are free or nearly so, from the Christkindlmarket and ice skating to ZooLights’ free-admission Mondays and exploring neighborhood light displays. Your biggest expenses will be accommodation, food and themed cocktails, not the holiday magic itself.