A Chic Chicago Holiday Itinerary

There is nothing like Chicago during the holidays. The city glows – literally – from twinkling trees along Michigan Avenue to festive hotel lobbies that look straight out of a movie set. As someone who calls Chicago home, I’m here to give you the exact itinerary I’d recommend to friends visiting during the season. Think classic holiday moments, cozy food stops, festive markets, and a few insider favorites that make this time of year so special.

Whether you’re coming for a long weekend or squeezing in a pre-Christmas getaway, here’s your perfect 3-day Chicago holiday itinerary (plus a full list of all the holiday things to do at the bottom!).

Day 1 – Magic on Michigan Ave

Morning – Coffee, Shopping & The Tree-Lit Stroll
Start your morning with a warm coffee from Ralph’s Coffee – truly the BEST vibes. It’s right inside of Ralph Lauren and since we are all having a Ralph Lauren christmas this year, this is the perfect stop. I highly recommend their gingerbread latte or peppermint hot chocolate. Also, I LOVE the RL Restaurant next door if you are able to get a lunch or dinner reservation (see middle pic below).

After coffee, walk down the Magnificent Mile while the lights are still twinkling – it’s the prettiest before the crowds pick up. The shops are dressed up for the season and the lights make everything feel a little more magical. Duck into your favorite stores for holiday gifts or just enjoy the window displays – Michigan Ave truly comes alive this time of year. There are a lot of shops but definitely pop into Nordstrom, Neiman Marcus, or Water Tower Place for some holiday shopping.

Early Afternoon – Christkindlmarket
No Chicago holiday trip is complete without a stop at Christkindlmarket. Grab a hot mulled wine in a souvenir mug, stroll the stalls, pick up a few ornaments, and snack on pretzels or strudel. It’s crowded, yes – but it’s the good kind of holiday chaos.

Lunch – The Walnut Room Tradition
Walk toward Macy’s to see the holiday windows and then head inside to the Walnut Room for lunch under the giant Christmas tree. It’s classic, cozy, and feels like stepping into the city’s history. It books up pretty far in advance so I definitely recommend a reservation but sometimes you can luck out and grab a last minute spot!

Early evening – Maggie Daley Park Ice Skating Ribbon
A long, winding ice ribbon through the park – more of an experience than a rink!

Evening – Dinner & Drinks with a View
Grab festive cocktails at Cindy’s Rooftop with incredible views overlooking the Bean and Millennium Park tree.

For dinner I would recommend The Hawksmoor, Bavettes or Maple & Ask if you are looking to really treat yourself! All are considered steakhouses but have a extremely good menu even if you aren’t in the mood for steak. If you aren’t in the mood for steak then I would suggest Alpana or Tre Dita.

Day 2 – Lights & Local Favorites

Morning – Breakfast in the Gold Coast
Start day two with brunch at 3 Arts Club Café inside RH. The courtyard is magical year-round, but during the holidays it feels extra romantic.

Late Morning/Afternoon – The Bean
Walk off brunch by visiting THE Chicago must-see, especially reflective and fun during the holidays.

Evening – Lincoln Park ZooLights
Spend the afternoon winding through Lincoln Park, then head into ZooLights, one of my absolute favorite holiday traditions. The displays get better every year and it’s perfect for couples, families, or girls’ trips.

Dinner and Evening Walk – The Chicago River
Walk the Chicago Riverwalk and grab dinner (so many great spots located alongside it with a view), which is so gorgeous in winter time. My favorite river spot is Pizzeria Portofino. Like most spots, I highly recommend making a reservation but it also doesn’t hurt to pop in and see if you get lucky!

Night – Broadway Show at the Chicago Theatre

End your day with a little sparkle by catching a Broadway show at The Chicago Theatre. With its iconic marquee lit up against the winter sky, it’s one of the most magical spots in the city during the holidays. Inside, the ornate ceilings, velvet seating, and old-Chicago charm make the whole experience feel special before the show even begins.

Day 3 – Holiday Strolls + Shopping

Morning/Early Afternoon – A Little Culture + Drake High Tea

Start your day at the Museum of Contemporary Art or nearby galleries. They have special holiday offerings, including members’ parties, extended hours, festive decorations (wreaths on lions!), and creative activities, making them great spots for holiday outings, shopping, and art discovery. You can expect themed events, discounts at the store, and unique seasonal experiences during December.

After a morning stroll through the galleries, make your way to The Drake for their iconic holiday high tea. It’s elegant, festive, and the perfect cozy break before the afternoon rush. Sip, snack, soak in the ambiance, and feel like you’ve stepped straight into a classic Chicago holiday postcard.

Late Afternoon – Museum of Ice Cream
This is such a fun, colorful, immersive experience that’s extra adorable during the holidays with festive installations, treats, and photo ops of their Pinkmas installation. Great for kids too! I might suggest a quick change into something more casual for the rest of the day if heading this route:)

Dinner – Trivoli Tavern or High Five Ramen (West Loop)

These are two of our favorite spots, especially during the winter, and they are located in the same alley! Trivoli Tavern is a fancier vibe with warm lighting, vintage charm, excellent cocktails, and the perfect holiday dinner atmosphere. High Five Ramen is a more casual experience, and instantly warms you up in the cold weather.

*Pro tip: If you choose to go the ramen route just know there is always a long wait (up to 2 hours) and no reservations but the ramen is 100% worth it. Put your name on the waitlist at High Five ramen and then go grab a drink or 2 at the Trivoli Tavern bar or Soho House next door until your seats are ready. Ps I wouldn’t recommend High Five Ramen for more than 4 people. It only holds about 20 people.

Evening – Santa Baby Bar in Wrigleyvillve
One of the most decked-out Christmas bars in the city – a true holiday explosion. If you want to celebrate a little longer, head across the street to Fox Bar inside Soho House or make your way up to Wrigleyville’s Santa Baby Bar. It’s an entire experience with 3 floors of decked out holiday decor and festive drinks.

More Chicago Recommendations

Here is my complete round up of must-do’s for planning your trip!

Millennium Park Ice Skating
Skate right under the skyline with the iconic Chicago tree twinkling beside you.

See the tree at Millennium Park
The city’s official Christmas tree – massive, magical, and worth the photo.

Walk around Michigan Ave
Twinkling trees, decorated storefronts, and classic holiday energy up and down the Magnificent Mile.

Magnificent Mile Lights Festival (late November)
Holiday kickoff with a parade, fireworks, and the first sparkle of the season.

Macy’s Holiday Windows
Iconic window displays that change every year – whimsical, detailed, and nostalgic.

Museum of Science & Industry Christmas Around the World
A forest of themed Christmas trees representing global traditions – magical for all ages.

Jack Frost Holiday Pop-Up in West Loop
Part outdoor festival, part market, part ice rink – super fun and very Instagrammable.

Winter at Gallagher Way
Ice skating, curling, a holiday market, rides, and cozy vibes right next to Wrigley Field.

Wrigleyville Winter Wonderland
Over-the-top holiday decorations, themed bars, and nonstop festive energy.

The Drake High Tea
Elegant, timeless holiday tea inside one of Chicago’s most iconic hotels.

The Drake Hotel Holiday Lobby
A true Christmas postcard moment – think twinkling garland and old Chicago charm.

The Peninsula Sky Rink
A rooftop ice rink experience with sweeping city views – chic, cozy, and exclusive.

The Peninsula Holiday Tea
Perfect for a more upscale holiday treat – refined, pretty, and delicious.

CTA Holiday Train
Elves, lights, and Santa himself gliding along the train tracks – adorable and purely joyful.

State Street Christmas decorations
Classic Chicago holiday décor lining the sidewalks from the Loop to River North.

Oak Street + Gold Coast holiday shopping
Designer stores, beautiful brownstones, and some of the prettiest decorations in the cit

Holiday pop-up bars (Santa Baby Bar, Jack Frost, Elf’d Up)
Over-the-top themes, fun drinks, and great photo ops for a girls’ night or date night.

Chicago Botanic Garden Lightscape
A stunning, immersive walk-through light experience – peaceful, magical, and breathtaking.

Navy Pier Light Up the Lake
Indoor lights, rides, ice skating, and plenty of family-friendly fun.

Chicago holiday concerts + performances (Joffrey Ballet’s Nutcracker, Symphony Center’s Merry Merry Chicago)
The most festive shows of the season – classic, cozy, and guaranteed to spark holiday spirit.

And that’s your chic little holiday playbook, friend. Chicago really knows how to turn it on this time of year. Even if you follow even half of this itinerary, you’re basically guaranteed main-character Christmas energy. Consider this your official permission slip to make magical memories, eat all the festive treats, and pretend you’re in a Hallmark movie – because honestly, in Chicago, you kind of are.