Lady’s Festive Itinerary for 4 Days in Chicago at Christmas

Today I want to bring you my itinerary for 4 days in Chicago at Christmas. This is a great time to see the highlights of the Windy City, as Chicago goes all-out for the festive season. From Christmas markets to trees, lights, and decorations, there’s a lot to get excited about in the run-up to December 25th. I’m here now and I can’t wait to show you the highlights. I’ve included a map, too.

4 Days in Chicago Itinerary

4 days in Chicago is an ideal amount of time to see the highlights of the city, experience its world-class food scene, and explore some local neighborhoods.

Going at Christmastime is fun because there are so many great things to do in Chicago in winter. Whether you love ice skating, shopping, or festive bars, there’s a lot to entertain.

Add to that fewer tourist crowds than in the peak summer season, and it’s an enjoyable time to be here.

Lake Michigan, Chicago

What to Pack for 4 Days in Chicago in Winter

In terms of what to pack for a 4-day Chicago itinerary in winter, the city’s weather can vary. On my trip the climate has been exactly like London.

The temperatures have hovered just above freezing, there’s been a bit of rain here and there, and I’ve enjoyed some beautiful sunshine.

Chicago can be much colder at this time of year, though. As such, it’s a good idea to check the forecast before you travel and pack accordingly.

Either way, you can use my winter packing list to get an idea of what to bring. You can modify it where necessary.

Chicago view at sunset

Where to Stay in Chicago

As far as where to stay goes, there are lots of options for accommodation in Chicago. Whether you’re looking for a hotel or apartment, the Windy City has a variety of places to choose from at a range of price points.

On this trip my other half and I are staying at the W Chicago – Lakeshore in Streeterville. Right on the waterfront, it has sweeping views of Lake Michigan and Navy Pier.

The interiors feature contemporary decor, the staff is friendly, and the room rates are refreshingly reasonable in winter. You can book a room here.

You can see more options and book accommodation in Chicago here. With so many good choices, you’re sure to find a place that fits your travel style.

Chicago Hotel Restaurant

Day 1

After landing at O’Hare Airport and taking a taxi to the W Lakeshore, we start our itinerary for 4 days in Chicago with a late lunch.

It’s a short walk through the skyscrapers to get to Beatrix, a modern restaurant with a cozy dining room. We settle in for a hearty winter meal of Brussels sprout salads and pistachio crusted whitefish. It fuels us for the rest of the day.

Chicago Riverwalk

By the time we finish, the sun is going down and the Christmas lights are coming on. We head over to the Riverwalk, a public space on the south bank of the Chicago River with great views of the city’s iconic architecture.

Chicago River at night

From the Wrigley Building to the Tribune Tower and Marina City (aka the Corncobs), we get awed by some of the city’s famous structures lit up at night.

Millennium Park

From the Riverwalk we head over to Millennium Park to see the big Christmas tree, admire the colorful lights on the Millennium Monument, and take in the ice skating rink in McCormick Tribune Plaza. It’s a great introduction to Chicago at Christmas.

Across the street we pop into the Chicago Athletic Association, a historic hotel with great holiday decorations in the upstairs bar. With wood paneling and an atmospheric fire, it’s one of the coziest places in the city.

Chicago Christmas Tree in Millennium Park


Leaving the hotel, our 4 days in Chicago continue as we walk a few blocks to get to the annual Christkindlmarket in Daley Plaza. This festive Christmas market is packed with stalls selling everything from mulled wine to pierogi dumplings.

The scent of melted raclette mingles with the sound of live music as we walk in. We buy some hot drinks to warm our hands, then spend an hour browsing the market.

We pop into shops and check out stalls full of Christmas ornaments, European gifts, cookies, handicrafts, and other festive finds. It’s an impressive market and a fun place to get into the seasonal spirit in Chicago.

Christkindlmarket Chicago

The Office

From the Christkindlmarket, our Chicago itinerary continues with a taxi ride to a speakeasy. The Office is in the basement of The Aviary, a hip bar affiliated with the city’s famous Alinea restaurant.

This place has come highly recommended by a friend who used to live in the city, not least because it has one of the world’s largest collections of rare vintage spirits.

A host leads us down to an unmarked door that opens to reveal an intimate room with low lighting and big chairs. We settle in and enjoy everything from unique Manhattans with banana liqueur to cool gin drinks of the bartender’s creation.

Chicago speakeasy


After drinks we hop in a taxi for the ride to Bavette’s. This famous steakhouse is everything I think of when I think of Chicago: upscale but casual, down-to-earth but cool, sophisticated but playful.

A friend who has a flat in Chicago told us it was his favorite steakhouse, so we knew we had to come here. His recommendation is spot on, too.

Everything from the Caesar salad with smoked whitefish (not on the menu, but locals know) to the steaks and chocolate cream pie goes down a treat. We love our waitress, too.

Chicago restaurant

Day 2

The next morning our itinerary for 4 days in Chicago at Christmas continues as we make our way to Blue Bottle Coffee for breakfast. This California-based company is one of our favorites in the US, and the lattes and banana bread set us up for the day.

After breakfast my other half heads to the office (he’s in town for a big work event), and I set off on a walk.

Back along the Riverwalk I go, taking in architectural masterpieces like the Merchandise Mart. This behemoth was once the largest building in the world.

Chicago River

Chicago Cultural Center

From the river I walk over to the Chicago Cultural Center, a 19th-century building in the Loop with free art exhibitions and famous stained-glass domes. I wander in, climbing the stairs to stand in awe of the largest Tiffany glass dome in the world.

On the other side of the building, I check out the Grand Army of the Republic (G.A.R.) Hall and Rotunda. This space is home to an equally impressive dome.

It also has beautiful 19th-century rooms that were designed for the social, political, and moral well-being of Civil War veterans and their families.

Chicago Tiffany Dome

Millennium Park

From the cultural center, my itinerary continues with a walk through Millennium Park. I take in the eye-catching Pritzker Pavilion, a bandshell designed by architect Frank Gehry in his signature flamboyant style.

I also walk past the Crown Fountain with its larger-than-life LED screens, through the Lurie Garden, and over to Cloud Gate, which is better known as the iconic Chicago Bean. The metallic sculpture reflects the city’s skyline and the surrounding park.

Chicago Bean


From The Bean I walk across South Michigan Avenue to have lunch at a restaurant called The Gage. This American classic has a great lunch menu full of soups, salads, sandwiches, and larger dishes.

I settle in at a corner table on the banquette in the back dining room and tuck into a roasted wild mushroom sandwich and a heaping side of fries. It’s the perfect winter lunch.

Magnificent Mile

After lunch I do some Christmas shopping on Chicago’s Magnificent Mile. This stretch of Michigan Avenue is home to everything from shops to restaurants and hotels.

Chicago Christmas Decorations on the Magnificent Mile

It’s also home to famous skyscrapers like the 100-story John Hancock Center. The 360 CHICAGO Observation Deck on the 94th floor has some of the best views of the Chicago skyline and Lake Michigan.

I do some shopping along the Magnificent Mile, popping into places like The Shops at North Bridge to see the Holly Jolly Lodge Christmas lounge as I go.

I also take in the Christmas tree and historic Chicago Water Tower in Jane M. Byrne Plaza, the castle-like Chicago Avenue Pumping Station across the street, and Fourth Presbyterian Church with its pretty cloister.

Chicago Avenue Pumping Station


In the evening, I meet up with my other half for a Christmas lights walk in Chicago. We stroll down Michigan Avenue and take in the Christmas trees near the river.

We then walk along West Kinzie Street to see the Christmas decorations in places like Moe’s Cantina. This place has gone all-out with a giant inflatable bear, a huge Santa chair, and larger-than-life ornaments suspended from the ceiling.

When dinnertime comes, we meet his coworkers at The Purple Pig, a famous restaurant with an extensive menu of meat and wine options (and lots of other dishes and drinks).

We tuck into a big family-style meal of everything from pork to duck, paella, and broccoli in the buzzing dining room.

Christmas bar in Chicago

Day 3

The following morning our 4 days in Chicago continue as my other half heads to the office and I meet up with an old friend for brunch in Streeterville. Egg Harbor Cafe is a family-owned restaurant with an extensive breakfast menu.

We order everything from smoked salmon Benedict to skillets heaped with eggs. It’s the perfect meal to catch up over, and a great place to start a day of sightseeing.

Chicago Architecture Boat Tour

And what a day of sightseeing it is. My itinerary continues with a short walk to the water, where I board a boat for a Chicago River architecture cruise.

Chicago Architecture Cruise

A company called Wendella operates architecture tours in the winter months, and my 90-minute ride takes me through the heart of the city on all three branches of the Chicago River.

As we go, the tour guide entertains us with information and stories about the famous buildings along the banks. From landmarks by Ludwig Mies van der Rohe to famous numbers like the Sears Tower (Willis Tower), we see it all.

The guide also fills us in on the history of Chicago, from Fort Dearborn to the Great Chicago Fire and the city’s world’s fairs. The tour is a highlight of the trip.

Chicago River view


After the tour I can’t help heading back up the Magnificent Mile and out to Lake Michigan for one more architectural highlight: 860-880 Lake Shore Drive.

Designed by Mies van der Rohe, it’s often considered Chicago’s 20th-century architectural masterpiece. So much so that I’ve wanted to see these side-by-side buildings since I took a class on modern architecture in college.

My professor spent so much time telling us how revolutionary these pared-back towers were compared to their heavily-ornamented predecessors that I knew I had to see them someday.

860 880 Lake Shore Drive

They’re every bit as impressive in person as they were on screen in the lecture hall, and I’m so glad I’ve made a point of seeing them.


Having ticked my architectural box for the day, I head to a late lunch at a casual place in Streeterville called Poke Poke. I settle in at an upstairs table and savor a big bowl of spicy tuna, salmon, and all the accompaniments.

Drinks in Lincoln Park

In the early evening I hop on the ‘L’ train and make my way to Lincoln Park to meet another old friend for drinks. We head to Love Street, a corner bar with red leather stools and friendly bartenders.

We sip creative mezcal cocktails and cozy winter warmers as we catch up and reminisce about our last meet-up in Wicker Park.

Chicago bar in Lincoln Park

Chicago Deep Dish Pizza

After drinks my other half and I head to dinner at a famous deep-dish pizza place called Pequod’s in Lincoln Park. This place is known for its heaping pies with crispy caramelized crusts.

We sit at the bar and tuck into a thick pizza topped half with veggies and half with meat. It’s as filling as it is delicious, and we leave feeling like we’ll be full for a week.

Day 4

The next morning is a sunny one, and our 4 days in Chicago continue with breakfast at the hotel and a trip to the lake. We meet a friend and her dog in the park by Ohio Street Beach, marveling at how warm it is for Chicago in winter.

Ohio Street Beach

Art Institute of Chicago

After our walk, we head to the Art Institute of Chicago. Established in 1879, it’s one of the oldest and largest art museums in the world. I’ve been looking forward to visiting this place for years, and I’m excited to get inside.

There are more than 300,000 works of art from all over the world and all through the centuries here. The world-class collection has everything from American art to Impressionism, Asian art, antiquities, and beyond.

We pick up a brochure and follow the highlights trail to see the most famous works first. From Van Gogh’s The Bedroom to Georgia O’Keeffe’s Sky Above Clouds IV and Edward Hopper’s Nighthawks, we’re awed the whole way through.

Art Institute of Chicago

We even see American Gothic, which gives me goosebumps. It’s hard to believe we’re standing in front of one of the most famous 20th-century American paintings.

We also admire heavy hitters and impressive works by everyone from Monet to Picasso, Kandinsky, and Seurat (he did the one from Ferris Bueller’s Day Off). We could spend days here, but even seeing the best of the museum leaves us inspired.

It also leaves us sad to say farewell to Chicago. We hop in a taxi at the museum, pick up our bags at the hotel, and continue to the airport. We spent so long looking at the art that we almost miss our flight, but it was worth it.

In fact, we feel that way about everything we saw and did (and ate) in Chicago. We could spend a lot more time here and not want to leave. If you get a chance to follow in our footsteps, I hope the same is true for you.

Art Institute of Chicago

4 Days in Chicago Itinerary Map

As promised, I created an interactive Google map of all the places I mentioned in this blog post. You can find it here. I hope it helps you plan the perfect 4-day trip to Chicago at Christmas!

Chicago Christmas bar

4 Days in Chicago at Christmas

I hope you’ve enjoyed my itinerary for 4 days in Chicago, and that it’s inspired you to get out and explore the Windy City in winter. It’s an amazing place, and it’s worth discovering the highlights of the season while you’re visiting. Happy travels!

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4 Days in Chicago at Christmas

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