This self-guided tour is perfect for guests that cannot join a scheduled Chicago Holiday Walking Tour.

Welcome to our self-guided Chicago Holiday Walking Tour! Experience the magic of the holiday season in the heart of the Windy City. This tour will take you through some of Chicago’s most iconic landmarks, all dressed up in their festive best. Along the way, you’ll discover rich histories, enchanting decorations, and heartwarming stories that embody the spirit of the holidays in Chicago.

Stop 1: Millennium Park Christmas Tree and Ice Skating Rink

201 E Randolph St, Chicago, IL 60602

What to See

• Chicago’s Official Christmas Tree: Admire the towering Christmas tree adorned with thousands of twinkling lights and ornaments.
• McCormick Tribune Ice Rink: Watch skaters glide under the city skyline or rent skates yourself for a memorable experience.
• Cloud Gate (“The Bean”): Don’t miss this iconic sculpture reflecting the festive surroundings.

Points of Interest

• Photo Opportunities: Capture the festive atmosphere with the illuminated tree and skyline as your backdrop.
• Holiday Music: Enjoy seasonal tunes often played around the rink and tree area.

Stories to Share

• Chicago’s Christmas Tree Tradition: In 1913, Chicago lit its first municipal Christmas tree, a 35-foot Douglas spruce, in Grant Park. Mayor Carter Harrison Jr. dedicated it as a symbol of hope and unity.
• Transformation of Millennium Park: Once a desolate rail yard, the park opened in 2004 and has become a central hub for Chicago’s cultural and holiday festivities.
• “The Bean” in Winter: Designed by Anish Kapoor, the Cloud Gate sculpture offers a unique view during the holidays, reflecting the lights and snow, creating a magical visual effect.

Stop 2: Chicago Cultural Center

Address: 78 E Washington St, Chicago, IL 60602

What to See

• Preston Bradley Hall: Marvel at the world’s largest Tiffany stained-glass dome, measuring 38 feet in diameter.
• Rotunda and Grand Staircase: Observe the intricate mosaics and marble detailing.
• Holiday Exhibits: Check for seasonal art installations and free concerts.

Points of Interest

• Warm Indoor Space: Take a break from the cold while enjoying the opulent interior.
• Information Desk: Pick up brochures about current exhibits and events.

Stories to Share

• A Palace for the People: Opened in 1897 as Chicago’s first public library, the building symbolized the city’s commitment to accessibility and education.
• Architectural Marvel: The Beaux-Arts building was designed by Shepley, Rutan, and Coolidge, showcasing lavish materials and craftsmanship meant to inspire visitors.
• Cultural Hub: Since 1991, it has served as the Chicago Cultural Center, hosting over 1,000 programs annually, all free to the public.

Stop 3: Macy’s on State Street (Formerly Marshall Field’s)

Address: 111 N State St, Chicago, IL 60602

What to See

• Holiday Window Displays: Stroll along State Street to view the elaborate, themed displays enchanting visitors since the early 1870s.
• The Walnut Room: Located on the 7th floor, it’s home to the Great Tree, a two-story Christmas tree decorated with hundreds of ornaments.
• Tiffany Ceiling: Inside the store, look up to see the largest unbroken example of Tiffany Favrile glass in the world.

Points of Interest

• Dining Experience: Consider making a reservation at The Walnut Room to dine next to the Great Tree.
• Shopping and Souvenirs: Explore unique gifts and holiday specials throughout the store.

Stories to Share

• Marshall Field’s Legacy: Established in 1852, the store became a retail pioneer, introducing concepts like the bridal registry and in-store dining.
• Holiday Windows Tradition: The animated window displays began in the early 20th century, delighting generations with stories like “A Christmas Carol” and “The Nutcracker.”
• The Great Tree: Since 1907, the Walnut Room has featured a grand Christmas tree, becoming a cherished Chicago tradition.
• Transition to Macy’s: In 2006, Marshall Field’s was rebranded as Macy’s, sparking local debate but continuing the store’s holiday customs.

Stop 4: The Palmer House, A Hilton Hotel

Address: 17 E Monroe St, Chicago, IL 60603

What to See

• Grand Lobby: Admire the French Baroque-style ceiling frescoes, chandeliers, and the majestic “Winged Angels” on the grand staircase.
• Historical Displays: Find exhibits showcasing the hotel’s rich history and famous guests.
• Lockwood Bar and Restaurant: A cozy spot to warm up with a drink or snack.

Points of Interest

• Art and Architecture: Pay attention to the intricate designs by architect John M. Van Osdel.
• Palmer House Brownies: Try the original brownie recipe created here.

Stories to Share

• A Love Story Built in Stone: Potter Palmer built the original hotel as a wedding gift for his wife, Bertha Honore Palmer. After it burned down in the Great Chicago Fire of 1871, he rebuilt it grander than before.
• Innovation and Luxury: The rebuilt Palmer House was the nation’s first fireproof hotel and featured modern amenities like electric light bulbs, telephones, and elevators.
• Invention of the Brownie: In 1893, Bertha Palmer requested a portable dessert for ladies attending the World’s Columbian Exposition, leading to the creation of the chocolate fudge brownie.
• Famous Guests: The hotel has hosted luminaries like Charles Dickens, Oscar Wilde, Judy Garland, and every U.S. president since Ulysses S. Grant.

Stop 5: Christkindlmarket Chicago at Daley Plaza

Address: 50 W Washington St, Chicago, IL 60602

What to See

• Festive Market Booths: Explore over 50 vendors selling handmade ornaments, nutcrackers, cuckoo clocks, and other gifts.
• Culinary Delights: Enjoy German specialties like bratwurst, schnitzel, potato pancakes, and Glühwein (hot spiced wine) served in collectible mugs.
• Daley Plaza Christmas Tree: A beautifully decorated tree that serves as the market’s centerpiece.
• The Picasso Sculpture: An untitled 50-foot steel sculpture by Pablo Picasso.

Points of Interest

• Live Entertainment: Check the schedule for carolers, dance performances, and appearances by the Christkind.
• Souvenir Mugs: Each year features a new mug design—great keepsakes!

Stories to Share

• German Heritage in Chicago: In the 19th century, German immigrants were the largest ethnic group in Chicago, greatly influencing the city’s culture and traditions.
• Origin of Christkindlmarket: Established in 1996, it was inspired by the 16th-century Christkindlesmarkt in Nuremberg, Germany. It’s now the largest Christmas market in the U.S.
• The Christkind: A fairy-like being from German folklore who brings gifts to children. The market’s Christkind opens the event with a prologue.
• The Picasso Sculpture: Unveiled in 1967, it was initially met with mixed reactions but has since become a beloved landmark. Its abstract form adds a modern contrast to the traditional market.

Additional Tips

• Stay Warm: Between stops, consider warming up with a hot beverage from local cafes like Intelligentsia Coffee (53 E Randolph St) or Caffè Rom (200 S Michigan Ave).
• Accessibility: The route is wheelchair and stroller friendly.
• Plan Ahead: Check the operating hours of Christkindlmarket and The Walnut Room, especially if visiting on a holiday.

This festive tour showcases the heart and history of Chicago’s holiday celebrations. From glittering lights to timeless traditions, each stop offers a unique glimpse into what makes the season special in the Windy City. We hope this journey fills you with joy and creates lasting memories. Happy Holidays!

A big shout out and thank you to Nikola at Structure Photography (http://www.structurephotography.org) for braving the elements with one of our Free Chicago Walking Tours and sharing some incredible pictures he captured while visiting Chicago. He shows that even on a not-so-perfect-day you can still get your great shot.

About Structure Photography & Nikola Olic

Nikola Olic is a photographer living and working in Dallas, Texas, focusing on architectural photography and abstract structural quotes that reimagine their subjects in playful, dimensionless and disorienting ways. His photography has appeared in various galleries, art events, museums, magazines, newspapers, and websites around the world.

Without further ado, please enjoy the photos Nikola captured on his visit to Chicago along with the location and information about each shot.

8:01am – 899 W Harrison St / UIC School of Architecture. The early morning gray was opportunely countered by the colorful public display across the street from the UIC School of Architecture, offering a seemingly conflicted visual space of a colorful public display and a gray colorless city behind it.

8:21am – 50 Ida B. Wells Dr / Roosevelt University Another way to improve the weather — at least temporarily — is to replace the gray background with a blue one, even if it belongs to a modern building and its glass facade.

9:02am – Prudential Plaza + Buckingham Fountain This photographs represents 3 rather than just one location. It was taken from Shedd Aquarium, and it depicts the water fountain of the Buckingham Fountain, decorating the uniform facade of the Prudential Plaza a few blocks behind.

9:41am – Jay Pritzker Pavilion The pavilion has ample opportunities for photography, with such a diversity of Chicago architectural options and styles offered around it. In this case, the overhead structures that help bring sound and lights closer to the audience also help frame a building near by.

10:00am – Shedd Aquarium Back to the Aquarium for more photographs, in this case lightly quoting famed Italian photographer Luigi Ghirri and his vertical dividing beams, used to frame distant water activity.

10:32am – Prudential Plaza The public space in front of the building offers a performance space and a Colosseum-like structure that can also be used to help frame and isolate interesting architectural details nearby.

11:16am – 432 W Lake St / Fulton River District From a particularly extended spot in the walking area in front one of the buildings facing the river, surrounding buildings come together in an unexpected visual space that combines and breaks and bends visual lines in dimensionless and disorienting ways.

11:33am – 432 W Lake St A small convenience store offers a unique and different view of the famed Marina City buildings, instantly recognizable to Chicago residents, even when reflected in a window which almost morphs the buildings into something else.

12:14am – Waterview Tower Another unique view of the famed Marina City buildings, this time reflected in an even less recognizable fashion, of the facade of the Waterview Tower.

1:47pm – The Bean / Cloud Gate One of the most recognizable visuals in Chicago, the Cloud Gate sculpture in Millennium Park (aka The Bean) helps a bird rest, while also providing cover for a building behind it.

2:52pm – Sofitel Hotel The striking building of the Sofitel hotel provides a sharp angle that can be used as a central figure in a photograph that balances the hotel and its facade with the empty Chicago sky, offering a quick break from the saturated architectural visual space of this fascinating city.

3:06pm – John Hancock Center The world-famous John Hancock Center has an interesting addition on its west side: a garage with a spiral driveway visible from the outside.

3:21pm – 840 N Michigan Ave The non-descript building near John Hancock center offers another view of the famous building, contrasting Hancock’s cross beams with this building’s horizontal facade sections.

4:11pm – 120e E Walton St Different sections of the building offer a unique opening towards the sky, and a unique light-shaped space that breaks the shadow in the early afternoon hours.

5:00pm – 1100ish N State St I had to “-ish” the address because I cant find it on Google Maps; Not the first time this happened with the dynamic city such as Chicago. The building offers a Picasso-like cubist reflection of — and reflection on — the famed Hancock tower a few blocks east from here.

5:21pm – 505 N St Clair St Eating pizza nearby, the similarly colored buildings a few blocks behind combine their similar facades and their sun reflections and reflections of each other, to provide an entertaining visual space.

6:11pm – 899 W Harrison St / UIC School of Architecture Back to the place where the walk started 10 hours ago, the improved light conditions provided new opportunities with the colorful public display, now worthy of its dedicated own photographic space.

This post contains affiliate links and I will be compensated if you make a purchase after clicking on my links.

With summer finally arriving in Chicago it’s about time to talk about all that the city has to offer. One of our favorite ways to experience attractions in Chicago AND save some money is by purchasing a Chicago Explorer Pass from Smart Destinations.

The Chicago Explorer Pass allows you to purchase admission to 3, 4 or 5 different attractions in Chicago for a discounted price. Below are our top 3 attractions. (Note: You can select from 28 different ones, so even if there isn’t something you like below make sure to check out all they have to offer.)

The 3-attractions Chicago Explorer Pass will cost $79/adult. The 3 destinations that we selected below would cost $114.92 at the gate for a total savings of $35.92 or 31%! If 3 attractions is not enough there are 4 attraction, 5 attraction and unlimited options as well.

Hop on, Hop off Big Bus Chicago 1-Day classic tour

Gate Price: $45.00

We’re guessing that after a 2-hour Free Chicago Walking Tour you’ll want to kick back and relax and there isn’t a better way to do than on the Big Bus Chicago 1-Day Class Tour with live guides, a comprehensive route that takes you through the best Chicago sites & gives you a chance to hop on and off at your leisure.

shoreline architecture river cruise

Gate Price: $45.92

We’ve said a million times (ok, not really). There is nothing better than being on a boat cruising the Chicago River. The sun. The beer. The gorgeous architecture. The incredible live guides.

Honestly, every guide for Free Chicago Walking Tours takes a Chicago River Architecture cruise each year. And most times we’re bringing our families along too. Every single year!

As a guest aboard the Shoreline Architecture River Cruise you will sail all 3 branches of the Chicago River: Main Branch, North Brand & South Branch. Heads up that this tour is CLOSED from November to April.

skydeck chicago

Gate Price: $24.00

Skydeck Chicago is perched some 1,353 feet above the streets of Chicago in The Willis Tower (formerly Sears Tower). From up there you can see parts of 4 different states and take a step out onto “The Ledge” which is a glass balcony that extends past the side of the building. Fair waring it is nerve-racking.

Make sure to bring your camera and if you’re able to try and go early on a weekday as the weekends can get really busy and sometimes the wait is more than an hour to get up there.

One of the greatest things about Chicago is the nightlife~ Chicago is full of great clubs, bars, and after hour eating establishments. Now that the weather is getting warmer, it’s time to switch from indoor bars to exciting outdoor rooftop bars! Rooftop bars in Chicago are great places to visit for many reasons; not only will you get to grab a drink in a cool establishment, but you can also grab a view of the Chicago skyline! Check out the list below and be sure to stop by one of these great locations.

The J. Parker

1816 N Clark St, Chicago, IL 60614

Source: The J. Parker

We put The J. Parker first on our list for a reason. Most of the popular rooftop bars are located in The Loop or River North, and we totally get it. They’re awesome. If however you’re looking for something a little different head north to Lincoln Park and to the 14th floor of the Lincoln Hotel and you’ll find yourself the beneficiary of panoramic views of Lincoln Park, the shores of Lake Michigan and a spectacular view of the Chicago skyline looking south.

My wife and I lived in Lincoln Park for a couple of years and grabbing a drink here in the summer never got old. Head to the Green City Farmers Market on Saturday morning and then cross the street to grab a cocktail and soak in the views. Now that’s a great start to the day!

Cindy’s Rooftop Restaurant

12 S Michigan Ave, Chicago, IL 60603

Source: Cindy’s Rooftop Bar

When people think rooftop bars in Chicago, they think of Cindy’s. Not only will this bar give you great views of Lake Michigan and Millennium Park, but you also get a five-star dining experience.

Cindy’s is open until 1am on weekdays, and 2am on weekends, making a great late night spot too for a nightcap drink or even a midnight meal. This bars rooftop is covered, so you can enjoy Cindy’s year round, even in the bitterly cold Chicago winters!

AIRE

100 W Monroe St, Chicago, IL 60603

Source: Hyatt Centric

AIRE is the hidden gem of rooftop bars. You will pay a bit of money to dine here, but remember, it’s about the atmosphere! There are very few rooftop bars in Chicago that offer the high end atmosphere that AIRE does. Make sure to plan your time here on a clear night, there is no awning covering the lounge area. If it’s a rainy or windy night, reschedule for another time. It will be worth it!

Drumbar

201 E Delaware Pl, Chicago, IL 60611

Source: Drumbar

Forbes magazine named Drumbar the best rooftop bar in Chicago, and they did so for a good reason. Drumbar was also named the “Best Whiskey Bar” by GQ Magazine. They have an incredible indoor lounge, as well as an outdoor terrace with downtown and speakeasy-style decor. Located at the top of the Raffaello hotel, this rooftop bar is a must-see for locals and tourists alike. With all cocktails being $16, you know exactly what you are going to pay. No hidden fees or upsells. Spots fill up fast, so be sure to fill out a reservation!

Raised

1 West Upper Wacker Drive, Chicago, IL 60601

Source: Raised Bar

Not only is Raised a great place to grab drinks, but they have an incredible menu. All of their menu items are made using ingredients sourced from within 200 miles of the restaurant. Sometimes, you want to grab a meal while you are at a bar, and this is the place to do it. The cool thing about this bar is that there are no reservations, making it a great choice for you and your friends when you just randomly decide that you want to attend a rooftop bar.

No matter which rooftop bar in Chicago you want to attend, going to either one of these locations means you will have a great night filled with memories!

Chicago doesn’t have a shortage of things to do. In fact, we’ve written about Chicago FREE Things to Do, non-free Chicago Things to do and the top paid tours in Chicago. Almost no matter what the number one question we receive is “what are the best non-touristy things to do?” Markets. Chicago Markets. And here are the best of the best.

These markets contain dozens of vendors all under one roof (or at least in the same vicinity if a roof doesn’t exist). It’s easy to explore new foods, new cultures, and check out all the best new “stuff” that is available. Instead of heading to an Italian restaurant, head on over to an Italian market where you can explore different restaurants and vendors, and even buy some food to take home with you!

Here is a list of the top four markets you MUST check out in the Chicago area.

Eataly

43 E Ohio St, Chicago, IL 60611

© 2013 Galdones Photography/Eataly

Ok, we admit it, this one is sort of touristy. But still, if you are looking for an authentic and eventful Italian marketplace, look no further than Mario Batali and Joe Bastianich’s Eataly Market. There are several different locations all over the world, but the Chicago location is actually the largest, spanning 65,000 square feet.

This marketplace is full of retail stores, restaurants, and ‘street sellers’ selling different authentic foods just like a real Italian marketplace. Not only will you get to buy delicious foods and wine, but you will also get an incredible experience.

They have a Nutella bar. You can walk around with a beer or glass of wine in your hand. Do you need more reasons to go?

French Market in Ogilvie Transportation Center

131 N Clinton St, Chicago, IL 60661

From Italy to France. The French Market in Ogilvie is an indoor, year-round, farmers market full of amazing foods, gifts, and other merchandise. The French Market brings in some of the best vendors that Chicago has to offer from all sorts of different neighborhoods. This marketplace contains smaller vendors who are entrepreneurs and families who own their own businesses. Not only are you getting some great stuff, but you are also supporting local small businesses in Chicago.This market’s vendors sell cheeses, meats, wine, seafood, and even ice cream.

Lincoln Park Farmers Market

1817 N Clark St, Chicago, IL 60614

The Lincoln Park Farmers Market is one of the most popular farmer’s markets in the Chicago area. This farmers market is a one-stop shop to get all of your in-season produce fresh from the farms themselves. Farmers from all over come to the Lincoln Park Farmers Market every Saturday morning to showcase their goods. Imagine buying fresh apples from a farmer in Indiana, or amazing grapes from the infamous southwest Michigan vineyards! There are so many great options here. This farmers market is open every Saturday from 7 am to 1 pm from May-October.

Logan Square Farmers Market

2363 N Milwaukee Ave, Chicago, IL 60647

The Logan Square farmers market is a one-stop shop for organic foods, retail merchandise, and live music. This market is year round, but it moves outdoors every spring! You can come visit this market on Sundays from 10 am – 3 pm. With new vendors all the time, you can come by and find something unique!