One of the oldest and largest art museums in the United States, the Art Institute of Chicago is home to a collection that spans 5,000 years.

The Art Institute of Chicago is one of the premier art museums in the world. /n The museum's collection spans 5,000 years and includes more than 300,000 works of art from around the world. The museum also offers a variety of educational programs and hosts a variety of special exhibitions throughout the year. Whether you're an art enthusiast or a casual visitor, the Art Institute of Chicago is a must-visit destination.

One of the oldest and largest art museums in the United States, located in Chicago.

Known for its iconic Cloud Gate sculpture, this 24.5-acre park also features the Crown Fountain and Pritzker Pavilion.

Millennium Park is a 24.5-acre park in the heart of downtown Chicago. /n The park is home to a variety of public art installations, including the iconic 'Cloud Gate', also known as 'The Bean', and the Crown Fountain. The park also hosts a variety of cultural events throughout the year, including concerts, festivals, and art exhibitions. The park also offers stunning views of the city's skyline and Lake Michigan. Whether you're a local or a visitor, Millennium Park is a must-visit destination in Chicago.

A popular park in Chicago, known for its public art installations and cultural events.

The Christkindlmarket is a unique shopping experience, offering traditional German products like nutcrackers, cuckoo clocks, and beer steins, as well as international holiday gifts, ornaments, jewelry, and high-quality arts and crafts.

The Christkindlmarket is a beloved holiday tradition in Chicago. /n The market, which is modeled after the traditional Christmas markets in Germany, offers a unique shopping experience. Visitors can browse through a variety of vendors selling traditional German products like nutcrackers, cuckoo clocks, and beer steins, as well as international holiday gifts, ornaments, jewelry, and high-quality arts and crafts. /n In addition to shopping, the Christkindlmarket also offers a variety of food and drink options. Visitors can enjoy traditional German foods like bratwurst, pretzels, and schnitzel, as well as sweet treats like strudel and gingerbread cookies. There is also a variety of beverages available, including hot spiced wine, German beers, and hot chocolate. /n The Christkindlmarket is a great place to get into the holiday spirit and experience a bit of German culture in the heart of Chicago.

A traditional German holiday market in Chicago's Daley Plaza.

One of the largest science museums in the world, featuring a full-size replica coal mine, a German submarine captured during World War II, a 3,500-square-foot model railroad, and the Apollo 8 spacecraft.

The Museum of Science and Industry in Chicago is one of the largest science museums in the world. It's a place where you can explore the wonders of science and technology in a fun and interactive way. The museum features a wide range of exhibits, from a full-size replica of a coal mine to a German submarine captured during World War II. /n The museum also offers a variety of educational programs and events, making it a great place for families and school groups. Whether you're interested in space exploration, the human body, or the natural world, there's something for everyone at the Museum of Science and Industry. It's not just a museum, it's a cultural experience that's sure to inspire and educate.

One of the largest science museums in the world, offering interactive exhibits.

One of the oldest zoos in North America, offering free admission and home to a wide range of species.

Lincoln Park Zoo is a free, family-friendly zoo located in the heart of Chicago. It's home to a wide variety of animals, from big cats and primates to reptiles and birds. The zoo offers educational programs and events, making it a great place for both fun and learning. /n The zoo is open year-round and features several unique exhibits, including the Regenstein Center for African Apes, the Kovler Lion House, and the Farm-in-the-Zoo. The zoo also has several dining and shopping options, making it a full-day destination. Whether you're a local or a tourist, Lincoln Park Zoo is a must-visit when in Chicago.

A free, family-friendly zoo located in the heart of Chicago.

One of the largest natural history museums in the world, housing extensive scientific specimen and artifact collections.

The Field Museum of Natural History is a renowned institution in Chicago, housing extensive natural history collections. It's one of the largest natural history museums in the world, offering a wide range of exhibits and educational programs. The museum's collections include over 24 million specimens and artifacts, covering everything from anthropology and botany to zoology. /n The museum is also home to Sue, the largest and most complete Tyrannosaurus rex skeleton ever found. Other highlights include the Ancient Egypt exhibit, the Evolving Planet exhibit, and the Grainger Hall of Gems. The museum offers a variety of educational programs and events, making it a great destination for families and school groups.

The Field Museum of Natural History is a renowned institution in Chicago, housing extensive natural history collections.

A 3,300-foot-long pier on the Chicago shoreline of Lake Michigan, Navy Pier is home to a variety of attractions including a Ferris wheel, theater, and children's museum.

Navy Pier is a must-visit destination in Chicago, offering something for everyone. /n The pier is home to a variety of attractions, including the iconic Centennial Wheel, the Chicago Children's Museum, and the Chicago Shakespeare Theater. There are also numerous dining options, from fast food to fine dining, as well as a variety of shops. The pier also hosts a variety of events throughout the year, including fireworks displays, festivals, and concerts. Whether you're looking for family-friendly fun, a romantic date night, or a day of shopping and dining, Navy Pier has it all.

A popular tourist destination in Chicago, offering a variety of entertainment and dining options.

Winter WonderFest is a seasonal indoor carnival held at Navy Pier in Chicago. It features a variety of rides, games, and holiday-themed decorations, making it a popular destination for families during the holiday season.

Winter WonderFest at Navy Pier is a must-visit destination for families during the holiday season. This indoor winter carnival features a variety of rides, games, and holiday-themed decorations. /n From giant slides and ice skating to festive food and drink, there's something for everyone at Winter WonderFest. The event typically runs from late November to early January, offering a fun and festive way to celebrate the holiday season in Chicago.

A festive indoor winter carnival featuring rides, games, and holiday decorations.

An indoor public aquarium housing over 32,000 marine animals.

Shedd Aquarium, located in Chicago, Illinois, is one of the largest indoor aquariums in the world. It houses over 32,000 aquatic animals from 1,500 species, including fish, marine mammals, birds, snakes, amphibians, and insects. The aquarium offers a variety of exhibits that showcase different aquatic environments and their inhabitants, from the Amazon River to the Caribbean Sea. /n Visitors can explore the Oceanarium, where they can watch dolphins and whales perform in a spectacular aquatic show, or visit the Wild Reef exhibit, which replicates a Philippine coral reef and features sharks, rays, and hundreds of species of fish. The aquarium also offers educational programs and experiences, including behind-the-scenes tours, sleepovers, and animal encounters. Whether you're a marine life enthusiast or looking for a fun family outing, Shedd Aquarium offers an unforgettable experience.

Shedd Aquarium is a popular indoor public aquarium in Chicago.

One of the great avenues of the world, the Magnificent Mile is a prestigious section of Michigan Avenue offering luxury retail, restaurants, museums and hotels.

The Magnificent Mile, or 'Mag Mile', is a prestigious section of Chicago's Michigan Avenue, running from the Chicago River to Oak Street. /n It's known for its luxury boutiques, large department stores, and international fashion houses, making it a shopper's paradise. But it's not just about shopping - the Mag Mile is also home to some of Chicago's most iconic architectural landmarks, including the historic Water Tower and the John Hancock Center. The area is also rich in culture and entertainment, with a wide range of restaurants, bars, and nightlife venues to explore.

A premier shopping district in Chicago, known for its architectural landmarks.

The Adler Planetarium is a public museum dedicated to the study of astronomy and astrophysics. It was founded in 1930 by Chicago business leader Max Adler. The museum is home to three full-size theaters, extensive space science exhibitions, and a significant collection of antique scientific instruments and print materials. In addition, the Adler boasts one of the world's most important antique astronomical instrument collections on display.

Adler Planetarium, located on Chicago's Northerly Island, is a must-visit for anyone interested in space and astronomy. Founded in 1930 by Max Adler, it was the first planetarium in the United States. /n The planetarium offers a variety of exhibits, sky shows, and interactive experiences that inspire exploration of the universe. It houses three full-size theaters, including the Grainger Sky Theater, the Definiti Space Theater, and the Samuel C. Johnson Family Star Theater. Each offers unique immersive experiences, from high-resolution visuals to surround sound systems. /n In addition to its shows and exhibits, the Adler Planetarium also conducts research in space science and is a hub for STEM education. It also offers stunning views of the Chicago skyline and Lake Michigan, making it a popular destination for locals and tourists alike.

Adler Planetarium is a renowned public museum dedicated to the study of astronomy and astrophysics.

A pedestrian waterfront located on the south bank of the main branch of the Chicago River, offering dining, boat rentals, and more.

The Chicago Riverwalk is a vibrant, pedestrian-friendly waterfront park in the heart of the city. /n The Riverwalk offers a variety of activities, from dining and shopping to boat tours and kayaking. The area is dotted with cafes, restaurants, and bars, making it a popular spot for dining al fresco. The Riverwalk also offers stunning views of the city's skyline, making it a popular spot for photography. Whether you're looking for a leisurely stroll, a romantic date, or a fun family outing, the Chicago Riverwalk has something to offer.

A scenic waterfront promenade offering dining, recreational activities, and stunning views of the city.

The Skydeck offers spectacular views spanning up to four states, a one-stop Chicago experience full of interactive exhibits and The Ledge, a glass balcony extending four feet outside the 103rd floor of Willis Tower!

Skydeck at Willis Tower is a popular tourist attraction that offers breathtaking views of Chicago. It's located on the 103rd floor of the Willis Tower, the second tallest building in the Western Hemisphere. The Skydeck features The Ledge, a glass balcony extending four feet outside the 103rd floor, providing visitors with an unobstructed view of Chicago. /n In addition to the view, the Skydeck offers interactive exhibits and a multimedia presentation about the city of Chicago. It's a must-visit for anyone wanting to get a bird's eye view of the city. Whether you're a local or a tourist, Skydeck at Willis Tower is a must-visit when in Chicago.

A popular tourist attraction offering breathtaking views of Chicago.

Experience the magic of the holiday season with a performance of 'A Christmas Carol' at the Goodman Theatre. This classic tale is brought to life with stunning performances and beautiful set designs.

The Goodman Theatre in Chicago is known for its high-quality productions, and 'A Christmas Carol' is no exception. This beloved holiday classic is a must-see for anyone visiting the city during the holiday season. The story of Ebenezer Scrooge and his journey from a miserly old man to a generous benefactor is brought to life with stunning performances and beautiful set designs. /n The theatre itself is a landmark in Chicago, known for its commitment to producing classic and contemporary works. The production of 'A Christmas Carol' is a highlight of the theatre's season, drawing in locals and tourists alike. Whether you're a theatre enthusiast or simply looking for a way to get into the holiday spirit, a visit to the Goodman Theatre for a performance of 'A Christmas Carol' is a must.

A classic holiday performance at Chicago's renowned Goodman Theatre. A must-see for theatre enthusiasts.

Experience the beauty of the Chicago Botanic Garden like never before with Lightscape, a stunning light show that transforms the garden into a winter wonderland.

The Chicago Botanic Garden is a must-visit destination in the city, known for its stunning displays of plants and flowers. But during the holiday season, the garden is transformed into a winter wonderland with Lightscape, a mesmerizing light show. /n As you walk through the garden, you'll be treated to a spectacle of lights and sounds that bring the plants and trees to life in a whole new way. From towering light sculptures to paths illuminated with thousands of twinkling lights, Lightscape is a unique and unforgettable experience. Whether you're a nature lover or simply looking for a magical holiday experience, a visit to the Chicago Botanic Garden for Lightscape is a must.

A mesmerizing light show at the Chicago Botanic Garden during the holiday season.

Experience the vibrant city of Chicago, Illinois, a bustling metropolis known for its stunning architecture, rich history, and diverse culture. Marvel at the city's skyline from the Skydeck of Willis Tower, or stroll along the Magnificent Mile for a shopping spree. Explore the world-class museums like the Art Institute of Chicago and the Field Museum. Enjoy the city's culinary scene, from deep-dish pizza to fine dining. Visit Navy Pier for entertainment and Lake Michigan for a scenic view. Sports enthusiasts can catch a game at Wrigley Field, while music lovers can enjoy a show at the Chicago Theatre. Don't forget to visit Millennium Park and see the iconic Cloud Gate, also known as "The Bean". Chicago offers a unique blend of urban exploration and Midwestern hospitality that leaves every visitor captivated.

Art Institute of Chicago

Millennium Park

Christkindlmarket

Start your day with a visit to the Art Institute of Chicago, one of the oldest and largest art museums in the United States. Explore the museum's vast collection of artworks from around the world.

Enjoy a lunch at a local restaurant in the Loop area, known for its variety of culinary options.

After lunch, take a stroll through Millennium Park, home to the famous Cloud Gate sculpture, also known as 'The Bean'. Don't forget to visit the McCormick Tribune Ice Rink for some ice skating.

Have dinner at a cozy restaurant in the River North district, known for its vibrant nightlife and food scene.

End your day with a visit to the Christkindlmarket, a German-style Christmas market, where you can enjoy hot mulled wine, traditional German food, and shop for unique holiday gifts.

Art Institute, Millennium Park & Christkindlmarket

Museum of Science and Industry

Lincoln Park Zoo

Begin your day with a visit to the Museum of Science and Industry, the largest science museum in the Western Hemisphere.

Have lunch at a local eatery in Hyde Park, known for its diverse food scene.

Spend your afternoon exploring the Lincoln Park Zoo, one of the oldest zoos in North America. During the holiday season, the zoo hosts ZooLights, a festive light display.

Enjoy dinner at a restaurant in the Lincoln Park neighborhood, known for its eclectic dining options.

End your day with a performance of 'A Christmas Carol' at the Goodman Theatre, a holiday tradition in Chicago.

Museum of Science, Lincoln Park Zoo & 'A Christmas Carol'

Field Museum of Natural History

Navy Pier

Winter WonderFest

Start your day with a visit to the Field Museum of Natural History, one of the largest natural history museums in the world.

Enjoy lunch at a restaurant in the South Loop, known for its trendy eateries.

Spend your afternoon exploring Navy Pier, a popular tourist destination with shops, restaurants, and the Centennial Wheel, a giant Ferris wheel with panoramic city views.

Have dinner at a restaurant in the Streeterville neighborhood, known for its upscale dining options.

End your day with a visit to the Winter WonderFest at Navy Pier, a holiday event featuring indoor ice skating, rides, and holiday decorations.

Field Museum, Navy Pier & Winter WonderFest

Shedd Aquarium

Magnificent Mile

Begin your day with a visit to the Shedd Aquarium, home to over 32,000 aquatic animals.

Have lunch at a local eatery in the South Loop, known for its diverse food scene.

Spend your afternoon exploring the Magnificent Mile, a premier shopping destination in Chicago. During the holiday season, the area is beautifully decorated with lights and holiday displays.

Enjoy dinner at a restaurant in the Gold Coast neighborhood, known for its luxury dining options.

End your day with a visit to the Chicago Botanic Garden for the Lightscape event, a walking trail illuminated with thousands of lights.

Shedd Aquarium, Magnificent Mile & Lightscape

Adler Planetarium

Chicago Riverwalk

Skydeck at Willis Tower

Start your day with a visit to the Adler Planetarium, the first planetarium in the United States.

Spend your afternoon exploring the Chicago Riverwalk, a scenic pedestrian trail along the Chicago River. During the holiday season, the Riverwalk hosts various holiday events and activities.

Have dinner at a restaurant in the West Loop, known for its vibrant food scene.

End your trip with a visit to the Skydeck at Willis Tower, where you can enjoy panoramic views of the city. During the holiday season, the Skydeck hosts holiday-themed events.

Adler Planetarium, Chicago Riverwalk & Skydeck

Daylight saving time: +1hr, begins second Sunday in March; ends first Sunday in November; note: the 50 united states cover six time zones

UTC-5

The CTA operates the nation's second largest public transportation system. It includes a network of buses and trains that cover the city and 35 surrounding suburbs. The 'L' train system has eight rapid transit routes and consists of 145 stations.

Metra is a commuter rail system that serves the city of Chicago and its surrounding suburbs. It operates 11 lines and 242 stations, making it an efficient way to travel to and from the city's outskirts.

Pace provides bus services throughout the Chicago suburbs and complements the service provided by CTA and Metra. It operates 241 routes, including express, local, and feeder bus services.

Divvy is Chicago's bike sharing system with thousands of bikes available at hundreds of stations across the city. It's a fun, affordable and convenient way to get around, especially when the weather is nice.

Ridesharing services like Uber and Lyft are widely available in Chicago. These services provide convenient, on-demand transportation throughout the city and suburbs. They can be accessed through smartphone apps.

Taxis are plentiful in Chicago, especially in the downtown area. They can be hailed on the street, at taxi stands, or booked via phone or app.

Chicago's Water Taxi operates on the Chicago River and provides a unique mode of transportation. It's a great way to see the city's architecture and avoid traffic during rush hour.

While driving can be convenient, it can also be challenging due to traffic and expensive due to parking costs. There are numerous parking garages and metered parking spots throughout the city, but be aware of restrictions.

Chicago is a very walkable city, especially in the downtown area where attractions are close together. The city's grid system makes it easy to navigate.

Chicago is a bike-friendly city with many bike lanes and paths, including the 18.5-mile Lakefront Trail. You can bring your own bike or rent one from a bike-sharing service like Divvy.

Several companies offer shuttle services to and from Chicago's two major airports: O'Hare and Midway. These shuttles can be a cost-effective option for travelers.

A Chicago classic, deep-dish pizza is a must-try. It's characterized by its thick, buttery crust, chunky tomato sauce, and generous layers of cheese. It's a staple in Chicago's culinary scene.

Deep-Dish Pizza

This sandwich is a Chicago original, featuring thinly sliced roast beef soaked in juices and served on an Italian-style roll. It can be ordered 'wet' (extra gravy) or 'dry'.

Italian Beef Sandwich

A Chicago-style hot dog is a steamed or boiled all-beef frankfurter on a poppy seed bun, topped with mustard, fresh tomatoes, onions, sport peppers, bright green relish, dill pickles, and a dash of celery salt.

Chicago-Style Hot Dog

A beloved snack in Chicago, Garrett Popcorn is known for its 'Garrett Mix', a blend of sweet caramel crisp and savory cheese popcorn.

Garrett Popcorn

A sandwich that originated in Chicago's Puerto Rican community, the Jibarito is made with flattened, fried green plantains instead of bread, and filled with meat, cheese, lettuce, and tomato.

Jibarito

A popular dish in Chicago's Polish community, Pierogi are dumplings filled with a variety of ingredients, such as potato, cheese, or sauerkraut.

Pierogi

A popular fast food in Chicago, Gyros are Greek sandwiches made with slices of rotisserie-cooked lamb, beef, or chicken, served on pita bread with tzatziki sauce.

Gyros

A Chicago original, Shrimp DeJonghe is a casserole dish that features whole peeled shrimp blanketed in soft, garlicky, sherry-laced bread crumbs.

Shrimp DeJonghe

A traditional Polish pastry, Paczki are deep-fried pieces of dough filled with sweet filling and covered with powdered sugar or icing. They are especially popular in Chicago on Fat Tuesday.

Paczki

A bitter liquor, Malört is a Chicago original. It's known for its strong, unique flavor that's often described as tasting like grapefruit and gasoline.

Malört

Another popular snack in Chicago, this popcorn is a mix of sweet caramel and savory cheese flavors, offering a unique and addictive taste experience.

Chicago-Style Popcorn

Chicago has a thriving craft beer scene, with many local breweries producing a wide variety of unique and flavorful beers.

Craft Beer

New Year's Day

New Year's Day (substitute)

Martin Luther King Jr. Day

Presidents' Day

Memorial Day

Juneteenth

Independence Day

Labor Day

Columbus Day

Veterans Day (substitute)

Veterans Day

Thanksgiving Day

Christmas Day

A beautiful outdoor park with hiking trails and waterfalls.

Starved Rock State Park

A national park on the shore of Lake Michigan offering a wide range of activities.

Indiana Dunes National Park

A large amusement park with a variety of rides and attractions.

Six Flags Great America

An art museum with a collection of over 31,000 works.

Milwaukee Art Museum

A private Catholic research university known for its historic campus, collegiate gothic architecture, and strong athletic tradition.

University of Notre Dame

A state forest known for its glacial landforms, such as kettles, moraines, and kames.

Kettle Moraine State Forest

The capital of Wisconsin, known for its vibrant cultural scene and beautiful lakes.

Madison

The capital of Illinois, known for its association with Abraham Lincoln.

Springfield

A major city in Missouri along the Mississippi River, known for its iconic Gateway Arch.

St. Louis

N Michigan Ave at night. Downtown Chicago during Christmas

Chicago skyline at night during Christmas from Adler Planetarium

Chicago is located in the Central Time Zone.

The city is known for its unpredictable weather. Always check the forecast before your trip.

Chicago is a very walkable city, but it also has a comprehensive public transportation system, including buses and the 'L' train.

Tipping is customary in Chicago. It's standard to tip 15-20% at restaurants and for services.

The city is known for its food. Don't miss out on trying a Chicago-style hot dog or deep-dish pizza.

Sales tax in Chicago is 10.25%, one of the highest in the U.S.

Chicago is a city of neighborhoods, each with its own unique character and charm.

The city is located on Lake Michigan, which can make it feel colder due to the 'lake effect'.

Chicago is a sports-loving city, home to the Cubs, White Sox, Bulls, Bears, and Blackhawks.

The city is very bike-friendly, with numerous bike lanes and bike-sharing programs.

Chicago is known for its music scene, particularly blues and jazz.

The city has strict smoking laws. Smoking is banned in all indoor public places and within 15 feet of any entrance.

Chicago's O'Hare International Airport is one of the busiest airports in the world.

The city is known for its architecture. Consider taking an architectural tour.

Chicago has a high sales tax on bottled water, so consider bringing a reusable water bottle.

The city can get very cold in the winter, with temperatures often dropping below freezing (32°F/0°C).

Chicago's summers can be hot and humid, with temperatures often reaching into the 80s and 90s Fahrenheit (27-32°C).

The city is known for its vibrant arts scene, including theater, visual arts, and music.

Chicago is a diverse city with a rich history of immigration, which is reflected in its food, neighborhoods, and festivals.

The city has a reputation for being windy, hence its nickname 'The Windy City', but this is more due to its political history than its actual weather.

January is the coldest month in Chicago, with snow and freezing temperatures, so pack warm clothes.

February is still quite cold with a chance of snow, but temperatures start to rise slightly.

March sees the beginning of spring, with temperatures rising, but still expect some chilly days.

April is a transitional month with temperatures ranging from chilly to mild, and occasional rain showers.

May is the start of the warm season, with pleasant temperatures and more sunny days.

June is a great month to visit Chicago, with warm temperatures and plenty of sunshine.

July is the hottest month in Chicago, with high humidity and plenty of sunshine.

August is still quite hot, but temperatures start to cool down towards the end of the month.

September is a pleasant month with mild temperatures, perfect for outdoor activities.

October sees the arrival of fall, with cooler temperatures and beautiful fall foliage.

November is a transitional month with temperatures dropping and the first signs of winter.

December is a cold month with a high chance of snow, so pack warm clothes if you plan to visit.

Chicago, often referred to as the "Windy City", experiences a wide range of weather conditions throughout the year, so it's important to plan your visit accordingly. 

Spring (March to May) in Chicago can be unpredictable, with temperatures ranging from 40°F to 70°F (4°C to 21°C). It's a good idea to pack layers and a waterproof jacket as rain showers are common during this season.

Summer (June to August) is typically warm and humid, with temperatures often reaching up to 85°F (29°C). However, it can occasionally get hotter, so don't forget your sunscreen, hats, and light clothing. Also, be aware that Chicago can experience severe thunderstorms during the summer months.

Fall (September to November) is a beautiful time to visit Chicago as the leaves change color. Temperatures can vary greatly, from 70°F in September (21°C) to 40°F in November (4°C). A light jacket and umbrella are recommended as rain can be frequent.

Winter (December to February) in Chicago can be quite harsh, with temperatures often dropping below freezing, sometimes as low as 20°F (-6°C). Snowfall is common and can be heavy, so pack warm clothing, including a winter coat, gloves, and a hat. 

Regardless of when you visit, keep in mind that Chicago's weather can change quickly. It's always a good idea to check the forecast before your trip and pack accordingly. Also, remember that the wind can make it feel colder than the actual temperature, especially near the lakefront.

Finally, don't let the weather deter you from enjoying all that Chicago has to offer. There are plenty of indoor attractions like museums, art galleries, and restaurants to enjoy if the weather isn't cooperating.

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5-Day Romantic Christmas Holiday Itinerary in Chicago

About Chicago, Illinois