Chicago in November: A Guide to Architecture, Art & More

Chicago Downtown Cityscape
© Jonathan S

Discover the Windy City's charm with this 4-day itinerary packed with architectural marvels, world-class museums, vibrant nightlife, and delicious food tours. Whether you're an art enthusiast, a history buff, or simply seeking a relaxing getaway, this guide has something for everyone.

Day 1 in Chicago: A Day of Art and Architecture

Explore Chicago's Architectural Heritage

Step back in time and discover the history of Chicago architecture and design at the Richard H. Driehaus Museum. Immerse yourself in the elegance of this museum, showcasing exquisite interiors and decorative arts.

Explore Chicago's Architectural Heritage
© Armita Z

Shop and Admire on the Magnificent Mile

Indulge in retail therapy and admire the stunning architecture of Chicago's premier shopping district, the Magnificent Mile. Browse designer boutiques, upscale department stores, and unique shops, all while taking in the city's iconic skyline.

Shop and Admire on the Magnificent Mile
© Ashish Chandra

Experience Chicago's Vibrant Theater Scene

Catch a captivating performance at one of Chicago's historic theaters, immersing yourself in the city's vibrant theater scene. From Broadway productions to local talent, there's a show for every taste.

Experience Chicago's Vibrant Theater Scene
© Hugo Gerardo Azurdia

Unleash Your Creativity at WNDR

Explore the world of design and creativity at the WNDR Museum, where interactive exhibits and immersive installations will ignite your imagination. This museum is a must-visit for anyone seeking a unique and engaging experience.

Unleash Your Creativity at WNDR
© WNDR Museum

Day 2 in Chicago: A Day of History and Culture

Uncover Chicago's Gangster Past

Delve into the fascinating history of Chicago's gangsters on a guided walking tour. Explore the city's notorious underworld, learning about infamous figures and their impact on the city's development.

Uncover Chicago's Gangster Past
© Moises Reyes

Explore the World of Natural History

Journey through time at the Field Museum, a renowned institution showcasing the wonders of natural history. Discover dinosaur skeletons, ancient cultures, and the diversity of life on Earth.

Explore the World of Natural History
© tarun kumar yerra

Museum Campus Exploration

Discover a collection of world-class museums in one area, perfect for a day of exploration. Visit the Shedd Aquarium, the Adler Planetarium, and the Field Museum, immersing yourself in science, history, and the wonders of the natural world.

Museum Campus Exploration
© Julio FERNANDEZ CASANOVA

Celebrate American Literature

Explore the world of American literature and writing at the American Writers Museum, showcasing the stories and voices that have shaped our nation's literary landscape. Discover the works of iconic authors and delve into the history of American writing.

Celebrate American Literature
© American Writers Museum

Day 3 in Chicago: A Day of Music and Entertainment

Cheer on the Chicago Bulls

Experience the electrifying atmosphere of a Chicago Bulls basketball game at the United Center. Cheer on the home team and enjoy the energy of the crowd as you witness the thrill of professional basketball.

Cheer on the Chicago Bulls
© Rob Lewis

Experience Legendary Jazz at Green Mill

Immerse yourself in the legendary jazz scene at one of Chicago's most historic jazz clubs, the Green Mill. Enjoy live music and soak up the atmosphere of this iconic venue, known for its rich history and intimate setting.

Experience Legendary Jazz at Green Mill
© limotodd

Enjoy Live Jazz and Dinner

Savor a delicious dinner and enjoy live jazz music at Andy's Jazz Club, a cozy and intimate venue known for its exceptional music and warm ambiance. This is a perfect spot for a relaxing evening of entertainment.

Enjoy Live Jazz and Dinner
© Tae Kim (coffeecup)

Laugh Your Way Through Chicago Comedy

Experience the legendary Chicago comedy scene at The Second City, a renowned improv theater that has launched the careers of countless comedic stars. Prepare for an evening of laughter and unexpected twists as you witness the talent of these improvisational masters.

Laugh Your Way Through Chicago Comedy
© The Second City

Day 4 in Chicago: A Day of Relaxation and Exploration

Lakefront Trail Stroll

Enjoy the scenic views of Lake Michigan and the city skyline on a walk or bike ride along the Lakefront Trail. Breathe in the fresh air, soak up the sun, and admire the beauty of Chicago's waterfront.

Lakefront Trail Stroll
© Jose Rivera Degracia

Family Fun at Maggie Daley Park

Spend the afternoon at Maggie Daley Park, a family-friendly park with various attractions. Explore the climbing walls, ice skating rink, and playground, or simply relax and enjoy the beautiful surroundings.

Family Fun at Maggie Daley Park
© P S

Explore the 606

Wander along the 606, an abandoned railway turned recreational space, complete with art installations and views. This unique urban oasis offers a peaceful escape from the city's hustle and bustle.

Explore the 606
© yu chen

Discover Graceland Cemetery

Explore the beautiful grounds and historical significance of Graceland Cemetery, a peaceful oasis in the heart of the city. Stroll among the monuments and learn about the lives of notable Chicagoans who have found their final resting place here.

Discover Graceland Cemetery
© Graceland Cemetery

References

Weather in Chicago

In November, Chicago's weather is typically cool to cold, with average high temperatures ranging from 8°C to 12°C (46°F to 54°F) and average low temperatures ranging from 2°C to 6°C (36°F to 43°F). It's not uncommon to experience some frosty mornings and occasional light snowfall, although significant snowstorms are less likely. To prepare for the autumn weather in Chicago in November, it's recommended to pack warm clothing such as coats, hats, gloves, and scarves. You may also want to consider bringing waterproof or water-resistant clothing to protect against potential rain or snow. Additionally, it's a good idea to check the weather forecast before your trip to ensure you're prepared for any unexpected weather conditions.

Transportation in Chicago

Getting around Chicago is relatively easy and affordable, thanks to its comprehensive public transportation system. You can use the Chicago Transit Authority's (CTA) network of train and bus lines, which includes the "L" train, to get around the city. You can purchase a Ventra card, which can be loaded with an unlimited CTA pass for $20, or a single-ride ticket for $2.50. The CTA operates 24 hours a day, and you can transfer twice in a two-hour period with a single fare. You can also consider using rideshare services like Uber or Lyft, or taking a taxi, but be aware that taxis from the airport can be expensive. If you're traveling with a group, you may want to consider renting a car or chartering a bus service. Additionally, you can walk or bike around the city, as many attractions are within walking distance of each other.

Dos in Chicago

Don'ts in Chicago