View along the Chicago River showcasing a vibrant mix of modern and historical architecture, with skyscrapers lining both sides of the waterway. A pedestrian bridge, busy with walkers, connects the city sides, under which tour boats and water taxis navigate the river. This urban riverscape highlights safe and scenic routes for solo travelers, providing a peaceful yet bustling atmosphere, perfect for exploring Chicago's architectural marvels and city life alone.

How To Plan Solo Travel in Chicago – A 3-Day Guide By A Local

Are you looking to do some solo travel in Chicago?  Look no further! In this post, I will share an ideal itinerary for planning an iconic solo trip to Chicago for 3 days!

As an Illinois native of 20+ years who has made countless visits to Chicago for fun and school, I have prepared this 3-day itinerary that, with my guidance and personal recommendations, will inspire you to create your own itinerary or simply follow what I have prepared in this post. 

Chicago is *that* city that offers a pretty fantastic mix of history, culture, and modern attractions in one place, plus more! 

From iconic landmarks like The Bean at Millennial Park to prestigious museums such as the Art Institute of Chicago, an incredible food scene, cultural neighborhoods, and world-class architecture and entertainment plans, experiencing Chicago solo is not only possible but probably the best way to soak in the city’s offerings. 

Ready to see what’s in store?

Let’s jump!

What To See and Things To Do in Chicago in 3-Days – Solo Travel in Chicago 

Day 1 – Explore The Loop + Discover Chicago’s Best Museums + Catch the sunset from the Willis Tower or John Hancock Building

Split image showcasing vibrant solo travel experiences in Chicago. On the left, the historic Wrigley Building towers over the bustling Michigan Avenue, surrounded by impressive skyscrapers and active city life, perfect for exploring alone and affirming that Chicago is safe for female travelers. On the right, the iconic Cloud Gate sculpture, also known as 'The Bean,' reflects the lively Millennium Park atmosphere with many tourists walking around, highlighting exciting things to do in Chicago alone.
The Loop (left) and The Bean AKA Cloudgate at Millennium Park in Chicago

🌅 Morning – Millennium Park + The Bean 

Grab breakfast at Goddess and the Baker at Millennium Park, then head to explore The Loop and all the iconic places to see at Millennium Park! 

Things to see at Millennium Park: 

  • Listen to music from the Jay Pritzker Pavilion or sit on the lawn for a bit.
  • Take a photo of yourself with the Bean (Cloud Gate).
View of the Jay Pritzker Pavilion in Millennium Park, Chicago, featuring its intricate network of stainless steel ribbons that form an avant-garde canopy over the outdoor concert stage. This architectural marvel is set against a backdrop of towering skyscrapers and lush green lawns, offering a dynamic and safe environment for solo travel in Chicago. A perfect blend of urban design and cultural activities, it exemplifies why Chicago is safe for female travelers and highlights engaging things to do in Chicago alone.
The Pritzker Pavilion – Chicago’s main outdoor amphitheater showcasing multiple free shows throughout the summer.
  • See the local crowd around the iconic Crown Fountain.
  • Walk around Maggie Dayley Park and see all the activities to do
    • Ice skating (Winter)
    • Walking the many parks and paths 
Split image capturing serene solo travel spots in Chicago. On the left, a tranquil view from Millennium Park with a large silver bandshell roof nestled among lush greenery, framing the vibrant skyline with its mix of modern and classic architecture—a peaceful yet dynamic setting for solo travelers, demonstrating why Chicago is considered safe for female travelers. On the right, a tree-lined promenade featuring ornamental planters along Grant Park, leading the eye towards a distant view of skyscrapers, perfect for leisurely walks and experiencing the culture and beauty of Chicago alone.
Chicago has a little bit of everything – great architecture with a side of nature walks.
  • Rock climbing 
  • Mini Golf 
  • Rollerblading, scooter and bungee
  • Tennis courts
  • See the gorgeous blooms at North Rose Garden 
  • Take a photo at Buckingham Fountain 

☀️ Afternoon – Get cultured at one of Chicago’s best museums

  • For lunch, if you’re looking for something light in a historic and uniquely Chicago setting, check out Pittsfield Cafe. For delicious Chicago-style hot dogs, check out Billy Goat Taven. 

After lunch, head to one of the best Chicago museums.

These are my recommended museums within the Chicago Loop. I recommend picking one so you can fully absorb and enjoy it. 

The Art Institue of Chicago 

Immerse yourself in a vast collection of world-renowned art from all over the world. 

At the Art Institute of Chicago, you can expect art from impressionist to early-European paintings, Asian prints and sculptures, American artists, and uniquely Chicago art. 

💡Pro Tip: This is one of the most famous museums in Chicago, so unless you want to wait for hours to get in, be sure to get there as early as you can or, better yet, pre-book fast pass tickets! Also, if you’re a Bank of America cardholder, you can access the Art Institute of Chicago for FREE only on the first weekend of any month. Check out other free entry opportunities here!

✅ BOOK your FAST PASS ticket to the Art Institute of Chicago 

Chicago Architecture Center 

For architecture lovers (and those interested), the Chicago Architecture Center boasts a great collection of the history of architecture in Chicago and the world. 

Chicago is a renowned city in architecture, so any opportunity to learn about the subject is a must-do in Chicago!

💡Pro Tip: If you book tickets to the Architecture Cruise, choose the combo ticket that includes admission to the Chicago Architecture Center for only $5 (usually $14). 

✅ PREBOOK your BUNDLE TICKETS to the Chicago Architecture Center + Architecture Tour

Chicago Fed Money Museum

Learn about the role of the Federal Reserve, the history of money and economics, notice the details in bank notes, and other fascinating things about money, both physical and digital. 

Admission is free, but make sure to bring a photo ID to enter. 

Mindworks: The Science of Thinking 

Hosted by the University of Chicago and located in the Chicago Loop, Mindworks is a fascinating museum that showcases a deep look into the human mind and behavior. It is exciting and interactive enough to help you come away with tangible tips to take home. 

Admission is free. 

Chicago Cultural Center 

Explore the beauty of one of Chicago’s most famous and visited cultural and architectural spots – the Chicago Cultural Center. 

It is most famous for its two beautiful, magnificent stained-glass domes, including the world’s largest stained-glass Tiffany dome, exquisite designs by designers Healy & Millet, and more. 

Though you can pop in and see the beautiful architecture, marble, brass, hardwood, glass, and mosaics interior designs for free, to really gain an in-depth look and appreciation for all the beauty, book a guided tour of the interiors. 

✅ BOOK your tickets for a guided tour of the interiors of the Chicago Cultural Center

Best Chicago Museums Honorable Mentions:

💡Pro Tip: Instead of buying and handling multiple tickets for all of Chicago’s main attractions, consider purchasing the Chicago CityPASS. Enjoy easy access to these museums, the Architecture tour, the 360 Chicago Observation Deck, and more! With the Chicago CityPASS, you get access to the Shedd Aquarium and the Skydeck Chicago (Willis Tower), plus your choice of 3 other attractions, including but not limited to the Field Museum, the Museum of Science and Industry, the Art Institute of Chicago, and much more, with a single ticket on your phone. 

🌃 Night – Catch the thrilling sunset from The Willis Tower or John Hancock Tower

Split image capturing exhilarating perspectives for solo travelers in Chicago. On the left, an aerial view from the Willis Tower Skydeck shows an expansive look over Chicago's sprawling cityscape, from dense urban blocks to distant suburbs, highlighting a top activity for solo travel. On the right, a smiling female traveler sits confidently on the transparent glass floor of the Skydeck, with the city's streets visible directly beneath her. Her relaxed pose and joyful expression underscore Chicago's appeal as a safe and inviting destination for female travelers seeking adventure alone.
The Skeydeck is located on the 103rd floor of the Willis Tower, where you can step inside the infamous Ledge glass box!

When it comes to what to do in the evenings alone, reserve tickets ahead of time for The Ledge at the Willis Tower Skydeck – one of Chicago’s most popular attractions at the famous Willis Tower! 

Formerly known as the Sears Tower (what I grew up calling it), the Willis Tower has 108 floors, with the 103rd floor being the Skydeck. 

At the Skydeck, you’ll see numerous exhibits retelling Chicago’s architectural history. The many signs will also detail what direction you’re looking at and what’s in view from all points of the Skyledge. 

When you’re ready, inch closer to The Ledge until you fully step into the (safe) glass box that sticks out from the 103rd building and offers full views of Chicago and beyond (including beneath you!).  

✅ BOOK your tickets for The Ledge at the Willis Tower Skydeck

For another great viewpoint in the city, check out 360 Chicago at the John Hancock Building! 

Ascend to the 94th floor of the building and enjoy the numerous activities there. 

From admiring the breathtaking views of Chicago and Lake Michigan to enjoying a cocktail and light bites, or if you’re looking for something a *tad* more adventurous, hop on the TILT activity.

The TILT is an attraction that straps you onto a platform on one side of the building, 1,000 feet above Chicago. As the glass tilts forward, you’ll view numerous Chicago sights, including Lake Michigan, the Magnificent Mile, and more!

✅ BOOK your tickets for 360 Chicago at the John Hancock Building

💡Pro Tip: If you want to save money and organize your entry into numerous Chicago attractions, consider booking the Chicago CityPASS! This ticket is seriously worth considering if you want to visit sights like the Art Institute, Skyledge, Chicago 360, and even hop on the Architecture Tour. 

For dinner, if you plan well in advance for a truly delicious meal experience, make reservations for Girl and the Goat by award-winning chef Stephanie Izard, one of Chicago’s best restaurants that serves New American style dishes in a modern and uniquely warm environment.  

Another great option is Topolobambo by chef Rick Bayless, which serves modern Mexican-inspired dishes. 

One of my favorite restaurants in Chicago for a while is his other restaurant, Frontera Grill (their milanesa torta and agua de horchata are incredible!). My parents have been to Topolobambo, and they only had amazing things to say about the food and dining experience. 

Day 2 – See Chicago’s World-Famous Architecture + Eat Deep Dish Pizza + Experience Chicago Theatre 

Split image showcasing popular solo travel experiences in Chicago. On the left, the Chicago River winds through a corridor of towering glass skyscrapers under an overcast sky, reflecting the dynamic urban landscape ideal for safe solo explorations, particularly for female travelers. On the right, a delicious Chicago-style deep-dish pizza with rich, bubbly cheese and a variety of toppings served on a wooden table, highlighting the famous culinary experiences available for solo travelers in the city. This image perfectly encapsulates engaging activities to do alone in Chicago, from architectural tours to indulging in local gastronomy.
Cruise down the Chicago River on the famous Architecture Tour and then have some delicious Chicago-style Deep-Dish Pizza!

🌅 Morning – Explore Chicago’s famous architecture on the Architecture Tour

Have breakfast at Beatrix, and then head off to see some of Chicago’s best examples of world-class architecture on the architecture tour. 

As you glide through the Chicago River, you will see sights like The Wrigley Building, the John Hancock, and the Willis Tower, plus many more iconic buildings and skyscrapers that make up the city’s recognizable skyline. 

✅ BOOK the Chicago Architecture River Cruise

⭐️ Looking for other 5-Star Chicago Architecture Tours? 

☀️ Afternoon – Explore the Chicago Riverwalk + Visit Navy Pier

Grab lunch at Beatnik On The River, and enjoy seeing the other boat tours, kayakers, and more on the river, plus people-watching on the Chicago Riverwalk. 

After a filling Mediterrenean-inspired lunch, head to Magnificent Mile and State Street to check out the shopping scene. 

For a midday pick-me-up, try one of Chicago’s best donut spots, Stans Donuts on Michigan Avenue, or if you’re on State Street, grab a sweet hummingbird cupcake at Magnolia Bakery. 

Visit Navy Pier and enjoy the action, from cultural events to riding the Ferris Wheel and capturing amazing views of the city and Lake Michigan. 

A split image capturing two dynamic scenes ideal for solo travel in Chicago. On the left, a female traveler poses on a modern glass balcony with Chicago's sweeping skyline in the background, featuring the distinctive outline of the Willis Tower against a blue sky dotted with clouds. The right side of the image showcases a bustling scene along the Chicago River with people kayaking and riverboats cruising between the high-rises, reflecting a safe and active environment for female travelers exploring Chicago alone.
Stroll through Navy Pier – one of the many places to take photos with the perfect Chicago backdrop!

There are plenty of restaurants, cafes, and bars at Navy Pier, but what I love the most is seeing the free concerts, taking in amazing city views (perfect for photos!), and people-watching. 

If you’re up for it, many Lake Michigan boat tours embark from here, which I also recommend from personal experience! 

I went on Chicago Buffet Lunch Cruise on Lake Michigan a few years back, and I still recommend it to friends and others looking for things to do in Chicago solo to add to their itineraries! 

🌃 Night – Chicago theater or stand-up comedy show

For dinner, try some deep-dish pizza! Places in the city that I recommend are:

To finalize another great night in Chicago, head out to a theater show at the Theater District’s Goodman Theater or watch stand-up.  

If you didn’t already know, Chicago has a wildly incredible theater scene, with over 200 theaters ranging from Broadway to local theater and, of course, stand-up comedy. A must-visit is the Goodman Theater, Chicago’s oldest and largest non-profit theater that offers theater shows of all genres. 

When it comes to comedy, Chicago is widely known for hosting the best shows in the country. It is often the start-up place for many famous comedians, from Amy Poehler to Bill Murray. 

Second City is the most famous comedy club, with more than 60 years of trajectory. It is absolutely a must-visit if you’re into the arts or just want to have a good laugh. Fun fact, many comedians on SNL got their start at Second City. 

Best theater in Chicago

Don’t have time for a show? Want an inside look into the workings and behind-the-scenes at the iconic Chicago Theatre? 

Book a Behind-the-scenes tour of the Chicago Theatre to see the interiors of the historic theatre, where big names like Frank Sinatra, Dean Martin, and more have played and left their mark behind!

✅ BOOK the Chicago Theatre Tour Experience

Best comedy clubs in Chicago

Day 3 – Discover Chicago’s Cultural Neighborhoods + Listen To Live Jazz or Blues or join a Ghost Tour

Split image celebrating the vibrant street art and cultural sculptures found in Chicago, a captivating aspect for solo travelers exploring the city. On the left, a whimsically painted Swedish Dala horse statue stands on a sidewalk, adorned with serene scenes of Swedish landmarks and the calm blue waters of Lake Michigan, symbolizing Chicago's rich tapestry of cultural influences. On the right, a colorful mural depicts a lively scene of dancers swirling in traditional Mexican attire against the backdrop of a detailed architectural structure, showcasing the city's diverse and inclusive art scene that appeals to female travelers seeking safe and enriching solo experiences in Chicago.
Chicago is oozing with diversity and cultural beauty all within the city, alone. It’s one of my favorite things about Chicago. Andersonville (left), Pilsen (right).

🌅 Morning: Explore Chicago’s neighborhoods  

Chicago has 50+ different cultural neighborhoods to explore, but the most popular ones to visit are: 

  • Pilsen – known for its vibrant Mexican community, amazing street art, murals, and delicious food.
Split image showcasing two vibrant murals in Chicago's Pilsen neighborhood, a testament to the city's rich cultural tapestry and a highlight for solo travelers. On the left, a mural features a group of Indigenous women portrayed with strong, dignified expressions, dressed in traditional garments, symbolizing the community's heritage and resilience. The right image displays the 'Pilsen' mural with a rainbow background and three individuals in medical scrubs, underlining the neighborhood's unity and its response to community health, reflecting a safe and culturally enriching environment for female travelers exploring Chicago alone.
Pilsen AKA “Little Mexico”
  • Chinatown – known for its primarily Chinese community, some of the best food in the city, Chinese murals, and sculptures. 
Split image featuring iconic landmarks in Chicago's Chinatown, an engaging destination for solo travelers. On the left, the iconic Pui Tak Center, with its ornate pagoda-style tower and detailed architectural accents, rises against a grey sky, showcasing the area's rich cultural heritage. On the right, the grand Chinatown Gate spans the street with its traditional Chinese architectural elements and vibrant blue and gold colors, welcoming visitors under a light drizzle. Both scenes capture the unique cultural experiences available in Chicago, proving it a safe and fascinating place for female solo travelers to explore alone.
Chinatown in Chicago
  • Little Italy – offers the best mom-and-pop Italian restaurants, bakeries, attractions like the Hull House opened by Jane Addams, and much more.  
  • Greektown –  home to excellent Greek food, plenty of Greek architecture, Greek supermarkets, and a great ambiance. 
Split image showcasing two famous locales in Chicago's Greektown, perfect for solo travelers. The left side depicts a vibrant scene with the Greektown signage prominently displayed against a backdrop of modern skyscrapers and classical architecture under a blue sky adorned with fluffy clouds. The U.S., Chicago, and Greek flags flutter around the Greektown neighborhood sign, adding a touch of movement to the serene cityscape. On the right, a detailed close-up of Greek-inspired architectural columns at a building entrance, illustrating the cultural richness accessible in Chicago. These locations underscore why Chicago is considered safe for female travelers, offering engaging solo activities and cultural exploration.
Greektown in Chicago
  • Andersonville – greatly known for it’s Swedish influence, tons of great restaurants, bakeries, and local shopping. 
This split image presents two charming scenes ideal for solo travel in Chicago. On the left, an iconic Andersonville water tower painted with the Swedish flag stands proudly against a blue sky, atop a red brick building, symbolizing the neighborhood's rich heritage. On the right, a hand holds a freshly baked, poppy seed-sprinkled chocolate babka in a paper sleeve, positioned against the minimalist decor of a cozy café with simple white tables and quirky animal-themed artwork. This image captures the diverse and safe experiences available in Chicago, from exploring cultural landmarks to enjoying delightful local eats alone.
Prominent Swedish influence in Andersonville – Lost Larson Bakery (right)
  • Lincoln Park – One of Chicago’s wealthiest neighborhoods, offering gorgeous architecture and many experiences from the Lincoln Park Zoo, Lincoln Park Conservatory, Chicago History Museum, and North Avenue Beach. 
This composite image showcases two iconic aspects of solo travel in Chicago. On the left, a view of the Chicago History Museum with a distinctive glass façade featuring the city’s flag. The museum is located in a bustling urban setting with cafes and a clear pedestrian path, inviting solo travelers to explore the rich narratives of Chicago's past. On the right, a serene cityscape view from Lincoln Park shows Chicago’s skyline over a tranquil pond surrounded by lush greenery, exemplifying safe and scenic spots for female travelers to enjoy solitude in a vibrant city. Together, these images highlight engaging and secure activities for those exploring Chicago alone.
Lincoln Park – The Chicago History Museum (left), views of Chicago from Lincoln Park Zoo (free) (right).

Though it won’t be possible to see all of Chicago’s incredible diversity (one of my favorite things about the city), pick one neighborhood that calls out the most to you, and enjoy it! Make an effort to grab breakfast and explore one of these neighborhoods to see how culturally diverse and rich Chicago and its residents are. 

However, if you want to experience just a little slice of a few of Chicago’s neighborhoods, consider a small-group tour of Chicago’s north and southside neighborhoods and discover Chicago’s popular northside neighborhoods, each offering their flair, beauty, and culture. 

☀️ Afternoon – Grab lunch at 3 Arts Club Cafe on The Gold Coast 

A bustling indoor restaurant scene in Chicago, showing solo and group diners in a relaxed setting with elegant décor. The venue features a large fountain as the centerpiece, surrounded by lush greenery and exposed brick walls, under a glass roof and crystal chandeliers. This image captures the vibrant dining experience and architectural beauty, suitable for exploring things to do in Chicago alone, illustrating why the city is safe and welcoming for female travelers.

Depending on which neighborhood you may find yourself in, if you’re in or near Lincoln Park, grab lunch at the beautiful 3 Arts Club Cafe in Chicago’s wealthy Gold Coast area. 

3 Arts Club Cafe has gained tremendous popularity in recent years thanks to more and more people discovering its stunning indoor courtyard-style dining area and multi-level luxury home shopping opportunities, as the cafe shares the space with Restoration Hardware. 

It’s a gorgeous space with a rooftop deck that opens in the summer and offers expansive views of Lincoln Park and Chicago. 

🌃 Night – Jazz or blues concert, listen to house music or a ghost tour

Did you know that Chicago is also known for being the birthplace of modern jazz, blues, and house music, among other genres? 

There’s no better way to finalize your last night in Chicago than with some live music, specifically modern jazz, blues, or listening to house music!

Best jazz and blues club in Chicago

Many of these jazz and blues clubs also have restaurants, so depending on time and mood, enjoy food and show, or stop by for dinner at:

Between the terror and life loss during the Chicago Fire, mobster gangster history, with characters like Al Capone and his doings during the prohibition era, H.H Holmes, one of America’s first serial killers, also committing most of his crimes in Chicago during the World’s Columbian Exhibition in 1893 – it’s safe to say that Chicago is still haunted by it’s creepy and mysterious history, today.

This is why Chicago is one of the best cities in the U.S. to do a ghost tour! As an avid ghost tour attendee (I seriously love them and try to go on one in whichever city I am visiting), a ghost tour in Chicago is a creepy, entertaining, and unique way to learn about the city’s history.

Whether you take a bus tour, walking, or even a scooter tour, passing through the infamous sights of murder, unsolved mysteries, and pure terror, make sure to check out the best ghost tours in Chicago to add to your evening itinerary.

Some of my favorite ghost tours in Chicago

💡 Bonus Tip: Not too much of a fan of creepy? Check out the 14 Best Night Tours in Chicago, where I share other tours that are perfect if you’re looking for something relaxed, fun, yet exciting to do in Chicago.

About Chicago

Chicago, also known as the Windy City, is a vibrant city with a rich history that attracts more than 55 million visitors annually (and growing). 

Established in 1833, Chicago rapidly grew into an industrial powerhouse, showcasing world-class modern architecture like the Willis Tower and John Hancock Center after the Great Chicago Fire of 1871. 

Today, visitors worldwide come to Chicago for its world-class museums, such as the Art Institute of Chicago, to see works of art like “American Gothic” and its diverse food scene, including the famous deep-dish pizza and Chicago-style hot dogs.

The city’s entertainment is equally renowned, with theaters like the Chicago Theatre, music festivals like Lollapalooza, comedy clubs, and more! 

Lastly, Chicago’s diverse neighborhoods, from Pilsen to Andersonville, offer unique city vibes with a dash of Midwestern charm, while its stunning lakefront and vibrant arts scene make it a must-visit destination!

Places to stay in Chicago

Some of the best hotels in Chicago are mostly found within the Loop and River North, especially if you want to explore the city. 

  • Virgin Hotels Chicago – in the Loop, beautiful spacious and clean rooms with views of downtown Chicago, and close to the Magnificent Mile. 
  • Chicago Athletic Association – housed inside a historic building in Chicago, in the heart of the city. Enjoy the spectacular rooftop bar with views of Millennium Park.
  • The Palmer House Hilton – located in Chicago’s theater and financial district, is just a block away from Millennium Park and the Art Institute of Chicago. 

How to move around Chicago 

  • The L – Chicago’s elevated train system. 
  • Uber/Lyft – ridesharing apps most commonly used in Chicago.
  • Water taxi – Hop on and move around the city via the Chicago River, from Union Station and Ogilvie Station to Michigan Avenue and more. 
  • Divvy bikes and scooters – Chicago’s bike and scooter ride-share throughout the city. 

Solo Travel in Chicago Questions

Is Chicago dangerous?

A vibrant and colorful mural titled 'Greetings from Chicago' displayed on an urban wall, featuring the letters of 'CHICAGO' filled with iconic symbols and landmarks. The images within the letters include a hot dog, the Chicago flag, the Cubs logo, graffiti art, a portrait of Ferris Bueller, and cityscapes including the Willis Tower. This mural represents the city's rich cultural scene and is a great photo opportunity for solo travelers exploring Chicago, highlighting the city's safety and numerous activities for individuals.

There’s no doubt that Chicago experiences high levels of crime, but before you rule out visiting Chicago solo, as a Chicagoland local and as someone who went to school in Chicago, it’s not as bad as the news describes. 

Be vigilant and aware of your surroundings, just as you would in any other city. Avoid walking late at night if you’re a solo female traveler or traveling with a group. If you go out, be sure to get an Uber instead of walking back to your hotel. 

When to visit Chicago solo?

A solitary traveler stands admiring the iconic Cloud Gate sculpture, also known as 'The Bean', in Chicago's Millennium Park. The sculpture's shiny, mirror-like surface reflects the clear blue sky and surrounding skyscrapers. This scene illustrates a popular and safe destination for solo travelers in Chicago, showcasing a must-visit spot that allows visitors to appreciate the city's architecture and vibrant urban atmosphere alone.

Chicago has plenty to offer anyone visiting solo any time throughout the year; it depends on what you’re looking for. 

Summer is magical in Chicago. As the locals call it, Summertime Chi is an experience you have to live, as it’s when the city truly comes alive. After 3 long and cold winter months, Chicago kicks off the warmer weather activities with festivals, events in the city, the beach opening, terraces, rooftops, and more! 

In the fall, the city offers gorgeous fall foliage, fun fall activities, Halloween pop-ups and events, Chicago’s version of Oktoberfest, and more!

Don’t rule out visiting Chicago in the winter! Winter brings many fun ways to experience the holidays in Chicago and even a little beyond. From ice skating, tree lighting, and the city sparkling a bit brighter as it’s decorated for the holidays. 

Just don’t forget to bundle up and prepare your Chicago winter wardrobe with the best staple pieces!

Spring in Chicago is witnessing a rebirth of nature, cherry blossoms, tulips, and more. 

Why you should visit Chicago solo?

Aerial view of downtown Chicago featuring a dense cluster of skyscrapers extending towards Lake Michigan, captured from a high vantage point. Prominent buildings pierce the skyline under a hazy sky, illustrating a bustling urban landscape. This image exemplifies the vast cityscape solo travelers can explore, emphasizing the diverse architectural experiences and safe, engaging environment Chicago offers to visitors, especially female travelers exploring the city alone.

Why not? Chicago has tons to offer for solo travelers! I think Chicago offers anything other major U.S. cities have but with a dash of Midwestern charm. Who knows, maybe your interest may be piqued after Chicago to visit other stunning and underrated Midwestern destinations! 

There are many things to do in Chicago by yourself, from great food experiences that you can’t have anywhere else to the beauty of Lake Michigan a few moments away and so much more. 

The Wrap-Up – A 3-Day Local’s Guide to Solo Travel in Chicago

At this point, you may be surprised with just how many incredible things come from Chicago – world-class architecture, the world’s best comedians, beloved musical genres, and a great gastronomic scene. 

I hope this post helped you see all the things you can experience while visiting the Windy City and that it inspired you to visit Chicago solo! 

When do you think you’ll be coming by, and what do you think you’ll be seeing when you visit? Let me know in the comments! 

To more travel moments like this,

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Hi! I'm the founder and writer behind Travel Notes and Things. I write posts about travel destinations, share travel tips and resources, as well as talk about transformative travel to help inspire Latinas to travel to their dream destinations!

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