Best Places & Restaurants in Chicago for Solo Travelers | Top Hotels & Tips

Published: 03 Mar 2025

Where Am I Going?

Million Dollar Park, one of the most famous places in Chicago, is a great place for single tourists to visit. The park is home to Cloud Gate (The Bean), a beautiful mirrored sculpture that shows off the city skyline and creates fantastic photo opportunities. It is entirely free to visit, and there is always a lot going on.

Things That Solo Friends Can Do

Take shots that Bean would be proud of.
Watch street artists play music and make art live.
Check out Lurie Garden, the hidden green space in the park.
Drop off your stuff at Crown Fountain, where digital faces in the summer spray water.
Go to Jay Pritzker Pavilion to see a show outside.

The Best Time to Visit

It’s best to take shots before 9 a.m. with fewer people.

Sunset Views: The golden hour lights on The Bean make for beautiful views.
Winter Wonderland: The snowy scenes in the park make it feel like a winter paradise.

Nearby Attractions to Explore

The Chicago Cultural Center has gorgeous buildings and free art shows.
Maggie Daley Park has ice skating in the winter and rock climbing in the summer.
The Art Institute of Chicago is one of the best museums in the world and is only a short walk away.

Pro Tip for Solo Travelers: Go on weekday mornings for a quiet experience. When you’re traveling alone, remember to bring a frame for selfies.

The Art Institute of Chicago Is Great for Art Lovers

Why Go?

The Art Institute of Chicago is a must-see for single art lovers in Chicago. With more than 300,000 works of art, it includes excellent works by Van Gogh, Monet, Picasso, and Grant Wood. This museum gives you a complete experience so you can look around at your own pace, no matter how interested you are in art.

🖀️ Something to Look At? (Exhibits You Have to See)

The Impressionist and Post-Impressionist Collection has works by Monet, such as Water Lilies, and Van Gogh’s works, such as The Bedroom.
The Modern Wing shows modern art and works by Picasso and Matisse.
Thorne Miniature Rooms: These are tiny, detailed rooms from different times.
Armor and Medieval Art: A unique collection of weapons and armor worn by knights.
American Gothic by Grant Wood is in the section on American art.

Traveler’s Pleasures Alone

Take your time; you don’t have to rush through the displays!
Enjoy the quiet; it’s a great time to think and get ideas.
You can take the audio tour on your own using the museum app.
Take a break at the museum café for coffee and a view of Millennium Park.

The Best Time to Visit

Monday mornings (before 11 a.m.): Less crowded, making it easier to enjoy art.
Thursday nights: Fewer people and admission is cheaper.

Places Nearby That Are Worth Seeing

Millennium Park is only across the street! Great for taking a walk after your stay.
Chicago Symphony Orchestra: For a great show close by, go to this one.
Grant Park is a lovely green space where you can unwind.

Pro Tip: Bring a notepad or sketchpad to write in a journal or paint. This museum is full of ideas.

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The Chicago Riverwalk Is a Beautiful Place to Walk Along the River

Should You Go?

The Chicago Riverwalk is one of the most beautiful urban walks in the United States. It has stunning views of the city skyline. Enjoy your free time, take pictures, or look for events that are good for traveling alone on this lively seaside promenade.

Activities with Friends

Take your time walking along the river and enjoy the famous buildings of Chicago.
Find a coffee shop or a snack along the river, like Giselle Coffee & Wine Bar.
At street events, listen to music and see artists.
Take a design boat tour to learn about Chicago’s most famous buildings.
Take a break at a wine bar and watch the sun go down.

The Best Time to Go on Vacation

Take a walk early, before 9 a.m., when there is no traffic.
Sunset: The lake shows off the golden light so beautifully.
Evenings: The city lights make for a great atmosphere at night.

Places in the Area to Check Out

The Wrigley Building is one of Chicago’s most beautiful pieces of architecture.
Michigan Avenue (The Magnificent Mile) is a great place to shop and see sights.
Navy Pier is a short walk away and offers more fun things to do by the water.
The River Theater stairs are a quiet place to escape the city’s noise. Find a spot to sit and watch the boats go by.

Navy Pier Is an Old Favorite Spot in Chicago

Why Should You Go?

Navy Pier is one of the most well-known spots in Chicago. It offers excellent Food, fun things to do, and lovely lake views. It’s a great spot for single tourists to enjoy the lively scene in Chicago without feeling like they don’t fit in.

Best Things to Do by Yourself

Ride the famous Centennial Wheel to see the city and lake from above.
Go to a live show; the Navy Pier offers free concerts, comedy shows, and street events.
Go on a lake ride 🖂 . Take a slow-paced boat trip to Lake Michigan to see architecture or a speedboat tour.
Go to the Chicago Shakespeare Theater to see great plays in a small space.
Try Chicago-style Food Get Garrett Popcorn or deep-dish pizza while you enjoy the lively pier scene.

Best Time to Visit

Evening: The city skyline looks beautiful at night.
Wed-Fri: Less traffic means more fun compared to the weekends.
Summer: Fireworks shows every Wednesday and Saturday night.

Not Too Far Away Are Places That Are Worth Checking Out

Ohio Street Beach is a quiet place by the lake that is only a short walk away.
The Museum of Contemporary Art is excellent for people who like modern art.
Chicago Riverwalk: Continue your trip along a beautiful riverbank path.

Pro Tip: If you buy your ticket online, especially on weekends, you can skip the lines at the Centennial Wheel.

Stunning Views of the City from the 360 CHICAGO Observation Deck

Why Go?

The John Hancock Center’s 360 CHICAGO has some of the city’s best views. This viewing deck is less crowded than the Willis Tower, so it’s better for people just visiting alone.

Very Important Events

On a clear day, the 360° views let you see the skyline of Chicago, Lake Michigan, and parts of Indiana and Wisconsin.
Do the TILT experience. Stand inside a glass box that tilts forward for an exciting city view.
Have a drink at Bar 94 and enjoy the view.
Take lovely pictures 📀; the floor-to-ceiling windows make things look like they belong in a painting.

The Best Time to Take a Trip

At sunset, also called “Golden Hour,” the sky changes colors and looks beautiful.
Late at night: The meeting is quiet, and few people are there.

Places Close By to See and Do

Oak Street Beach is a great place to relax after your trip.
The Magnificent Mile is the best place to eat and shop in Chicago.
Water Tower Place is well-known for its unique stores.

Tip for Solo Travelers: Visit right before sunset to see views of the area both during the day and at night.

Go to Lou Malnati’s Pizza and Try Their Famous Deep-Dish Pizza

Why Do You Want to Go?

If you go to Chicago, you must try the famous deep-dish pizza. Lou Malnati’s is one of the best-known places to get it. This is the place to go for people who are going alone and love good Food. It’s famous for having soft dough, gooey Cheese, and thick tomato sauce.

What Should I Order? (Dishes You Must Try)

The Malnati Chicago Classic features deep-dish pizza with lean sausage, fresh mozzarella, and vine-ripened tomato sauce.
Buttercrust Pizza has a crispy, flaky crust with an extra layer of flavor.
House Salad is a crispy, light side dish that pairs perfectly with cheesy perfection.

Advice for Eating Alone

Sit at the bar for faster service and a great way to meet other people in the area.
Get your deep dish in the perfect size for one person.
Go to lunch or early dinner when it’s not as busy to avoid long wait times.

Nearby Places That Are Worth Seeing

The Magnificent Mile – Looking at shops will help you eat the rest of your dinner.
The 360 CHICAGO Observation Deck is close to the city’s most beautiful views.
The Chicago Riverwalk is a great place to walk after eating pizza.

Tip for Solo Travelers

Baking a deep-dish pizza takes about 30 to 40 minutes, so get a drink and enjoy the cozy setting while you wait.

The Allis is a Cozy Place to Work and Drink Coffee

Why Do You Want to Go?

The Allis is an excellent place for a solo traveler to find a stylish, quiet café to work, read, or rest. This café is inside Soho House Chicago and has a chic, peaceful setting with nice seats and a beautiful interior.

The Best Things to Order

Matcha Latte – Smooth, creamy, and great for a caffeine boost.
Avocado Toast – A tasty and healthy way to start the day or eat a snack.
Freshly Baked Pastries – Perfectly paired with coffee.

Why It’s Great for People Who Travel Alone

A cozy and quiet space that’s great for reading, writing in a journal, or working on your PC.
Soft seats and stylish chairs make it a place to relax.
There is a good mix of locals and tourists, so it’s a good spot to talk to strangers or watch people.

When to Go

Before 10 a.m. – It’s less crowded and a great way to start the day.
2:00 to 4:00 p.m. – The best time for working and enjoying a coffee.

Places Close By to Visit

Fulton Market District – This cool spot has unique shops and restaurants.
Willis Tower Skydeck – See Chicago atop one of the city’s tallest buildings.
The West Loop is home to some of the best dining spots in the city.

Tip for Solo Travelers: Bring a book or laptop, find a quiet corner, and enjoy a hot coffee.

Eataly Chicago: A Heaven for Italian Food

Why Do You Want to Go?

If you love Italian Food, this substantial Italian market is a dream come true. It has restaurants, cafés, and shops that sell authentic Pasta, pizza, Cheese, and sweets. You can go here for a full meal or a quick bite. People who like good Food and a lively atmosphere will love this place.

What Should I Eat? (Foods You Should Try)

Fresh Pasta – From scratch, try making fresh Pasta, like Cacio e Pepe or Tagliatelle al Ragu.
Naples-Style Pizza – Thin, crispy, and tastes just like pizza from Italy.
Wine & Cheese – Authentic Italian wines paired with a selection of cheeses.
Classic Desserts – Cannoli and tiramisu are the perfect sweet endings to your meal.

Benefits for Solo Travelers

Instead of ordering one big meal, get small plates to try different foods.
Sit at the bar for quick service and friendly interactions with the staff.
Explore the market—you’ll find unique Italian ingredients and gourmet treats.

When Would Be the Best Time to Visit?

Weekdays (Before Noon) – Less crowded, making it easier to find a cozy spot.
Evening (5–7 p.m.) – Lively but not overwhelming.

Nearby Places to Visit

The Magnificent Mile – Just a short walk away, perfect for shopping and sightseeing.
Millennium Park – A great place to walk after a delicious meal.
Chicago Riverwalk – Take a relaxing stroll along the river after indulging in Italian delights.

Tip for Solo Travelers: What should I try? Ask the staff! They love recommending authentic Italian dishes.

The Second City: See a Comedy Show

Why Do You Want to Go?

Chicago is the birthplace of improv comedy, and The Second City is where legends like Tina Fey, Steve Carell, and Bill Murray started. If you love live comedy, this is a must-visit spot!

What Should I Expect?

Hilarious Sketch & Improv Shows – The lineup changes every night, so there’s always something new!
Interactive Experience – Sit close to the stage, and you might become part of the show.
Lively Atmosphere – A fun, friendly crowd makes it easy to enjoy solo.

Tips for Solo Travelers

Sit in the Front Row – Performers love engaging with the audience!
Arrive Early – Grab a great seat and enjoy a drink at the theater bar.
Try an Improv Class – Feeling Bold? Sign up for a beginner’s improv workshop!

Nearby Places to Visit

Old Town Bars & Restaurants – Perfect for a post-show drink or late-night snack.
North Avenue Beach – A peaceful lakeside walk after the laughs.

Fun Fact: Many Saturday Night Live (SNL) comedians started their careers at The Second City.

The Green Mill: A Legendary Jazz Club

Why Do You Want to Go?

Step into the past at The Green Mill, one of Chicago’s most iconic jazz clubs. This historic venue was a favorite of Al Capone, and it still carries that 1920s speakeasy charm with its dim lighting, vintage décor, and incredible live music.

What Should I Expect?

Live Jazz & Improv Music – Enjoy world-class performances every night.
Speakeasy Vibes – Feels like stepping into a hidden Prohibition-era bar.
Mix of Locals & Tourists – A welcoming spot for solo travelers.

Tips for Solo Travelers

Arrive Early – Seating is first come, first served!
Order a Classic Cocktail – Try a Manhattan or Old Fashioned for an actual jazz-era experience.
Sit at the Bar – Great for meeting fellow jazz lovers and friendly bartenders.

Nearby Places to Visit

Aragon Ballroom – Another legendary venue for live music.
Uptown’s Late-Night Food Scene 🍔 – Perfect for a post-show meal.

Fun Fact: Rumor has it Al Capone used a secret underground tunnel beneath The Green Mill to escape the police

Blues Clubs in Chicago: Check Out the City’s Music Scene 🎶

Why Do You Want to Go?

Since the blues originated in Chicago, you must experience live blues music here! Whether you love soulful guitar solos or high-energy performances, these clubs will give you an authentic and unforgettable music experience.

The Best Blues Clubs to Visit

Kingston Mines is Chicago’s oldest and largest blues bar, featuring two stages with nonstop live music.
Buddy Guy’s Legends – Owned by blues legend Buddy Guy, this club is a must-visit for great music and Food.
Rosa’s Lounge provides a small, cozy atmosphere that resembles an authentic neighborhood blues bar.

Tips for Solo Travelers

Go on a weekend night – The energy is incredible!
Stand by the stage – Feel the music up close.
Talk to the performers – Many blues artists love chatting with the crowd after their show.

Nearby Places to Visit

Chicago’s Jazz & Blues Museums – Learn about the city’s rich musical history.
Late-Night Food Spots – Enjoy classic Chicago comfort food after a night of live music.

Pro Tip: Some blues clubs offer free live music on certain nights. Check the schedule before you go.

Outdoor & Nature Vacations for Solo Travelers

Find Peace in Lincoln Park & Lincoln Park Zoo

Why Should You Go?

Lincoln Park is the perfect escape from Chicago’s busy streets. This 1,200-acre green space offers a free zoo, peaceful walking paths, and stunning lake views—ideal for solo travelers looking to relax.

Things to Do Alone

Explore the Lincoln Park Zoo – One of the oldest and best free zoos in the U.S.
Walk the Nature Boardwalk – Spot wildlife and enjoy the fresh air.
Relax at North Avenue Beach – Soak up the sun or people-watch.
Visit Alfred Caldwell Lily Pool – A hidden oasis with peaceful streams.
Check out the Chicago History Museum – Learn about the city’s fascinating past.

Best Time to Visit

Morning (Before 10 a.m.) – Enjoy the quietest, most peaceful moments.
Sunset – Watch the lake shimmer under the evening sky.

Other Nearby Nature Spots

Lincoln Park Conservatory – A stunning indoor garden with exotic plants.
Peggy Notebaert Nature Museum – A butterfly haven with interactive exhibits.
Old Town Chicago – A charming area with unique shops, cafés, and historic buildings.

Solo Travel Tip: Pick a quiet spot in Lincoln Park, bring a book or journal, and enjoy the view.

Garfield Park Conservatory: A Hidden Gem for Nature Lovers

Why Should You Go?

Want a lush, tropical getaway without leaving Chicago? The Garfield Park Conservatory is one of the most extensive indoor gardens in the U.S., featuring thousands of plant species inside stunning glass-domed rooms. It’s the perfect place to enjoy nature year-round—even in winter!

What to See & Do?

Walk Through the Palm House – Towering palm trees and exotic plants surround you.
Explore the Fern Room – Waterfalls and hidden pathways create a prehistoric vibe.
Visit the Desert House – See rare cacti and air plants worldwide.
Capture Natural Beauty – One of Chicago’s best photo spots for nature lovers.
Relax in the Outdoor Gardens – A peaceful escape for reflection and quiet time.

Pros of Solo Travel Here

Calm & peaceful – Ideal for a solo mindful retreat.
Free entry – No ticket needed!
No rush – Wander at your own pace and soak in the beauty.

Best Time to Visit

Weekday Mornings – Fewer visitors, making it extra peaceful.
Winter Escape – Stay warm in a tropical paradise while Chicago freezes outside.

Nearby Places to Explore

Garfield Park Lagoon – A peaceful spot for paddling or quiet reflection.
West Loop Cafés – Grab a coffee and plan your next adventure.

Fun Fact: Due to its stunning architecture and vast plant collection, the Garfield Park Conservatory is often called “landscape art under glass.”

Best Hotels & Hostels in Chicago for Solo Travelers

Choosing the right place to stay is essential for any solo traveler. Whether you’re looking for a budget-friendly hostel, a boutique hotel, or a luxury stay, Chicago offers plenty of options.

Best Budget Hostels in Chicago ($-$$)

If you travel solo and want to save money, these hostels offer affordable prices, safety, and social events. Located in prime areas, they are perfect for meeting fellow travelers.

HI Chicago Hostel – Best for Meeting New People

Location: South Loop, near Grant Park
Price Range: $40 – $70 per night

Why Stay Here?

One of Chicago’s top-rated hostels
Daily social events for solo travelers to connect
Shared kitchen & complimentary breakfast
Walking distance to The Loop, Art Institute & Millennium Park

Solo Traveler Tip: Stay in a dorm for socializing or book a private room for more privacy.

Freehand Chicago – Stylish & Affordable

Location: River North
Price Range: $50 – $100 per night

Why Stay Here?

A mix of boutique hotel & hostel vibes – budget-friendly but stylish

Dorms & private rooms available

Home to Broken Shaker, one of Chicago’s best cocktail bars
Close to Navy Pier, Riverwalk, and Magnificent Mile

Solo Traveler Tip: Head to Broken Shaker for a fun night out and to meet fellow travelers.

Chicago Getaway Hostel – Best for Relaxing

Location: Lincoln Park
Price Range: $35 – $80 per night

Why Stay Here?

Located in a safe & quiet neighborhood
Cozy common area, Free Food, and bike rentals
Close to Lakefront Trail & Lincoln Park Zoo

Solo Traveler Tip: A great option if you want to be close to the city but away from the crowds.

Best Mid-Range Hotels for Solo Travelers in Chicago ($$–$$$)

If you’re traveling solo and want more comfort and privacy without spending a fortune, these mid-range hotels offer the perfect balance of style, location, and affordability.

Hotel Versey Days Inn by Wyndham – Artsy & Fun

Location: Lincoln Park
Price Range: $100 – $180 per night

Why Stay Here?

A new, artistic hotel with a unique style
Walking distance to bars, restaurants, and Lake Michigan
Cozy, quiet rooms with a trendy boutique vibe

Solo Traveler Tip: Stay here if you want affordability & style in a lively area.

The Chicago Hotel Collection – River North

Location: River North
Price Range: $120 – $200 per night

Why Stay Here?

Designed for solo travelers with stylish décor & social areas

Great coworking spaces for remote workers
Close to Chicago’s best restaurants & nightlife
A perfect mix of comfort, style & affordability

Solo Traveler Tip: If you’re a digital nomad, this hotel has fantastic workspaces.

The Moxy Chicago Downtown – Cool & Fun Stay

Location: River North
Price Range: $130 – $200 per night

Why Stay Here?

Instagram-worthy hotel with stylish décor
Lively social scene & a fun, youthful vibe
The lobby bar is perfect for meeting locals & travelers 🍹

Solo Traveler Tip: If you love trendy hotels near nightlife, Moxy is a perfect choice.

Best Boutique & Luxury Hotels for Solo Travelers ($$$ – $$$$)

For solo travelers who love style, comfort, and breathtaking views, Chicago has some of the best high-end hotels with top-notch service and prime locations.

The Robey – A Super Chic Stay

Location: Wicker Park
Price Range: $200 – $300 per night

Why Stay Here?

Located in Chicago’s trendiest neighborhood 🌿
Features a stunning rooftop bar with skyline views 🍸
A perfect mix of modern elegance & vintage charm

Solo Traveler Tip: Stay here if you want a stylish escape from the busy city center!

The Gwen – A Solo Luxury Escape

Location: Magnificent Mile
Price Range: $250 – $400 per night

Why Stay Here?

Chic & elegant – perfect for solo travelers who love comfort & style ✨
Close to Lake Michigan, top restaurants, and designer shopping 🛍️
Features a rooftop terrace with breathtaking city views 🌆

Solo Traveler Tip: Ideal for a peaceful, high-end stay in the city’s heart!

London House Chicago – The Best River Views

Location: Downtown, by the Chicago River
Price Range: $250 – $450 per night

Why Stay Here?

One of Chicago’s most iconic luxury hotels
Has a rooftop bar with panoramic city views
Steps from The Loop, Chicago Riverwalk & Millennium Park

Solo Traveler Tip: Stay here if you love breathtaking views & city lights.

FAQs

1. What do you do in Chicago by yourself?

If you’re traveling alone, Chicago has many things to do. You’ll find something fun here whether you like art, history, Food, or nature.

Must-Do Activities:

Take famous pictures in Millennium Park and The Bean.
Walk along the Chicago Riverwalk and enjoy the water views.
Visit The Art Institute of Chicago, home to world-class art.
Take an architecture boat tour for stunning skyline views.
Enjoy live jazz at The Green Mill or a comedy show at The Second City.
Try deep-dish pizza at Lou Malnati’s or visit Eataly for gourmet Food.

2. May I go to Chicago by myself?

Yes, of course. Chicago is one of the best places for solo travelers. It’s easy to navigate, has excellent public transport, and plenty of solo-friendly activities.

Why Chicago is Great for Solo Travelers:

Walkable areas like the Lakefront Trail
Efficient public transport (CTA buses and trains)
Safe, solo-friendly places: museums, parks, cafés, and live music venues

3. Is Chicago an excellent place for people to meet?

Yes. Whether you want to meet new people or explore alone, Chicago has plenty of opportunities.

Social Hotspots:

Rooftop bars and jazz clubs in River North and Wicker Park
Cafés, coworking spaces, and live music venues
Food tours, fitness classes, and walking tours

4. How do adults in Chicago make friends?

Making friends in a big city can be challenging, but Chicago offers plenty of opportunities.

Ways to Connect:

Join group activities like yoga, dance lessons, or comedy workshops.
Visit jazz bars and music venues.
Go to networking events or coworking spaces.
Join brewery tours and food tastings.
Start conversations in cafés, bars, and local events.

5. Is it safe to walk around downtown Chicago by myself?

Yes, but like any big city, stay aware of your surroundings. Downtown areas like The Loop, River North, and Magnificent Mile are generally safe, especially during the day.

Safety Tips for Solo Travelers:

Stick to well-lit areas and avoid empty streets at night.
Use public transport or rideshare services after dark.
Keep valuables secure in crowded places.

Solo Traveler Tip: Stay near busy areas like Michigan Avenue or the Riverwalk if you are exploring late.

6. What is well-known to buy in Chicago?

Chicago has excellent shopping spots for unique souvenirs and local specialties.

Popular Chicago Souvenirs:

Garrett Popcorn – Famous caramel and cheese mix
Chicago sports gear – Bulls, Bears, Cubs, or Blackhawks merchandise
Chicago-style hot sauce and spices for food lovers
Local artwork from the Chicago Art District
Luxury shopping on The Magnificent Mile

7. Is Chicago a romantic place for couples?

Yes. Chicago is a fantastic city for couples and solo travelers alike.

Romantic Experiences (also great solo):

Sunset boat tours on the Chicago River
Rooftop dining at Cindy’s or LondonHouse
Evening walks through Millennium Park and Navy Pier
Lake Michigan cruises with stunning city views

Last Thought

Chicago is a dream city for solo travelers, offering the perfect mix of exciting activities, iconic landmarks, delicious Food, and plenty of opportunities to explore at your own pace. There’s always something to do, whether indulging in deep-dish pizza, strolling along the Riverwalk, admiring world-class art, or taking in stunning skyline views.

Why Solo Travelers Love Chicago

Walkable and Safe – Easy-to-navigate streets and accessible public transportation.
Endless Attractions – There’s always something for tourists, from museums to live music venues.
Welcoming Atmosphere – There are plenty of social events where locals and travelers can connect.
Incredible Food Scene – Chicago-style hot dogs, deep-dish pizza, and world-class coffee.

Final Thoughts

Traveling to Chicago alone is a chance for freedom, adventure, and unforgettable experiences. Whether staying for a weekend or a more extended trip, this city welcomes you with open arms and endless excitement.

Pack your bags, book your flight, and get ready to make incredible memories in Chicago.