You’re going to Chicago! Great choice. From the moment you arrive in this city, it acts differently. The skyline comes first. Then the food. Next, the energy of the streets. More than 70 museums, 580 parks and 26 miles of Lake Michigan coastline await you. From history buffs to live music lovers, to those who just want to eat really well, this Chicago travel guide has it all.
This blog will include the best places to visit in Chicago, hidden spots, best places to eat, neighborhoods, and how you can plan your trip so that you will remember it for years.
Quick Answer
One city has it all, and that’s Chicago! See the sun set over Lake Michigan, ride a boat along the Chicago Riverwalk, taste the very best deep-dish pizza and touch Cloud Gate, all in one day. Food, culture, history and outdoor fun are the best elements combined in the best things to do in Chicago. Stay for a weekend or a week! In any case, this metro area will continue to delight you.
Why Chicago Is One of America’s Most Exciting Cities
What Makes Chicago Worth Visiting?
For nine consecutive years, Chicago was selected as the Best Big City in the U.S. The city serves up world-class food, beaches for no charge, and beautiful architecture. Each time you visit, it’s as if it’s new. There’s always something else to do and see here.
How Many Days Do You Need in Chicago?
Three days are enough to do the highlights. Five days to explore the neighbourhoods. With one full week, you’ll experience the whole of Chicago, foodie tours, day trips, and so much more.
Is Chicago Good for First-Time Visitors?
Yes, completely. Chicago is easy to navigate, welcoming to visitors and has a lot to offer the family. Public transport is fairly good. Most of the top places to visit in Chicago are close to each other in downtown Chicago.
Top Must-See Attractions in Chicago
Millennium Park
Home of the Famous Cloud Gate (The Bean)
Most people start their sightseeing in Chicago at Millennium Park. Approach Cloud Gate (the giant silver Bean) and admire the view of the whole skyline. There is no charge, it is open daily, and it’s always fun.
Navy Pier
The city’s iconic Navy Pier is located on the shores of the lake and offers Ferris wheel rides, Chicago boat tours, restaurants and summer fireworks. It is one of the most popular tourist attractions in Chicago that’s suitable for all ages and groups.
Willis Tower Skydeck
At Willis Tower, Skydeck Chicago is more than 1,300 feet above the ground, on a glass ledge. The downtown Chicago skyline extends for miles. One of the most thrilling Chicago destinations in the city.
360 CHICAGO Observation Deck at John Hancock Center
360 CHICAGO at the John Hancock Center gives wide open views of the Chicago skyline and Lake Michigan. The TILT experience leans you out over Michigan Avenue. A top pick for anyone who loves observation deck views.
The Magnificent Mile
Michigan Avenue’s Magnificent Mile is one of the top shopping spots in the nation. This is where luxury brands, excellent restaurants and renowned hotels line up. A lovely afternoon walk.
Chicago Riverwalk
The Chicago Riverwalk follows the Chicago River right through the middle of the city. Walk it, eat while walking it or take a Chicago boat tour. One of the cheapest and most laid-back activities in Chicago.
Buckingham Fountain
One of the World’s Largest Fountains
One of the world’s largest fountains is the Buckingham Fountain in Grant Park. Its evening light and water show is free, making it a great photography spot. Easy to visit and always worth seeing.
Best Architecture and Sightseeing in Chicago
Chicago Architecture River Cruise
The #1 Rated Tour in the City
The Chicago architecture tour by river is the single best experience in the city. A live guide takes you past over 50 landmark buildings while telling the stories behind each one. This is the number one Chicago guided tour — book early because it sells out fast.
Best Walking Tours in Downtown Chicago
Downtown Chicago walking tours explore the history of Chicago on foot. Perfect for Chicago cultural attractions enthusiasts and for anyone interested in the history and stories behind the buildings. Local guides make it come alive.
Helicopter Tours
A helicopter tour is a great way to experience luxury in Chicago. Overhead view of the whole skyline of Chicago and the entire lakefront. One of the most impressive Chicago scenic locations you can ever see.
Chicago Gangster & History Tours
These walking tours follow the streets of Prohibition and Al Capone’s old haunts. It’s one of the most original (and fun, great history, and great storytelling) things to do in Chicago.
Best Museums in Chicago You Should Not Miss
The Art Institute of Chicago — World-Class Art Collection
With more than 300,000 works of art, the Art Institute of Chicago has been the top museum in the world for four consecutive years. A great art lover’s experience in Chicago. Allow 2-3 hours.
Field Museum — Meet Sue the T. Rex
SUE, the most complete T. rex skeleton ever discovered, is at The Field Museum. It’s on the Museum Campus and is definitely a must-see destination in Chicago for families and history lovers.
Shedd Aquarium — Marine Life in the Heart of the City
Dolphins, beluga whales and thousands of sea creatures make their home in the middle of the city at the Shedd Aquarium. One of the best places to visit in Chicago, and one of the family-friendly activities in Chicago for visitors of all ages.
Museum of Science and Industry
The Museum of Science and Industry is the biggest science museum in the Western hemisphere. Located in Hyde Park Chicago, it has a real German submarine and incredible interactive exhibits. A top Chicago vacation idea for curious visitors.
Adler Planetarium
At the end of the Museum Campus is the Adler Planetarium. Fabulous city views outside, great space inside. A calm and beautiful Chicago destination to add to your list.
Fun Outdoor Activities in Chicago
Lake Michigan Beaches
Oak Street Beach and North Avenue Beach are the best beaches in Chicago for the summer. You’re surrounded by sand and water, and the Chicago skyline is directly behind you. They are both easily accessible from the heart of the city and free.
Lakefront Trail
The Lakefront Trail is an 18-mile-long trail along Lake Michigan. Level, mowed, open and maintained throughout the year. These are some of the most beautiful places in the city to run, bike or walk. Totally free.
Lincoln Park Zoo
One of the Best Free Things to Do in Chicago
Lincoln Park Zoo is one of the few remaining “free” zoos in the country. It is located within Lincoln Park, one of Chicago’s most beautiful green spaces. A wonderful family and solo outing.
Chicago Botanic Garden
The Chicago Botanic Garden is located approximately 25 miles north of the city, and it’s filled with peaceful paths and lovely fall colors. A peaceful retreat from all the hustle and bustle of downtown.
Free Things to Do in Chicago (No Budget Needed)
Free Attractions That Are Worth Every Zero Dollars
Chicago is brilliant for budget travelers. Great free spots:
- Millennium Park
- Lincoln Park Zoo
- Chicago Cultural Center
- Grant Park
- Buckingham Fountain
- All 24 city beaches
- The Lakefront Trail
- Garfield Park Conservatory.
Free Festivals and Outdoor Events by Season
Most of Chicago’s biggest festivals are free:
- Chicago Blues Festival
- Taste of Chicago
- Chicago Jazz Festival
- Lollapalooza
- Chicago Air and Water Show
- Christkindlmarket
- Chicago SummerDance
Free Neighborhood Walking Experiences
Some of the best free things to do in Chicago this weekend are simply walking around.
- Try Pilsen for murals
- Wicker Park for indie shops
- Chinatown Chicago for food and culture
- Old Town Chicago for historic streets
- Hyde Park Chicago, near the new Obama Presidential Center.
Best Things to Do in Chicago for Couples
- Romantic Sunset River Cruise
One of the most romantic things to do in Chicago is to take a sunset cruise along the Chicago River or Lake Michigan. Golden Hour of the day in the city sky. For the complete experience, take a dinner cruise.
- Rooftop Bars with Stunning City Views
There are no better places for couples to eat and drink than rooftop restaurants and bars in Chicago. Chicago’s best luxury activities for a special night out.
- Fine Dining Experiences You’ll Remember
Some of the best restaurants in the country can be found in the West Loop Chicago, and River North Chicago. Book ahead and enjoy a real Chicago luxury experience at the dinner table.
- Lakefront Walks and Observation Decks at Night
After dark is a magical time to walk the Lakefront Trail. Or head to 360 CHICAGO for a nighttime affair at the top of the tower with epic views of the Chicago skyline.
- Best Date Night Ideas in Chicago
Top romantic picks:
- Sunset Architecture Cruise
- Dinner in West Loop
- Live jazz at Green Mill
- Rooftop drinks at LondonHouse
- Navy Pier fireworks in summer
- Christkindlmarket in winter
- Comedy show at The Second City
Family-Friendly Things to Do in Chicago
Chicago Children’s Museum at Navy Pier
The Chicago Children’s Museum at Navy Pier is hands-on and made for young kids. Great for family activities Chicago — especially on rainy or cold days when you need an indoor plan.
LEGOLAND Discovery Center Chicago
LEGOLAND Discovery Center Chicago is a fully built LEGO world right in the city. Rides, builds, and colorful displays. One of the top family-friendly things to do in Chicago for children under 10.
Brookfield Zoo — A Full Day of Family Fun
Brookfield Zoo is bigger than Lincoln Park Zoo and sits just outside the city. Over 400 animal species make it a brilliant full-day outing. A great pick among Chicago family destinations.
Best Indoor Things to Do in Chicago with Kids
When the weather is bad:
- Chicago Children’s Museum
- LEGOLAND Discovery Center
- Shedd Aquarium
- Field Museum
- Museum of Science and Industry
- Adler Planetarium
- Museum of Illusions Chicago
Unique and Hidden Gem Experiences in Chicago
Wrigley Field Tour
Wrigley Field was built in 1914. Behind the scenes tour will take you to the dugout, locker rooms and press box. Even if you aren’t a baseball fan, it’s a truly one-of-a-kind Chicago experience.
The Second City
World-Famous Comedy Shows
Here in the Second City on North Wells Street, celebrities such as Tina Fey and Bill Murray began their careers. Comedy will be performed live nightly. One of the best places for entertainment in Chicago.
Garfield Park Conservatory
The Garfield Park Conservatory is free, beautiful, and almost always quiet. One of Chicago’s best hidden gems and a lovely scenic location far from the tourist crowds.
Exploring Chinatown
Chinatown Chicago, along Wentworth Avenue, is colorful, lively, and full of great food. A genuine Chicago cultural attraction that many visitors miss entirely. Don’t be one of those visitors.
Pilsen
Chicago’s Colorful Arts and Culture Neighborhood
Pilsen has giant street murals, great tacos, and the National Museum of Mexican Art. One of the best unique places to visit in Chicago for a real local feel.
606 Trail (Bloomingdale Trail)
The 606 Trail is a 2.7-mile elevated path through four neighborhoods. Bike it or walk it. Great views, great energy, and one of the coolest free Chicago adventure activities in the city.
Best Food Experiences in Chicago You Have to Try
Chicago Deep-Dish Pizza
The deep dish pizza of Chicago is thick, cheesy and filling, unlike any pizza in the world. Best places to eat: Lou Malnati’s, Giordano’s Pizza, Pequod’s Pizza, Gino’s East. Try at least one.
Chicago-Style Hot Dogs
Mustard, neon relish, onion, tomato, pickle, sport peppers and celery salt are the ingredients in a true Chicago hot dog. Pick up one at Portillo’s for the correct experience.
Italian Beef Sandwich
Beef, cut into slices and marinated in gravy, rolled up. Get it “dipped” at Al’s Beef or Mr Beef in Old Town Chicago. It’s an Italian beef sandwich, the Chicago original!
Food Tours in Chicago
Chicago food tours are one of the most enjoyable things to do in Chicago. Try:
- Chicago Food Planet Tours
- Tastebud Tours (Fulton Market)
- Chicago Pizza Tours
- Chinatown Food Tour by Chicago Food Tours
Best Restaurants for Every Budget in Chicago
- Budget: Portillo’s, Al’s Beef, Birrieria Zaragoza (theme items)
- Mid-range: Girl & the Goat, Bavette’s Bar & Boeuf, GT Fish & Oyster
- High-End Dining: Michelin-starred dining at its finest, Alinea, Smyth, Ever, Oriole
Best Neighborhoods to Explore in Chicago
- The Chicago Loop is downtown, the heart of the city, so get your day-one here!
- River North Chicago is a good place for art galleries and Chicago nightlife.
- Lincoln Park is green, laid-back, and stuffed with good cafes.
- Wicker Park has its own unique sort of energy and is creative and independent.
- West Loop Chicago is where all the best new restaurants keep opening.
Each neighborhood in this city tells its own story — and all of them are worth walking through.
Seasonal Guide: Things to Do in Chicago All Year
Summer
Enjoy a swim at Oak Street beach, watch the fireworks at Navy Pier, attend Lollapalooza at Grant Park, savor the Taste of Chicago festival, and ride an open-air Architecture River Cruise. The best time to do things in Chicago is in the summer.
Fall
Enjoy fall colors in Walk Lincoln Park, a last-minute Chicago architectural tour, arts fairs in Pilsen and outdoor dining in the West Loop before winter.
Winter
Free ice skating at Millennium Park, shopping at Christkindlmarket, live games with the Chicago Blackhawks or Chicago Bulls and deep dish pizza for cozying up after a cold walk down the lakefront.
Spring
Tulips at the Chicago Botanic Garden, outdoor dining returns to the West Loop, Chicago Cubs first games at Wrigley Field, and bike riding on the 606 Trail when the trees turn green.
Budget Tips and Best Time to Visit
When you are searching for top attractions in Chicago, visit the Chicago CityPASS to save up to 40-50% on attractions such as the Shedd Aquarium, the Field Museum and 360 CHICAGO. If you are going to three or more paid stations, it’s worth buying.
What Is the Best Month to Visit Chicago?
Chicago is best visited between June and August. Summer is the time for warm weather, open beaches and the city’s largest festivals. For less of a crowd, visit during weekdays, or September or October for more beautiful weather.
How to Avoid Crowds in Chicago
Whenever possible, visit during the week and not on the weekends. Visit busy attractions, such as Cloud Gate and Willis Tower Skydeck, in the early morning. September and October are also great months, since it is still a nice and cool time of the year, the tourist crowds are reduced, and the fall colours in the city’s 580 parks are gorgeous.
Where to Stay and Getting Around
Best neighborhoods to stay in:
- River North Chicago
- Gold Coast Chicago
- Lincoln Park
- West Loop Chicago
- South Loop Chicago
Budget hotels
HI Chicago Hostel | Freehand Chicago | Moxy Chicago Downtown
Mid-range: Hotel Zachary | Swissôtel Chicago | Renaissance Chicago Downtown
Luxury: The Langham Chicago | Four Seasons Hotel Chicago | Waldorf Astoria Chicago | LondonHouse Chicago
Getting Around Chicago — Transportation Guide
Chicago is an easy city to navigate once you know what to do. The CTA train system runs throughout the city, biking is popular along the lakefront, and downtown Chicago is very walkable. Private car service in Chicago is the best option for visitors looking for flexibility, as it ensures a stress-free and comfortable experience.
How to Use the CTA Trains and Buses in Chicago
The El Train is a famous CTA line that connects all of the major neighborhoods to downtown, and is colour-coded. The cost for one ride is $2.50. Get a Ventra card and tap-and-go without paying transfer fees all day long.
Best Bike Rental Options in the City
Divvy Bike Share operates throughout the city with stations in convenient places – ideal for quick trips along the Lakefront Trail or across neighborhoods.
Options:
- Divvy Bikes
- Bobby’s Bike Hike (near Navy Pier)
- Bike and Roll Chicago
Is It Easy to Walk Around Chicago?
Very easy, yes. The city of Chicago is one of the most walkable big cities in the United States. The downtown core is easy to traverse on foot due to its flat topography, signage and man-to-man layout. The main tourist spots in and around Chicago are within easy walking distance of one another, such as Millennium Park, The Magnificent Mile and the Chicago Riverwalk. Comfortable shoes are all that is needed, and you’ll be just fine.
Private Car Service in Chicago: The Most Comfortable Way to Explore
If you wish to visit Chicago without any pressure at all, a private car service Chicago is the right option. No parking. No CTA timing. No surge pricing for rideshare. All that is needed is a comfortable and clean car and a professional driver who will deliver you where you need to go and on time, every time. Private car service offers O’Hare airport services, Midway airport car service, a Chicago corporate transportation transfer and more, including full-day transportation for sightseeing in Chicago. Perfect for business travellers, couples, families and anyone looking for a Chicago luxury experience from the moment they arrive. To make a reservation for your ride, visit blackcarserviceschicago.com.
If you want to see Chicago without any stress at all, a private car service Chicago is the way to go.
Why Choose Black Car Service Chicago?
Black Car Services Chicago ensures that every trip is hassle-free. 24 hours a day, every day of the week, and beyond — professional chauffeurs, clean luxury fleet, timely pick up, airport meet and greet, and so much more. From executive airport transfers to Chicago, a chauffeur-driven tour of the city, or simply a reliable ride from your hotel to Chicago, it’s all got a smooth ride through the city. Licensed drivers, insured vehicles and comfortable interiors from the first moment you get in.
Reserve a car rental at blackcarserviceschicago.com and explore Chicago in style!
Conclusion
Why Chicago Should Be Your Next DestinationThere’s just a great city, Chicago. The skyline stops you. The food keeps you. Every time you think you will get to the end of the neighborhood, you are drawn back again. Whether you’re riding the Cloud Gate at Millennium Park, having a late night laugh at The Second City, or strolling through the murals in Pilsen, this city will provide you with one memorable experience after another. 2026 is the year of new openings and exciting events in Chicago. There are more things to do in Chicago. Make your travel plans, pack your bags and head to see what everyone’s talking about! It’s time for you to come to the Windy City.