This realistic List of Best Places to Visit in Chicago helps you plan an adventure in “The Windy City”.

Chicago, Illinois is one of the biggest cities in the United States. Visitors come to the capital of the Midwest to enjoy its architecture, parks, museums, and food.

This post includes affiliate links that will earn us commission if you make a purchase via these links.

Chicago is the key city in the state of Illinois. It is also the third largest metropolitan area in the United States. Over 9 million people live in or near Chicago.

The size alone does not make Chicago a worthy destination. But rich history, beautiful architecture, and scenic lakeshore put “The Windy City” on a map for most travelers.

There are a lot of places in Chicago you could consider the best spots to visit. But unless you have a full week, you will have to pick the sights you visit and skip.

This List of the Best Places to Visit in or near Chicago tries to make this selection easier for you.

1. Frank Lloyd Wright Home & Studio

Frank Lloyd Wright Home & Studio is the best place to visit on your trip to Chicago, Illinois. One of the most prominent architects and designers in America lived in Oak Park at the turn of the centuries.

This house museum is in Oak Park, west of Chicago. You would need to budget about an hour to get to the Home from the Loop. Take a subway or a train.

It is a good idea to get a tour ticket in advance. You will learn a lot about the famous architect and his Prairie School style on a 60-minute house tour.

Enjoy original Frank Lloyd Wright furniture pieces, murals, and architectural designs. You could even take some with you by buying a lamp or a placemat at the Museum Shop.

2. Chicago River Architecture Cruise

No visit to Chicago is complete without a Chicago River Architecture Cruise. This is a great way to experience the city.

You could board a 75- or 90-minute cruise at Michigan Avenue or Navy Pier. A handful of companies offer their own versions of this cruise.

You will see the city landmarks from a comfortable boat. Enjoy the Wrigley Building, Tribune Tower, Merchandise Mart, and Willis Tower.

You could return to any of these buildings later once you find the ones you like. Think of the Chicago River Architecture Cruise as a taster of this city.

3. Chicago Lakefront Trail

The Chicago Lakefront Trail is a must-visit destination in “The Windy City”. This 18.5-mi (30-km) paved path connects South Shore with Edgewater neighborhoods.

You could bike the full length of this trail. But it makes more sense to only walk on a few trail sections. There is a breeze from the lake year round. Wear a warm jacket unless you hike the trail in the summer.

You should head to the trail section near Grant Park and Shedd Aquarium if you are after the Skyline views. This area some of the best views of the Chicago skyscrapers.

You could also choose to take the trail to Lincoln Park in the north or Jackson Park in the south. Enjoy the scenic waters of Michigan Lake as you navigate the Lakefront Trail.

4. Millenium Park

Millenium Park has been on the map of the city for less than 20 years. Yet, it has become an iconic Chicago landmark. Every visitor to “The Windy City” stops by Cloud Gate.

This stainless steal structure is great for capturing reflections. But there is more to see in Millenium Park than “The Bean”.

Head to the Millenium Monument on Wrigley Square. It is a replica of an older peristyle. This way, the park ties together different times in the history of the city.

Or check out free classical music festival at Jay Pritzker Pavilion if the dates of your trip work out. There is a free classical music festival that takes place every year at this venue.

5. Frederick C. Robie House

The Frederick C. Robie House is another fantastic place to visit in Chicago. Nicknamed the Robie House, it is the second Frank Lloyd Wright house on this List.

Widely considered the crown jewel of the Prairie School style, this home is open to guided tours. Fascinating design elements await you in this Hyde Park house.

Prepare to be amazed by the beauty of the exterior and interior of the house. You will see the Prairie School elements first hand.

Most visitors go on a 45-minute house tour. You could double your exploration if you add a self paced audio tour of the neighborhood.

6. Garfield Park Conservatory

The Garfield Park Conservatory is a hidden gem in Chicago. This free greenhouse has an astonishing variety of exotic plants. While there is no fee to visit it, you should get a reservation in advance.

You will see palms and bromeliads in the Palm House. Head to the Fern House to see an indoor pond with koi fish and evergreen ferns.

The Desert House and Aroid House are also certain to leave a impression. Look for a desert rose, live baseball plant, and one-of-a-kind cacti.

The area around the conservatory is among the most dangerous in Chicago. Make sure you visit during daylight. And skip the rest of Garfield Park. You are better off catching a subway train to Oak Park.

7. Lincoln Park

Lincoln Park is a green oasis in the north of Chicago. It is a great place to visit on a trip to “The Windy City”. This park has plenty of sights for you to choose from.

You could visit the free Lincoln Park Conservatory. Look for orchids, pitcher plants, and cycads in this Victorian Glass Building.

The Lincoln Park Conservatory has an great number of fruit plants. See papayas and clementines. And check out Buddha’s Hand and Sausage Trees. You have likely never seen such plants before, have you?

Check out free Lincoln Park Zoo or grab a bite at the historic Café Brauer. You could take a stroll around the South Pond afterwards.

8. Oak Park Walking Tour

An Oak Park Walking Tour is the final Frank Lloyd Wright attraction to visit in Chicago. But instead of one house, you could see 28 different homes.

They all date to different times. Some of them follow more traditional designs, while others are in full-on Prairie School style. Only one thing makes them similar: they were all designed by Frank Lloyd Wright.

All of these houses are private residencies. Be respectful to private property as you admire these landmarks from the walkways.

You could choose between a free self-guided tour and an audio tour from the Frank Lloyd Wright Studio and Museum. The latter tour costs $10 and puts a time limit on your exploration.

9. Grant Park

Grant Park is a scenic destination in the center of the Loop. Chances are you will visit Grant Park as you explore the Lakefront Trail and nearby Millenium Park.

This park is home to Buckingham Fountain. It is one of the largest fountains in the world and a sight to see. It will take a good minute to just loop around it.

The fountain works from May to October. You could also catch a light and music show every night during that time. No worries if your trip brings you to Chicago in the winter or spring.

You could heat to Grant Park to see the holiday lights and displays in the winter. It gives you a reason to enjoy this central park even in the off season.

10. Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower is a perfect way to get a bird’s-eye view of Chicago. The tallest skyscraper in the city is still among the highest buildings in the world.

You will enjoy fantastic views from this observation deck. All the major landmarks in the city will be right below you. You could use the Willis Tower to scout your next attraction in Chicago.

Blue waters of Lake Michigan will be also on full display. You might even see the east shore on a clear day. These towns are already in Indiana and Michigan.

You could also stand on the Ledge some 1,353 ft (412 m) above the ground. This experience is not for the faint of heart. Large crowds and a steep price are the only downsides of a visit.

11. Lake Michigan Architecture Cruise

Lake Michigan Architecture Cruise is a great addition to any summer trip to Chicago. A boat tour gives you a different look of the Chicago Skyline.

All of the tallest buildings will be on full display. The greenery of the Lakefront Trail brightens up the concrete jungle. You will learn about the reversal of the Chicago river and underwater tunnels.

A few tour operators offer one 90-minute tour of the Chicago River and Lake Michigan. This could be an excellent way to see the best of the two worlds.

Keep in mind that you will lose some time passing through the Chicago Harbor Lock. But this could be a memorable experience in itself.

12. Matthiessen State Park

Matthiessen State Park is the furthest attraction from Chicago on this list of Best Places to Visit Near the City. You would need a rental car and hiking boots to enjoy this park.

A beautiful canyon, powerful creek, and scenic waterfalls await you in Matthiessen State Park. You could explore them all as long as it did not rain heavily the night before.

Low water creek crossings might be flooded then. In this case, you would have to resort to only hiking the rim of Dells Canyon.

You could pair a visit to this park with a few hikes at nearby Starved Rock. Together these parks make a great day trip to Northern Illinois.

13. 360 Chicago

360 Chicago is another place to keep in mind when visiting the top attractions in Chicago. It is the second tallest observation deck in the city.

Head to 875 North Michigan Avenue, the former John Hancock Building. You will see Chicago from 1,000 ft (305 m) above the ground.

All towers of the Near North Side and the Loop will be on full display. You will also see a beautiful shoreline of Lake Michigan thanks to the location of this building.

General admission to 360 Chicago is a bit cheaper than at Skydeck Chicago. You could use the savings to buy a drink at the CloudBar or take a thrill ride at the Tilt.

14. Starved Rock State Park

Starved Rock State Park is a beautiful place to visit within a 1.5-hour drive from Chicago. You should stop by this park if you already made it to Matthiessen State Park.

Starved Rock is a hiker’s park. You will see a handful of sandstone canyons, waterfalls, and creeks. Enjoy the wooden boardwalks and stairs as hike between the different sights.

You could start your adventure at the Eagle Cliff Overlook. You will get scenic views of the Illinois River. Go to Lonetree Canyon next. Admire a waterfall in Wildcat Canyon before returning via French Canyon.

It will be difficult to keep track of the different canyons. Hop in your car to reach St Louis Canyon and Illinois Canyon. Or make it a full day adventure by hiking the entire Canyon Trail out and back.

15. Navy Pier

You cannot discuss the best places to see in Chicago without mentioning Navy Pier. This historic location is a center of action.

The Pier dates back to 1916. It has a museum, a ferris wheel, a theater, and an event venue. Countless restaurants and shops are on Navy Pier. There is even a hotel.

Navy Pier is the best spot to see the fireworks. The best show takes place on the New Year’s. You could also see the fireworks every Wednesday and Saturday night between Memorial Day and Labor Day.

You could start a Lake Michigan cruise right from the Pier. Take a short walk to Ogden Slip and board a Chicago River Architecture cruise. Or hike to the sights of the Loop via the Lakefront Trail.

16. Ernest Hemingway Birthplace Museum

Frank Lloyd Wright was not the only famous resident of Oak Park. As a matter of fact, Ernest Hemingway was an Oak Park native. The Nobel Prize winning writer was born in this Chicago suburb.

You could visit the Birthplace Museum as you enjoy your walk around Oak Park. You might not notice this modest 1890 Queen Anne house among the gorgeous Frank Lloyd Wright buildings.

Head inside to tour the Birthplace Museum. You will learn about the writer’s family and childhood years. Look for the beautiful furniture and art pieces.

Keep in mind that the Ernest Hemingway Birthplace Museum tours often run over the posted time. But this could be great news for the fans of his works.

17. University of Chicago Campus

Chicago is home to a handful of renowned universities. If you are looking to take a stroll on a historic campus, look no further than the University of Chicago.

Most of the buildings in the Main Quadrangle are in Gothic Collegiate style. Harper Memorial Library, Haskell Hall, and Stuart Hall are beautiful buildings covered in ivy.

Take a look at Rockefeller Memorial Chapel. It is the tallest building on campus. The chapel is just a block away from the Robie House.

Head to the Joe and Rika Mansueto Library if you like contemporary architecture. Its elliptical dome is quite a bit different from the early 20th century halls.

18. Jackson Park

Jackson Park rounds up the list of Best Places to visit in Chicago. This park is a nice addition to a trip to Hyde Park or Woodlawn.

You could visit this park after touring of the Robie House or walking around the University of Chicago campus. It could be a short stop as you are waiting for a train back to the Loop.

Head to the Museum of Science and History. This museum is in the the 1893 Palace of Fine Arts. Enjoy the views of this historic building.

You will find Jackson Park even more fascinating if you visit Chicago in spring. The park cherries will be in full bloom, making it a popular photo spot.

Takeaways: Best Places to Visit in Chicago

Chicago is a great city to visit in the Midwest. There are a lot of best places you could visit on a trip to Chicago. In fact, you might have to cut down your list to squeeze everything in one trip.

Every traveler will find something to like in “The Windy City”. This is true for architecture geeks, history lovers, outdoor enthusiasts, art connoisseurs, and foodies.

Seasons are a thing to be aware of when planning a trip to Chicago. Winter is a real deal. The wind chills could make your exploration far less enjoyable. If you can, try visiting the city in the summer or fall.

You could enjoy the great outdoors on a summer trip. Take a stroll on the Lakefront trail or swim in Lake Michigan. Head to Oak Park to see the Frank Lloyd Wright houses.

The fall is a gloomier and colder season in Chicago. But you could see amazing fall colors in the parks. Spend more time indoors admiring the conservatories and house museums.

Transport, Places & Stay, & Restaurants

Use public transport as you navigate between different sights in Chicago. Subway (L trains), Metra trains, buses, and bikes make it easy to reach your next destination.

Beware of your surroundings. Not all neighborhoods in Chicago are equally safe. Some of the best places to visit are in the rougher neighborhoods like Garfield Park.

Consider staying in the Loop. The places to stay in this neighborhood are near everything in the city. Take a look at Hotel Blake, an Ascend Hotel Collection Member and Hyatt House Chicago West Loop.

Make sure to try a deep dish pizza and a Chicago hotdog while in town. Book a table at one of a handful of Michelin Star restaurants in the city. Or stop by Time Out Market for a taste of Chicago.

Take a look at this Video List of the Best Places to Visit in or near Chicago. And visit the YouTube channel for the latest videos.

Frequently Asked Questions

Safe realist travels!