Should You Visit Chicago?

Are you thinking about visiting Chicago, Illinois? Here's what you need to know before planning your trip.

Is Chicago worth visiting?

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Yes, it's worth visiting this city for three to five days because of the many great activities. Chicago is a booming metropolis that sits on the edge of Lake Michigan. It is a thriving and diverse city that has theater, shopping, and high-reaching skyscrapers. It's also home to the Willis Tower (previously the Sears Tower), which at one time was the world's tallest building. Visitors appreciate the many museums, sporting events, and entertainment options around town. We first visited in 2017 and have returned several times. During our time here, we fell in love with its many kid-friendly museums and parks as well as its great cosmopolitan atmosphere. Chicago is loved by visitors for many reasons, and is routinely on national "best of" lists, including Money's Best Places to Travel in 2023.

Chicago’s Elevated Train Chicago’s Elevated Train

Reasons to Visit Chicago

There are countless landmarks, museums, and iconic sights in the area. Some of the most famous are the Art Institute of Chicago, Adler Planetarium, and the Museum of Science and Industry. Notable landmarks include the famous Willis Tower - formerly the Sears Tower, Buckingham Fountain, and the iconic Cloud Gate (the bean).

Theatre Productions
Theater is big here with many of the major Broadway productions visiting the city. There is also an endless list of smaller, local theaters to choose from.

With everything from award-winning luxury restaurants to local dives, this city has something for everyone. It also has very distinct local flavors and dishes that create an identity and bring great pride to the locals. While you're in town you have to try the famous deep dish pizza, Chicago style hot dogs, and Italian beef.

It has a wide range of activities at night, with everything from theater and comedy clubs to dance venues, sporting events, and local bars. It's easy to fill many evenings with whatever activity appeals to you. Popular bars and clubs include the Smart Bar, Beauty Bar, and Le Nocturne.

The city is the birthplace of such interesting styles as modern gospel and the Chicago style blues.

There are countless neighborhoods that are filled with boutiques, local vendors, and art galleries. The city has some of the country's best shopping opportunities, and the most notable area is the famous Michigan Avenue and the Magnificent Mile.

While you don't immediately think of beaches when you think of Chicago, there are some nice beaches by the lake. If the weather is nice, it's a great area to spend some time.

Christmas Markets
Shopping is a highlight of a trip to the city, and the Christkindlmarkt is not to be missed.

Is Chicago worth visiting in the Summer?

Summer is the high season for travel in Chicago, so expect more visitors and higher prices. This destination is quite popular with tourists, and in the high season it's even busier than usual as this is when most people like to visit. Expect crowds to be large, and prices to be a bit higher than normal. However, there's plenty to do here this time of year, too. Summer really is the best time to visit Chicago, but even then the weather can be surprisingly cool. Particularly by the lake, you'll want to come prepared for the windy chill.

The weather in Chicago is fairly warm during summer, and stays around 25°C (77°F). But it can get as warm as 30°C (87°F) at times, too. It's also quite rainy during this season, so be prepared.

The activities of the city are numerous, and this is a great time of year to explore all of them. From family-friendly attractions to romantic getaways, as well as budget-friendly things to do, there's something for everyone. Famous landmarks, museums, tours, and more are all available. You'll also find it quite easy to get around on foot, because this is a very walkable city, especially in the nice weather. You'll find plenty to do during summer, as you'll be able to lounge on the beach, spend time at the museums, and discover the big city activities. Also, you'll be able to grab some drinks at a bar.

Summer Weather in Chicago
Avg Temp
Avg Rain
July 25°C (77°F) 100 mm (3.9 in)
August 24°C (76°F) 90 mm (3.5 in)
September 20°C (68°F) 96 mm (3.8 in)

Is Chicago worth visiting in the Autumn?

This is the shoulder season for travel in Chicago. This destination is quite touristy, so in the shoulder season you can still find plenty of crowds, but better prices.

You'll find the weather to be very nice here during autumn with average temperatures around 14°C (56°F).

Autumn is a great time of year to explore the numerous museums and landmarks around town. They are fun for the whole family as well great for couples. During this season it's fun to experience the beautiful scenery, the museums and landmarks, and the Christmas markets. Also, you can experience the big city activities and the live music.

Autumn Weather in Chicago
Avg Temp
Avg Rain
October 14°C (56°F) 56 mm (2.2 in)
November 7°C (44°F) 56 mm (2.2 in)
December -1°C (31°F) 71 mm (2.8 in)

Is Chicago worth visiting in the Winter?

The weather in Chicago can be quite cold during winter, and averages around -4°C (25°F). But be prepared for much lower temperatures, too.

The low season for travel in Chicago is during the winter. This destination is quite touristy, but in the low season you'll see fewer crowds and much better prices. Unless you have a high tolerance for cold weather, the winter may prove itself unbearable in Chicago.

You'll like that you can take public transit easily in the winter, too. You can get around quickly while avoiding bad weather if needed. This is a great time of year to wander through the museums, take in a show, and dine out at amazing restaurants. Also, you can enjoy the evening activities, listen to some live music, and enjoy the city's energy.

Winter Weather in Chicago
Avg Temp
Avg Rain
January -4°C (25°F) 47 mm (1.9 in)
February -2°C (29°F) 35 mm (1.4 in)
March 5°C (41°F) 93 mm (3.7 in)

Is Chicago worth visiting in the Spring?

Spring is the shoulder season for travel in Chicago. This destination is quite touristy, so in the shoulder season you can still find plenty of crowds, but better prices.

Keep in mind that it can be fairly rainy during spring, and temperatures hover around 11°C (52°F).

You'll find plenty to do during spring, as you'll be able to find the best deals at the shops, browse through museums, and admire the wonderful scenery. Also, you can check out the live music scene and the nightlife.

Spring Weather in Chicago
Avg Temp
Avg Rain
April 11°C (52°F) 108 mm (4.3 in)
May 17°C (63°F) 75 mm (3 in)
June 23°C (73°F) 100 mm (3.9 in)


What is Chicago most famous for?

Chicago is most famous for its thriving sports scene, its iconic local cuisine, and its world class shopping at the Magnificent Mile. The city is very popular for its museums, theatre productions, food, nightlife, music, and shopping. Many people love the beaches and christmas markets, too. It is often described as multicultural, edgey, cosmopolitan, diverse, and vibrant.

What is the most famous sight in Chicago?

The most popular sight in Chicago is The Willis Tower (previously the Sears Tower). You can see prices and costs for this and other sights in Chicago on our travel costs page.

Or, see tickets, activities, and tours for The Willis Tower (previously the Sears Tower) and other attractions here.

How touristy is Chicago? Is it a popular city to visit?

Chicago is a popular city for tourists and travelers. Here are some of the most popular activities and tours. (Prices in US Dollars)

  • Chicago Murder Mystery Tour: $35
  • Chicago Loop Walking Tour: $60
  • Small-Group Sightseeing Boat Tour in Chicago: $75
  • Private Chicago Highlights Driving Tour: $190
  • Chicago Shoreline Adventure Boat Tour: $90
  • Workers Cottages of Oldtown Triangle Walking Tour: $45
  • Chicago Walking Tour - West Town: $50
  • Art Institute of Chicago Private Expert Guided Tour: $74

How long should I spend in Chicago?

The ideal length of time for a trip to Chicago is at least three or as many as five days. Since Chicago has a variety of activities such as dining, nightlife, music, and shopping, most people need this much time to see and do everything here.

If you have a specific amount of time for your trip, see our advice about how much time to spend here: Should I spend 1, 2, or 3 days in Chicago?, Should I spend 3, 4, or 5 days in Chicago?, and Should I spend 1 or 2 weeks in Chicago?.