Should I spend 1, 2, or 3 days in Chicago?

Should you spend 1, 2, or 3 days in Chicago?

Many visitors spend three to five days in Chicago during their visit. If you're not sure how much time you might need here, we have the answers because there's so much to see and do. This city offers a number of attractions to explore, including the museums and landmarks, the big city activities, the theatre, and the restaurant scene.

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.

Do you have one or two days to visit Chicago? Here's our comprehensive breakdown of how much time you might need for your trip along with some suggestions for things to do.


Is one day enough time in Chicago?

With only one day, you might feel a bit pressed for time when it comes to exploring the main attractions. After all, The popular city of Chicago has many activities and attractions for visitors. To fully embrace Chicago, a longer visit is better. Most travelers tend to allocate at least 3 or as many as 5 days to browse the museums, enjoy the city's energy, spend an evening at the theatre, and taste delicious cuisine. Nevertheless, if your schedule is limited, we can provide some suggestions to maximize your visit.

How to spend a day in Chicago

When visiting Chicago, you can't miss the Willis Tower (previously the Sears Tower) as it's one of the most famous places in the world. Make sure you give yourself enough time to enjoy it.

Don't miss an evening at the theater while in town. Whether it's a musical, opera, ballet, or a famous Broadway-style production, Chicago is known for its wide range of shows. 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.


A few tour suggestions include:

  • Chicago Scavenger Hunt by Operation City Quest ($10)

Chicago is a very walkable city. With only a day in the city, you'll have no trouble exploring the local sights. The city has many restaurants, sights, and hotels that are easily accessible on foot.

Is a weekend (two to three days) enough time in Chicago?

To do everything that Chicago has to offer, you'll need more than a weekend, but two or three days does allow you a bit more time to explore. You'll have a chance to experience at least some of the highlights. In addition to the great museums and landmarks and fun big city activities, visitors can enjoy the food, nightlife, and live music. By staying a night or two, you'll be able to take advantage of the most interesting activities found here, and we have some suggestions below.

Chicago’s Elevated Train Chicago’s Elevated Train

How to spend 2 days in Chicago

With a weekend (two to three days) in Chicago, you'll have a bit more time to enjoy everything that the city has to offer.

Chicago is famous for it's world-class attractions, museums, and landmarks. You'll want to spend at least a day exploring one or more that you're interested in the most. 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).


A few tour suggestions include:

  • Art Institute of Chicago Skip-the-Line Guided Museum Tour ($133)
  • 2-Hour Chicago Lakefront and Museum Campus Segway Tour ($75)
  • Skip the Line: American Writers Museum Admission Ticket ($16)

The delicious food of Chicago is one of the main highlights of a trip to the region. Dining out is one of the highlights of a trip. Make sure you take the time to taste as much of it as possible during breakfast, lunch, and dinner at some of this city's best restaurants. And consider a food tour or cooking class. You can easily fit one into your schedule since many are just a few hours or half a day. 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.


A few tour suggestions include:

  • Chicago Walking Food Tour With Secret Food Tours ($89)
  • Chicago Small Group Food Tour ($69)
  • Chicago Food Tour with The Magnificent Mile and Millennium Park ($155)

Public transit in Chicago is easy and efficient. In just a few days, you should be able to get around the city quite easily. There's a subway (the "L"), a commuter well, as well as buses and countless taxis available.

More Info

If you're looking for more information about Chicago, we have even more advice to help you plan your journey.

Budget Your Trip is all about finding out how much everything costs so that you can travel cheaper and longer. Created by avid travelers Laurie and Bryan, our goal is to help you plan your next trip on the right budget. With average daily travel costs that are calculated from the budgets of real travelers, plus an analysis of hotel and tour prices, you can find out how much money you need to plan your next adventure. We also have plenty of travel advice, accommodation reviews, and activity suggestions.

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