Should I spend 1 or 2 weeks in Chicago?

Should you spend 1 or 2 weeks 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 weeks 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 week enough time in Chicago?

One week is more than enough time to see everything that Chicago has to offer. Many visitors prefer to spend three to five days here, so you'll be able to take in all of the museums and landmarks, the big city activities, the theatre, and the restaurant scene at your own pace. We have a few suggestions of things to do while you're visiting, and then you can take a day trip if you're looking to explore further around the area.

How to spend a week 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.

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.

With its diverse attractions, Chicago awaits with plentiful neighborhoods, attractions, and activities. Set aside a day to explore the city's historical and cultural sites as well as the special neighborhoods that give the city its own personality. It is a quintessential big city with unique neighborhoods, a diverse population, and and all of the energy that comes with vibrant city life.


A few tour suggestions include:

  • Chicago River Architecture Walking Tour ($34)
  • Chicago Architecture Center River Cruise aboard Chicago's First Lady ($54)
  • The Escape Game Chicago: Epic 60-Minute Adventures in River North ($46)

This city is very popular for nightlife. After the sun goes down, head out to one of the many popular venues around town. 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.

Shopping in Chicago is very popular, and it's easy to see why. Spend time exploring the many shops and boutiques to find the perfect gift, souvenir, or outfit. 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.


A few tour suggestions include:

  • Private Shopping Tour from Chicago to Fashion Outlets of Chicago ($138)

Live music is very popular in Chicago, so make sure you spend the evening exploring some of the more popular venues. The city is the birthplace of such interesting styles as modern gospel and the Chicago style blues.


A few tour suggestions include:

  • Chicago Monday Night Blues Summer Concert Aboard a Tall Ship ($99)

The beautiful beaches await you in Chicago, so spend the day (or several, if you can) relaxing on the sand or swimming in the water. 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.


A few tour suggestions include:

  • Chicago Architecture Center River Cruise aboard Chicago's First Lady ($54)
  • Chicago River 90-Minute Architecture Boat Tour ($37)
  • Chicago Architecture River Cruise ($54)

Chicago is known to be such a beautiful destination, so just exploring and taking it all in should be one of the top things to do on your list. The water makes this city a truly unique place to explore, and the world class architecture is not to be missed.


A few tour suggestions include:

  • Walking Tour of Chicago Loop: Home of the Modern Skyscraper ($60)
  • Your Way or the Highway: 2-hour Customized Private Walking Tour in Chicago ($220)
  • Historic Homes and Cottages of Wicker Park Walking Tour ($45)

After you've explored most of Chicago, take a day trip to one of the many beautiful destinations nearby.

As the live music scene is so popular in Chicago, make sure you spend another evening finding more of the area's best places to take in a show. Often, many of the local venues are near one another, so you can hop from place to place.

Because Chicago offers so many famous sights, landmarks, and museums, you should dedicate at least another day to see the places you haven't seen yet. You can spend multiple days browsing through the city's amazing museums, and some of them are worth a second visit, too.

There are plenty of restaurants you haven't tried yet, so don't miss another amazing meal at local places for lunch and dinner. Try to go out of your way to find the small, locally owned places that offer the charm and ambiance that can only be found in Chicago.

Is 2 weeks enough time in Chicago?

Two weeks is more than enough time to see pretty much everything in Chicago. You can move at your own pace and relax in your hotel. You could also use Chicago as a base for exploring the nearby destinations. You'll find some great day trips in the region.

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How to spend 2 weeks in Chicago

With 2 weeks in Chicago, you'll have plenty of time to enjoy everything the city has to offer at your own relaxed pace. You'll want to spend plenty of time relaxing on the beach, perusing the musuems, experiencing the city's neighborhoods, dining at local restaurants, hopping around the bars and clubs, hanging at the music venues, and browsing the shops. You can also relax at your hotel, or casually explore this city looking for hidden gems. Also, consider taking some day trips to nearby destinations where you can explore more of the region.


A few trip suggestions:

  • Chicago Architecture Center River Cruise aboard Chicago's First Lady ($54)
  • The Escape Game Chicago: Epic 60-Minute Adventures in River North ($46)
  • Chicago River 90-Minute Architecture Boat Tour ($37)
  • Chicago Architecture River Cruise ($54)
  • Chicago River Architecture Tour with Small Boat Upgrade Option ($49)

More Info

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

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