4 days in Chicago – Complete guide

por Postcards from IvI

Chicago is a city I’ve always wanted to visit. Known as the windy city, Chicago is popular for its amazing architecture, pizza style and Al Capone. This post provides information about accommodation, transportation, things to do and some tips for spending 4 days in Chicago.

Chicago is located in the state of Illinois and it is the third largest city in the United States. The city is very large but still super neat and clean. Chicago has a very modern vibe and offers travelers a variety of activities. It is a fascinating city and it certainly has a place among my top 3 of favorite cities in the US.

Plan a trip to Chicago - Complete Guide


When to visit Chicago?

The best months to plan a trip to Chicago are from April to October. In summer days, the hot weather can be pretty suffocating but you can always enjoy the beach. In winter, the cold temperatures can be extreme and you can’t do some activities like the boat tours on the Chicago River.

I visited Chicago on December and I was probably lucky because I enjoyed some sunny days and temperatures were around 15°C. The best thing about visiting Chicago in December is that you can see all the Christmas decorations and visit the Christmas markets.

How to get to Chicago?

You can get to Chicago from other US cities by plane, car, bus or train. The city has two airports: O’Hare International Airport and Midway International Airport.


  • Train: Both airports are connected to the city by the CTA train. The CTA Orange Line provides service directly to Midway Airport. The travel time to downtown is 25 min and the ride costs USD$2.5. The CTA Blue Line provides service directly into O’Hare Airport. The travel time to downtown is 45 min and costs USD$5. For using Chicago public transportation you need to get a Ventra Card that you can buy at machines at stations.
  • Private Transfer: the most comfortable option to get from the airports to the city is to book a private ride airport transfer. Book a private transfer from O’Hare Airport here.

Find more information at Chicago Transit official page.

How many days should you spend in Chicago?

The windy city is a really large city and there are many places to visit so I recommend staying for a minimum of 3 days in Chicago. I spent a total of 5 days in the city and would have stayed more. I think 4 days in Chicago is the perfect lenght for visiting the city’s main attractions without a rush.

If you only have two days to visit the city, check out this 48 hours in Chicago Itinerary.

Where to stay in Chicago

If you want to be close to the main attractions, the best neighborhoods to stay are: The Loop, River North, Magnificent Mile. This is the area where most of the hotels and hostels are concentrated.

Getting around Chicago

  • Walking: If you stay in the center of the city, you can walk to most of the attractions. The urban design of Chicago makes it great for walking.
  • Subway/Buses: The subway/Metro in Chicago is a great option for getting around and it’s also kind of an attraction itself because in some parts the rail route is elevated and goes between the buildings and streets of the city center. To use the Chicago subway you can buy 1, 3, 7 and 30 day passes or pay individually for each trip. At any station you can buy the “ventra card”, a rechargeable card that serves to pay for both Metro and bus trips.
  • Uber/Lyft: Both companies are widely used in the United States. Uber Pool is sooo cheap, sometimes it was cheaper than taking the subway!

Facts and recommendations for travel to Chicago

Chicago CityPASS – How to save money in Chicago

If you’re planning on visiting many of the city attractions, I recommend buying the Chicago CityPASS which saves you 51% off admission to the top 5 attractions in the city. The attractions included in the pass (which I’ll detail later) are:

Skydeck Chicago

Shedd Aquarium

The Field Museum

Observatory 360° Chicago or Museum or Science and Industry

Adler Planetarium or The Art Institute of Chicago

More information about Chicago CityPASS here

Info & tips for planning a trip to Chicago

Things to do in 4 days in Chicago

  • Admire the city’s architecture

Chicago stands out for its modern and contemporary architecture. The first skyscrapers were built in this city. After the great Chicago Fire that left much of the city destroyed in 1871, Chicago was rebuilt. This was the beginning of the “School of Chicago”, an architectural style that developed towards the end of the nineteenth century and was characterized by the use of new materials and techniques in construction.

Walking the streets of Chicago is like being in an outdoor architecture museum. It’s really fascinating to look up and see all those skyscrapers that seem to have no end.

There are different architecture tours in the city, like this 75-minute architecture cruise tour including an interior tour of the Rookery Building, a historic landmak of the city.

  • Millennium Park

Millennium Park is a huge and super-interactive park. Some of the main attractions in the park are:

Cloud Gate or “The Bean”: a steel sculpture that reflects the city’s skyline and park. The Bean is on everyone’s Chicago bucket list so be patient and get there early if you want a picture without people because it’s one of the most crowded attractions in the city.

Jay Pritzker Pavilion: A concert pavilion designed by architect Frank Gehry.

Crown Fountain: a fountain designed with screens that project the faces of the city’s citizens.

Info & tips for planning a trip to Chicago

  • Navy Pier

Navy Pier is an ideal place to go for a walk. The views of Lake Michigan and the city are beautiful. This landmark offers a variety of attractions for all ages to enjoy: Ferris wheel, children’s museum, restaurants and shops. You can also take a boat ride along Lake Michigan.

Info & tips for planning a trip to Chicago

  • Chicago River

Chicago River is bordered by the huge skyscrapers and crossed by different bridges. You can cruise down the Chicago River to see the city’s architecture on a 45-minute tour, which is offered by several companies. Please note that the tours don’t run during winter.

However there is no need to spend money to see the river, you can walk along Chicago Riverwalk, the waterfront that borders the river and has places to sit and enjoy the view.

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  • Chicago 360 ° John Hancock Center

You can’t leave Chicago without visiting one of the observatories. 360° Chicago is located on the 94 floor of the Hancock Center building. The views of the city and Lake Michigan are magnificent. The entrance to this viewpoint is included in the Chicago CityPASS.

Info & tips for planning a trip to Chicago

  • Skydeck Chicago – Willis Tower

If you love city views as much as I do, you can’t miss the view from Willis Tower (formerly Sears Tower). This 442 m high skyscraper was the highest in the world at the time of its inauguration . You will love visiting the Skydeck located on the 103 floor, where you can look down and see the city through the glazed floor. It is one of the most touristic attractions so make sure to get there early and plan to spend at least one hour there. The entrance to this attraction is included in the Chicago CityPASS.

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  • Grant Park

Grant Park is a huge urban park, in fact the Millenium Park is within it. It is an excellent place to have a picnic in summer, walk around, see the sculptures and enjoy the views from Chicago’s skyline.Info & tips for planning a trip to Chicago

  • Chicago Museums

There are many museums in Chicago worth visiting, I’m going to mention only a few:

-The Art Institute of Chicago is one of the most important art museums in the world, where you can see renascentist, impressionist and modern art. The museum is huge, and and you can easily spend hours there. If you love art, it’s a must see. Don’t miss the view of the city from the museum’s terrace.

-The Field Museum is a natural history museum. There are many objects related to nature, history and culture. One of the main attractions is the skeleton of the largest Tyrannosaurus Rex that has been found.

-Shedd Aquarium is an excellent choice for those who travel with children.

All these museums are included in the Chicago CityPASS.

Info & tips for planning a trip to Chicago

The Field Museum

  • Chicago Tours

Chicago is famous for its mob and crimes in the 1920s, under the command of Al Capone. A good option to learn more about this topic is to take the Chicago Crime and Mob Tour.

Other interesting tours are the pizza tour, the architecture tour and the segway tour. If you book tours through Get Your Guide you can always cancel the bookings for free:

Info & tips for planning a trip to Chicago

  • Chicago Cultural Center

This is place is not usually mentioned in the “Things to Do in Chicago” guides, but I recommend to visit it if you have the time. The building was formerly the Central Library of the city and today it is a Chicago Landmark. The interior architecture of the building is beautiful and very interesting. Entrance is free.

Info & tips for planning a trip to Chicago

  • Magnificent Mile

The Magnificent Mile is a section of Michigan Avenue where you will find the best clothing stores, restaurants and some historic buildings. Even if you don’t plan to go shopping, the Avenue and the surrounding area is very nice, especially at night when the lights come on.

  • Try the Pizza!

One of the things that make Chicago city famous is its pizza! Chicago-style pizza is made with thick, deep dough, stuffed with cheese and plenty of tomato sauce. You can try it at one of the most famous places in town: Giordano’s.

Info & tips for planning a trip to Chicago

  • Walk the city

As I always say, the best way to get to know a city is walking it, exploring the unknown streets and discovering places that aren’t listed in any guide. The whole downtown Chicago is great for this because there are many hidden alleys, and on every block there is a building worth admiring.

4 days in Chicago - Complete Guide

Have you been to Chicago? What did you like the most? I hope this post has helped you plan your 4 days in Chicago. If you have any doubts please leave your comment below 🙂

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