I have wanted to visit Chicago for many years. After a frustrated attempt to travel to the city in 2014, I finally managed to fulfill my desire to visit Chicago in December 2017. This post provides information about accommodation, transportation, itinerary and some tips for to plan a trip to Chicago on your own.
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.
On this post you’ll find:
- When to visit Chicago
- How to get to Chicago
- How many days should you spend in Chicago
- Where to stay in Chicago
- Getting around Chicago
- Things to do in Chicago
When to visit Chicago?
The best plans 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 and Midway, and both are connected easily to the city by the CTA train. Southwest Airlines is a low cost US airline, a great option for cheaper flights between Chicago and many other U.S. cities
How many days should you spend in Chicago?
The city is quite large and there are many places to visit so I recommend a minimum stay of 4 days. I spent a total of 6 days in the city and would have stayed more. 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.
- Dewitt Hotel and Suites: Excellent Value for money. This was the place where me and my boyfriend stayed. We paid USD $300 for 5 nights in double occupancy apartment. The apartments are simple and the building is The rooms are simple but have all the commodities of an equipped apartment. The location is great,it is just a few blocks from the 360 ° Chicago and Magnificent Mile. Click here to check the updated prices and photos.
- Freehand Chicago: A hostel with the coolest design. If you’re looking for affordable accommodation in a central location, Freehand Chicago is the place to go. Click here to check the updated prices and photos.
- Chicago Athletic Hotel: A building from 1893 which used to be a private club and was restored into a unique boutique hotel. The location is excellent, right in front of the Millenium Park. The hotel also has a restaurant at the terrace and a famous Shake Shack on the ground floor. Even if you don’t stay here, I recommend checking out the building because it’s beautiful. Click here to check the updated prices and photos.
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!
As I mentioned before, the city offers many activities for visitors. 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:
–The Field Museum
–Observatory 360° Chicago or Museum or Science and Industry
–Adler Planetarium or The Art Institute of Chicago
Things to do in Chicago – Plan a trip to Chicago
- Architecture of Chicago
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.
- 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. It’s the most touristic place so be patient and go really early if you want a picture without people.
–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.
- 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 the Michigan Lake.
- 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 60-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.
- 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.
- 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.
- 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.
- 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.
- 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:
- 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.
- 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.
- 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.
Have you been to Chicago? What did you like the most?
Disclaimer: This post contains affiliate links. That means, if you click on certain links within this post and make a purchase, I earn a small commission at no extra cost to you. Read more about it here.