Chicago Travel Guide

Being the third biggest city in the United States, Chicago offers plenty for all walks of life. From tons of great sightseeing opportunities, restaurants and sports, Chicago ranks as a must see city on your next trip to the USA.

I had the privilege of visiting Chicago in 2015 and can honestly say it is one of my favourite cities. It is known as The Windy City, but ironically that has nothing to do with the weather conditions there.

Chicago is in the state of Illinois which is located in the Midwest. It is situated next to Lake Michigan and has beautiful canals running through the city centre. The amazing skyline is what makes Chicago one of the most recognisable cities in the world.

When To Go?

Chicago is known for having very cold winters, so unless you like being cold and seeing snow, the best time to visit the city is sometime in April or May, or in September or October. That is when the city will be the warmest.

If you go during the summer months of say June, July and August you will have to compete with big crowds at all the major sightseeing spots and the museums. This is also the time when accommodation prices rise to cater for the hordes of travellers that will impend on the city.

Alternatively, if you are willing to brave the bitter cold temperatures of the winter months and are happy to do things indoors, then it could be a good time for you to visit as accommodation will be a lot cheaper.

Things To Do in Chicago

Willis Tower

Willis Tower Chicago

Willis Tower, also known as Sears Tower, is one of the most famous skyscrapers in the entire world. A visit to Chicago would not be complete without a trip up to the top of this tower which gives breathtaking 360 degree views of the city. It is also a learning experience as it shows how the city was built and shows where the landmarks are. Willis Tower was built in 1970 and was the tallest building in the world from 1973-1998.


Chicago Museums

Chicago is blessed with some of the best museums in the country and is a big part of why people travel to the city. The Field Museum of Natural History and Museum of Science & Industry are absolute must see. Also nearby is the hugely popular Adler Planetarium as sell as Shedd Aquarium. By buying a City Pass you can get yourself access to all of these places at a much cheaper discount than if you wanted to go individually.

Navy Pier

Navy Pier Chicago

One of the more popular landmarks in Chicago is Navy Pier. Built in 1916 and spanning over 1km, it is a popular meeting point that hosts fantastic restuarants, gardens, shops, family attractions and exhibitions. Families will enjoy the carnival rides and arcade area and there is little doubt why they call Navy Pier the top leisure destination in the Midwest. Each year it will attract close to ten million visitors, so it is clearly a must see.

Go to the Theater

Chicago Theatres

Well known as a famous theatre town, Chicago has plenty to offer in terms of entertainment. We suggest you head down to the Theatre District during your stay as there are too many theatres to count. You could also check out a site like to get a full rundown of all the plays that are currently on and a review of each one. The Chicago Theatre and Oriental Theatre are two of the most popular theatres in town.

Millennium Park

Chicago Millennium Park

Millennium Park is Chicago’s answer to Central Park in New York. It spans a massive 99,000m square and is a popular meeting point in the city. Each year it will attract in excess of four million people and is well known for the famous Cloud Gate structure. Other features include the Crown Fountain, Wrigley Square, Exelon Pavilions, Jay Pritzker Pavilion, Boeing Gallery and Nichols Bridgeway. So in other words, there is plenty to see!

Where To Stay

Chicago is spread out over ten different districts. As you can imagine it is a massive city and there is good public transport, but it is recommended that you stay somewhere pretty central when visiting for the first time.

“The Magnificent Mile is a top area to stay”When I visited I stayed in Downtown Chicago and felt this gave me great access to all the major sights, plus put me in a close position to the theatre district and great restaurants. It is also perfect if you enjoy shopping with tons of great shops to choose from.

Be sure to check out what is known as the Magnificent Mile which is basically in the middle of the Loop’s. You will be walking distance from sights such as Navy Pier and Millennium Park. Plus very close to public transport to get you out to the museums or sports stadiums.


Chicago Trains

Buses are probably the best way to travel in Chicago. They operate 24 hours in the central part and will be able to get you all over town, especially to all the sights you want to see. If you plan on visiting the museums, then travelling by bus is absolutely the best way.

If you fancy travelling by train then look up Metra as they operate the trains in the city. Travelling into or out of Chicago by train is a good option too, as the city is the is historically the rail hub of the entire United States. Those trains are operated by Amtrak.

Renting a car or catching a taxi are other options, but the traffic in Chicago is insane at the best of times. Unless you are an experienced driver in big cities, it may not be for the faint hearted. Another good option is to hire bikes, with little bike hubs located all over the city.


Ahh who could forget Michael Jordan and the Chicago Bulls of the 1990s?! The Bulls are probably one of the most recognised sports brands in the world and catching a game at the United Center is an incredible experience to say the least.

“You must go to a Chicago Bulls game!”Chicago also boasts two MLB teams (which is baseball for those who don’t know). The two teams are the Chicago Cubs who play at Wrigley Field, which is famous for being the oldest National League ball park in the country. Then there is the Chicago White Sox who play at US Cellular Field.

The Chicago Bears are the football team and they are massively popular, playing their games at Soldier Field. If the Bears are playing while you are in town, do all you can to get a ticket!

Then there are the lesser teams such as the Chicago Fire of the MLS, Chicago Red Stars (women’s soccer team), Chicago Sky (women’s basketball) and Windy City Rollers which are a skate team.

Soldiers Field Chicago

Travel Tips


You will find that Chicago is quite an expensive city, so ensure you are cashed up when visiting, especially if you are visiting in the warmer months. Hotels are very pricey and so are restaurants, but public transport is affordable.


If you stay in the downtown area where it is well populated and open, you should be very safe. However the further you go out, particularly the South Side, you should keep your wits about you. Dial 911 if you have concerns.


Chicago is well known as one of the greatest restaurant towns in America. No matter what type of cuisine you are looking for, you will be able to find it. The city is famous for the deep dish pizza and the Chicago hot dog. Very popular!


There are plenty of shopping opportunities in the city whether you are after high end shops, or if you are on a budget. If you visit the Magnificent Mile and surrounding areas, there will be no shortage of opportunities to shop.

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