Chicago has grown from a Midwestern American outpost with a population of 200 folks when it was founded in 1833 to become America’s third-largest city after. This cosmopolitan city with 1,315 high-rise towers was once nothing more than a forest of foul-smelling onions that grew widely and rampantly. The Native Americans in the region called the onion “Checagou,” which European settlers pronounced as “Chicago.”
In the years in between Chicago’s rise from a small Chicago River settlement in the early 19th Century to the booming metropolis of today, the city has been defined by industry, notorious mobsters, police corruption, and political hot air, which helped bring about the nickname, “The Windy City” – along with the vibrant breeze that flows across Lake Michigan.
Today, Mob activity and corruption are a relic of the past, and this iconic city has become a friendly city that is low on pretentious air. Moreover, Chicago is a cultural Mecca with great cuisine, world-class museums, brilliant architecture with a skyline that brings about wonder, and 28 miles of shoreline that house 24 beaches that outline the western border of Lake Michigan, which is the fifth-largest lake in the world.
In addition, along Chicago’s Magnificent Mile, there are malls and boutiques that make for some of the best shopping in the world. And for those who avoid that particular scene and crowds in general, you will find miles of walking trails along Lake Michigan, a tree-lined shore along the Gold Coast, and open, green spots in spacious Grant Park.
Chicago’s Gris System is incredibly basic and getting around is really simple. It all starts with the Loop. This Central Downtown District is the heart of the City and the rest of the districts are named on their distance and directions for the Loop.
Near North, Near West, Near South, Far Northwest, Far West, Far South West, Far South East. so you always know where you are and where you are going. There are a few exceptions to this, with districts such as Lincoln Park, Magnificent Mile, and the Gold Coast but overall it’s all pretty straightforward.
Where to Stay
When visiting the City you are likely to want to be in the heart of the city, so while there are options outside of the center we tend to gravitate towards the central hotel’s Districts. Reasonable Hotels can be found abundantly in the following areas:
- The Loop
- Magnificent Mile
- River North
- Gold Coast
- Lincoln Park / Old Town
Any of these districts will provide adequate lodgings in excellent central locations. Check out our Full Guide on where to Stay in Chicago for more detailed information and some great hotel Recommendations.
Chicago ‘L’ by Rene Schwietzke on CC2.0
Most places, Attractions, and things to see and do are all centrally located and most are within walking distance. on top of this Chicago has a top-notch Transport system with Buses and L – Trains making up for any journey that cannot be walked. Along with an army of Taxis, Uber, and Lyft cars for those times when you need door-to-door.
Based on this Hiring a car is not really necessary in Chicago and to be honest with the poor traffic along with limited and expensive parking it really isn’t worth it at all. We only hire a car if we are heading AWAY from the City, or using Chicago as a starting point for a Road trip, such as Route 66, and then we only Hire a Car AS we leave the City.
You can read more about Chicago’s great public transport here.
To and From the Airports
There are two main airports serving Chicago. O’hare International and Midway Airport. Whichever you fly into getting to and from the center is very simple and can be very cheap too. If you avoid the Taxis and Shuttle buses and simply hop straight on the L Train you can be Downtown in minutes for only $5.00 from Ohare and $3.00 from Midway!
Again we have gone into detail about this in our transport guide here
Things To Do in Chicago
Chicago is a city of great culture and has some real world-class museums. Any “Must see list” or itinerary normally has a good few of the city’s museums on it and we whole heartily agree. In fact, the Cities Museums make the number 1 spot on our list of things to do in Chicago! Museums to Check out include:
- Art Institute of Chicago
- Field Museum of Natural History
- The Museum of Science and Industry
- Alder Planetarium
- Chicago Children’s Museum
- Chicago History Museum
Read More about Chicago’s Great Museums Here
Aquariums are probably one of our favorite places to visit (apart from maybe a good bar) and Chicago’s John G Shedd Aquarium is a really great one. There are some phenomenal aquariums in US Cities and the Shedd ranks right up there with the best. While falling short of Georgia and Monterey Bay Aquariums it easily ranks 3rd place.
The Star Attractions are the Beluga whales and Dolphins, sea otters, and Sea Lions along with the impressive Caribbean Reef exhibit. There is a whole lot to see with over 32,000 animals and 5 Million Gallons of exhibits.
Lincoln Park Zoo
Lincoln Park is worth a trip in itself, A wonderful large open expanse featuring coastal walks and spectacular views of the City Skyline. However, the Jewel in the Parks Crown is the Lincon Park Zoo. Featuring Penguins Polar Bears, Monkeys, Chimps, Gorillas, Big Cats including Lions and Pumas, Zebras Giraffes, and a whole lot more. They even have a breeding group of Black Rhinos!
What more is this pretty solid collection if completely free! 365 days a year. On this basis, it’s hard to find fault at all!
Ravinia Festival by Donna Sutton on CC2.0
Chicago is a City Of festivals and different events year-round. Many people head to Chicago just for these festivals alone. While You may want to avoid these big dates as the crowds will rise and the prices soar, you may also be in the City at exactly the right time as things really come alive at festival time!
January or Early February
- Chicago Restaurant Week
- Chinese New Year Parade
- Chicago Auto Show
- St. Patrick’s Day Parade
- Chicago Blues Festival
- Ravinia Festival
- Chicago Gospel Festival,
- Chicago Pride, the
- Old Town Art Fair and
- Wells Street Art Festival
- Taste of Chicago
- Pitchfork Music Festival
- Chicago Jazz Festival
- Riot Fest
- Chicago Gourmet
- Chicago Film Festival
- Dance Chicago
We have more details on our when to Visit Chicago Page.
In a City built from towering Skyscrapers, one of the best things to do is head up high to get a truly breathtaking view of the incredible CityScape. The View from a few thousand feet up is truly mindblowing and we definitely recommend getting up at least one of Chicago’s great Observation Decks.
The Willis Towers (formally SearsTower) Skydeck is 1,353 feet up on the 103rd floor of the tower and is the highest Observation Deck in the USA. It features an Enclosed Balcony with a glass floor for the crazy brave to test their nerve on.
The 360 Chicago is a little closer to the ground, but not by much, From here you get stunning views up and down the coastline along with one of the best views of the city itself. Its Thrill option is “The Tilt” a moving window that leans you out over the plunge below!
Whichever you choose (We recommend both!) You will get stunning views of the city, Lake Michigan, and 4 different States at the same time! Try and time one for Sunset to see the best of the city as the sun dips and the city lights up!
Saving Money on Paid Attractions
As you can see there is a lot on offer in Chicago, but visiting a number of these attractions can really end up costing a large chunk of money, Just visiting the Shedd, The Skydeck and the Field Museum can cost up to $150! for a family of 4, it gets expensive fast!
One great way to See More and Pay Less is to consider an Attractions Pass. Chicago has Several Available, The Go Chicago Pass, the Official Chicago CityPASS, and the Chicago Explorer Pass. All offering Slightly different attractions and Experiences. To decide which pass would suit you best Take a look at our Chicago City Pass Guide.
For other ways to Save Money on Your Chicago Trip Take a look at our Money Saving Guide here.
Like many built-up areas, the city has set aside large areas of green space for residents and tourists to enjoy. Places to get away from the hustle and bustle of the city and enjoy a touch of nature. Chicago’s brutal seasons mean these parks take on different roles depending on the weather. Relaxing walks and finding solitude is the order of the day whereas in the summer the parks come alive with festivals and people escaping the City and relaxing.
- Lincoln Park
- Grant Park
- Millennium Park
- Jackson Park
Check out our full guide to the best things to do in Chicago, or our Free things to Do in Chicago for more info and other great attractions.
Like most big cities there are fantastic shopping opportunities in the City the Magnificent Mile is awash with high-end luxury and fabulous boutiques. Water Tower Place is a fantastic vertical mall packed with shops and restaurants.
There are also two Outlet Malls where you can head for some serious discount shopping. The Premium Outlets Chicago is probably the better of the two but the Fashion Outlets of Chicago is far closer to the center and will take far less time out of your trip.
Chicago has a fantastic Cuisine and Dining scene and people head to Chicago simply for the food so eating and drinking is an activity to do in its own right so let’s discuss this further.
Chicago Cuisine and Dining
The Dining Scene in Chicago is really thriving and restaurants line every street. Variety is vast and you can choose anything from cheap Hotdog joints to familiar fast food and chain restaurants right up to 3 Michelin Starred restaurants that will blow your mind.
Chicago has a proud food heritage and many culinary delicacies such as Deep Pan Chicago Style Pizza, Amazing Hotdogs to wipe the floor with New York, and hearty Italian Beef Sandwiches.
We discuss exactly what and where to eat in our Chicago Dining Guide here
Weather is not the City’s best selling point. Locals tend to grin and bear it, making the most of the elements. Visitors need to do the same. The City is stifling hot during the summer, and blisteringly cold during the winter with frequent heavy snow. Cloud and rain are persistent nuisances year-round and the wind from Lake Michigan can cut to the bone!
Overall the weather is something to work with and just accept. Appropriate clothing and proper planning along with a good sense of humor and robust spirit are essential to not letting the weather get the better of you.
Our full guide will help you get the best out of any trip to Chicago whatever the Weather.
Have Your Say?
We always love hearing from you so if you have any comments or questions about our post or visiting Chicago in general Fire away in the comments below!