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How To Get The Most Out Of A City Break To Chicago

The USA has its fair share of incredible cities, but there is arguably nowhere more unique than Chicago. Chicago lies on the southern shores of the mighty Lake Michigan, an area that is sometimes referred to as ‘America’s third coast’ thanks to the staggeringly long coastlines of the great lakes.

It’s the third largest city in the USA with 9.5 million people calling the Chicago Metropolitan Area home, and probably has one of the most iconic skylines in the world- pictures of the city’s skyscrapers from across the lake have become pretty iconic, and can only be achieved in perfect conditions!

It is famed for its deep dish pizza and has featured in many movies, from the Blues Brothers to The Dark Knight, and is packed to bursting with culture and history.

Whether you are making a big move and starting a new life here, or simply visiting for a perfect vacation, there are a few things you’ll need to know in order to maximize your time in this midwestern metropolis.

Let’s take a look at some of the things you should know before you visit the stunning Chicago.

The Best Time to Visit

Chicago really is one of those cities that you can visit at pretty much any time of the year and have a great time- but that does come with a few caveats.

The summer months are clearly the best time for those looking to enjoy the outdoor activities the city offers, like sunning yourself at the beach, relaxing in the parks or cruising the beautiful rivers on a boat.

If you’re looking to have some fun in the sun with friends, enjoy the city’s gorgeous parks and lakeside, and try doing something like a Chicago scavenger hunt to explore the city; then summer is the time for you. 

If you fancy yourself as a bit more of a winter bird, then there is still plenty to see and do during the winter months- but you have to be prepared for snow and bitter cold.

The parks have that magical snow covered feel, and of course all of the world class museums and galleries are open year round.

The city at Christmas time is a whole new kind of magical, and the autumnal period has to be seen to be believed!    

The Lake Effect

This is one of the main caveats to visiting in the winter.

‘The Lake Effect’ is the cause of Chicago’s changeable weather, and it describes the effect that the massive Lake Michigan has on the city. 

The Great White North is on the city’s doorstep, and it can be the case that arctic winds and cold air ‘skate’ across the frozen surface of the lake and slam into the city.

It’s a pretty spectacular thing to experience- but Chicago in the winter is not for everyone.

Getting There

Getting to Chicago at any time of year could not be easier.

Here are the main three methods for accessing America’s Windy City.

By Air

There are two International airports on the outskirts of the city- Midway International, and O’Hare International.

Both offer incredible international links, but O’Hare is the larger of the two- in fact, pre-pandemic O’Hare was the second busiest airport in the world, with 538,211 aircraft movements.

Each airport is connected directly to the city’s rail network, and can be accessed with real ease from the city.

By Rail

America has a famously poor rail network considering its size, but luckily for us, Chicago acts as a kind of ‘rail hub’ for the entire east coast and Canada.

It can be accessed from all the major cities in the east, and even from places like LA in the west.

By Road

One of the many things America is famed for is the great road trip.

The highway infrastructure in the country is expansive and high quality, and the lakes and surrounding area make for great driving, so road tripping is a superb way to arrive in Chicago.

The only thing to note is that Chicago is notoriously difficult when it comes to traffic. Pre-arrange a parking space, and plan to leave the car there for the duration of your stay!

Getting Around

Despite its gargantuan size, Chicago city center is incredibly walkable- and for the most part, visitors shouldn’t be too worried about the wider metropolitan area.

As with many other cities around the world, there are three main ways of exploring:

On Foot

It has long been said that the best way to truly experience a city is by wandering its streets- and Chicago is no exception to this.

It’s a beautiful city to explore on foot; filled with parks, lakeside paths and wide open streets offering soaringly spectacular views of the city’s buildings.

The city is nicely laid out in the classic American grid pattern, so navigation is easy and the lack of hills is a welcome surprise!

By Train

Chicago’s metro system, the ‘L Train’ or ‘the loop’, is an incredible service and offers amazing coverage of the downtown area.

It’s quite literally a circle with offshoots into the surrounding areas, so it’s easy to use, inexpensive and covers pretty much everything you could want to see in the city. 

On the River

One of Chicago’s most iconic sights is the series of bridges which cross the Chicago River And are surrounded by impossibly tall buildings- but many people forget that the river is actually an excellent way to see the city.

It runs inland from the lake, then parallel to the city’s center. Booking a river sightseeing cruise, or utilizing the river taxis, is a superb way to get around and is great fun too!

You can also check out the banks of the river that have been turned into beautiful public spaces and riverside walkways.

Where to Stay

There are several areas that are considered ‘downtown’, and a few surrounding neighborhoods, each with something different to offer- from business to casual, Chicago has it all.

The Loop

The Loop not only refers to the metro system, but also the district at the very heart of the city.

Although this area is aimed more towards business people, there are plenty of luxury hotels with amazing views and stunning locations.  

West Loop

The West Loop district is conveniently located on the imaginatively named Green and Pink lines, and rather obviously lies west of The Loop.

Here the vibe is altogether more relaxed, the food is stunning and the night life and urban culture is amazing.