How to Get the Most Out of a City Break with the Family in Chicago

An overhead view of the Chicago highrise skyline

Let’s face it, vacations as a family can be challenging. Getting everyone packed, organized and out the door can be a nightmare- and you have only just begun. 

Make your vacation as easy as possible by visiting one of the USA’s greatest cities, Chicago.  

One of the USA’s last great cities, it offers everything that its bigger brothers, New York and LA do, without any of the hassles. Layed out over an incredibly easy-to-navigate grid system and offering an excellent public transport network, you’d never know that this is America’s 3rd most populous city, home to nearly 9 million Americans.

You won’t find any of the record-breaking traffic jams like in LA, the streets are less cramped and cleaner than New York’s, and there is an incredible amount to see and do. 

Famed for its deep-dish pizza, amazing nightlife and incredible architecture, this city has a lot to offer for families looking for an unforgettable city break, and it offers a relatively stress-free travel experience.  

We all know that family vacations can be chaotic without some serious organization, so follow this guide to help you maximize your next family holiday- don’t miss out on amazing experiences because of logistical headaches! 

Keep it breezy and enjoy ‘The Windy City’.

This post is part of our series Discover the USA

When to Visit Chicago

Chicago is pretty much an all-year kind of city- although certain times might not be as suitable as others. 

Thanks to its proximity to the Great White North, Chicago can get pretty cold during the depths of the winter. And by pretty cold; you can expect heavy snow and ice.

The gigantic Lake Michigan can give the city a Siberia-like feel as the wind skates across the lake and slams the city with cold air dragged down from the north. If winter is your thing, then it’s a spectacular sight, but many families might want to choose a different season. 

Chicago in freezing wintery weather

Summer is packed with free festivals celebrating music, arts, culture and food; and the temperature usually settles around 20-25°C. It’s a great time of year to enjoy the city’s amazing parks and stunning shoreline. Exploring the city is a great pass time, and admiring the striking skyline against summer skies is a marvel.   

Another favored time of year is the incredible autumnal season. The temperature is good enough to be outdoors, the skies are clear and bright, and the color change in the trees and forests surrounding the city is a truly gorgeous spectacle- people travel from all over the world to enjoy the change of season in this area.  

Getting There 

As previously mentioned, getting to Chicago could not be easier.

By Air

There are two international airports on the perimeter of the city’s metropolitan area; Midway International and O’Hare International. Both offer connections all over North America and beyond, and each has its own link to the city’s train network.

By Rail

The USA’s train network is notoriously beautiful, slow and expensive to use; but having said that, Chicago’s connections with other east coast cities, and even New Orleans in the south, are remarkably good. Accessing the city from Canada via train is relatively easy too, making international train travel a great option.

By Road

If you are road-tripping to the city, then make sure you have already organized a place to park, as with any city, parking can be a problem.

The roads in the area are comprehensive and quite beautiful to drive, thanks to the surrounding lakes – Chicago is a great stop on any family road trip.

Millenium Park in Chicago on a sunny summers day

Where to Stay in Chicago

The Loop

Chicago’s city center accommodation in ‘The Loop’ area is mainly focused on business travelers, but the rooms are reasonably priced- much more so, in fact than in other major cities in the country. 

You’ll find many double or twin rooms in highrise hotels with multiple beds and great views, and the odd office space- but families can always be accommodated. 

There are plenty of accommodations to be found online throughout the city, but if you’re visiting for a short holiday or long weekend, then making sure you’re near The Loop is a good idea. It’s where most of the action is, and it contains the highest density of culture and attractions. 

West Loop

If you’re a group of foodies looking for a potentially quieter area, then West Loop is a great idea. You get all the benefits of being close to the city center, with the added bonuses of great food and a more relaxed atmosphere.   


Lakeview is a great area for families looking for a peaceful and relaxing area to escape the hustle and bustle of the city center.

It’s a very safe area filled with green spaces and great family attractions. You’ll find excellent food served in relaxed restaurants and it’s a great place to spend the day outdoors by the lakeside, or in the many parks. 

It’s also home to the Chicago Cubs baseball team for the sports fans out there!   

Getting Around in Chicago

Despite being quite large, it is not difficult to navigate your way around Chicago’s city center. 

On Foot

Thanks to the incredibly well-organized grid system, the city center is extremely walkable for people of all ages and abilities, and taking part in a Chicago scavenger and treasure hunt is a unique way to get to grips with the city and will take you to the greatest attractions and iconic landmarks in the area.   

By Train 

If you don’t fancy walking, then the train and metro systems in the city are by far the most useful way to travel. 

The Loop’ is not only the neighbourhood but also the train system that encircles the city’s financial district. Everything you could want to see in the city can be accessed from here. 

By Bus

Whether it’s catching a CTA Bus or chartering your own bus in Chicago, it couldn’t be easier to get around the city with shared transportation.

Particularly if you’re travelling as a group, a Chicago bus charter service can be a great way to get between the city’s key attractions and take day trips beyond the city.

By Boat

Seeing the city by boat is a pretty special way to explore Chicago.

You can grab a river taxi on the Chicago River for a quick ride through the highrise district. You’ll have access to Chinatown, Michigan Ave. and many of the city’s most central areas from a whole new vantage point.  

A boat on the river in Chicago

Things to See & Do in Chicago with Kids

Just strolling around Chicago, you will be struck by the incredible architecture on display in this city.  Iconic structures make up the city center, and gorgeous buildings push the boundaries of design and engineering.

The Skyline is incredibly famous and one of the most recognizable in the world, so here are some ways you can enjoy the sights the city has to offer. 

Millenium Park 

Millenium Park was constructed for the Millenium, obviously, and is a part of an incredible series of green spaces containing some of the city’s best cultural hotspots. 

See live music, visit Burnham Park Harbor, watch the skaters at Grant Skate Park, enjoy the fountains of Grant Park and chill out in these awesome nature-filled spaces with the stunning highrise buildings leaning over you. 

The Bean

Officially called The Cloud Gate, it’s one of the city’s most iconic art installations after having appeared in several movies and TV shows. 

It reflects the city’s most iconic structures and distorts them in a fascinating way, and was designed by Anish Kapoor; a world-renowned sculptor.

The bean in Chicago on an autumn day


360 CHICAGO is a great family-friendly activity located in one of the city’s most iconic buildings; the massive John Hancock Center. Standing at 100 storeys tall, it is one of the most striking buildings in the area, and there is an incredible panoramic observation deck on the 96th floor. 

The Art Institute of Chicago 

The Art Institute of Chicago is one of the country’s finest art galleries and offers some of the world’s finest collections of sculpture, ceramics, textiles and paintings on the planet.   

Shop the Magnificent Mile

Nowhere embodies the buzz of the city like the Magnificent Mile. 

Packed to the brim with culture, great international cuisine, entertainment, and world-class shopping, there is something for everyone here, and you can truly experience the city’s heart.

The Ledge  

Located on the side of Chicago’s tallest building, the Willis Tower, this glass-floored observation deck will terrify and delight kids and adults in equal measure. Stand high above the streets and enjoy a unique perspective on the city.

The views from The Ledge are stunning, and the vertigo-inducing drop will be something to tell the entire family about! 

Create Lifelong Memories

Make sure your next visit to Chicago is stress-free and easy for your whole family so you can maximize your time in this incredible city. 

Making the most of Chicago is a much more manageable feat than it is in other cities around the States.

Make full use of the public transport system, explore the city on foot, see the sights and create lifelong memories with your family that don’t involve any stress or nightmarish logistics.

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