You are here

5 reasons to add Chicago to your USA holiday

Published 29 June 2016

Bronwyn Griffiths

Bronwyn Griffiths

Apart from a few 1980s film references (Ferris Bueller and Blues Brothers), deep dish pizza and a giant ‘bean,’ there’s not much widely known about Chicago. Or at least, I didn’t know much when I visited as part of an epic road trip in 2005. Much to my surprise though, this vibrant city proved to be so wonderful that I chose to return recently. And much to my further delight, I liked it even better the second time! Here are a few reasons why:

An aerial view of the Chicago skyline at sunrise

It’s a great alternative to New York

If you’ve already done the Big Apple, then Chicago should be next on your list. The city is packed with an incredible array of museums, green spaces, public art, and a notably thriving theatre/comedy scene. All of the buzzing aspects that make New York so loveable but without feeling so claustrophobic. But unlike the crowded island of Manhattan, Chicago has room to breathe, enabling it to hold onto the cultural diversity that New York has started to lose. I also really liked the fact that, like New York, the trains run 24 hours a day but unlike the NYC subway system, Chicago’s L (short for 'elevated') trains are above ground so you can see the city as you move through it.

People on North Beach in downtown Chicago

You can enjoy a beach holiday too

The first time I visited Chicago, I stood at the edge of Lake Michigan puzzled. I knew I was inland, but this epic body of water looked suspiciously like the sea. This Great Lake is edged by 26 miles of beautiful sandy beaches that you can walk to from the city centre. There's an option for everyone: 31st Street Beach is great for those with small children and Montrose Beach is the perfect spot for dog-lovers. North Ave Beach is on the edge of Lincoln Park, so after exploring Chicago’s excellent zoo, you can try out some of the activities like volleyball and jet skiing. My favourite though is the Kathy Osterman Beach, also known as Hollywood Beach, which is a beautiful place to take a break and enjoy great views of the Chicago skyline.

Four glasses of craft beer

The city has a great cocktails and craft beer scene

In 2014 GQ dubbed Chicago “the greatest drinking city in America” thanks to its booming craft beer scene and innovative cocktail bars. With over 50 breweries in the city alone, you can spend an afternoon getting a taste for the local hops alongside some international guests at a specialist bars like Quenchers Saloon near Logan Square. One of my most interesting experiences in Chicago was at The Aviary in West Loop. It’s a cocktail bar but feels like a restaurant, with your drinks made by one of many bartenders partially hidden inside a caged kitchen. They even have their own ‘ice chef’, giving it a very ‘next level’ vibe. If you’d prefer something a little more light-hearted, head to the fun Tiki bar Lost Lake in Logan Square. Their predominantly-female bar team make a killer ‘Tic-Tac-Taxi’, which is exactly what I needed after my second. One of the city’s most exciting new bars is GreenRiver, curiously situated on the roof of a medical building. Located 18-floors up, the terrace has incredible views for you to sip and savour the city (and capture the perfect Chicago selfie).

The food is world famous

I expected to just eat Deep Dish pizza on my first trip here. After all, isn’t that what Chicago is most famous for? Surprisingly, the city is actually the heart of the American foodie scene with 22 Michelin-starred restaurants and the home of the ‘Oscars of Food’, The James Beard Awards. While the option is always there, you don’t have to blow your budget to find great eats in Chicago. I had some tasty tacos at Big Star in Wicker Park and slurped on some excellent broth at High Five Ramen in West Loop, whilst nearby Avec has the fashionable small plates/communal tables dining experience perfected.

With the city’s large Italian population (one of the largest in the USA), I also highly recommend dining on Italian at Eataly: just off the Magnificent Mile, it houses 20+ restaurants and food counters over 2 floors with savoury upstairs and sweet below.

A bike path along the water in Chicago

It’s a great city for cycling

If like me you’re an avid cyclist then you will love Chicago. It’s very flat with wide streets and, like many European cities, was developed with cycling in mind. The city has its own excellent bike sharing scheme called Divvy, and you can also buy one secondhand from Working Bikes on Western Ave for a very reasonable price. This is a great option if you are staying for a week or more plus you can donate it back to this great community scheme when you leave.

Of course, the weather in the Windy City can at times be a little brutal, which is why the public transport system is exceptionally cyclist-friendly. Not only can you take your bike on the train outside of peak hours, but the buses all have a bike rack on the front so you can secure it there for free.

Don’t miss the most iconic cycle route for visitors: the 18-mile Lakefront Trail taking in the city, the beaches and the best of what this amazing city has to offer.

Visit the Windy City on our Chicago, Niagara & New York Escorted Tour, or add a stop on your own tailor-made itinerary.

You might also like:

8 Things to Do in New York City

The Best Cities in the US


Featured in this blog:

Select an option below to contact one of our experts now, about anything you need

Alternatively, you can email us, request a call back, or live chat with a consultant

Call free on 0800 707 6010

We're open every day from:
9:00am to 8:00pm Mon-Fri
9:00am to 6:00pm Sat
10:00am to 5:00pm Sun and Public Holidays

We're open every day from:
9:00am to 8:00pm Mon-Fri
9:00am to 6:00pm Sat
10:00am to 5:00pm Sun and Public Holidays

Send us your number and we'll call you back.

Your details

When would you like us to call you?
Your details:

Your details

When would you like us to call you?
When would you like us to call you?
Add additional information?
Speak to us about:
Discuss a Trip List

Live Chat