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Holidays in Chicago

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Travel Tips for Chicago


See all TravelTips for Chicago
 Field Museum of Natural History

posted by bwentzel

My two boys are at the dinosaur stage and this place just fascinated them. Sue, the huge t-rex was the highlight but there's so much more to this museum than just dinosaurs, if you get the chance to look round!!

 31st Street Beach

posted by cwise

I hadn't really considered that Chicago would have beaches, but it does! This was near our accommodation so we stopped by quite a few times. You get a park and a beach in one, which to my mind, is the way to do it!

 Lakefront walkways

posted by rwise

There are so many lovely walks to go on in Chicago, with the lake on one side and the city on the other it's really pretty, and not as windy as i'd expected either!!

 Chicago Cultural Center

posted by bdale

The first free cultural centre in America, I always go here to see what's happening when i'm in Chicago. I've seen plays, music, singing, art installations and more! This time I saw a sculpture exhibition by Aristotole Georgiades which was great.

 Sears (Willis) Tower

posted by wchristopher

I just love this magnificent building, I never knew it was 9 skyscrapers in 1 until I saw it up close. The skydeck is amazing, and although my boyfriend made it out onto the "ledge" I was far too afraid!!

dealchecker's guide to Chicago


Chicago is situated in the heart of the Mid West on the shores of Lake Michigan. It is commonly known as the 'windy city' however the origins of this name are widely debated.

How To Get To Chicago

O'Hare International Airport is where all Chicago flights touchdown and since it is almost 30 kilometres from the heart of the city itself it is always worth looking into car hire from Chicago Airport if you want to avoid public transport and take your travels out on the open road. Buses and trains run throughout the city and the suburbs, making it easy to navigate and there is even a free tram that travels between the main attractions, making sightseeing while on holiday in Chicago a simple pleasure.

Where To Stay In Chicago

Accommodation during holidays to Chicago comes in all shapes and sizes, with the most modern, upmarket hotels located in the famous Chicago Loop area, whilst the smaller, more unique inns are located close to the Magnificent Mile. For people who want to spend as little money as possible there are bed and breakfast options and hotels near the airport, creating a great opportunity for an inexpensive stopover during cheap holidays in Chicago.

What To Do In Chicago

With an annual international film festival, a host of theatres to rival Broadway in the centre and cultural and educational destinations such as the Museum of Science and Industry or the Art Institute of Chicago, you will never have a minute to spare during your holiday to Chicago. Skyscrapers such as the Willis Tower offer visitors the chance to get an eagle-eye view of the city and Lincoln Park Zoo is a great place to visit with the whole family.

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