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City Breaks in Chicago

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Travel Tips 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 a large cosmopolitan city with plenty of attractions, but it still retains some small-town all-American charm. It's a great place for a cheap city break for art lovers and architecture fans, but sports fanatics and shoppers are well catered for too!

One Weekend in Chicago

If you're like us, holiday time is hard to come by so a cheap weekend break in Chicago could be just the ticket. Book a cheap Chicago flight and get stuck in - the airport is in the north so for quick transfer times look for a hotel in Chicago North. See the view from Willis Tower, wander the galleries of the Art Institute of Chicago and be entertained on Navy Pier. Downtown is the place for shops, restaurants and partying til late.

More Attractions in Chicago

If you're lucky enough to have more time, you can use your city break to Chicago to explore a little more. Lincoln Park Zoo is a wonderful place with old buildings and plenty of animals, and what's more it's free! Take the time to see Buckingham Fountain in Grant Park, with shows every hour. Take an architectural tour to learn about hidden gems, catch a baseball match at Cellular Fields, or get back to nature at the Shedd Aquarium or the Peggy Notebart Nature Museum.

Best Times to Visit Chicago

Although known as the Windy City, this isn't strictly true! Summers are pleasantly warm but you'll need to wrap up if you're off on a Chicago break in the winter as snowfall is plentiful. This is the best time to get a bargain as the cold scares off most of the tourists, but if you're similarly put off, look out for March and October offers which are often cheaper than closer to the summer.

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