Route 66 is pretty much the ultimate road trip destination, both in the US and across the rest of the world. If you’re planning to take on the whole thing, I reckon it’s well worth spending some time in Chicago before you get going. Need convincing? Well, read on to get to grips with the city’s appeal!

Chicago: where Route 66 begins

Probably the most obvious reason to dedicate a dollop of your break to Chicago is that it’s where Route 66 starts. So, if you’re driving the whole thing, you’re going to be here anyway – at least for a little while. It’s packed with attractions, so it seems a bit silly to do nothing more than arrive, hop in a car and skedaddle (though I totally understand the urge get started on an epic journey like this straight away!).

Willis Tower

Of all Chicago’s attractions, Willis Tower is one of the best-known and, depending on what floats your boat, the most exciting. The tallest building in the western hemisphere, it juts a whopping 1,450 ft into the air. The best bit, though, is that there are two ways you can appreciate this serious height.

The first of these is a visit to the Skydeck, which is at 1,353 ft and on the 99th floor. Head up here and you can look forward to 360-degree panoramas of the city and far beyond. In fact, on clear days you can actually see up to four states from here, which is pretty impressive! The second is the Ledge. This is a bit higher up, being on the 103rd floor, and consists of four glass boxes that stick out just over 4 ft from the building. Go into one of these and you can look straight down into the city below – and, believe me, it’s a seriously long way down.

Chicago Cultural Center

Chicago’s also a decent place to soak up a little culture, and one of the best places to do so is the Chicago Cultural Center. The great thing about coming here is you get all the excitement of the sizeable itinerary of shows, exhibitions and lectures, as well as the wonder of the building itself. In fact, taking a building tour is among the real highlights of coming here.

These don’t run on a daily basis, though, so it pays to plan ahead. Wednesdays, Friday and Saturdays see them kick off at 13:15 local time from the Randolph Street lobby. Be prompt, since only the first 20 people there get to go. The piece de resistance is the stained glass Tiffany dome, which at 38 ft in diameter is the largest in the world. The glass is cut into the shape of fish scales, and at the top of the dome you can spot the signs of the zodiac.

Navy Pier

One of Chicago’s top attractions, Navy Pier is the place to go if you’re after pure unadulterated fun. Home to a 150 ft high Ferris wheel, IMAX cinema, the Chicago Shakespeare Theatre and several museums, this site also boasts loads of free weekly shows. It’s worth remembering a few of the city’s hidden gems are tucked away here, too, like the Smith Museum of Stained Glass Windows.

Plus, there’s also a decent selection of rides to keep the Ferris wheel company. These include a carousel, the Wave Swinger (I’ll let you wait and find out what that is for yourself!) and much more. So, don’t forget to leave time to try them.


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