“It is hopeless for the occasional visitor to try to keep up with Chicago- she outgrows her prophecies faster than she can make them. She is always a novelty; for she is never the Chicago you saw when you passed through the last time.”
– Mark Twain, Life on the Mississippi
Chicago is a big city that, as Twain so accurately noted, is always evolving. There are some great travel guides available here, here, and here to help make the city more manageable for your average tourist. For some recommendations from a local Chicagoan that hopefully go beyond what you might find in your average travel guide, keep reading.
Chicago is among the most bike friendly cities in the world and its greatest resource is its people. The Chicago Cycling Club provides a unique opportunity to get out there and experience the best the city has to offer of both. It’s free to participate in the rides and bikes can be rented for the day at reasonable rates. The average rider can easily participate in the social rides.
At 15-20 miles they may sound a little intimidating but they go at an easy pace and incorporate lots of stops to check out the sights along the way.
Chicago is also famous for its architecture. The architecture boat tour is extremely worthwhile and you should make sure to catch it while you still can. The Sears Tower (the author refuses to call it Big Willy) is one of the more prominent features of the Chicago skyline and a common tourist destination for its unique view. The problem is it’s a little too common. There are often long lines on the weekend and once you get to the top the view is mostly of the suburbs. Heading to the Signature Lounge at the John Hancock Building is a better option that provides a more advantageous view of both the city and the lakefront. The view you should really check out, though, is the one from Cité. It’s an amazing French restaurant at the top of Lake Point Tower that has a great brunch and a 360 degree view of all there is to see. Oprah’s condo is also located in this building so you may even run into her while you‘re there.
If museums are more your speed, Chicago has a lot to choose from. The Chicago History Museum provides some insight into what makes the city tick. In addition to its exhibits the museum hosts events and tours around the city that are worth checking out. Another fun option if you’re of age and in town on the first Friday of the month is First Fridays at the Museum of Contemporary Art. Adler Planetarium hosts a similar event called Adler After Dark on the third Thursday of every month. Both of these events provide visitors the run of the facilities in a sociable setting and sometimes even a sneak peak at exhibits that haven’t opened yet.
Eventually you’re going to get hungry. Billy Goat Tavern is a fun spot to grab a quick burger. Yes. They really do pronounce it “cheezborger.” For a more formal meal I’d recommend Bandera’s. It’s conveniently located above Michigan Avenue so you can watch all the tourists go by as you enjoy their delicious fare and nightly live music. For more of a local flavor you might stop by Twin Anchors . Their ribs were a favorite of Frank Sinatra’s and the restaurant itself was featured in the movie the Dark Knight.
After dinner, head up to the Green Mill for some superb live jazz music. The lounge served as a speakeasy during prohibition and was a frequent hangout of Al Capone’s, as well as the setting for the real life events immortalized in the movie The Joker is Wild. The crowd is always a lot of fun as the venue attracts music lovers of every age and creed. It’s a bit of a hike from the downtown area but it’s worth it. If comedy is more your speed, Second City is a Chicago institution that’s as much fun as it’s cracked up to be. After enjoying a show you might be able to catch a few of the comedians at the Old Town Ale House around the corner. Alternatively, if you’re trying to keep your dining and entertainment on a budget grab some accoutrements at the French Market and have a picnic in Millennium Park while taking in the free concert series at the Jay Pritzker Pavilion.
The great thing about Chicago is that there is a bar on practically every corner. If you’re trying to find a specific crowd, here’s a quick rundown of where to look. The Viagra Triangle and the nearby bars on Rush and Division are a favored stomping ground for tourists who are only in town for a few nights and forgot to pack their dignity. Hordes of young people go there looking for debauchery and, as the name implies, a number of creepy old men do the same. They are easily identifiable and, as such, easily avoidable. Boystown is obviously a blast for obvious reasons. Fancier clubs and lounges can be found in the River North, West Loop, and Old Town areas. The college age and recently graduated crowd tends to hang out in Wrigleyville and Lincoln Park.There are some really fun bars in Lakeview for the marginally more mature crowd. Bucktown/Wicker Park is the new up and coming area. It attracts a diverse crowd of people. Don’t let the hipsters scare you away. There are some really cool, chill bars there.
Follow the masses of people as they leave the bars and you‘re bound to stumble upon a hot dog or pizza joint that‘s open for a late night snack. For something a little different and unique to Chicago, you might want to head to Wieners Circle. The hot dogs are delicious and the burgers have been described by some as possibly the best the city has to offer. The cheese fries should not be consumed before you have a good buzz going but once you’re at that point, they’re a must. Wieners Circle is about more than the food, though. It’s about the experience. If you have delicate sensibilities (or really any sensibilities at all), it might not be the place for you but it’s a Chicago institution for better or for much, much worse. Brave it if you dare. Just don’t order the chocolate shake.
This post could never cover everything there is to see and do in the great city of Chicago. If anyone has any recommendations they’d like to add, please feel free to toss them in the comment section – we’d love to hear from you!
