Offbeat Chicago Guide

Cool and Offbeat Things to Do in Chicago

There’s a lot to do in Chicago. Understatement. Chicago is the third-largest U.S. city in terms of population, and it’s considered the “Second City” in terms of cultural and financial happenings. So, how do you plan an itinerary for the Windy City? Here are some tips on what to look for and what to avoid, offbeat-style.

Don’t Get Stuck In the Loop

The downtown Chicago area encompasses the neighborhoods of the Loop, the Near North Side, and Near South Side, but is generally just referred to as “the Loop.” While you shouldn’t ignore the wonderful sights here, you’re likely to have a run-of-the-mill tourist experience unless you branch out. While in the Loop, though, be sure to check out Grant Park, Willis Tower (formerly the Sears Tower), and keep your eyes peeled for tons of outdoor sculptures by the likes of Picasso, Joan Miró, and Marc Chagall.

Free Summer Events in Millennium Park and Grant Park

Use Public Transit

It’s cheap to get around Chicago if you plan it right. You can buy single-day passes, three-day passes, or seven-day passes depending on how long you’re staying, or just cough up $2.25 any time you hop on the bus or L-train. It might be better, in the long run, to get the passes ahead of time, since you can only pay with cash (exact change) if you don’t have a ticket when you get on board. Besides being convenient, it will save you some money. Say you are staying a week and you use public transit an average of 3 times a day. You’d end up spending $47 on transportation that week. The seven-day pass sells for just $23, and you can use it as many times per day as you want. Vending locations for these passes are easily found on CTA’s website.

Visit Hyde Park

The South Side of Chicago is notorious for being the bad part of town, but in truth, it’s a mix of affluent neighborhoods and low-income neighborhoods. It may be gritty, but it’s not all bad. One advantage of its poor reputation is that the South Side tends not to be overflowing with tourists. True, there’s a lot to be found on the North Side, but if you need a day to mellow out and see how locals enjoy Chicago, Hyde Park is worth the visit. You’ll find some houses and buildings designed by Frank Lloyd Wright if you take a walk through the neighborhood.

Also, if you prepare yourself for the possibility of rats, Promontory Point is a great little park to visit right on the lake. It offers the best view of Chicago’s skyline from within the city limits, and parking is free. It’s a popular choice for couples getting married, so depending on the season you might get to do some bride-watching. You can also go swimming or have an impromptu barbecue. And for a year-round spot to visit in Hyde Park, check out the Smart Museum of Art. It’s part of the University of Chicago and has a huge permanent collection (over 9,000 works) featuring Frank Lloyd Wright, Degas, Goya, Ansel Adams, and more. You’ll also be able to see what’s considered the city’s best showcase of student work.

Venture North!

As we’ve just mentioned, the North Side of the city is quite happening. Garfield Park and Lincoln Park are two popular neighborhoods about a ten-minute ride on the L-train from downtown. In Garfield Park, you’ll find a world-renowned conservatory for some convening with nature no matter what the weather. It’s free and home to hundreds of plants from around the world. There’s a smaller conservatory in Lincoln Park, but if you’re a nature freak it’s worth the trip over to Garfield Park.

Lincoln Park

If you’d rather not hop all over the city for fun, stick to Lincoln Park as there’s more to see and do. You can visit the zoo, browse new and used records at Dave’s – a local independent music store – and if you have a suit jacket and room on your credit card bill, dine at Alinea. Frequently listed as one of the top 5 restaurants in the country, and in the top 10 worldwide, you are sure to have one of the most memorable meals in your life here. Be warned that the price of decadence is not cheap; you will spend $150 per person on the 13-course tasting, or $225 for the 24-course tour. On the other hand, there aren’t many places that serve pheasant flavored with smoldering maple leaves and apple shallot jelly. This is a must for foodies but is best saved for a longer stay in Chicago, as the average meal here lasts 4 hours.

Wicker Park

Other notable neighborhoods to the North are Wicker Park and nearby Noble Square. Vegetarians will be happy to find Handlebar in Wicker Park, a bicycle-themed bar and restaurant with many vegan options. Here you’ll also find Myopic Books, the oldest and largest used bookstore in Chicago.

Chicago Myopic Books

There are poetry readings almost every evening and Experimental Music Mondays. Definitely poke your head in here if you’re artistically inclined. For weekend fun, you’ll find The Hideout in Noble Square. Saturday night dance parties hosted by local dj’s are all the rage right now, and Chicagoans really dig this divey bar. It’s cash only but a great spot to let loose and just dance.

Plan Ahead

Remember that CTA pass we suggested buying? Here’s where it really comes in handy. Some neighborhoods you really don’t want to miss (but are more spread apart) are Roscoe Village and Avondale, Lincoln Square, Uptown, and Andersonville/Edgewater.

Roscoe Village/Avondale

In Roscoe Village, you’ll find the city’s best vegetarian restaurant hands-down. Called Victory’s Banner, the menu also features vegan options and 100% organic products. It’s run by a religious sect from India that practices meditation, and the atmosphere of the place is really interesting. If you’re looking for more All-American eats, head over to Hot Doug’s in nearby Avondale. You’ll get the best hot dogs and fast food Chicago has to offer, and yes, they have veggie dogs as well.

Lincoln Square

Moving over to Lincoln Square, you’ll find a host quirky establishments. Book Cellar is an independent bookstore/cafe that offers free wifi. Feel free to relax with a cup of coffee or glass of wine, curled up with a book on one of their comfy couches. Should you feel like splurging on a unique fashion find, Savvy Seconds and 1sts is a high-end vintage store bursting at the seams with wonderful wardrobe additions. As this is one of the hippest neighborhoods in Chicago, you’ll be able to find lots by way of shopping or live music just by wandering down Lincoln Avenue.


Over in Uptown, the city’s defining entertainment district, you’ll find tons of theatres and music venues. A favorite haunt for local artists and musicians in the Green Mill. They host a weekly slam poetry night and feature live jazz, which many residents feel captures the heart of Chicago. It actually used to be the number one hangout spot for gangster Al Capone.

green mill chicago
Green Mill, a famous gin mill in Uptown Chicago – image by flickr/swanksalot


Finally, if you’re looking for a very happening place to hit the town, be sure to visit Andersonville in Edgewater. A diverse and densely populated community, you’ll find an eclectic mix of locally-owned independent shops and restaurants, concentrated around Clark Street at Berwyn Avenue. Highlights include the Hollywood Mirror, a thrift store with tons of wacky finds. For something with a little more class, kick off the night with a cocktail at Marty’s. This intimate little bar can fill up pretty quickly, but offers a nice patio in the summer and serves great drinks.

So, there you have it – a hodge-podge of shops, restaurants, and things to see in the most American of big cities. The last tip we have for you is to plan ahead, but leave room for spontaneity. Don’t be afraid to explore. Have fun in Chicago!

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