Visiting Chicago - a Native's Guide

16 Things You Must Do While Visiting Chicago

Tim Searles
Chicago is a great city and I'm not just saying that because I live here. It's also a big city. I've lived here all my life and I still don't believe I've seen all of it. Currently the third largest city in the United States Chicago is the happy medium of cities such as New York City and Los Angeles. Most people like it because it has hustle and bustle, but not as crazy as those other two cities. Some like it for the suburban living. Others like it for the food options. Some like it because it's right on Lake Michigan. Whatever your reason Chicago is a great place to live and to visit.

If you're thinking of visiting Chicago, most people will keep you in the downtown areas. While there are some great things to see downtown, Chicago is more than just what is on the postcards. I wanted to provide you a guide of things you should see and do that span the dimensions of the city. So here you have it... a native's guide to Chicago.

1. Visit the Lincoln Park Zoo - Chicago's only free zoo. It's in our Lincoln Park area and I recommend taking pubic transportation here. You can attempt to drive, but street parking is next to impossible. There is a parking lot that starts at $17 for three hours of time.

2. Eat at one of our Harold's Chicken Shacks. There are a number of them to be found in Chicago; most of them are found on Chicago's South Side. If you've never had Harold's fried chicken, you are in for a treat! Get a six wing dinner with hot sauce and a side of fries and you'll go back home a happy person! Take it back to your hotel and watch people wonder where that great smell is coming from.

3. Tour Northwestern University. One of Chicago's most prestigious academic institutions, Northwestern University is found in the northern suburb of Evanston, IL. Catch a Wildcats game depending on what sports season it is or tour the campus during one of the scheduled tour times. You can take Chicago's purple line into Evanston from downtown during rush hour, or take the Red Line to Howard Street and transfer to the Purple Line; you'll be getting off at the Davis Street stop.

4. Take a drive down Lake Shore Drive. For a great scenic tour of Chicago take a drive down Lake Shore Drive. Found on the lake, Lake Shore Drive spans about fifteen miles. Some of the sights you'll see are the Museum of Science and Industry, Solder Field (home of the Chicago Bears), Chicago Museum of Natural History, Navy Pier, North Avenue Beach, and an array of parks, apartment buildings, boats and beaches.

5. Get a slice of deep dish pizza. I have an article that'll tell you where the best pizza places are in Chicago are. You can click here to read it. If you want a quick overview, either go to Lou Malnati's on Wells & Kinzie downtown or Pizzeria Uno on Ohio & Wabash Streets downtown. Most people will tell you to go to Giordano's and they are an option... but remember this is a native's guide... not a tourist's guide.

6. Eat a hot dog with at least five condiments on it. Have you ever had sauerkraut, sport peppers, raw onions, sliced tomatoes, mustard, sweet relish, and celery salt on your hot dog at the same time? If not, welcome to Chicago! Be sure to try the Chicago-style hot dog before leaving our city.

7. Stop by Greektown and Chinatown. These are two of our well-known neighborhoods. Neither are very huge, but they are very authentic. From the people to the restaurants you will notice how authentic our neighborhoods can be.

8. Ride one of our "colored" trains. In case you didn't know, our train system is separated by colors. For example, there is the Red Line, Blue Line, Green Line, Purple Line... just to name a few. They go to various parts of the city, but most of them come through downtown at some point. The Orange Line goes to our Midway Airport, and the Blue Line goes to our O'Hare Airport. If you want to avoid the costs of a taxi-ride to your hotel, consider taking the train into downtown. The ride will be about 45 minutes, but you won't have to deal with expressway traffic this way.

9. If you come in the summer, come in time for the Taste of Chicago - our biggest food festival of the year. This festival usually happens between late June and early July, ending after Independence Day. You have a host of restaurants and food places that provide samples of their food for a nominal cost. This ten day festival literally takes up most of Grant Park including a fireworks display towards the end of the festival. This is a family-friendly event with something for everyone other than stuffing yourself with tasty Chicago food.

10. Shop on the Magnificent Mile. For those with the money to do so, I recommend shopping down Michigan Avenue north of the Chicago River. If you can't shop there you can still window-shop there. You'll find a lot of specialty stores and our Water Tower Place is a great stop to eat and take in more specialty shopping. Our bus system runs plenty through the Magnificent Mile so if you get tired of walking, a number of buses will happily take you down Michigan Avenue for as far as you want to go.

11. Eat Garrett's Popcorn (I recommend the Caramel Crisp). I have an article about why you should stand in line for this stuff, you can read it here. This is a 60-year old tradition that is true to Chicago. Anyone that comes in or out of Chicago must try this popcorn.

12. Take a boat ride or dinner cruise down the Chicago River. There are tours that run daily down the Chicago River, or spend a bit more for a 2-3 hour dinner cruise down the river. Either way you're sure to get some great sights of Chicago that you may not get on foot.

13. Drive south of 95th Street. Most people don't consider doing anything past downtown. I recommend that anyone who is willing to go to the South Side of Chicago to drive as far south as you can to get a good glimpse of the breadth of Chicago. There isn't much tourism past the middle of the south side but I still recommend the drive if you have the time.

14. See the Blue Man Group. The Blue Man Group has been playing for some time in Chicago at the Briar Street Theatre in Lakeview. I saw this show in New York City and it was great, so I definitely recommend you see it in Chicago. It's not playing in the theater district, only at the Briar Street Theater. Go to http://www.blueman.com/tickets/chicago to get tickets, or http://www.blueman.com to learn more about the production.

15. Play Whirlyball. I've played this a couple of times for a corporate function and it is fun. If you're trying to figure out what Whirlyball is... it's Lacrosse meets bumper cars meets basketball. Located at 1880 W. Fullerton Pkwy there's nothing like it in Chicago. Go to http://www.whirlyball.com to learn more about it. I'd recommend going in a mass group to get the most excitement out of it.

16. Take a trip to Navy Pier and the Chicago Children's Museum. The Chicago Children's Museum is free on first Sundays thanks to Target's sponsorship. It is an atmosphere where children young through teenage years can have fun in an interactive and learning environment. For more information, go to http://www.chicagochildrensmuseum.org/. Navy Pier has a lot to offer its visitors. Unique shops, a ferris wheel, boat rides, and more are available at Navy Pier. For more information, go to http://www.navypier.com.

I hope that you enjoy your time in Chicago! If you tried one of these options let me know how the experience was for you. Chicago is one of those city's that you'll want to come back to... mostly because you didn't do half of the stuff you wanted to the first time.

Published by Tim Searles

I am currently involved in web development, consulting, and freelance writing. I also love music, art, having fun, and life.  View profile

6 Comments

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  • Julie Darleen9/19/2009

    Bookmarking in hopes of visiting Chicago soon! Thanks.

  • Marie Anne St. Jean9/18/2009

    I visited Chicago only for a day so didn't see much at all. Did see a bit of Navy Pier and ride the ferris whee, and stopped in Hard Rock Cafe long enough to buy a t-shirt. Thanks for the tour.

  • ADSpencer9/17/2009

    I still have a few of these I haven't done yet, like the free zoo--thanks for the list! I'll try to keep it in mind next time I'm visiting my grandparents in Zion.

  • Brandon Miller9/17/2009

    I have only been to Chicago once. I spent a week there with a church youth group feeding homeless people. Very cool city!

  • Shea Rossetti9/17/2009

    I've been to Chicago several times, but the only thing I did that you recommend was go to Navy Pier. I loved what I did see though!

  • Joshua Huffman9/17/2009

    This is nice. I don't think I could survive in Chicago. Traffic is insane, haha.

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