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A Chicagoan’s Weird, Wild and Sort of Wacky Travel Guide to Chicago

Chicago local Dr. Jamil Abdur-Rahman of The Twin Doctors Travel Bag shares the best of cool Chicago.

While many may affectionately call this bustling metropolis by the lake, this Gotham of America’s breadbasket, this hub of transport, business and culture the nation’s “Second City”; I as a proud Chicagoan am here to tell you that Chicago takes a back seat to no one and nowhere! So, as a city that is truly second to none, Chicago has a little something to offer everyone. From those visitors with highbrows to those visitors who are browbeaten. From those visitors with the virtues of a saint to those visitors with the vices of a sinner. If you can’t find something to do in Chicago, well then my friends simply put, you’re just not looking hard enough.

Frank Sinatra once said of Chicago that “it’s my kind of town”. And after a visit to Chicago, well I bet my bottom dollar that it will be your kind of town too. So come with me friends as we spend a virtual day as newly arrived tourists exploring some of my city’s hidden, offbeat and slightly spooky treasures.

From Ghostly Congress Hotel to Awesome Dove’s Luncheonette

Ah what a lovely morning!!! Look at that big, beautiful orange sun rising over Lake Michigan. I doubt that there are many lakefront views of a Chicago sunrise better than the one that we are enjoying right now from room 441 at the legendary Congress Hotel. If you’re like me, then you probably were a little bit concerned that unruly ghosts, goblins and a general assortment of things that go bump in the night might keep you up last night. What, with all of that talk about the Congress Hotel being haunted and all you know? But no, you and I, we slept like babies last night.

The Congress Plaza Hotel at Michigan Avenue and Congress Parkway in Chicago, USA.

The Congress Plaza Hotel at Michigan Avenue and Congress Parkway in Chicago, USA. Photo by Ivo Shandor.

And now we’re hungry. We could just order some room service, I guess. But where is the fun in that? No, ordering room service is so passé. Let’s get out of this hotel and let’s eat some good food. And let’s not only eat some good food, but let’s eat that good food where Chicagoans go when they want to eat good food. Yeah, let’s go to Wicker Park. I hear that there is an awesome little restaurant there called Dove’s Luncheonette.

Wow, can you believe this restaurant? The vintage 60’s and 70’s Chicago-style Jazz and Blues music is really creating an awesome atmosphere in here isn’t it? Man, if that music doesn’t get your blood pumping early in the morning, then I don’t know what will? Now I don’t know about you, but I’m ready to eat!

This counter style seating in here certainly is unique isn’t it? It makes the place feel really quaint doesn’t it? Almost like we’re eating breakfast with about 50 or 60 of our closest new friends. Oh man, hold me back!!! Holy Cow, did you see this menu!!! Check out the food here!!! It looks like Dove’s Luncheonette is ground zero in Chicago for breakfast food that is an imaginative fusion of both classic American and Norteño Mexican breakfast cuisines. I don’t know about you, but I’m going to get the Enchiladas De Hongos, with a side of buttermilk pancakes of course. Oh here, sorry, I didn’t mean to hog the menu. Take a look at it and see what you want to eat so we can order up and then chow down.

Man, that place was a gem! The food was awesome! The people were friendly. You won’t find anything like that along the Magnificent Mile, that’s for sure. Hah hah!! Looks like we are doing Chicago like Chicagoans do Chicago doesn’t it? No tourist traps for you and me. Nope, just original Chicago treasures. You know what? Last night before going to bed I read a customer review of Dove’s Luncheonette. The guy said “Okay, this restaurant is the sweet, sweet birth child of all my favorite things: Mexican & Southern culture, blues [and] Tejano music, 1970s cinema, DINERS, the Mojave desert, rockabilly, children & some really great bathroom soap. I was destined to love it! And honestly [while there], I [just] wanted to tuck myself away off into some corner with a strong cocktail, a book & my existentialist feelings”. And you know what, that about sums it up for me too. I couldn’t have said it any better myself. And now, let’s walk some of that food off.

Walk Wicker Park

You and me, we’re in Wicker Park right? Now, I’ve been told that when Wicker Park locals want to take a walk, they like to kick things up a notch…..literally. You know what? We’re here, so let’s do it! Let’s kick things up a notch with our walk too. Let’s kick them way up, like above ground up.

Let’s go to Chicago’s elevated Bloomington Walking Trail. Now I read somewhere that folks around here call the Bloomington Trail “The 606”. I wondered why, so I did a little research. Turns out that “606” is the zip code prefix for Chicago; and with the Bloomington Trail being a one of a kind walking trail, it was given “The 606” moniker by the locals.

The 606 in Chicago

The 606 in Chicago

The 606 is an elevated old abandoned rail line, hence the reason that I said that we should “kick things UP a notch with our walk”. The trail is elevated, so we are going UP. Get it?

Through a joint public-private partnership, The 606 was converted from an abandoned rail line into a green space. Prior to the development of The 606, the neighborhoods surrounding the now very green walking trail had some of the smallest amounts of green space per capita in the city of Chicago. This lack of green space led developers to convert the old Bloomington rail line into the public green space that it is now. Today, at almost three miles long, The 606 is a “recreational and cultural trail” that visitors can walk, run and bike; all while enjoying an ever emerging gallery of rich and diverse foliage, organized “Trail Mix Events” and “The 606 Arts Program.”

Biking Chicago & The 606

Oh man, I’m so full. Dove’s Luncheonette must have put at least an extra 5 pounds on me! No worries though, we will burn off all of those extra calories that we ate once we hit The 606. But how should we get to The 606? You want to walk? We could walk I guess, but where’s the fun in that? Oh I know, let’s get a Divvy bike instead. I heard that Divvy is Chicago’s official bike sharing system, and that Divvy has over 4500 bikes stationed throughout the city at more than 475 stations. And surprise surprise, with that many stations there is a Divvy station located just a few blocks from where we are now. So let’s head on over and get two Divvy bikes. The concept of these Divvy bikes is so awesome man! If we lived in Chicago, I would get a Divvy bike membership for sure. But since we are only visiting, the Divvy bike 24-hour pass is perfect.

So now that we’ve got two of those famous blue Divvy bikes, and now that we have cycled the mile or so over to the Churchfield entrance of The 606, let’s hit the trails. Wow, I think that it is so cool that the trails accommodate bikes, runners and walkers. The mix of people here really creates a very cosmopolitan and urban feel doesn’t it? Plus, I have to admit. I feel like a bit of a voyeur here riding these trails as they snake through residential neighborhoods. With intimate views into people’s homes and yards, I really do feel like we are being given a sneak peek into the lives of every day Chicagoans. How cool, and sort of Creepy McCreeperson is that?

I have to say though; what I think I really like most about The 606 is its arts program. The arts program features a full range of both visual and performing art exhibits and exhibitions. Some of the exhibits and exhibitions are temporary while others are permanent. All of them though are cool. And these exhibits and exhibitions, along with the frequent “Trail Mix Events” series activities make it really easy to spend hours and hours just hanging out along The 606.

The 606 in Chicago

The 606 in Chicago

Unfortunately though friend, you and I don’t have hours and hours to spend on The 606 today. We still have so much more to see and do around town; but I tell you what. Anyone who wants to enjoy some tranquil urban greenery while getting a little bit of exercise in the Windy City; especially if they want to do this all while also checking out some really cool art and hanging with some really cool people, then they need to come to The 606. But alas, our time here is done. Doesn’t it feel like the nearly three miles of trail just passed way too quickly? Oh well, gives us an excuse to make another visit to The 606 next time we are in Chicago now doesn’t it?

Weird Museums: International Museum of Surgical Sciences

So what’s next? How about a true, if not slightly under appreciated Chicago original? Yeah, I’m talking about the International Museum of Surgical Sciences. It is only four miles from the easternmost point of The 606 to the museum, and with these Divvy bikes we can take North Avenue most of the way down. Doing that, we can knock out that journey in no time. So let’s do it, what do say? Next stop? The wonderfully weird, sort of wacky and slightly creepy International Museum of Surgical Sciences.

International Museum of Surgical Sciences

International Museum of Surgical Sciences

Man, between doing three miles on The 606 and another four miles over to the museum here; I’m starting to feel a wee bit hungry believe it or not? What about you? Well, after we leave the museum, we need to get lunch. But not just any old lunch. Nah, we need to get a famous deep dish Chicago pizza. After all, can you come to Chicago and not get a Deep Dish pizza? I don’t think so. In fact, doing that literally might be a criminal offense in this city. So we will have to ask someone inside of the museum what is the best place around here to go for a deep dish pizza. But first, let’s secure our bikes and head on in to the museum.

International Museum of Surgical Sciences

International Museum of Surgical Sciences

The International Museum of Surgical Sciences is housed in a mansion that was built in 1917. The museum itself, which claims to be “North America’s only museum devoted to surgery” first opened its doors in the year 1954. Currently, the museum is opened everyday other than Mondays, with operating hours from either 10AM to 4PM or 10AM to 5PM depending upon the day. From the miraculous to the macabre, from the gross to the glorious; The International Museum of Surgical Sciences is packed with exhibits and artifacts that tell the story of surgery’s evolution from trepanation (the burring of holes in the skull to treat a wide variety of aliments) to modern day organ transplantation. And I can’t believe that we covered the nearly 10,000 square feet of exhibition space in as little time as we did. I guess when you are having fun, time really does fly! That is ok though.

Maybe we can come back later on tonight for the museum’s “Candlelit Historic Homes Tour”. I hear that that thing is awesome! The museum describes the tour as follows; “bathed in warm candlelight, [this] unique exploration of [the museum building] delves into the architecture of the space and the lives of its original occupants. Highlights from the [museum’s] permanent collection invite guests to layer their experience of the property as an historic dwelling and modern-day Museum – as much enchanted by its elegant past as it is haunted by the morbid curiosities it houses today”. Man, if that narrative doesn’t get you interested in the candlelit tour, then you may be deader inside than some of those cadavers that we saw in the museum.

Chicago Deep Dish Pizza

Okay, back on our Divvy bikes you and me. Now let’s head on over to The Art of Pizza. One of the museum’s curators said that The Art of Pizza was recently recognized by the Chicago Tribune for having “the #1 Deep Dish Pizza” in Chicago. And, The Art of Pizza is only three miles away from the museum; so, what better place to go than that for a real Chicago-style deep dish pizza? Hell, we will even be there in 10 minutes or so on these bikes. So lets go, I’m hungry!!!

The Art of Pizza

The Art of Pizza

Man this place is sort of nondescript isn’t it? Hardly the kind of place you’d expect to find the city’s “# 1 Deep Dish Pizza”. Just hidden away in what almost looks like a strip mall. But let’s head on inside. Well, I don’t know about you, but the first thing that strikes me is the smell of the pizza in this place. It is so thick and welcoming that it feels like it is giving me a long sweet warm embrace. Good Lord, have I died and gone to heaven? If I have, well then eternity is going to be absolutely blissful!

The décor in here is simple enough now isn’t it? What, with all of the wood paneling? I like it though. It is like they know that they don’t need a whole lot of sizzle to lure you in here when their steak (or should I say when their pizza) is all that and then some. So let’s take a seat, order, dig in and then eat! I’m going to have Art’s Stuffed Meaty Delight with ground beef, onions and spinach. What? I didn’t hear you. What did you say? Can you have a slice of my pizza? Uh, you know that I love you; and you know that I would do almost anything for you, but no. You cannot have any of my deep dish Chicago pizza. Get your own. The largest deep dish pizza in this place only costs $29.25. I think you can manage that even on your worst day!

Chicago Pubs & Lounges

Alright, I don’t drink; but I know that you like to “get loose” every once and while when you’re on vacation. And what better way to “get loose” after eating Chicago’s best deep dish pizza than to visit a local bar that features turtle racing? Regardless of whether or not you drink, watching turtles race has got to be entertaining for everyone! So off to Big Joe’s 2 & 6 Pub we go. And thankfully, we are looking at another short 3-mile bike ride to get there. Man, these Divvy bikes were an awesome investment weren’t they? You can get around the city quite easily using them in large part because the city of Chicago has so many dedicated bike lanes. I’m convinced that these blue little bikes have saved us both time and money today. Oh look, there it is off to the right there. Let’s secure these bikes and get inside.

Big Joe’s 2 & 6 Pub

Big Joe’s 2 & 6 Pub

Holy Cow, this place is crowded! I guess turtle racing is pretty darn popular in this town! Well, let’s buy some beer. I know that you’ll drink more than your fair share of the suds, and whatever you don’t drink, we can just give it to other patrons. But we’ve got to buy some beer. After all, the more beer we buy, the more turtle racing tickets we get. The more turtle racing tickets we have, the better our chances of having one of our ticket numbers called. And if one of our ticket numbers is called, we win the right to be a “turtle jockey” for one of the 6 different turtle races. If our turtle wins it’s race, then both the turtle and it’s “jockey” go on to the next round. The winning turtle from each of the original 6 rounds then participates in the 7th and final turtle race of the night. The winning “turtle jockey” of the 7th and final race then has his or her name placed in a raffle for a free trip to Las Vegas.

Dude, I tell you; I couldn’t believe it when your ticket number was called for the very first race. And my God, your turtle, what was his name again? Yeah that’s right, “Speedy the Shell Shoveler”, good Lord Speedy was fast! He absolutely dusted the competition during the first race. The final race of the night now, well that race was another story. I thought that that sneaky little turtle in the center lane; he was a ringer I am quite sure; well I thought that he had you and your turtle dead to right. But nope, you guys pulled it out in the end! And now you’ve been entered into a raffle to win a free trip to Vegas. Man, Big Joes 2 & 6 Pub was awesome! Do you think though that you are steady and sober enough to ride that blue little bike of yours my friend? Here, how many fingers am I holding up right now? Yeah, you got. I’m not holding up any fingers; just two thumbs. You’re good to go. I’m not sure that you will be after this next stop though. So let’s beat a path 1.3 miles over to The Green Mill Cocktail Lounge.

The Green Mill Cocktail Lounge is known most for three things­–– good old fashion Chicago-style jazz, poetry slams and the Mob. Tonight we are in luck. Two of those three things will be at the lounge. The night at The Green Mill will start out with the “Uptown Poetry Slam”. The poetry slam will run from 7PM to 10PM. It will include spoken word performed by special guests as well as the opportunity for people from the audience to recite their own poetry. Too bad I’m not much of a poet or I ‘d get up there on that stage and let it flow!! How awesome would that be? What about you? Do you have any lyrical prose that you’d like to share on stage tonight? If you do, I’ll have my camera ready.

The Green Mill Jazz Club.

The Green Mill Jazz Club.

Oh man, check this place out! God, walking into The Green Mill Cocktail Lounge feels like taking a step back in time. Look at that stage. I can just imagine big bands from an era by gone up there just getting down! And I bet that the Moonshine was flowing here during the Prohibition Era. You know, they say Chicago’s own Al Capone use to frequent The Green Mill? In fact, that’s the booth right there that they say he use to frequent while here at the lounge. And, it has a good view of both the front and back doors of the establishment. Probably not a bad idea for a man like Al Capone. After all, I heard that he had a few enemies.

I once read that there is a tunnel that can be accessed through an “escape hatch” here at The Green Mill. The article I read said that the tunnel runs underground, between The Green Mill and another close by building. Reports are that Capone and his men would use this tunnel to escape authorities when they came to the lounge looking for Capone. I would ask management here if we could check the tunnel out, but everything that I’ve read also says that visitors are not allowed into the tunnel. Too bad!

Man oh Manischewitz, that poetry slam was phenomenal! But the jazz, man the Jazz was otherworldly! The acoustics in this old building are some of the best that I’ve ever heard. The horns sounded so deep and rich, and the strings were ethereal. Dude, I don’t want to leave. But we have to. It’s getting late. And while The Green Mill frequently has an afterhours jam session, I’m too tired to stay for that! The crowd here was great though, and the service was top notch. Plus, call me a slouch. But I really did appreciate that there was no dress code here. So let’s hit those blue Divvy bikes one more time. But first……how many fingers am I holding up? Yeah perfect, you got it! No fingers, just two thumbs. Let’s go. You’re good to get on your bike. Now, let’s find the closest Divvy station and drop these bikes off. They really made our getting around the city so much easier today didn’t they? After we’ve dropped them off, let’s get either an Uber or a city cab and head back to the Congress Hotel. I am spent!

Well here we are, back at the Congress Hotel. What an absolutely awesome, thoroughly exciting day we had exploring The Real Chicago. Man, the Second City this is not. Chicago is first in my book every day of the week and twice on Sundays. Now, after the day we had Lord knows that I am tired. And while I am sure that I will have absolutely no trouble sleeping, the stories of the Congress Hotel being haunted are freaking me out just a little bit. From what I have heard, the Congress Hotel was recently named “Chicago’s Most Haunted Hotel”. From stories of Al Capone’s ghost haunting the North Tower of the 8th floor, to stories of a mischievous little ghost boy haunting the rooms and the hallways of the 6th floor; the Congress Hotel has been known to illicit chills and goose bumps from more than just a few guests. From the ghostly shadowy figure of a women who stands at the foot of the bed in room 441, a woman who waits for the guests sleeping in that bed to go to sleep before then violently kicking that bed and startling them awake; the Congress Hotel has been known to………whoa whoa whoa wait!! What room are we staying in? Damn, that’s what I thought! Room 441!! Man, it may be a long sleepless night here in Chicago after all. Oh well, I guess we will have more stories to tell!!!

Dr. Jamil in Guilin – Lingchuan Guangxi, China.

Dr. Jamil in Guilin – Lingchuan Guangxi, China.

About the Author: Dr. Jamil Abdur-Rahman or “Dr. J” as he is more commonly referred to is both a dedicated husband and a devoted father to two son’s and one daughter. He is also a board certified Obstetrician/Gynecologist, a retired Captain in the U.S. Army Medical Corp, an avid traveler, a not so enthusiastic runner and a licensed private pilot who calls the Chicagoland home. After participating on season 22 of CBS’ ‘The Amazing Race,’ he and his twin brother were inspired to start, an interactive viewer centered social and medical information platform that serves to inform, enlighten, motivate, educate and entertain in the name of a healthier planet. They also pen the The Twin Doctors Travel Bag.

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