Chicago- The Worst Place To Visit Ever?

Chicago- The Worst Place To Visit Ever?

As March nears we are in the process of making plans to travel literally coast to coast to screen our most recent film “Mattress World” at film festivals. Our first stop will be Vegas for the Vegas Media Expo followed shortly by the LA Women’s Film Festival, followed shortly by the Lichtfield Hills Film Festival in Connecticut. We didn’t really expect to become such accomplished travelers in the course of our careers as filmmakers but we aren’t complaining too much: we love to travel and to visit new places. In the end, though, we are happy to call Chicago home. 


Lets face it, we’re from Chicago and we’re pretty proud of that fact. We’re proud of our pizza, proud of our hot dogs, proud of our sports teams (whether or not they win) and heck, we’re even proud to be called “The Second City”. Our city teems with theatre and film, with summertime concerts and events, with food, with politics, and business but apparently it’s a lousy place to visit.

This last was brought to our attention by a gentleman we met during our visit to LA last March for a previous film festival. We got to chatting about where we were from and the conversation went something like this:

Him: Hey, where’re you in town from?

Us: Chicago- we’re just here for the film festival.

Him: Chicago! I went to Chicago once and it was the worst experience I ever had.

The Worst!
He went on to explain that he and some friends had flown into O’Hare and had a several hour layover in Chicago and figured they’d see some of the sights while they waited. They hopped a cab but didn’t know where to tell the driver to take them. The driver was surly and unhelpful and offered no suggestions. They eventually made it downtown but still didn’t know where anything was, where to go to get something good to eat or what was worth seeing and had no one to call for pointers. They finally made their way back to the airport frustrated and disappointed and feeling like Chicago didn’t have much to offer.

This was not the kind of response we were used to getting when we told people we were from Chicago. Occasionally we encounter someone who doesn’t take Chicago seriously because it occupies that vast uncharted wilderness between New York and LA. Worse, it’s part of the Midwest home of the corn fed. But even these naysayers describe Chicago as “friendly” and admit there are a few things worth doing around town and few regional specialties worth eating if you happen to find yourself in the area.

Was all this just lip service? We hope not! We are travelers ourselves and know that it’s hard to find your way around any city. And we know that if the Guy-From-LA had any buddies in Chicago that they would’ve been delighted to show him around town. Maybe that’s the key to a good Chicago visit: a buddy to show you around.  So we were kicking around the idea of making a short film: How To Visit Chicago While On Layover. It would include how to get downtown from the airport, what stop to get off at, a few highlight sights to see, a few good places to eat, and how to get back again in time for your flight. The only problem we are having? Figuring out what sights to include and what places to eat.

So help us out: if your buddies only had a few hours in town and were downtown in the Loop- where would you tell them to go? What would you want them to see and do so that they would never, ever, EVER be inclined to say that Chicago was the worse place they ever visited.


Leave a comment
  • Typical NY, LA, ethnocentric thinking. Like they are the center of the universe and we are a bunch of hillbilly farmers.

  • I would tell them to take the blue line to jackson then the red line to lake- there is shopping along lake street and they can quickly stop by millenium park for a classic "look-i've-been-to-chicago" picture. Plus the Art Institute is just down the street and there are plenty of restaurants to choose from. And if they have the time, they can hop back on the red line go north a couple stops to Chicago/State and eat deep dish pizza at Giordanos or Gino's East and can say they walked along Mag Mile.
    We also covered this topic a couple months ago on ChiU- this is what college students suggested people do if they only have a short time in the city:
    Great post! Can't believe anyone would say Chicago is the worst city to visit!! And for the record- all the cab drivers I have had here have been very kind and would definitely have suggestions as to where to go.

  • I work for an international company with offices in nearly every major city around the world. with the headquarters in Chicago, many of these people visit for training, etc. Of those that I ask about Chicago compared to other US cities like LA and NYC. Nearly ALL have said they LOVE Chicago way better.

    I believe them too, especially when they hail from cities like Buenos Aires, Sao Paulo, London, Sydney, you name it.

    I don't like this article...what, so the guy went downtown on a whim with no travel book, no suggestions, no nothing and expected to just fall into all the sights and things to do? ANY city would fail to do that. It's all ridiculous to me. How could they not find Grant Park, explore the River Walk, see would reknown architecture, 1000s of (in my opinion) the BEST restaurants in the world?

  • So let me get this straight. The guy just wonders off into a big city, has one bad cab driver, can't find anything by himself, and somehow this is the cities fault? Has this person heard of the internet or a map?

  • I agree with Mugen. I was in New York for a short time a few years ago. I didn't get to do everything but i wouldn't be slow enough to think based on that short window of time there was NOTHING to do. Who does that? So you didn't know where you were or where to go. Did you ask? Grab a travel guide or think that the magic welcome fairy would be there waiting to take you by the hand? This is more poor effort than a "bad visit." Just like anything you get out of it what you put in.

  • It's hard to see everything in just a few hours, so they'd probably have to stick to the Loop. I'd have them meet me at my office, and I'd take them to Willis Tower (just to say they'd been there), the Art Institute, and the Chicago Cultural Center. I'd also advise them against doing anything as idiotic as planning a last-minute tour of a city and expecting to be dazzled without preparation or effort on my part. So very L.A.

  • Depends--my first visit to Chicago I was not impressed, second--same way. Third--I figured out how to ride the train from OHare-cheap and easy. But its hard for a visitor to figure out where to go once you get off the train! By my 4th visit, I had that figured out as well as I brought a good map with me, and I was no longer timid about asking for directions, even with my very southern accent. People downtown were very nice, one lady even walked with me to my destination. What a person wants to see can be very individualized, but any visitor should see the lake front parks, at least one of the wonderful museums, eat Garretts popcorn, see and go inside a few of those beautiful old buildings. If you are serious about making this film "what to do during a layover" then include the "bean", a look at the lake, one or two buildings, and eats--popcorn, candy, pizza, hot dogs. Actually, nothing "sells" a place like food, so put a lot of attention on eating!
    And I'm from a place where food is king and queen of everything done--and sorry to say, I've never eaten food as good in Chicago as I get at home (due south of Chicago until you hit water).
    I am now a fan of Chicago--traveled north 8 times in the past year and got to see something different each trip! Much better than New York City and I won't even compare LA with Chicago!!

  • Not that you shouldn't make the movie; but these guys jump in a cab and ask the harassed third world immigrant struggling to pay the lease on the vehicle where they should go? They were at the airport which has at least one booth with tourist information, maybe dozens of such.

  • Definitely show them how to get to the Blue Line and show them how that actually works. I remember my first time visiting, when I arrived at the platform, it was stunning to see that I couldn't use my credit card to buy a ticket. Though there was an ATM in the area, nobody could give me exact change, so I had to hike back to the Hilton with my luggage to find someone with change for a $20.

    But the Blue Line would be key since you don't want to waste a layover in traffic.

    Depending on how long you have, there are a few stops to recommend. For a short trip, you would try the Damen stop for Wicker Park. Though there are many many places to go, some possibilities would be tacos at Big Star or a prohibition-era drink at the Violet Hour.

    If there is more time and you want a bite, you could continue your trip further south to clark and lake. From there, walk north to other nightlife and gastro opportunities. Off the top of my head, I think of Manhattans at Gilt Bar; Karaoke at Blue Frog; a sandwich at Xoco; drinks at Public House, bull and bear English, Rockit; or even dining at Mortons. If you want to go even more mainstream, you can hit up Hard Rock Cafe or House of Blues from that stop too. Lastly, they can just take a walk down Clark, La Salle, Dearborn or State to look at architecture. All of this is within "walking" distance to the stop at Clark and Lake.

    I'd also keep in mind, when making this documentary, that people flying in to Chicago might not be used to using their feet to get around and they will most likely be dealing with luggage.

    Good Luck!

  • In this day and age, if they can afford to fly to Chicago, they can afford a mobile device with something like Yelp on it. I mean, how hard is it to do click a few phone buttons?

  • It's no surprise. People in LA are in their own world. They're pretty ignorant, rude and disingenuous above all.
    What does LA have? smog, bad food, fake people and earthquakes.
    oh and riots! ;)

    @Karis, I would not recommend two trin lines, may as well get off at Jackson. The Art Institute is just a couple of blocks off the Blue line stop anyhow. No need to complicate or lengthen things.

    If you're going to do some sort of film, perhaps it best to do a series of films each targeted at specific likes, or the top attractions...

    If it's summer time and sunny, I would recommend a ride up and down lake shore.
    The Hancock's Signature room/lounge for premier views and not having to pay for observatory admission
    Otherwise being near the parks is always beautiful. IF you;re on layover, theres not much point in trying to go into anything like a museum. best to take a weekender trip to see the sights for that.

    Theres always apps too for figuring out where to go. The Chicago Way app is great for finding things right nearby .

  • The Chicago Cultural Center is a great place to start. One can spend hours in this building learning about Chicago, visiting art exhibitions in the various galleries, admiring the Tiffany dome, and so on. It is a good idea when one is a tourist in a new place to go to the cultural center of that place.

    I definitely recommend going to the Hancock Center for a drink in the lounge if the day or night is clear. This offers a fantastic view of the shoreline. If it is cloudy or foggy, skip it for sure.
    If you are into shopping, hit Michigan Avenue.

    I don't know how someone couldn't find good food in Chicago. There has been such a huge gastronomical explosion over the past decade that it's hard to not find yummy victuals. I am not a huge pizza fan, but I always recommend that my visitors try Chicago pizza. It is definitely different than the za one gets in other parts of the world. Chicago steakhouses are also fun to visit and very typical of Chicago fare.

    If you get a bad driver anywhere in the world, get a second opinion (again, I vote for a tourist or cultural center). Don't base your opinion on one visit. Americans can be too quick to judge; keep an open mind and welcome new experiences!

  • I have not read all the posts so these may be included already- gallery district on Huron and Superior, Peggy Notebart Nature Museum and Butterfly Conservatory, Lincoln Park Zoo, North Avenue Beach, Adler, Field, DuSable, Shedd of course, stroll down Milwaukee Avenue between Damen and Wood, Wrigley Field, Take a Windella or other such cruise down the River or the Lake, Navy Pier, Chicago Historical Museum, The Financial District, Cruise down Lake shore to Foster and back, Willis Tower observation deck and the Hancock, same thing. Eat at Wishbones, Billy Goat, Harry Carry, Keefers, Grand Lux, Cheesecake Factory, Tea at the Drake or the Four Seasons, Uno Pizza, Rosebud, Spiaggia, Red Canary, Mado, Tavern On Rush or Carmines, Hugo's Frog Bar

  • I came across this:

    Chicago Bucket List

  • The first thing I would have asked this guy is why didn't he stop into a hotel and ask a concierge? I used to work in hotels in Chicago and now anywhere I go, if I'm unfamiliar is go into a large hotel, see the conceriege and ask them what to do! It is a very simple thing and plus they usually have a ton of brochures to look through where you can find the best and worst tourists traps. Even the worst are great as long as they're memorable. There's so much to do that you can't list them all here anyway, sounds like others gave some pretty good ideas.

  • tell them to call MR. CHICAGO a professional tour guide who also works at the airport, call my mobile unit 224-688-2128 fo the best information!

Leave a comment