City Photography Tips & Tips for Photographing Chicago

I’ve had the chance to visit Chicago several times for work over the past four years, and it quickly became one of my favorite cities to visit.  Throughout those visits, one of the things I’ve really loved is constantly finding new and interesting ways to capture it through a camera lens.

So I wanted to pull together my best Chicago photography tips and examples, but you can also consider these general city or urban photography tips since the principles typically apply.  It’s so satisfying to come back from a trip with photos you know are super cool, and these tips will help you consider new photo spots or angles to consider.

Other Chicago adventures for your enjoyment!

A Detailed First-Timer’s Guide to Chicago

Why The Chicago Architecture Foundation River Cruise Is A Must-Do

Chicago Guide:  Where to Eat & Drink

Hiking In Starved Rock State Park, A Perfect Chicago Day Trip

Tips for photographing Chicago (& urban photography tips overall)

With cities that have lots of tall buildings, you’ll often feel hemmed in and it can be hard to get good angles looking upward.  Where you can, look for breaks in the buildings where you can have some open space to try things out, or play around with perspective in ways that can really show how huge the buildings are.

And time of day is key.  It’s best when possible to get out and photograph at different times of day, as the light changes constantly and different parts of the city will “pop” at different times.  Sunrise and sunset are always reliable for getting some good shots.  Beyond that, blue skies with clouds are your best bet, and interesting gray skies with clouds are next.

There’s not a lot you can do with dull flat pale gray overcast with no clouds or blindingly bright sun, so you may need to find ways to minimize the sky in that case, and just focus on other things (like building details).

I’ve broken out the city photography tips and examples into several different areas through the rest of this post.  Some are categories of photos (architecture, nature vs. city), some are more technique-driven (light pinpoints, reflections), and a few are how to photograph specific Chicago landmarks.

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Architecture

Chicago’s architecture history is amazing, and I never tire of photographing the fascinatingly diverse styles of buildings—particularly juxtaposed against each other.  But most cities have cool buildings and at least *some* interesting architecture history, so it’s worth seeing what you can capture.

In Chicago, I always start along the river, and it’s definitely worth taking an Architecture Foundation River Cruise on a nice day to get a great angle on some of the buildings.  Obviously one of the best angles is shooting upwards from down below, especially with blue skies behind.

But shooting across the river, capturing a bridge in there, etc. is always a good option as well.

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Shooting from below can be an especially effective technique for uniquely-shaped buildings like this one (one of my favorites, called The Pencil Building).  Angles like this really help emphasize how narrow it is at the bottom, holding up that entire giant building!

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We’ll talk more about little details later, but don’t forget that some of the coolest architecture has fascinating little details that you shouldn’t forget…in this case, if I’d only focused on the whole building (which is, admittedly, awesome), you wouldn’t have noticed the gorgeous carvings and the ornate gold around the doors.

Or in the second pic below, it’s easy to just walk by the big pillars that “guard” the Riverwalk entrances, but there is SO much detail on them!

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Reflections in buildings

I am a SUCKER for reflections, in all sorts of ways (and we’ll get to a couple others).  But one of the best aspects of city photography is catching the reflections of buildings in…other buildings.  I do it so much that it was honestly difficult choosing which photos to feature here.

I love how, in this first pic below, it’s almost as though the building is PART OF the sky.

In the second and third pictures, you’ll notice that I framed the reflection perfectly so it truly looks like a building-within-a-building.

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Here are a few more examples of building reflections in other buildings.  This is a unique tip for urban photography in a way that you can’t really do in any other setting, so take advantage of it!

You’ll see in this first pic below that I also played around with more of a wide angle shot, which I think turned out cool (minus that creepy face projection they do).  For reference, that first shot is Crown Fountain, right outside of the Bean in Millennium Park.

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But it’s not always buildings we’re reflecting into, but all sorts of shiny surfaces (we’ll talk about water in-depth later).  I love this first shot, of the ferris wheel at Navy Pier, and of course the Bean also provides tons of opportunities (SO much more on that below).

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Use light pinpoints

So this is really only possible to do well if you have a “real” camera where you can fully control your aperture, but it’s a technique I’m obsessed with and is a great tip for city photography.  It can be especially helpful in certain mid-morning and late afternoon times when the sun is in your way no matter what.

Basically, you want to get your aperture quite tight, like usually in the 14 to 22 range (will depend on the camera, amount of light, etc).  Ideally you want your light source (whether the sun or something else) to be partially behind or glinting off something…so in this first pic below, I set it to where the sun was partially behind the building and peeking out.

This creates, as you can see, a beautiful starburst with the light pinpoint.

For reference, I took these shots with my Sony a6400 mirrorless camera

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Nighttime is magical…use the lights

Speaking of light, nighttime in cities (and Chicago especially) is gorgeous!  I never get tired of photographing Chicago on the river at night, and it’s possible because there are so many lights, and they reflect off the water, giving me enough light to get a good picture if I just carefully stand still.

In some cities though, or even in other parts of Chicago, you’ll probably need a tripod to keep the camera from shaking.

One “hack” for this if you just want to capture a quick photo but don’t have a tripod, is to set your camera (or phone) somewhere stable and sturdy where you don’t have to touch it, then set the camera timer for 2-3 seconds, hit the button, then stop touching it.  This can mimic the benefits of a tripod and remote (though obviously if there are lots of people around, the ground will be shaking and you don’t want your camera stolen).

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If there’s enough light, you can capture some moving objects as well, like this boat that was making its way up the river.

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Snow and the twinkle lights or Christmas lights in the winter can offer some fun shots, and if you’re along the Chicago River you should also find out when they’re doing “Art on the Mart” or other building light projections, which can be really fun to capture.

What I love about this one is that you can see an awesome reflection in the base of the building on the left.

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Reflections in water

Now for more reflections!  Here are some examples, both big and small, of how you can use water to your advantage.  First off, larger bodies of water (on a still day) can offer beautiful reflections of surrounding buildings.  Chicago’s lakefront (and occasionally the river) can be great for this.  This specific shot was taken close to the Adler Planetarium.

But guess what—it rains a lot in the world!  So puddles and similar small bits of water can also give you super cool serendipitous opportunities to capture a building’s reflection or show a unique tableau in the water.  The three pics below are examples of this.

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Related to reflections…shadows are great

So maybe you don’t have any water handy in your particular urban photography venture…that’s fine!  Shadows can be a really cool way to highlight interesting aspects of a building or statue, provide complementary perspective, or just use harsh overhead lighting in the middle of the day to your advantage.

I love this first pic of the art installation, which was taken at the Adler Planetarium, as an example.

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Look up!

Honestly this is one of my general travel tips, not only a city photography tip…people are often so focused looking down and straight ahead, that they miss all the beautiful details or cool happenings up above.  And for photography, these can be some pretty great shots if you’re lucky.

Here are just a few examples of pointing my camera upwards (besides all the architecture ones at the beginning).  As you can see, having a pretty blue sky and some interesting clouds does make this a lot more effective.

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Manufacture perspective for size, depth, or distance

This is one of my favorite photography tips in general, and one I use constantly.  You can set up shots in a way that really leans into perspective, giving a sense of size or direction.

For instance in this first pic, I’ve made sure there’s an item in the foreground to kind of “anchor” the shot and make it more interesting, as well as give a better sense of depth and distance.

You can use people this way in shots, and that’s a great tip for city photography in particular (relative to size of buildings).  Or you can use something else, like in the third photo where the small boat really gives you a sense of the huge buildings.

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You can really use this technique well with things like bridges, railways, underpasses, and similar items to give the viewer a feeling of distance and direction.  With the examples below, they’re framed in a more interesting way so that it’s like the bridges to to infinity.

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There are so many different ways to play with perspective, and they result in SO much more interesting photos than just a straight-on shot.  Here are a few more examples to inspire you.  You can play around with your wide angle lens to manufacture perspective as well (on iPhones you can now do this by zooming out further).

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So here’s a specific example of using this technique to show better perspective, and I’ll show you the “boring” version as well.

This is an art installation in Chicago that’s out in one of the neighborhoods.  In the first two photos I’ve tried to get an interesting angle, using one of the sets of legs in the foreground for a visual anchor and to really highlight size.

And this is how it looks if I just get a snapshot of the art installation with the buildings in the background.  As you can see, it isn’t nearly as interesting…

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The famous landmarks

Obviously, we can’t talk about Chicago photography tips without hitting on a few of the “must do” sites such as the Bean.  But that’s true of other cities too, they each have their own “iconic photo opportunity” and you really have to consider a few things—time of day, crowds, and whether it’s better up close or far away.

For the Bean, it really depends…and the great thing is that I’ve found almost anything works.  It’s such a fun art installation to photograph any time of day, with or without people (because of the reflections), and up close or far away.

Because it’s reflective, what you really have to think about is using the reflections to your advantage.  Below are a few of my favorite examples.  During COVID they stopped letting people get close to it, so I highlighted the negative space around it, building reflections, and also some light pinpoints during harsher sun times.

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But as you can see below, when people are allowed to get up close and personal, that doesn’t make the photos worse (except that was with an older camera, so the quality isn’t quite as high).  You get SUPER cool reflective angles up close, and the tourists add an extra element of fun to the shots.

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Look for intersecting lines or angles

Similar to our discussion of perspective, in cities you can find all sorts of interesting lines and angles.  Look for where these angles intersect and you’ll often find great shots framed up for you.

In this first pic below I love how the different railroad lines give you straight and angled intersections, with the cityscape framed up in the background.

In the second pic, that diagonal lakefront edge makes an otherwise-straightforward city/lake shot much more interesting.

Look for juxtapositions of nature and city

Just like intersecting angles can be helpful, finding other contrasts can add texture and interest to your photos.  One of my favorite city photography tips is to find where urban and nature intersect.

In Chicago, for instance, there’s a beautiful little (free) botanical garden called Lurie Garden, right behind the Bean.  My last trip was in late April, and I was able to capture some lovely flowers with the skyscrapers in the background.

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Obviously sunset and sunrise can be awesome

I never get tired of photographing sunrise (UNDERRATED!!) or sunset anywhere I go.  The colors and light are gorgeous, but it can be a bit more challenging in a city due to all the buildings.  So as we’re talking about tips for city photography, we have to think about sunrise and sunset a bit differently.

First, you want to get up high…in a city like Chicago, this is often easy due to the rooftop bar culture.  But you can go a step further, as Chicago has two different skyscrapers with observation decks, Skydeck at Willis Tower (103rd floor, has a glass ledge) and 360 Chicago (94th floor, previously John Hancock building).

On my last visit I did 360 Chicago for a cocktail and sunset view, and wasn’t disappointed.  The best view is actually from the women’s bathroom 🙂

It’s a little more difficult, but you can get some pretty shots on the river as well, from ground-level.

And sunrise, just wow!  Because Chicago’s lakefront faces east, you can often get stunning sunrise photos.  These were a lucky capture one cold winter morning when I was on a run along the Riverwalk, and when I saw the sunrise that was developing I raced back to my hotel (which was close to the lakefront) to try and get up high for a shot.

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Small details (e.g. neighborhoods)

I mentioned at the outset that we’d come back to all the beautiful details you should consider with urban photography.  This requires really paying attention, but you can find all sorts of fun, quirky, beautiful, or unique small details on buildings or out in the neighborhoods that will make great photos.

Below are a handful of examples that I love, showcasing different ways to highlight the details.

The architectural details can really pop when looking upward as well, as the examples below showcase.

Dapples of light

This is a really specific type of photo to capture, but it’s one of my big tips for city photography, and for Chicago photography especially.  Because the buildings are tall and often block out the sky, you have to look for other elements of interest to include in your shot.

The light reflecting off other buildings, or off the river, can provide texture and light within photos that keep them from feeling flat and boring.  Here are a few examples.

Pay attention to how you frame your shot

One of the most critical tips for urban photography, Chicago photography and, in fact…any photography…is framing your shot.  Considering the elements of the shot, the rule of thirds, and how the lighting and sky are (or aren’t) working in your favor can make a big difference.

I’ll share a specific “good” and “bad” example below.  The first shot is…fine.  It’s a historic building in Chicago that is now the stayPineapple hotel, where I stayed on my most recent trip.  It’s an okay shot and does show the details of the building.

BUT, in the second shot I moved my camera to the left to capture some of the surrounding elements, and I think it is so much better.  You get much more interesting sky (they were taken about 15 minutes apart) plus the fun colors from the mural.

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Pay attention!  Serendipity knocks…

Perhaps the most important urban photography tip is to be paying attention…often the best photos are a combination of lucky timing, paying attention, and moving quickly to snap the perfect pic.

The first photo below is one of my favorite examples of this.  I’d been on my feet all day exploring the city and taking photos, was nearing a 25,000-step day in fact, and all I wanted to do was veg.  I was just around the corner from my hotel when I saw these ballerinas doing a photo shoot…which I managed to snag my own amazing photo of!

There are a few other examples below as well, lucky moments that I happened to notice and capture for posterity.

Don’t sleep on winter

No question, winter weather can make city photography really tough…you’re more likely to have overcast or dull skies, fog, etc.  But with some luck and planning you can still capture good pics.  Below are a couple I’ve loved (first uses perspective, and the second lighting interest.

One specific tip for photographing Chicago…

I had never heard of this until my most recent trip, so it may be more of a locals thing, but on a beautiful day it gave me the most beautiful photos!

Head out to the Adler Planetarium for some of those iconic city skyline photos, and enjoy walking up and down the lakefront for a number of interesting angles.

And the fact is…sometimes you just get unlucky with the weather.  Nothing to be done but snap a few photos and move on.  The weather in Chicago (and many other cities) can change on a dime, so make the most of it when you have good weather, and don’t sweat it if you don’t.  Find a great local restaurant and have some food and a snack 🙂

Hopefully this has given you lots of ideas and examples with detailed tips for photographing Chicago, and tips for city photography overall!

Other city photography inspiration you’ll love:

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