Chicago Photography: 100 Exciting Images of Life in the Windy City

My long-time home of Chicago is this month’s Featured Travel Destination, and I thought the best way to introduce the city was to present a collection of 100 images from the Windy City. This collection of Chicago photography covers everything from the vibrant ethnic neighborhoods to the cultural events to the everyday tasks like getting around town.

We’ve got street art, museums, skyline, snow, festivals, concerts, and many other glimpses into Chicago life. These images don’t necessarily capture the entirety of life in Chicago. Your own experience may vary. All photographs copyright Quirky Travel Guy.

1) Starting off with one of Chicago’s most recognizable features, its skyline.

chicago skyline

2) And the skyline in stormy weather.

skyline storm

3) And again from the lakefront.

skyline me

4) And from above, looking down from the Willis (Sears) Tower.

skyline above photo

5) Go higher still and look at a shot from the window of a plane. Everything looks so small, like Mr. Rogers’ neighborhood!

chicago skyline from plane

6) A portion of the skyline as seen from the vibrant streets of Chinatown.

chinatown picture

7) A visit to Chinatown is a great way to spend a day.

chinatown chicago

8 ) An aging piece of street art from Chinatown.

chinatown street art

9) Here’s a slightly more futuristic and modern piece of art near Wicker Park.

chicago future art photo

10) The predominantly Mexican neighborhood of Pilsen does not take a back seat when it comes to awesome art. Look at all the detail that went into this one.

pilsen mural

11) Hey there, cowboy!

street art cowboy

12) Pilsen is home to the Mexican Art Museum, one of the best free attractions in Chicago and one of the top things to do in Chicago during the winter.

mexican art museum

13) A very different kind of museum, the Field Museum, takes visitors back millions of years. It’s one of Chicago’s best museums!

field museum chicago

14) Get your fill of vintage planes at the Museum of Science & Industry.

museum science industry planes

15) The imposing Art Institute of Chicago houses some of the city’s most impressive art.

art institute of chicago

16) Inside, you’ll find Seurat’s famous “A Sunday on La Grande Jatte.” One of my favorite Family Guy episodes is where Stewie visits the museum and stares deeply into the picture, in a parody of Ferris Bueller’s Day Off.

seurat sunday painting

17) And you’ll find lots of really old statues and sculptures.

old statues

18) Everything about the Museum of Contemporary Art is cool. Even the staircases, which make for some cool geometry when viewed from above. Note the fish pond at the bottom.

museum contemporary art stairs - chicago photography

19) I love modern art because you can take wheelbarrows full of Christmas bulbs and popcorn and call it a masterpiece. Look how pretty!

wheelbarrows art - chicago images

20) The Garfield Park Conservatory is the place to go to get your botany fix. The ferm room is cool, showing how Chicago would have looked ages ago.

conservatory fern room

21) Then there’s the cacti, my favorite plants, because they’re so strange.

conservatory cacti

22) If animals are more your thing, check out the Lincoln Park Zoo, the largest free zoo in America.

chicago zoo giraffe

23) The zoo is open year-round, which is great for winter animals like polar bears. They like to get up close and personal with visitors.

zoo polar bear - chicago pics

24) Ducks and geese enjoy the lake and harbors even when it’s cold outside.

chicago ducks

25) I don’t know if you’ve heard, but it can get a little cold in Chicago during the winter.

winter chicago photos

26) The weather can lead to the formation of dangerous ice projectiles. I don’t know what this sign is supposed to accomplish. Are you supposed to wear a helmet? Look up into the air while walking around?

caution falling ice

27) Cars buried under feet of snow. I have a separate post with several more Chicago blizzard photos.

buried cars

28) And whiteout conditions on major roads.

north ave snow - chicago photography

29) And business closures.

store closed blizzard

30) Then, it’s time to shovel out.

shovel van

31) The mail delivery doesn’t stop.

postal delivery snow

32) In December, the Christkindlmarket takes over downtown. The open-air festival features a traditional German market with novelty items and food for sale.


33) The Parade of Lights also rings in the holiday season. Kermit the Frog, Frosty the Snowman, and Rudolph are among the winter luminaries who make appearances.

rudolph parade

34) Christmas isn’t the only time for parades and festivals in Chicago. The pride parade hits Lakeview in late June.

chicago pride parade

35) Kids enjoy sweet treats at the Puerto Rican festival in Humboldt Park. Free festivals like this are one of the best ways to live cheaply in Chicago!

puerto rican fest kids

36) No city has more music and street fests in the summer. Robyn dances on her own at Pitchfork.


37) Kid Cudi is in pursuit of happiness at the DMB Caravan Festival.

kid cudi

38) The Congress Theater hosts a bunch of rock shows. Good for them for not using the pretentious “theatre” spelling.

congress theater

39) Sometimes the street musicians are almost as good as the famous ones. Always look around on the sidewalk for unexpected Chicago photography opportunities!

street musician

40) Young fans await a My Chemical Romance concert.

concert crowd

41) The biggest music fest of all is Lollapalooza, which reigns for three days in early August each summer.


42) Up to 90,000 fans come through the front gates each day.

lollapalooza entrance

43) White people with cameras! Kim Schifino from adorable indie pop duo Matt & Kim crowd surfs at Lolla.

lolla matt & kim

44) Sidewalk art pops up at Lolla.

lolla chalk logo

45) Lolla takes place in Grant Park, home of the Buckingham Fountain.

grant park fountain - chicago photography
Any Chicago photography collection has to include a shot of the fountain!


46) Driving to Grant Park is never advised, but you can find parking if you insist.

grant park entrance

47) Nearby is the world-famous Cloud Gate Sculpture, otherwise known as the Bean. You may even catch a wedding in front of the reflective structure.

bean wedding

48) I miss the giant eyeball that used to surprise people downtown.

giant eyeball

49) The Congress Hotel was built back in the 1890s. This shot was taken while exploring Chicago at night.

congress hotel

50) The Chicago flag flies high.

chicago flag

Click here to see the second half of our 100 Chicago images post, including photos of Chicago sports, the lakefront, downtown architecture, and some less-touristy neighborhoods.

And for photo essays from other Windy City-based photographers, click here to see Urban Matter’s list.

22 thoughts on “Chicago Photography: 100 Exciting Images of Life in the Windy City”

  1. Great pictures! I never seem to take enough when I travel.

    The blizzard sign was so funny to me! Considering when DC went through the Snowmaggedon, we were shut down for over a week! It was just as much snow or less than shown in those picutres.

  2. Scott,

    My disdain for snow keeps me south bound during the winter, but I think just once I would have to attempt experiencing this snow thing at least once…maybe during the holiday. If nothing else it would provide a stark contrast to the beautiful photos that you have displayed here. I might have to do just that… soon as I summon up enough courage!!

  3. First of all, popcorn IS art – just not as great art as chocolate in my opinion. Second, that “caution – ice is falling” sign is hilarious! Third, I love gigantic photo essays and am enjoying yours. Chicago looks like fun a fantastic city to visit in all seasons. I’d love to visit in winter and see the lake when it’s frozen 🙂

  4. HOLY SMOKES!!! What an ambitious undertaking to post all these photos, but what neat photos you captured!!!!!!! I like how you broke it up in 2 posts and I LOVE the array of life, culture and vibrancy you captured. Super neat to see Chicago via your eyes. Thx for sharing!

  5. I never get tired of seeing photos of Chicago (but prefer to actually be there). I especially like all of the snow pics the one of the Congress Hotel at night. Well done!

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