Chicago City Pictures: 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 city pictures covers everything from the vibrant ethnic neighborhoods to the cultural events to the everyday tasks like getting around town and dealing with blizzard conditions in winter.

We’ve got street art, museums, skyline, snow, festivals, concerts, and many other glimpses into Chicago life. These images capture a large slice of life in Chicago. All photographs copyright Quirky Travel Guy.

Chicago City Pictures: Skyline and Neighborhoods

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.

chicago city pictures - 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

Photos of Plants and Animals in Chicago

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

Chicago Blizzard Photos

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. These Chicago city pictures came during one of the Windy City’s biggest snowstorms, which piled up more than 20 inches in two days.

buried cars

28) And caused 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

Chicago Festivals and Music Photography

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 late July or early August each summer. I’ve seen so many unforgettable concerts here!


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
The fountain is a must in any collection of Chicago city pictures!

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

grant park entrance

Pics of Downtown, City Life, Public Transit

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 - chicago city pictures

50) The Chicago flag flies high.

chicago flag

51) This statue of Cubs broadcaster Jack Brickhouse is a lot more lonely ever since the giant Marilyn Monroe statue arrived to steal all the attention.

Jack Brickhouse Marilyn Monroe

52) The tourists have to get their shot of Marilyn!


53) She towers over Michigan Avenue. (Note: Marilyn is no longer in Chicago. Find this statue in Palm Springs now!)

marilyn monroe statue

54) Everyone loves to get a picture taken with the Marilyn Monroe statue, but this girl wins the prize for the cutest pose.

marilyn statue girl

55) The iconic Chicago Theatre.

chicago theatre

56) A photo taken while walking across the Chicago River. I agree with the many folks who say that taking an architecture boat tour on the river is the best way to get to know the city!

chicago river
This is one of my favorite Chicago city pictures!

57) I love the concept of the water taxi.

water taxi

58) The skyscrapers look regal shrouded in fog.

foggy building

59) A statue of Jean Baptiste Point du Sable, regarded as the first permanent resident and “founder” of Chicago.

jean baptiste

60) It’s no problem finding a taxi downtown.

taxi downtown

61) And there’s always the CTA buses.

cta bus

62) Or the L trains.

cta loop

63) Walking down to the station.

cta station

64) These steps are both gritty and pretty.

cta steps

65) The train arrives in Wicker Park with the Willis Tower in the background.

train wicker park

66) A view of the Flatiron Building in Wicker Park.

flatiron building

67) You may stumble upon a movie or tv show filming in Chicago. The Transformers filming downtown was pretty sweet to witness. Here, some cop show films at Six Points in Wicker Park.

tv show filming

68) Chicago still has a decent number of independent record stores. I’ve seen famous folks like Fred Schneider of the B-52s checking out the vinyl collection.

reckless records

69) The bikes are everywhere in the city. Sometimes you can even find those weird modified bikes. I hope this guy has good balance!

modified bike - chicago city pictures

70) Downtown is the one part of the city where I’m wary of biking around.

biker downtown

71) I’d much rather bike along the lake on the trail.

lakeshore trail

72) It’s funny seeing bike corpses all over the place.

bike corpse

73) Lakeshore Drive is rarely this empty. Pity the poor saps who have to commute everyday on this road.

chicago city pictures - lakeshore drive

Random Chicago City Pictures

74) It doesn’t get much better than summer on the lake in Chicago. Go swimming, play in the sand, or rent a jet ski if you like!

chicago beach

75) Especially for the kids.

beach family chicago photo

76) Meanwhile, winter is more ideal for kids who want to try ice skating. I have an entire article dedicated to winter activities in Chicago!

ice skating girls

77) Look out for that Zamboni man!

chicago zamboni pic

78) While we’re on the subject of skating, remember when the Blackhawks won the Stanley Cup? I got to witness a couple of Stanley Cup parades downtown.


79) Mike Ditka! The mural honors the greatness of the Chicago Bears legend.

art ditka

80) World Pillow Fight Day brings people of all backgrounds together to beat the crap out of each other.

pillow fight day

81) At last year’s World Pillow Fight Day, I got to hang with the Peep. How many people can say that?!

peeps character

82) When it comes to atmosphere, there’s no place like Wrigley Field. It might be the most celebrated stadium in all of Major League Baseball.

wrigley field

83) You can buy a hot dog at the game, or head over to the Wiener Circle to get yelled at as you order. It’s a hilarious late-night atmosphere!

wiener circle

84) It’s hard to believe I had never had real deep dish before moving to Chicago, because now I can’t get enough. It’s one of the best Chicago foods!

I love the gooey cheese being on the bottom, and the sauce and parmesan on top. Here’s a guide to the best Chicago pizza tours.

deep dish pizza

85) The Taste of Chicago festival is always a great place to try new foods, although the prices are pretty expensive. I usually can’t justify buying anything more than the sample portion.

taste of chicago

86) The Mexican groceries on the west side are amazing. Dirt-cheap produce!

grocery produce

87) This pic probably seems meaningless, unless, like me, you’re from Pennsylvania, where booze can only be sold in state stores. The first time I saw the liquor aisle at a CVS, my mind was blown.

cvs liquor

88) Just off Michigan Ave, the storefronts never end. This is a great part of the city if you love shopping.

chicago storefronts

89) I prefer the view from inside Water Tower Place. Not as cool as the old Horton Plaza shopping mall in Downtown San Diego, but close.

shopping mall inside

90) You could always head to Navy Pier. I’m not sure why you’d want to do this, but you could. Navy Pier is kind of a tourist trap, and locals don’t often visit. But it can be a decent place to spend an hour.

navy pier

I consider Navy Pier to be one of the more overrated places in Chicago.

91) This guy is the best thing about Navy Pier.

navy pier statue

92) The pigeons are living large in Chicago.


93) Of all the statues in Chicago, Honest Abe Lincoln might be my favorite.

abe lincoln statue

94) Sometimes the Chicago police go old school. Kids love to see the horses come out!

horsey policeman

95) Robert Morris, George Washington and Haym Solomon stand in front of the Wilco towers. There are so many statues in the city of Chicago!

statues wilco towers

96) More surprising Chicago photography: A chunk of ancient Egyptian pyramid embedded in the Tribune Tower! This building has pieces of several other buildings lodged in its exterior.

tribune tower

97) On top of the world (or at least the city) at the Willis Tower Skydeck.

willis tower skydeck

98) Those bridge-covered streets are kinda creepy. Those are the elevated subway tracks.

lake street

99) There’s a lot of cool stuff going on near the boulevards in Logan Square. I lived in Logan Square for several years. It is definitely one of the best neighborhoods in the Windy City!

logan square boulevards

100) You can never have too much Bean! It always looks cool when the summer sun is shining upon it.

bean chicago

That’s it for our collection of Chicago city pictures! The sights are so amazing in this city, that I can never stop creating new images. And for photo essays from other Windy City-based photographers, click here to see Urban Matter’s list.