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.
2) And the skyline in stormy weather.
3) And again from the lakefront.
4) And from above, looking down from the Willis (Sears) Tower.
5) Go higher still and look at a shot from the window of a plane. Everything looks so small, like Mr. Rogers’ neighborhood!
6) A portion of the skyline as seen from the vibrant streets of Chinatown.
7) A visit to Chinatown is a great way to spend a day.
8 ) An aging piece of street art from Chinatown.
9) Here’s a slightly more futuristic and modern piece of art near Wicker Park.
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.
11) Hey there, 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.
13) A very different kind of museum, the Field Museum, takes visitors back millions of years. It’s one of Chicago’s best museums!
14) Get your fill of vintage planes at the Museum of Science & Industry.
15) The imposing Art Institute of Chicago houses some of the city’s most impressive art.
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.
17) And you’ll find lots of really old statues and sculptures.
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.
19) I love modern art because you can take wheelbarrows full of Christmas bulbs and popcorn and call it a masterpiece. Look how pretty!
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.
21) Then there’s the cacti, my favorite plants, because they’re so strange.
22) If animals are more your thing, check out the Lincoln Park Zoo, the largest free zoo in America.
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.
24) Ducks and geese enjoy the lake and harbors even when it’s cold outside.
Chicago Blizzard Photos
25) I don’t know if you’ve heard, but it can get a little cold in Chicago during the winter.
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?
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.
28) And caused whiteout conditions on major roads.
29) And business closures.
30) Then, it’s time to shovel out.
31) The mail delivery doesn’t stop.
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.
34) Christmas isn’t the only time for parades and festivals in Chicago. The pride parade hits Lakeview in late June.
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!
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.
38) The Congress Theater hosts a bunch of rock shows. Good for them for not using the pretentious “theatre” spelling.
39) Sometimes the street musicians are almost as good as the famous ones. Always look around on the sidewalk for unexpected Chicago photography opportunities!
40) Young fans await a My Chemical Romance concert.
41) The biggest music fest of all is Lollapalooza, which reigns for three days in late July or early August each summer. I’ve sen so many unforgettable concerts here!
42) Up to 90,000 fans come through the front gates each day.
43) White people with cameras! Kim Schifino from adorable indie pop duo Matt & Kim crowd surfs at Lolla.
44) Sidewalk art pops up at Lolla.
45) Lolla takes place in Grant Park, home of the Buckingham Fountain.
46) Driving to Grant Park is never advised, but you can find parking if you insist.
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.
48) I miss the giant eyeball that used to surprise people downtown.
49) The Congress Hotel was built back in the 1890s. This shot was taken while exploring Chicago at night.
50) The Chicago flag flies high.
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.
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!)
54) Everyone loves to get a picture taken with the Marilyn Monroe statue, but this girl wins the prize for the cutest pose.
55) The iconic 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!
57) I love the concept of the water taxi.
58) The skyscrapers look regal shrouded in fog.
59) A statue of Jean Baptiste Point du Sable, regarded as the first permanent resident and “founder” of Chicago.
60) It’s no problem finding a taxi downtown.
61) And there’s always the CTA buses.
62) Or the L trains.
63) Walking down to the station.
64) These steps are both gritty and pretty.
65) The train arrives in Wicker Park with the Willis Tower in the background.
66) A view of the Flatiron Building in Wicker Park.
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.
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.
69) The bikes are everywhere in the city. Sometimes you can even find those weird modified bikes. I hope this guy has good balance!
70) Downtown is the one part of the city where I’m wary of biking around.
71) I’d much rather bike along the lake on the trail.
72) It’s funny seeing bike corpses all over the place.
73) Lakeshore Drive is rarely this empty. Pity the poor saps who have to commute everyday on this road.
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!
75) Especially for the kids.
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!
77) Look out for that Zamboni man!
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.
80) World Pillow Fight Day brings people of all backgrounds together to beat the crap out of each other.
81) At last year’s World Pillow Fight Day, I got to hang with the Peep. How many people can say that?!
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.
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!
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.
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.
86) The Mexican groceries on the west side are amazing. Dirt-cheap 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.
88) Just off Michigan Ave, the storefronts never end. This is a great part of the city if you love shopping.
89) I prefer the view from inside Water Tower Place. Not as cool as Horton Plaza, but close.
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.
91) This guy is the best thing about Navy Pier.
92) The pigeons are living large in Chicago.
93) Of all the statues in Chicago, Honest Abe Lincoln might be my favorite.
94) Sometimes the Chicago police go old school. Kids love to see the horses come out!
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!
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.
97) On top of the world (or at least the city) at the Willis Tower Skydeck.
98) Those bridge-covered streets are kinda creepy. Those are the elevated subway tracks.
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!
100) You can never have too much Bean! It always looks cool when the summer sun is shining upon it.
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.
omg, you did it!! I don’t even know if I have 100 photos of any place yet (have to dig around in my folders) Love your photo #3, looked like you are flying into Chicago!
It’s fun to see Chicago from the air because all the massive buildings are so small.
Great collection Scott! Makes me want to visit Chicago soon!
Thanks Mark!
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.
We were only shut down for a couple days here, luckily.
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…..as soon as I summon up enough courage!!
Everyone has to have a few snowy experiences now and then!
Love the street art photos! And I can’t believe cars actually get covered by snow like that; I’ve never been anywhere in the winter that’s gotten more than a few feet. Yikes!
That was from 2011, it was the worst storm I’ve ever seen.
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 🙂
Chocolate art – now that is fun! Winter in Chicago does provide a lot of interesting sights.
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!
Thanks Courtney. It was ambitious but fun to put together.
You said that you missed the giant eye sculpture – what happened to it!?
I think it was moved to another city. Its whereabouts remain in question!
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!
Thanks. I agree, photo essays are fun.
So happy to see this post as I may be coming down from Toronto in June. Although I need more food photos and less snow photos!
I need some more food photos myself. I usually dig in without remembering to snap pics.
Great photos! The images of the Chicago winter remind me not to return in the winter though – it was just too cold! 😉
At least this winter was easy. Very little snow and 87 degrees in March!