A Fall Photo Tour of Chicago

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I've now been to Chicago three times this year — in the late winter/early spring, in the summer, and now in the fall. It's a great city any time of year, but I think Chicago in the fall might actually be my favorite.

If you're considering a trip to Chicago this fall, here's what you might be able to expect to find downtown:

A wind-swept Navy Pier:

Perhaps an Oktoberfest celebration:

Or maybe a boat race on Lake Michigan under dark skies:

The Tiffany dome inside the Cultural Center over a wedding celebration:

Chicago Cultural Center

“The Bean” in Millennium Park:

Bright fall colors:

The last few weeks of Buckingham Fountain running in Grant Park:

Maybe an Open Streets celebration on a weekend afternoon:

Chicago Street Performers

Other kinds of street performers:

A lively Chicago River:

And plenty of people looking up Marilyn Monroe's skirt:

Have you visited Chicago in the fall? What are your favorite parts of the city this time of year?


  • Aaron says:

    Great photos, love Chicago. Was already thinking about a return Fall trip (never been in the Fall), even more so now! Wanna go for a drive along Lake Shore Drive all the way up to Evanston and also see what Grant and Millenium Park and the lakefront are like with all the beautiful colors.
    Aaron recently posted..Atlanta: The Georgia Aquarium

    • DangerousBiz says:

      I really love Chicago, too, and last weekend was gorgeous, for the most part. Definitely go soon if you can!

  • Beautiful! I do think that every city in the world looks at its best in the fall. Orange leaves make my eyes go crazy! Even though I am from Montreal and get lots of classic fall foliage, I would be curious to visit my south neighbor, especially Chicago now!

    • DangerousBiz says:

      I agree that orange and red leaves make any city better! It also didn’t hurt that we had some sun, too — always makes the colors more vibrant!

  • We’re in Chicago right now and we love the colors of the fall! With the warm weather, I don’t even mind that it’s October, a month that I usually don’t like at all. Love your photos of Buckingham Fountain and the Bean.
    Dani | Globetrottergirls recently posted..Our Perfect London Day Off the Beaten Path

    • DangerousBiz says:

      Chicago continues to surprise me every time I visit. I never really would have expected fall colors in a big city, but they were definitely there! I’m glad you liked my little photo round-up. ๐Ÿ™‚

  • Lindsey says:

    Oh my gosh Amanda! I was in Chicago last weekend too! ๐Ÿ™‚
    Did you see how big the waves were on Saturday? I couldn’t get over how big and frothy they were and we watched them crash into the break wall along Lake Shore Drive.
    I had never been to downtown Chicago before and I was pleasantly surprised how beautiful it is! Having only ever been through Chicago on the interstate or the airports I had no idea how much I was missing out on.

    • DangerousBiz says:

      You were there last weekend too? No way! I didn’t see much of the waves on Saturday, as I had a wedding to go to that afternoon. But they were pretty intense down at Navy Pier on Friday, that’s for sure!

      Glad to hear you were pleasantly surprised by Chicago. I always am, too!

      • Lindsey says:

        My friend just moved up there and I went to visit for the weekend. We drove all up and down Lake Shore Drive, went on the architecture boat tour on the river and took a bike ride. Oh, and we walked to Wrigley Field and came across the 25th Anniversary celebration of Ferris Bueller’s Day Off, it was hilarious! ๐Ÿ™‚
        I want to check out the aquarium and the museum that has the whales and dinosaurs at it the next time I am in town. I heard they are both great!

        • DangerousBiz says:

          A 25th Anniversary celebration for Ferris Bueller’s Day Off?? Are you kidding?? I’m so sad I missed that!!!

          My family went on the architecture boat tour, too. I really enjoyed it! Will write up a review about it on here soon, I think.

          • Lindsey says:

            Wouldn’t it be crazy if we happened to be on the same boat tour?! LOL We went Sunday afternoon at 3:30, how about you? ๐Ÿ™‚

            I guess the Ferris Bueller screening set a world record! We tried to get in but it was sold out, darn! They had actors dressed in the clothes from the movie and they even had Cameron’s Dad’s car out front along with cardboard cutouts that you could get your picture taken with, it turned out to be a lot of fun and we just happened upon it. ๐Ÿ™‚

          • DangerousBiz says:

            That WOULD be crazy! We, too, went on Sunday afternoon, but we were on the 1:30 cruise.

            Fun about the Ferris Bueller thing, even if you couldn’t get inside. It’s those random finds like that that I love most about traveling.

  • Audrey says:

    Looks like a great time of year to visit! I haven’t been to Chicago yet, but I find that I really enjoy visiting cities in autumn. The summer chaos is gone and the cool breeze makes the city feel so alive and inviting. ๐Ÿ˜€
    Audrey recently posted..Local Montreal & The Underground Art Scene

    • DangerousBiz says:

      I also LOVE fall colors. I think I could enjoy any place with orange and red leaves on its tress! And, while autumn here in the Midwest is often quite rainy, the sunny days are stunning.

  • Suzy says:

    No offense to Marilyn Monroe, but that statue is a tad creepy! I was just thinking of heading to Chicago some weekend this fall. Looks gorgeous this time of year.
    Suzy recently posted..Redhead Reviews: Going On Location in New York City

    • DangerousBiz says:

      Haha, that statue was definitely… interesting. Especially because there were actually underwear painted under that skirt!

      But yes, Chicago is definitely nice this time of year, as long as you can catch it on a sunny day!

  • This is a lovely photo essay! You really captured some of my favourite areas of Chicago. I was there a year ago and attended Oktoberfest during that time as well! I have some funny video footage of a couple dancing with a hot dog mascot…LOL
    Nomadic Samuel recently posted..Smiles of Thailand | Photo Essay | Part 1

    • DangerousBiz says:

      Thank you, Samuel! Did you go to the Navy Pier Oktoberfest, too, or another one in the city? Too funny about the hot dog mascot… I wish I would have seen that!

  • Jim says:

    Always love reading your blog- great photos again. Almost want to add this to our bucket list.
    Jim recently posted..Magnificent Monday: Smiles can light up the world.

    • DangerousBiz says:

      Thanks so much, Jim. I really appreciate the kind comments! You should definitely add Chicago to your bucket list if ever you’re in the U.S. It’s a great city!

  • Erik says:

    I went to college in Chicago’s suburbs. I was always amazed living there how livable a big city it was and how my hometown of Detroit was tragically it’s opposite. I was lucky enough to work at an amazing travel bookstore (now closed) on Michigan Avenue for a few years, and there was something romantic about commuting by train to work everyday.

    I haven’t been there in seven years, might be time for a trip back.
    Erik recently posted..Australia- 10 Years Later- The Good & The Bad

    • DangerousBiz says:

      Chicago really does seem like a really livable big city. I think I could definitely call it home for a few years someday.

  • Suzanne says:

    LOVE Chicago~ not so much the Marilyn Monroe sculpture, most locals feel its irrelevant too. Most interesting new thing on last trip to learn about was the artifacts on the Chicago Tribune building. Really cool!

    • DangerousBiz says:

      Yeah, the Marilyn statue was so random. But I like random things, so I didn’t really have a problem with it. Lol.

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