Chicago, Instagram, North America, United States

Instagramming … Chicago.

Chicago Instagram
(Last Updated On: September 6, 2019)

I just came back from a long weekend in Chicago! Even though it’s a short one-hour flight from Toronto, I’d never once visited the Windy City. It now competes with San Francisco for being my all-time favorite American City.

Recommended reading: This post about the best things to do in Chicago or this one full of local tips about how to spend 48 hours in Chicago

Instagramming Chicago

The front desk of my hostel in Wicker Park, Holiday Jones. A fairly new hostel, you can book a private room here starting at around $27 US or 20 euros per night.

Chicago Instagram

Bangers and Lace, a bar just across the street from the hostel serves up a fabulous drink list in a beautiful setting.

Chicago Instagram

It’s still Christmas at Macy’s.

Chicago Instagram

Having fun with “The Bean” in Millenium Park.

Chicago Instagram

Chicago Instagram

The park looks pretty, even in wintry cold temperatures.

Chicago Instagram

Then it was time to warm up and have a drink with a view at the Signature Lounge in the John Hancock Center.

Chicago Instagram

Chicago Instagram

The buildings in Chicago all seem to have such character and charm.

Chicago Instagram

This includes the interiors, such as this one in the Fine Arts Building – America’s oldest artist colony.

Chicago Instagram
Checked out the last day of Winter WonderFest where Navy Pier is transformed into an indoor amusement park. It even included this skating rink!

Chicago Instagram

Although it was cold, it was nice to wander around Navy Pier and see frozen Lake Michigan.

Chicago Instagram

Chicago Instagram

Then this happened and the photographer in me went a little crazy.

Sunset that night in Chicago left me speechless. It was very different from viewing Iceland’s Geysir Geothermal Field at sunset only 2 weeks before – but equally as stunning and powerful.

Chicago Instagram

Chicago Instagram

Chicago Instagram

Chicago Instagram

Sadly, it was time to leave and head back home to Toronto. But not before getting treated to one last sunset!

Chicago Instagram

If you like my photos, follow me on Instagram (@cherylhowardblog) to see updates from my life in Toronto and on the road.

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  • Reply reeta @houseofanais January 16, 2014 at 9:00 am

    Such beautiful photos of Chicago – I like especially the frozen lake landscape!

    • Reply Cheryl Howard January 16, 2014 at 12:36 pm

      Thanks Reeta. Yes, winter has it’s own lovely beauty! I personally can’t wait for Spring though. 🙂

  • Reply Adam January 16, 2014 at 12:31 pm

    Love the photos Cheryl! I never really thought of Chicago as very colorful but your photos do a good job of disproving my theory.

    • Reply Cheryl Howard January 16, 2014 at 12:35 pm

      Adam – Thanks! It certainly is a colorful city. That sunset was incredible.

  • Reply Devlin @ Marginal Boundaries January 16, 2014 at 1:44 pm

    I sometimes forget how gorgeous my hometown is, thanks for making me just a tiny bit homesick… ok that’s over now =P

    • Reply Cheryl Howard January 16, 2014 at 3:19 pm

      It’s a great city! I’d love to return during the summer. =)

      • Reply Devlin @ Marginal Boundaries January 21, 2014 at 11:02 am

        Summertime is great in Chicago, sooo many damned festivals, I’d recommend the neighborhood ones instead of doing the Taste. Also ton’s of art shows in Logan Square & Bucktown on the Northside as well as Pilsen & Bridgeport on the Southside, plenty of street art style stuff.

        • Reply Cheryl Howard January 21, 2014 at 3:14 pm

          Thanks Devlin, I definitely need to get back there during warmer weather instead of 3 days post winter cold vortex. 😀

  • Reply Andrea January 17, 2014 at 7:39 pm

    Awwww – we missed you by like 2 weeks 🙁

    • Reply Cheryl Howard January 19, 2014 at 6:03 pm

      Awww – darn!! Would have been fun to hang out. 🙂

  • Reply Leigh Powell Hines January 20, 2014 at 9:20 pm

    Your photos of Chicago are beautiful. Love them, Cheryl.

    • Reply Cheryl Howard January 21, 2014 at 4:01 am

      Thank you Leigh! I’ve become a sunset addict, I think. 🙂

  • Reply Kea January 21, 2014 at 6:55 am

    I’ve only hung out at the ORD airport on multiple occasions, but someday I’ll actually get out of there and visit the city like it deserves. Awesome pictures!

    • Reply Cheryl Howard January 21, 2014 at 9:34 am

      Thanks Kea. You must get there soon and hopefully, you’ll love it as much as I did.

  • Reply Maria January 21, 2014 at 7:03 am

    Stunning – Instagram is so much fun and really shows how you can get great shots with so little. The propeller is my fav Cheryl.

    • Reply Cheryl Howard January 21, 2014 at 9:38 am

      Thanks Maria! The camera’s in the iPhone are of a really good quality, as are the photo editing apps. And an iPhone certainly makes for lighter packing then heavier camera equipment does.

  • Reply Dan January 21, 2014 at 1:30 pm

    The sunsets are amazing but you had me at the beer on top of the world.

    • Reply Cheryl Howard January 21, 2014 at 3:13 pm

      Ha ha, yeah hear ya there! The view was fantastic, but the food/drinks too overpriced for my taste.

  • Reply AmandaHalm January 21, 2014 at 1:33 pm

    Grew up in Chicago. You’re making my city look good. Really nice photos, especially love the one with all the lights.

    Now I miss it… Cheers!

    • Reply Cheryl Howard January 21, 2014 at 3:12 pm

      Thank you Amanda. I’m so happy you like my photos. 🙂

  • Reply Frank January 22, 2014 at 1:57 pm

    Looks cold! Great photos Cheryl!
    Frank (bbqboy)

  • Reply Mary @ Green Global Travel January 22, 2014 at 11:09 pm

    Every one of these photos are beautiful! I had several friends post pictures by “The Bean” within the last few months. You don’t look TOO cold in the pictures! 🙂 Thanks for sharing.

  • Reply IGTT News: Instagram fastest growing social media network {and more} #IGTravelThursday | Skimbaco Lifestyle | online magazine January 23, 2014 at 12:02 am

    […] case you missed last week… a great photo journal from Chicago. Cheryl shares her trip to Chicago in photos that reflect the city perfectly. I hope you’ll enjoy visiting Chicago via […]

  • Reply Stephanie - The Travel Chica January 23, 2014 at 6:47 pm

    I’ve been to Chicago many times, but it’s been a while, and I never went there with a “photographer’s mindset.” I will wait for summer though 🙂

    • Reply Cheryl Howard January 24, 2014 at 1:25 am

      Ha ha, I don’t blame you. I’m starting to get tired of the extreme cold. Toronto’s been brutal this year too, same polar vortex as Chicago had. BURR!!

  • Reply In The Pipeline Chino House January 24, 2014 at 12:05 pm

    […] Hello gorgeous Insta-Chicago. […]

  • Reply Laura @Travelocafe January 26, 2014 at 9:39 am

    Well, great job. It looks amazing! Keep on instagramming…

    • Reply Cheryl Howard January 26, 2014 at 10:41 am

      Thanks so much Laura. Your comment means a lot. 🙂

  • Reply Jennifer February 27, 2014 at 6:38 pm

    Fantastic photos! My husband is from Chicago and his family still lives there. Chicago is a great city and I’m glad to see you enjoyed it so much even with the Polar Vortex!

    • Reply Cheryl Howard February 27, 2014 at 8:10 pm

      Thank you Jennifer! I’m still swooning over that sunset.

  • Reply Tamara Gruber April 18, 2014 at 8:34 pm

    I love the picture with the phone taking the picture — very meta. It was a gorgeous sunset.

    • Reply Cheryl Howard April 20, 2014 at 2:01 pm

      Thanks Tamara. It was a pretty spectacular moment in my life. 🙂

  • Reply Brianna April 23, 2014 at 9:14 pm

    Great photos of one of my favorite cities. I’d live there if it weren’t for the brutal winters.

    • Reply Cheryl Howard April 23, 2014 at 10:06 pm

      Thank you Brianna! This past winter was the worst, especially with all those polar vortexes happening. I loved Chicago but I could never see myself living in the US. I want to go back to Europe ASAP. 🙂

  • Reply Deb May 3, 2014 at 6:39 am

    These are great photos Cheryl, well done! Dave and I haven’t been to Chicago yet. Maybe we’ll take a road trip this summer to check it out. Your photos are making me want to go! I’ve always wondered where that silver water bubble thing was from, now I know. It’s a Bean not a water bubble:)

    • Reply Cheryl Howard May 3, 2014 at 7:26 pm

      Thanks Deb! Means a lot coming from you guys. This was also my first visit there, hope you guys can get there soon too as it’s a fantastic city! 🙂

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