Instagramming … Chicago.

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.

Founder of cherylhoward.com. Canadian in Berlin. Frequent traveller now at 43 countries and counting.

38 Comments

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

  2. 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!

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

  4. 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.

  5. 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.

  6. 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!

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

  8. 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. šŸ™‚

  9. 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:)

  10. 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! šŸ™‚

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