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.
Bangers and Lace, a bar just across the street from the hostel serves up a fabulous drink list in a beautiful setting.
It’s still Christmas at Macy’s.
Having fun with “The Bean” in Millenium Park.
The park looks pretty, even in wintry cold temperatures.
Then it was time to warm up and have a drink with a view at the Signature Lounge in the John Hancock Center.
The buildings in Chicago all seem to have such character and charm.
This includes the interiors, such as this one in the Fine Arts Building – America’s oldest artist colony.
Checked out the last day of Winter WonderFest where Navy Pier is transformed into an indoor amusement park. It even included this skating rink!
Although it was cold, it was nice to wander around Navy Pier and see frozen Lake Michigan.
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.
Sadly, it was time to leave and head back home to Toronto. But not before getting treated to one last sunset!
If you like my photos, follow me on Instagram (@cherylhowardblog) to see updates from my life in Toronto and on the road.
Such beautiful photos of Chicago – I like especially the frozen lake landscape!
Love the photos Cheryl! I never really thought of Chicago as very colorful but your photos do a good job of disproving my theory.
Adam – Thanks! It certainly is a colorful city. That sunset was incredible.
Thanks Reeta. Yes, winter has it’s own lovely beauty! I personally can’t wait for Spring though. š
I sometimes forget how gorgeous my hometown is, thanks for making me just a tiny bit homesick… ok that’s over now =P
It’s a great city! I’d love to return during the summer. =)
Awwww – we missed you by like 2 weeks š
Awww – darn!! Would have been fun to hang out. š
Your photos of Chicago are beautiful. Love them, Cheryl.
Thank you Leigh! I’ve become a sunset addict, I think. š
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!
Stunning – Instagram is so much fun and really shows how you can get great shots with so little. The propeller is my fav Cheryl.
Thanks Kea. You must get there soon and hopefully, you’ll love it as much as I did.
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.
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.
The sunsets are amazing but you had me at the beer on top of the world.
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!
Thank you Amanda. I’m so happy you like my photos. š
Ha ha, yeah hear ya there! The view was fantastic, but the food/drinks too overpriced for my taste.
Thanks Devlin, I definitely need to get back there during warmer weather instead of 3 days post winter cold vortex. š
Looks cold! Great photos Cheryl!
Frank (bbqboy)
Thanks so much Frank! š
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! š Thanks for sharing.
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 š
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!!
Thank you Mary! š
Well, great job. It looks amazing! Keep on instagramming…
Thanks so much Laura. Your comment means a lot. š
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!
Thank you Jennifer! I’m still swooning over that sunset.
I love the picture with the phone taking the picture — very meta. It was a gorgeous sunset.
Thanks Tamara. It was a pretty spectacular moment in my life. š
Great photos of one of my favorite cities. I’d live there if it weren’t for the brutal winters.
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. š
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:)
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! š