Collected by JM
909 W Belmont Ave, Chicago, IL 60657, USA
111 S Michigan Ave, Chicago, IL 60603, USA
Wow. The last time I was here was on a high school field trip 35 years ago, and the museum has definitely grown. What an amazing collection—I could have spent days here, but I only had two hours. I followed the museum's suggested top 10, and...
220 E Chicago Ave, Chicago, IL 60611, USA
Not only does the Museum of Contemporary Art have great exhibitions on local and renowned artists, but the interior architecture of the museum itself is also an attraction. They also provide unusual events and tours—curator-led tours, musicians on...
2391 N Stockton Dr, Chicago, IL 60614, USA
Streeterville, Chicago, IL 60611, USA
The architectural boat tour of downtown Chicago is the single best way to see this city in a whole new way. From first-timers to lifers, it doesn't matter how long you've been in town, this perspective is going to be new to all. There are many...
201 E Randolph St, Chicago, IL 60602, USA
After walking the entire city I easily decided Millennium Park is hands-down Chicago's best attribute. I imagine the weather's not always as perfect as it was on my visit, but in the summer that attraction is unbeatable. (Ok, Central Park has it...
875 N Michigan Ave, Chicago, IL 60611, USA
Skip the ticketed admission to the John Hancock Observatory on the 97th floor and take the elevator to the “Signature Lounge at the 96th” floor of the John Hancock Tower at no charge. The Chicago skyline glitters at night, but sorry...
565 W Jackson Blvd, Chicago, IL 60661, USA
Lou Mitchell’s diner has been open in the same location since 1923; so long, in fact, that diner patrons witnessed the heyday of Route 66, which started right here next to Union Station. The Chicago city council renamed Jackson Street “Lou...
Old Town, Chicago, IL, USA
Located a short train ride from the Loop, this wrought-iron doorway marks the entrance to Chicago’s Old Town. You'll find plentiful shopping and restaurant options in the neighborhood, as well as St. Michael’s Church, one of the city's oldest...
401 N Franklin St, Chicago, IL 60654, USA
I have two pieces of advice for you regarding the Doughnut Vault: 1. Go early. They open at 8am Tuesday-Friday and 9:30am on Saturdays and if you want a breath of a hope of a chance of getting a doughnut before they sell out, you want to be there...
1927 W North Ave, Chicago, IL 60622, USA
You like pizza? You like beer? You'll like Piece. If you're a lover of craft beers then you should be familiar with Piece Pizzeria & Brewery in Wicker Park, but just in case I haven't made it clear enough - you should. Sundays you can get a pie...
2900 W Belmont Ave, Chicago, IL 60618, USA
Even though Kuma's Corner has only been around since 2005, it is already a Chicago institution. Supporting the local heavy metal music community, and paying tribute to bands by naming its burgers after groups like 'Slayer' and 'Iron Maiden,' this...
2148 N Milwaukee Ave, Chicago, IL 60647, USA
3411 N Halsted St, Chicago, IL 60657, USA
Boasting the slogan 'Meat free since '83,' The Chicago Diner isn't going to win everyone over. However, if you are vegetarian, or even want to get your vegan on, this is the place for you. With an extensive menu of food and drink, the friendly...
50 W Randolph St, Chicago, IL 60601, USA
A perfect buttermilk old fashioned donut is fresh and hot with crispy crunchy edges underneath a melting sugary glazy and the minute I’ve eaten one, I’m already dreaming about the next one. Do-Rite hits all these marks with room to spare, which...
5148 N Clark St, Chicago, IL 60640, USA
In the center of Andersonville, a trendy neighborhood on Chicago's far north side, you'll find a bar with 18 different Belgian beers on tap. One of my favorite memories at The Hopleaf (and let me stress, these are blurry memories) involves teasing...
737 W Randolph St, Chicago, IL 60661, USA
A visit to Chicago's historic meat-packing district at any time is, in and of itself, a bit of an adventure. The area has certainly seen enough transitions to bring in the hip and happening in recent years. However the best reason to visit,...
Unnamed Road, Chicago, IL 60614, USA
The Patio at Cafe Brauer is a great place to relax over a cold brew while taking in the scene of a nearby nature walk and pond with the city skyline in the distance. A respite to enjoy the energy of people out enjoying their diverse city,...
3020 N Lincoln Ave, Chicago, IL 60657, USA
Like most good thrift stores, the Brown Elephant is hit or miss. Sometimes you can find great books, T-shirts, and super-cheap vinyl—other times, nothing appeals, and you just wander around until your feet hurt. This shop is well organized,...
1472 N Milwaukee Ave, Chicago, IL 60622, USA
This charming little store on Milwaukee is stuffed with vintage goods in primo condition. Beautiful chunks of costume jewelry and frilly fascinators share space with lush leather handbags and sparkling glassware. Nothing in the store is cheaply...
1513 W Foster Ave, Chicago, IL 60640, USA
Adam and Skye Rust admit that they have a thing for taxidermy. And bones. And teeth. Adam has even made an animated sculpture where taxidermied mice circle and dance à la "Three Blind Mice." They travel the globe to find the strangest and...
812 W Belmont Ave, Chicago, IL 60657, USA
Hollywood Mirror is my favorite vintage, retro, tchotchke-filled store of randomness in Boystown. It’s incredibly crowded but amidst the clutter you’ll find Halloween costumes, vintage lunch boxes, Mardi Gras beads, feather boas, 60’s style...
1854 W North Ave, Chicago, IL 60622, USA
Quimby’s says they specialize in “unusual publications, aberrant periodicals, saucy comic booklets and assorted fancies” and if that description doesn’t grab you, then this isn’t your kind of place. However, if this is your kind of place then you...
1960 N Western Ave, Chicago, IL 60647, USA
Old school ice cream parlor and soda shop with homemade candy and ice cream since 1921 in the same location in Bucktown. I wish the little jukeboxes on the tables worked but clearly it’s not hampering their business as there’s a line out the door...
1379 N Milwaukee Ave, Chicago, IL 60622, USA
Reckless Records specializes in DVDs, vintage vinyl and used CDs of all kinds from Top 40 music to every obscure band that ever put out an album. The workers at Reckless have a reputation for being the tiniest bit elitist and because of that...
1564 N Milwaukee Ave, Chicago, IL 60622, USA
A good used bookstore is a glorious thing and Myopic is one of the great ones. They have a giant selection of new, used, rare and out of print books on 3 floors, they’re well organized, they're open until 11pm and there’s a store cat! There's also...
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