Wonderful brunch at a diner opened by the chef behind Girl & the Goat. Both inventive menu items and classics in an unimpeachably cute Wes Anderson-like setting. I loved the Went to China biscuit.
Walk along the river on the pedestrian pathway and wave to the tour boats going by, while the cars whiz above. (I recommend taking a sunset tour too, if you have a chance!)
Wonderful Midwestern ice cream. Compares favorably with anything in SF, LA, NYC.
A hipster newcomer that nails it, in large part due to its well-crafted drink program. Staff are dressed impeccably in tropical prints, banana earrings, etc. Lush plants and filtered sunlight.
You've got to go to a Cubs game if you're even mildly interested in America, Chicago dogs, or baseball. A classic like Fenway.
I was worried that this Chicago mainstay would be tired after so many years, but it's still so, so good. It was easy for me to get a seat at the bar as a party of 1.
Tiki bar with beautifully presented drinks, both classic and new-school. Caution! Long lines on Friday and Saturday nights. Would recommend weeknights or close to closing time.
The bar in the building formerly known as the Sears Tower. Expensive drinks, but you're there for the views. Skip if foggy.
Kickass modern art collection. I was floored by how many famous modern pieces they have. Go straight to the modern wing and get a crash-course on who's who in 20th century art.
Cocktail lounge -- no bar, just couches. Curious and fascinating drinks -- like an old-fashioned in a globe of ice, which you break with a slingshot so that it all falls into your glass.
The most delightful and enchanting dinner I have ever had? Reservations a few months in advance. Save for a special occasion, unless you're in from out of town -- then go for it!
Driving to the airport and want a pre-flight drink in one of America's most historical tiki bars? Check. Don't expect craft cocktails, though. This place is old school.
