Our “Second City”

Stop number one when re-creating Ferris Bueller’s Day Off. Yes, it is home to that one painting (Seurat’s A Sunday on La Grande Jatte). It is also where Madeleine works. Sorry, she cannot get you in for free.

Free and open to the public seven days a week. Taking up an entire city block, the stunning landmark building is home to the world’s largest Tiffany stained glass dome. A must-see!

For more than 25 years, the Chicago Architecture Center’s expertly trained docent volunteers have led the CAC River Cruise, sharing fascinating stories behind more than 50 buildings along the Chicago River.

Tom gives it two thumbs up.

Take a stroll along the river that changed direction in 1900. Sorry St. Louis. Grab a drink at City Winery or a beer at The Northman Beer & Cider Garden. Rent a kayak if you’re feeling adventurous.

Walk (or run) the path of greatness tread by Catharine Found. The Clarence Buckingham Memorial Fountain, one of the largest in the world, is located at Columbus Drive and Congress Parkway in Grant Park

A classic Chicago stop for burgers and beer tucked under the EL train.

Willis Tower or Hancock Tower, take your pick, go to the top. The latter has a bar the former a food hall (prices relative to elevation).

Even in September.

The Cubs are playing the Cincinnati Reds at 1:20pm on Saturday 9/28. Grab breakfast at Little Goat Diner before the game.

Go berserk like Spencer and Fisher over some dinosaurs, ancient objects, and groundbreaking science. If you’re looking for a souvenir, skip the gift shop and find a Mold-A-Rama machine.

Pack a picnic basket and enjoy a free outdoor concert or dance performance at the Pritzker Bandshell. Take a mirror selfie at Cloud Gate “The Bean.” Take a lap on the Maggie Daley Skating Ribbon.

Not for the claustrophobic. One of our favorite bookstores of all time with four insanely packed floors of used and new books. Just watch out for the puddles in the basement when it rains.

Hope it’s warmer for you.

White Sox vs. Angels at 1:00pm on Thursday 9/26.

Come listen to the unedited version of NPR’s comedy news quiz show performed Thursday evenings at the Fine Arts Building on Michigan Avenue.

Nope, not Giordano’s or Lou Malnati’s. Come here for some Star Trek on the TV, Punk Rock on the stereo, and great pizza.

Though Madeleine would vote Bungalow by Middle Brow.

Schubas Tavern. Eat dinner at Tied House before or after the show.

Metro. We would recommend dinner or just a drink at Uncommon Ground.

Clever Coyote is located on the second floor.

The Up Room is located on the 13th floor.

Wormhole Coffee knows the real drug is not caffeine but nostalgia. Bonus points for spotting the Xmas gift miracle of ‘84.

Jazz and gangsters

Decide for yourself if you are team Vienna Beef or team Chicago Red Hot.

Any Chicago Dog “Madeleine Style” would be sans celery salt. Ugh.

Chicago is a record town. High Fidelity was set here for a reason. Signal Records is our favorite.

We also like Reckless Records & Dusty Groove.

If someone offers you a shot of Malort, don’t take it.