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Chicago in the fall. It’s the best time to be here. Now summer is pretty wonderful in The Second City but the scene can be a bit manic. Autumn in Chicago is the more contemplative and refined season, when drinking and doing turns to observing and thinking. If you’re planning on traveling here this 2014, I recommend visiting us in a month that ends in -BER. Here’s why.


  • Chicago in the fall is mild, clear and sunny. No temperatures in the triple digits, no walls of snow. Average temperature in September: 65; October: 53; November: 40; and December: 27.

Below: Chicago Botanic Garden in November.

Botanic Gardens Chicago Red Berries

  • Chicago in the fall is more beautiful than any other time of year. The light is incredible (I take my best photos in September) and the fall foliage turns to every shade of red, orange and yellow.

Below: Chicago Botanic Garden in November.

Chicago in the Autumn Chicago Botanic Garden

  • People look their best in Chicago in the fall. The sleeveless smocks of summer reveal a myriad of flaws and there’s nothing attractive about dressing like the Michelin Man to face a January day in The Windy City. But autumn in Chicago flatters: black tights paired with leather ankle boots, light cashmere sweaters, colorful scarves, berets placed askew, tweed blazers: it’s difficult not to be fashionable in October.
  • Fewer tourists in Chicago in the fall means shorter lines and better rates.
  • Chicago’s best events of the year are held in autumn. Specifically:
    • The Bank of America Chicago Marathon
    • The Chicago Humanities Festival and Chicago Ideas Week
    • The Chicago International Film Festival
    • The SOFA (Sculptural Objects and Functional Art) exhibit, One-of-a-Kind sale, and Renegade Craft Fair

Below: Louis Thompson glass bottle at SOFA.

Autumn in Chicago: Louis Thompson glass bottle at Sculptural Objects and Functional Art

  • The college kids have returned, livening up the Near West Side, Lincoln Park, Hyde Park and Evanston again. Both Northwestern (in nearby Evanston) and the University of Chicago (in Hyde Park) are often listed among America’s most beautiful college campuses. I recommend taking the short drive south along Lake Michigan to see the U of C architecture when the campus is teeming with coeds. While you’re in the area, take a tour of the Frank Lloyd Wright Robie House and a walk-through of the Oriental Institute Museum, a world-renowned showcase for the history, art, and archaeology of the ancient Near East.

Below: photo from the Oriental Institute Museum.

Oriental Museum Horse

  • All of Chicago’s major sports teams — the Bears, Bulls, Blackhawks, Cubs and White Sox — play between September and December. Chicago is one of only four U.S. cities to have teams from the five American Major Professional team sports.
  • Chicagoans are into Halloween. Walk around neighborhoods like Lincoln Park on October 31 and compare the over-the-top decorating competitions, cute little costumed kids, and peek into the lit-up, open-doored McMansions and contemporary homes that are closed-off the other 364 days of the year. End your evening at the outlandish and hilarious North Halsted Street Halloween Parade.

The Points Guy, a travel blogger I read daily, shares my appreciation for Halloween in Chicago in his post Best Cities to Celebrate Halloween.

Lincoln Park at Halloween

Chicago restaurants break-out their comfort food menus in the autumn. Try the pork shoulder entree at Avec, the french onion soup at Mon Ami Gabi and any item served at North Pond, the quintessential Chicago fall restaurant.

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If fall is the best season to visit Chicago (and it is), my assertion begs the question, “what are the best things to do in Chicago in the fall?”

I can think of dozens of great things to do in Chicago in the fall off the top of my head, but if forced to narrow them down to just a handful, I recommend the following activities.



The Chicago Botanic Garden is my favorite outdoor space in the area, and one of the top things to do in Chicago at any time, but especially fall when the colors are most vivid. The attraction encompasses 385 acres of land, nine islands, 26 gardens, 4 natural areas and an internationally renowned bonsai collection. In addition to horticultural displays, the Garden presents a wide variety of exhibitions, including fine photography and an array of artwork. An indoor/outdoor cafe is available.

Fluffy weeds Chicago Botanic Gardens

Chicago Botanic Gardens Path

Chicago Botanic Gardens Building

Chicago Botanic Gardens Fountain

The Chicago Botanic Garden is located 20 miles north of Chicago in Glencoe, and it is accessible by car, train or bicycle.

Next best thing to walking the Chicago Botanic Garden: Walking the Morton Arboretum.


If you drive to the Chicago Botanic Gardens, return to downtown Chicago via scenic Sheridan Road, which runs along Lake Michigan, past multi-million dollar homes, through brilliant fall foliage and straight to the resplendent Baha’i House of Worship in Wilmette.

Only eight continental houses of worship have been built around the world and all are unique, nine-sided domes (most resemble orange  juicers). The one in Wilmette is made entirely of white concrete inscribed with writings and symbols of many religions.

Obviously you can visit the Baha’i House of Worship any time of the year, but I believe its best captured in the autumn light.

Bahai Temple Wilmette

Bahai Temple Chicago

Chicago Bahai Temple

Next best thing to visiting the Baha’i House of Worship: Visiting The Elks Veterans Memorial


No, I DO NOT recommend RUNNING in the Chicago Marathon! That’s masochistic. I recommend observing it (with drink in hand).

Every year half of Chicago hauls their furniture to the curb, breaks out the bagels, mixes up a few batches of bloody marys, scrawls some signs and digs out their noisemakers to support the 45,000+ runners from 100+ countries participating in the Chicago Marathon It’s kind of a party. My favorite vantage point is the intersection of Wells Street and North Avenue where an Elvis impersonator performs each year.

The 2014 Chicago Marathon will be held on October 12.

Next best thing to cheering on the Chicago Marathon runners: Cheering on the North Halsted Street Halloween Parade contestants.


Jon Hodgman. Rick Bayless. Ian Frazier. Gary Shteyngart (travel writing GOD). Dan Savage. Jonathan Safran Foer. Temple Grandin. The Chicago Humanities Festival corrals the most interesting, erudite, humorous and relevant people, ships them to Chicago, and makes them talk for an hour for the benefit of you and me. Their mission? Creating opportunities for people of all ages to support, enjoy and explore the humanities. Who knew learning could be so much fun. It’s the best of the cerebral things to do in Chicago.

The 25th Anniversary Festival kicks-off on October 25 (2014).

Next best thing to getting cultured at the Chicago Humanities Festival: Getting cultured at Chicago Ideas Week.


Every year I go. Every year I lust after the dazzling, sparkly, fragile things I can’t afford. Every year I go home empty-handed.

SOFA is the annual Sculptural Objects Functional Art + Design show held at Navy Pier (the ONLY reason to ever, ever go to Navy Pier).

From the SOFA website:

SOFA CHICAGO, the largest and longest continually-running art fair in Chicago, is a mainstay in its cultural and social calendar. Mary Daniels, senior arts writer, The Chicago Tribune, wrote, “New art forms never before seen and rich artisan traditions come together in a synergistic explosion of creativity at SOFA CHICAGO… A sense of discovery and surprise always permeates this show, one of the most anticipated cultural events in this city.” Jim Yood, critic and historian, Art + Auction and Chicago Public Radio/WBEZ-FM, said, “SOFA’s high-end, cutting-edge mix clearly has global appeal. It’s a really wonderful art fair.”

Everything is fabulous. And expensive (some pieces reach the six figures). There’s no harm in dreaming, right?

Sculptural Objects and Functional Art Scott Jacobson Gallery Piece

Sculptural Objects and Functional Art Louis Thompson Glass

Sculptural Objects and Functional Art Marta Klanowska Chamois

Sculptural Objects and Functional Art Louis Thompson Glass Bottles Blue

SOFA 2014 begins on October 31.

Next best thing to salivating at SOFA: Salivating at the One of a Kind Show and Sale. Again, extraordinary handmade creations by talented artists, except these prizes are actually affordable.


So there you have it: the best things to do in Chicago in the fall. I don’t want to brag but — I’ve traveled the world, and — Chicago’s got it all! Natural beauty, culture, shopping, architecture, etc. all wrapped-up in a nice little Midwestern package for you to dig into!

See you in September…

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Finally! 10 straight days at home in Chicago for the first time since June. No work travel, no leisure travel, no personal obligatory travel. No suitcases, no miniature toiletries, no Project Runway marathons. My own food, my own bed, my own car, my own house. Heaven!


Cats! Ez attacking my feet beneath the covers, malevolent Mia chasing Ez across the bed (and over my back), Mia now batting the cord to the venetian blinds above my head to get my attention.

5:08 a.m. and there goes the ‘L’ train, shaking my bed. And here comes the sun (damn Eastern exposure) — over the ‘L’ tracks and straight through the catawampy blinds destroyed in protest during one of my frequent absences.

The sound of the wind whipping across Lake Michigan reaches right up into my bed and judging by the non-stop whir of my furnace it’s a cold one out there today. Too cold to walk to the gym. And too cold to go to the store for groceries. Yet, I have no food in my house…

I’m checking-in to a hotel.



Chicago’s obviously a big, cosmopolitan city with more luxury hotels than you can shake a stick at, but ask any in-the-know local and you’ll probably learn that the Waldorf Astoria Chicago is generally regarded as the best of the bunch. It’s the only AAA five-diamond hotel in The Second City with 5 out of 5 bubbles on Tripadvisor and Travel + Leisure ranked it 44th on their World’s Best Hotels 2013 list. And for today — a chilly late-autumn weekend — I can think of no better place to stay in my fair city. Some hotels just fit certain seasons, and the Waldorf Astoria Chicago especially shines in The Fall.

To be specific, here are 40 reasons to love the Waldorf Astoria Chicago during a blustery November weekend:


  • The Waldorf Astoria Chicago is situated in the heart of the city, dangerously close to the best shopping ($$$$) and restaurants ($$$$). I could throw a Manolo Blahnik from my balcony and hit Barney’s


  • The roasted mushroom appetizer in Balsan is umami heaven
  • Bernard’s is Chicago’s coziest boîte and my new hangout
  • Subtle nods to Coco Chanel and Dior throughout the property (check-out the corset-styled drapes in the lobby)
  • Original, unique, Louvre-worthy artwork by Dawn ClementsJavier Marin and others
  • That insane, 8-foot-wide starburst chandelier in the lobby (modeled after one of Coco Chanel’s brooches)

Waldorf Astoria Chicago chandelier


  • The Waldorf Astoria Chicago accepts and awards Hilton HHonors points
  • Tipping is discouraged
  • A small fleet of Lexus vehicles are available (complimentary) on a first-come, first-served basis to transport guests within a two-mile radius of the hotel
  • Free wi-fi
  • Gratis newspaper delivery
  • Shoeshine service on the house
  • Pets welcome (I left Ez and Mia at home)


  • The Waldorf Astoria Chicago lobby features marble floors, classical busts, and a nickel ribbon wall
  • Private cobblestone entry

Waldorf Astoria Chicago Lobby


  • Scored a courtesy upgrade!
  • The suites, the suites, the suites. Did I mention the suites? Spacious, spacious suites
  • Large, private entryways. It doesn’t sound like much, but they make you feel like you’re living in a Manhattan Upper East Side penthouse rather than staying in a standard hotel room
  • Champagne and platinum color scheme (classy)
  • Artwork (the bright colors contrast nicely with the champagne/platinum and lend a feminine touch)
  • High ceilings, airiness and plenty of natural light
  • One-touch lighting, doorbell and privacy button

Living Room

  • A working fireplace! Perfect for today. Or any day in Chicago in November, really
  • Massive balcony
  • Chicago skyline and glimpses of Lake Michigan
  • 180 degrees of windows
  • Copies of Chicago Social magazine

Waldorf Astoria Chicago Guest Living Room

Waldorf Astoria Chicago Guest Balcony

Waldorf Astoria Chicago Skyline


  • iPhone charging deck + speakers (although it does not accommodate an iPhone 5)
  • Beds composed of clouds. I fell asleep with the tv on (NOT classy)
  • Silence! Like sleeping in a tomb. I overslept without any sounds  of the city to wake me


  • Elaborate master bath with mosaic tile floors, marble walls, an oversized soaking tub, shower the size of a racquetball court,  and toilet telephones (?)
  • TVs embedded in the mirrors
  • Ferragamo bath products

Waldorf Astoria Chicago Guest Bathroom


  • High-end silver fixtures, top-notch linens (the draperies cost more than I earn in a year), crown molding and beveled mirrors
  • A hotel gift of Elysian Spa & Health Club products
  • Custom stationery
  • Microwave, in-room ice and wet bar


  • The Waldorf Astoria Chicago gym is ridiculously equipped
  • Complimentary fitness classes, including pilates (high-tech machines available) and gyrotonics (whatever that is)
  • Lap pool, private locker room, whirlpool, sauna and steam room

Waldorf Astoria Chicago gym

Well, that was a wonderful little respite from reality. Although I already miss Ez and Mia. Time to return home.

“Car, please?”

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