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Three Perfect Days: Chicago

Nicknamed “The City of Big Shoulders,” Chicago sets the bar pre y high.But with its strollable neighborhoods, sunny lakefront parks and thriving food scene, America’s third-largest city more than carries the load

Author Layla Schlack Photography Bob Stefko

The Elysian Hotel lobby

Picture 1 of 14


Chicago lines its lakefront with miles of urban beaches

12th Street Beach On a little island near the Adler Planetarium, this uncrowded beach feels as if it’s miles from the city.

North Avenue Beach (shown below) Just beyond Lincoln Park, this spot offers amazing skyline views and a beach house that looks like a boat. Locals love it, so you may find a bit of a crowd.

63rd Street Beach The big draw here is history: A woman who once dared to bathe without a skirt on was legendarily arrested on this beach, and there’s a lovely bath house built in 1919. Concerts and volleyball courts are bonuses.

Osterman Beach A boardwalk and shallow wading area make this a favorite destination for families with small children.

Montrose Beach This vast stretch is where locals come to hang out and party. You’ll find people grilling and dogs frolicking, with ample space for everyone.


What do John Candy, Tina Fey and Mike Myers have in common? Aside from being hilarious brunettes, they’re all alumni of Chicago’s Second City improve theater, along with countless other heavies, from Joan Rivers to 30 Rock’s Jack McBrayer. Opened in 1959, Second City forged a new genre somewhere between standup comedy and theater. Experience it for yourself at one of the nightly shows. Appearing this month are South Side of Heaven, a hilarious look at Chicago’s South Side, and Fair & Unbalanced, a revue of some of the theater’s greatest hits. You’ll probably see some future Saturday Night Live stars here, which is why the theater continues to be such a draw and also why you should book early.



Jeanette Tremblay
Prints and drawings department, art institute of Chicago museum
“My summer evening guilty pleasure is Margie’s Candies in Bucktown. It opened in 1921 and exudes history (and kitsch!). My all-time favorite is the coconut ice cream sundae.”

Grant Achatz
Chef, Alinea, Aviary and Next
“One of my favorite places in Chicago is a Japanese restaurant called Katsu. It has been open for 23 years, yet very few people know about it. The sushi is some of the best I have had outside of Japan.”

Laurel Gray
Concierge, The Ritz-Carlton
“I like to do a lot of vintage shopping, and one of my favorite places is LuLu’s at the Belle Kay. It’s great for accessories, hats, shoes, jewelry, things like that. I’ve gotten some good stuff there over the years.”

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2 Responses to “Three Perfect Days: Chicago”

  1. Dave Says:
    April 3rd, 2014 at 4:03 pm

    On my first visit to Chicago, I did spend a few days there and you were right! I wanted to MOVE there. I have since been back more than 20 times and each time is a new adventure. I love it there!

  2. VICKIE Says:
    November 27th, 2015 at 11:28 am

    love it good to know while I visit chicago

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