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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

DAY 1 | This is not a trip on which to count calories, starting with breakfast at local favorite Original Pancake House (1). The enormous, fluffy, oven-baked omelets and the loaded baked apple pancake are house specialties—you’re on your own to answer the age-old question of sweet or savory. Fortified, you set out to explore the Gold Coast (2). Once home to the city’s steel magnates and retail tycoons (along with Abraham Lincoln’s son), this has been a posh neighborhood since soon after the Great Chicago Fire of 1871. Feel the lake breeze and drift into posh boutiques such as Shrine haberdasher and the Euro-inspired Sarca, as well as more well-known brands such as Marc Jacobs.

Journeying south, you eventually hit the Magnificent Mile, Chicago’s shopping mecca, marked by the Water Tower (3). One of the only structures to survive the fire, this building looks like a fairytale castle, and to fashionistas it kind of is. Familiar clothing outlets like J. Jill and Lacoste line the shiny interior alongside the shimmering storefronts of several jewelers.

Take a quick diversion off of Michigan Avenue for lunch at Portillo’s Hot Dogs (4). The Chicago-style dogs—with pickle relish, hero peppers, chopped tomato, onions, mustard and a pickle spear on a poppyseed bun—are delicious. An equally good choice, though, is the heartier Italian beef sandwich with hot and sweet peppers, served au jus. The thinly sliced roast beef and roasted sweet peppers melt into the now-soggy bread, with the hot peppers and giardiniera (Chi-town’s signature mix of pickled veggies) adding just the right amount of kick.

You roll yourself out of the restaurant grateful that your next activity involves sitting and amble south- east to the Chicago River for the Chicago Architecture Foundation’s boat tour (5). Cruising down the waterway, you’ll get a who’s who of great architects—Mies van der Rohe, Daniel Burnham and Charles B. Atwood, to name a few—who masterminded career-defining structures to make their mark on the city. The volunteer guides, mostly practicing or retired architects, also spin the fascinating tale of how the city fathers rebuilt very deliberately after the Second Industrial Revolution– era fire, creating parks and beachfront all around the bustling downtown.

Ninety minutes later, you step off the boat with a great appreciation for the city’s past. Ready to learn about its present, you make a quick stop at the Chicago Cultural Center (6). Regulars come here for the expertly roasted Intelligentsia coffee and WiFi, but stick around for the rotating art exhibits, mostly the work of local artists.

Check into the Elysian Hotel (7), a posh, almost unmarked villa set back from the street to make you feel as if you’re escaping the city for a night. Take a few minutes to explore your massive room and soak in the view from the balcony. The rooftops below are planted with grass to absorb rainwater and provide insulation. The foliage ripples slightly, making for an urban landscape like none you’ve ever seen. But you don’t have too much time to take it all in—you’ve got to eat.

Tonight’s dinner is at Rick Bayless’ much-lauded Frontera Grill (8). You can’t go wrong with anything on the menu at this upscale Mexican cantina. The food is fresh, flavorful and perfectly accented by a spicy cocktail called the Michelada Moderna—like a Bloody Mary but made with beer. Feeling adventurous, you try the goat taquitos, which arrive sprinkled in queso fresco and turn to butter in your mouth. Linger over dinner, taking in the clubby digs before you retire to the cloudlike king bed at the Elysian.


(1) Original Pancake House 22 E. Bellevue Pl.; Tel: 312-642-7917
(2) Gold Coast East of Clark Street and north of Chicago Avenue
(3) Water Tower 806 N. Michigan Ave.; Tel: 312-742-0808
(4) Portillo’s 100 W. Ontario; Tel: 312-587-8910
(5) Chicago Architectural Foundation boat tour Southeast corner of the Michigan Avenue Bridge at Wacker Drive; Tel: 312-922-3432
(6) Chicago Cultural Center 78 E. Washington St.; Tel: 312-744-6630
(7) Elysian Hotel 11 E. Walton; Tel: 312-646-1300
(8) Frontera Grill 445 N. Clark St.; Tel: 312-661-1434

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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