Chicago, IL - Jim Flynn's BestWeekends

Chicago, IL

Chicago, IL Overview

Anyone who has spent any time in Chicago quickly falls in love with this charming city. I lived there twice in my career and both my kids were born there, so it has a special place in my heart. Despite winters that can be quite brutal (ever been stuck in O’Hare in February?), Chicago has much to recommend it as a terrific weekend destination. You’ll find world class accommodations and dining, one of the best art museums in the world, a rich cultural tradition, the Cubs and Wrigley Field, Navy Pier, wonderfully diverse neighborhoods and in the Magnificent Mile, one of the best shopping stretches anywhere. Add a lakefront location (is there any other city that has urban beaches?), a gorgeous skyline, friendly Midwestern people, authentic Chicago Blues and that Saturday Night Live incubator, Second City and it will quickly go to the top of your “must see” lists.


When To Go

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Getting There

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Getting Around

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Things To Do

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Dont Miss

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Good to Know, Good to Go

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Special Things

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Where To Stay

Peninsula Hotel

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OVERVIEW Since 1928 Peninsula Hong Kong has set the world standard for exceptional service, style and comfort. In 2001 Peninsula Chicago opened and quickly reached the pinnacle of American hotels. It is consistently rated one of the top three or four hotels in the country. Hotel entry is at street level where you are whisked...…

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Sofitel Hotel

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OVERVIEW Sofitel Hotels are a favorite of ours and are recommended in our New York, Washington, DC and LA profiles. As I have said before you get a 4 star experience at a 3 star price. Their weekend rates are amazingly reasonable given the style and ambiance you enjoy. The Chicago hotel is no exception,...…

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Trump International Hotel

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OVERVIEW Say what you want about Donald Trump, the man knows how to do a hotel right and the Chicago incarnation is no exception. Located in the Loop beside the Chicago River, the soaring 92 story Trump is a bold design against the Chicago skyline. The views from the signature floor to ceiling windows are...…

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Where To Eat

Gibson’s Bar and Steakhouse

There may be better steaks in town, but it is tough to beat the vibe at Gibson's in the heart of the Gold Coast. A favorite of locals for years, it is also a "must stop" for visiting celebrities and sports stars. Seldom will you dine here without seeing someone famous. You just can't help…

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Le Bouchon

I have a soft spot for French bistros and they don't come more authentic than Le Bouchon, a low-key, relaxed, bistro, which from the outside, looks like a traditional Irish/European pub. Inside, the tiny restaurant is intimate and classically decorated with warm booths, colors of beige and red, wicker baskets, floral arrangements and historical French…

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Les Nomades

If pedigree means anything to the success of a restaurant, then it explains Les Nomades perch atop the list of Chicago restaurants. Owner Mary Beth Liccioni and her husband Chef Roland spent a portion of their career working with acclaimed chef Jean Banchet at Le Francais in Wheeling and later bought the restaurant from Banchet.…

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Advance Search

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May 2020: Little Nell

This months featured property is… charming and sweet. THE ROOMS In 2017, Champalimaud Design refreshed all 86 rooms and suites and all guest floor corridors. The approach was to reinvigorate the spaces to be fresh, light and welcoming, utilizing palettes of blue, tan and grey to complement the relaxed nature of Aspen. Key features include… read more.

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