City Guide: Chicago


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The tenth in our new City Guide series, this travel guide to Chicago, Illinois, features the most pertinent information about the area. Use the menu below to jump among sections for suggestions on where to stay, insider tips, restaurant recommendations and more.


 Chicago City Overview & Map

View of the Chicago skyline and Grant Park
View of the Chicago skyline and Grant Park - ©

Hunkered down at the southwestern edge of oceanic Lake Michigan, Illinois’ largest city (and the nation’s third-largest metropolis) has endured devastating fires, Al Capone’s corruption and beleaguered baseball teams. Yet its hearty Midwestern character not only endures but flourishes, with dazzling architecture, gritty blues, innovative theater and comedy, rich cuisine and a welcoming heartland disposition.

Most visitors stay in or near the downtown area, and there are ample attractions here, such as the nation’s tallest skyscraper, the Willis Tower, built as and still commonly referred to as Sears Tower; the art deco masterpiece The Chicago Board of Trade Building; and the resplendent civic green space of Grant Park. The postmodern public art of Millennium Park and the world-renowned Art Institute of Chicago can constitute an afternoon alone.

But for a truer taste of the city, venture out into the neighborhoods, exploring the North Side’s theaters, bars and clubs (and vintage baseball stadium, Wrigley Field) or the bohemian havens of the West Side, where, in Wicker Park, an independent arts scene thrives and Polish and Ukrainian cultural attractions offer a taste of the city’s Slavic roots. Enjoy a beer and sausage to bridge the Old World with the New.

 Chicago Travel Tips

Cloud Gate sculpture
Cloud Gate sculpture - © Sterling E. Stevens

When to visit, tastemaker tips and what to do in Chicago.

When to Visit Chicago

Peak season is June – August, when locals take full advantage of the parks and beaches along the lakefront. And Chicago’s rich cultural scene offers ample opportunities to escape the chill in winter.

Tastemaker Tips

Want to experience Chicago like an insider? Follow these tips from notable individuals in the travel, design, food, fashion and hospitality industry.

Andrew Harper, Editor in Chief of The Hideaway Report, Andrew Harper Travel

Andrew HarperThe Willis Tower (formerly the Sears Tower) has the tallest observation deck in Chicago, but because it’s located in the center of the city, it doesn’t have the best views. I prefer ascending to The Signature Lounge at the 96th in the John Hancock Building. This aerie at the northern end of Michigan Avenue provides sensational panoramas of the whole of Chicago’s downtown, and it can be accessed for the price of a cocktail. The tables on the left have the best positions.

Joe Colucci, Travel Advisor, Andrew Harper Travel

I would recommend an architectural cruise and two half-day trips to the Art Institute of Chicago, one to enjoy its masters' collection and the second to explore The Modern Wing. Also, stroll down Michigan Avenue (the Magnificent Mile) and stop at Millennium Park, which is one of the city's most gorgeous bits of urban planning. While there, don't miss the Cloud Gate sculpture, locally known as "The Bean," a stunning site-specific work.

  Hotels: Where to Stay in Chicago

Four Seasons
Four Seasons

Their names may have a familiar ring, but The Four Seasons and The Peninsula continue to set the standard for lodging in Chicago. Both are located along the Magnificent Mile, the dizzying stretch of Michigan Avenue that runs from the Chicago River to Oak Street.

  Restaurants: Where to Eat in Chicago

Spiaggia Ravioletti
Spiaggia Ravioletti - © Spiaggia

Chicago chefs are able to take advantage of the bounty of the heartland, with its incredible variety of produce and livestock, as well as dairy products from Wisconsin and fruit from the orchards of Michigan.


No one can argue about one attribute of this restaurant: The view is magnificent, as Everest is perched on the 40th floor of the Chicago Stock Exchange. The interior is low-key, with pale colors and discreet lighting. The food, however, will certainly grab your full attention. Chef Jean Joho hails from Alsace, and he combines that heritage with top American ingredients, as in a starter of crusted Berkshire pork cheeks with a choucroute salad. Among the main courses, you could find fillet of sole meunière with mousseline potatoes and petite capers, or rack of lamb with slow-cooked fava beans, fingerling potatoes and mint pistou. The wine list contains more than 1,600 selections. Closed Sundays and Mondays. 

Les Nomades

This is one of the prettiest restaurants in the city, set in a turn-of-the-century brownstone. The menu is contemporary French. Look for the rich assortment of house-made pâtés served with cornichons and toasted brioche. Main courses might include Arctic char with maitake mushrooms, forbidden rice and tapenade in a yellow tomato-lemongrass sauce; or braised beef short rib with root vegetables and trumpet royale mushrooms in a shallot sauce. The extensive wine list has 17 selections by the glass. Closed Sundays.


The city’s finest Italian restaurant overlooks Oak Street Beach and showcases the talents of chef Tony Mantuano. The main dining room has been redesigned for its 30th anniversary. The seasonal menu changes, but look for pastas such as ravioli with foie gras, hazelnuts, rhubarb and 18-year-old balsamic vinegar; or potato gnocchi with ricotta sauce and black truffles. Main courses might include Atlantic hake with Petrossian caviar, oyster cream and onion confit; or a free-range veal chop with asparagus, wax beans and baby arugula.

  Things to Do: Sightseeing in Chicago

Spirit stones arranged in the style of a classical Chinese garden at the Field Museum
Spirit stones arranged in the style of a classical Chinese garden at the Field Museum

Don't overlook these iconic sightseeing attractions while visiting Chicago.

  Chicago Itinerary Suggestions

A visit to Buckingham Fountain makes for a perfect day in Chicago
A visit to Buckingham Fountain makes for a perfect day in Chicago - Photo by Hideaway Report editor
Green Mill Cocktail Lounge
Green Mill Cocktail Lounge - © Mike Powers

Want to learn more about travel to Chicago? Read our in-depth articles from The Harper Way, The Hideaway Report and Traveler Magazine on topics such as shopping, food, wine, art, culture and more.

  Trip Ideas: Destinations to visit from Chicago

Frank Lloyd Wright Home & Studio
Frank Lloyd Wright Home & Studio

Discover the best destinations around Chicago as recommended by our team of well-traveled editors.

Stay tuned for more from our City Guide series, detailing what to do, eat and see, and where to stay, in Andrew Harper's favorite cities around the world.

Want our full travel guide to The United States? Purchase a copy in the Harper shop.

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By Hideaway Report Staff

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