Chicago may go by the moniker Chi-town, but make no mistake: The Windy City is anything but timid. From bold art and awe-inspiring landscapes to comedy clubs and groundbreaking jazz, your next destination doesn’t hold back. Savor the energy of the city, and when the day is done, hide in historic Chicago hotels or relax to the lullaby of the rushing river with a balcony view. As Nelson Algren once famously penned, “Chicago is an October sort of city even in spring.” While we’d be delighted to tell you that the Windy City boasts golden and rust-colored foliage year-round, it’d be more accurate to assume Algren was writing about the invigorating feeling the city gives you when set your heart to exploring.
Historic Hotels in Chicago
Some of the best places to stay in Chicago have stood the test of time, much like the Toddling Town itself. In the Chicago Loop, book iconic Chicago lodging near the city’s contemporary masterpieces at the Art Institute of Chicago and Millennium Park:
- Congress Plaza Hotel: Located across the street from Buckingham Fountain, Congress Plaza Hotel doesn’t even pretend to be a product of this century. Since its doors opened in 1893, the grand lobby has welcomed many famous guests, including Theodore Roosevelt and Woodrow Wilson, and the brick walls have witnessed history in the making.
- The Palmer House Hilton: Since its completion in 1875, The Palmer House Hilton, too, has hosted its share of presidents and celebrities—James Garfield and Mark Twain should sound familiar. After a day browsing the exhibitions at the Chicago Cultural Center, pause for a moment of reflection at the bean-shaped “Cloud Gate Sculpture” before returning for a relaxing night of cocktails and fine dining at Lockwood, or order in and draw a hot spa bath.
Where to Stay in Chicago with a View of the River
On the banks of the Chicago River, you’d never believe that the winters here are snowy and the summers balmy, because the urban waterway rarely slows down. Although serene and romantic, a lazy river this is not. If the water calls to you, wine and dine on a dinner cruise and follow the current out to picturesque Lake Michigan.
The Hyatt Regency Chicago and Wyndham Grand Chicago Riverfront are both located directly south of the Chicago Riverwalk and are exquisite options for decadent vacation brimming with amenities and fine dining:
- Book an event in one of the elegant ballrooms at the Wyndham and host the day-after brunch for a friend’s nuptials at the Hyatt Regency. Nothing says new beginnings quite like the sight of a river reaching the Great Lakes.
- Or, better yet, treat yourself to a waterfront suite after the last glass of Champagne has been sipped. Order a bottle to your room and settle in by the window with a good book.
About Those Comedy Clubs
There’s nothing more stylish than a sincere belly laugh, and Chicago will help you unleash your most elegant self. North of the Loop, the chortles flow like water rushing out to Lake Michigan. One of the most beloved comedy clubs in the U.S.—The Second City—is located in Old Town Triangle, and as you follow North Avenue, you’ll embark on quite the comedy crawl.
Line up an itinerary with shows at UP Comedy Club, Zanies Comedy Night, and The Comedy Clubhouse. Stay nearby at Hotel Lincoln Chicago, where your comfort is no laughing matter. You can even chase a late night with in-room breakfast or lean into the after-hours amenities in the 24-hour fitness center. All that laughing is energizing, after all…
From the Magnificent Mile to Wrigley Field, Chicago will revive and inspire you to be who you want to be and pursue the adventures that intrigue you. Whether you plan to relax to the sounds of water on the river banks or take comfort in a chorus of good humor, book cheap hotels in Chicago with Travelocity. We’ll match the lowest price on the hotel of your choice, so just like the Windy City, don’t be shy, traveler.