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Sofitel Chicago Water Tower - Chicago Hotels
Rating: 4.5 Stars
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Sofitel Chicago Water Tower

20 E Chestnut St, Chicago 60611 - Map
 
 
4.7 out of 5 (2,636 reviews)
Located 1 block from Rush Street nightclubs, Oak Street shopping, and the Magnificent Mile, this 32-story Gold Coast hotel is …More
Loews Chicago Hotel - Chicago Hotels
Rating: 4.5 Stars
$249
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Loews Chicago Hotel

455 North Park Drive, Chicago 60611 - Map
 
 
5.0 out of 5 (11 reviews)
Located in Streeterville, this hotel is within a 15-minute walk of Tribune Tower, Wrigley Building, and Chicago Children's …More
Hard Rock Hotel Chicago - Chicago Hotels
Rating: 4.0 Stars
$209
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Hard Rock Hotel Chicago

230 North Michigan Avenue, Chicago 60601 - Map
 
 
4.3 out of 5 (3,536 reviews)
On Michigan Avenue and across from Millennium Park, this rock-inspired hotel occupies the 36-story, Art Deco-style Carbide …More
Hotel Felix Chicago - Chicago Hotels
Rating: 4.0 Stars
$175
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Hotel Felix Chicago

111 W Huron St, Chicago 60654 - Map
 
 
4.1 out of 5 (2,284 reviews)
Hotel Felix Chicago is 5 blocks from the Magnificent Mile, one of America’s most dazzling thoroughfares. It’s a 7-minute cab …More
Trump International Hotel & Tower Chicago - Chicago Hotels
Rating: 5.0 Stars
$475
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Trump International Hotel & Tower Chicago

401 N Wabash Ave, Chicago 60611 - Map
 
 
4.8 out of 5 (1,080 reviews)
Located in Near North Side, this luxury hotel is within a 10-minute walk of Wrigley Building, Tribune Tower, and Ford Center …More
The Drake Hotel Oak Brook - Oak Brook Hotels
Rating: 3.5 Stars
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The Drake Hotel Oak Brook

2301 York Rd, Oak Brook 60523 - Map
 
 
Situated in Oak Brook, this hotel is within 1 mi (2 km) of Oak Brook Golf Course and York Woods County Forest Preserve …More
Millennium Knickerbocker - Chicago Hotels
Rating: 4.0 Stars
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Millennium Knickerbocker

163 East Walton Place, Chicago 60611 - Map
 
 
4.3 out of 5 (3,423 reviews)
This 1927 landmark Chicago hotel is a half block from Michigan Avenue/Magnificent Mile shopping, two blocks from Oak Street …More
Hotel Allegro, a Kimpton Hotel - Chicago Hotels
Rating: 4.0 Stars
$159
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Hotel Allegro, a Kimpton Hotel

171 W Randolph St, Chicago 60601 - Map
 
 
4.3 out of 5 (2,620 reviews)
Located in the Loop's theater and business districts, Hotel Allegro Chicago - A Kimpton Hotel is next to the Cadillac Palace …More
Club Quarters, Central Loop - Chicago Hotels
Rating: 3.5 Stars
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Club Quarters, Central Loop

111 West Adams Street, Chicago 60603 - Map
 
 
4.3 out of 5 (4,625 reviews)
Club Quarters is a club-like hotel in the center of the Loop, Chicago’s central business district. A short walk to Symphony …More
Raffaello Hotel - Chicago Hotels
Rating: 4.0 Stars
$216
Check availability

Raffaello Hotel

201 E Delaware Pl, Chicago 60611 - Map
 
 
4.3 out of 5 (3,254 reviews)
Located on Chicago's fabled Gold Coast, this boutique hotel is adjacent to the John Hancock Tower, steps from stylish shops …More

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    Where to stay in Chicago

    Chicago Hotel Guide

    Home to the Willis Tower, one of the tallest buildings in the western hemisphere, Chicago, Illinois, flaunts one of the tallest skylines in the world. The Willis Tower stands tall in the Chicago Loop, which is the downtown area often considered the heart of all the city action. The architectural splendor and alluring city life invite visitors to experience the charm of the Windy City all-year round, so book your Chicago vacation today right here on Expedia.com.

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    Hotels

    Those who love to shop ’til they drop regard the accommodations along Magnificent Mile as some of the best hotels in Chicago. These accommodations that line the famous shopping district are just steps away from the upscale shops and department stores that provide retail therapy at its finest.

    Meanwhile, other visitors prefer staying at Chicago hotels near the shore of Lake Michigan or at resorts with views of the Chicago and Calumet Rivers. Regardless of whether you like to spend your vacation in towering high-rises along the Chicago skyline or in accommodations within walking distance of the famous Navy Pier, you can acquire cheap hotel deals in Chicago that will exceed all of your Windy City expectations.

    Transportation

    The Chicago Transit Authority (CTA) offers one of the best ways of traveling around Chicago. The CTA buses and trains offer reliable and affordable service to areas in and around the city. Commonly called The L, the train system is based on color-coded line. To ride, travelers must purchase transit cards at any CTA station. As for the bus, stops are around four blocks apart on major streets, and you can ride with preloaded money on transit cards or with exact change. Some train and bus routes do run all night, so check the map schedules for early morning or late night transportation.

    Walking in downtown is another easy way of getting around in Chicago. Although vacationers find the streets simple to navigate, those trying to drive in the Loop may face traffic and hefty parking fees. For hassle-free transportation, hail a taxi as the fares are cheaper than in other major cities.

    Travel Basics

    When it comes to exploring the city, navigating is quite easy when compared to other complicated city layouts. In general, blocks include roughly 100 addresses, and each block is around one-eighth of a mile. Therefore, an eight-block stretch is generally more or less one mile. With a few exceptions, most avenues run north to south, while streets run east to west. Although Chicago is considered a safe city, as is the case with any city, you’ll want to avoid looking lost or acting like an unfamiliar tourist.

    Weather

    Don’t underestimate the windiness in the Windy City. This destination experiences all kinds of gusts of wind from Lake Michigan during every season, from cool breezes in the summer to nose-freezing bursts in winter. Chicago serves up frigid temperatures, snowflakes, and blustery winds from November through March. If you can brave the low digit temperatures, you’ll find cheap hotels deals in Chicago during the winter months.

    For warmer temperatures and a more pleasant outdoor experience, visit Chicago any time between April and October. The spring and fall temperatures are mild, while the summer months generally bring temperatures ranging in the mid-80 degrees Fahrenheit. With that being said, the nights do tend to cool down, so bring layers to prepare for chillier temperatures.

    Throw caution to the Chicago wind when it comes to booking your getaway, as there are tons of things to do to keep you busy regardless of the season in this city hot spot. Browse our vast selection of hotels, car rentals, and flights to Chicago right here on Expedia.com, and book the hottest deals around today.

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    *For these packages, package savings is at least equal to the cost of the flight or hotel if booked separately. Note: For packages including flights, you will be charged by the airline for the flight, but your savings on the package will equal the cost of the flight.