Chicago is a fantastic place for a vacation any time of year. With a large variety of activities and attractions, a vacation in Chicago will appeal to travelers of all ages with diverse tastes and preferences. Get ready for some fun Chicago adventures. If you’re planning a getaway in Chicago, Expedia can make booking your vacation both convenient and affordable. With plenty of great deals on Chicago resorts to choose from, you’re sure to find incredible rates when you use Expedia to book your trip.

On the hunt for luxurious accommodations during your trip to Chicago? Expedia can connect you with some of the best Chicago resort hotels. With Expedia’s great deals, you can indulge in luxurious amenities like fine dining, thrilling recreational activities, and state-of-the-art fitness centers. If you’re in the mood for pampering and deep relaxation, Expedia can help you find Chicago resorts with spa services like massage and skin care treatments. You deserve to relax and indulge on your getaway! If you’re on a budget and think you can’t afford a Chicago vacation resort, think again and take a look. Expedia offers a number of cheap vacation packages at top resorts in Chicago that will make you forget your worries during your stay and let you enjoy the pampering you deserve.

Depending on your lodging wishes, Expedia offers great deals on the sizes of rooms and luxury suites at different resorts in Chicago to meet your needs. Want to spoil yourself with an amenity-rich luxury suite during your vacation? Expedia can help you find a great place for your stay within your budget. Or, perhaps you need a small room or even multiple rooms? Expedia’s easy online booking lets you reserve whatever type of room you need quickly and conveniently. Chicago resort is waiting for you.

Expedia will save you money and time when booking your reservations at a Chicago resort so you can enjoy your vacation and not worry about planning and your accommodation budget. There are endless ways to create new and memorable travel experiences while enjoying Chicago. Let Expedia connect you with the best resorts in Chicago today!
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All Hotel & Resort Deals in Chicago

Find the Best Resorts in Chicago

Expedia can help you find the best resort deals in Chicago. Filter by popularity, hotel star rating or resort name to find the ideal resort package in Chicago for you and your family.

W Chicago Lakeshore

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644 N Lake Shore Dr, Chicago, IL
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The 33-story W Hotel, offering superb lake and city views, is 2 blocks from Ontario Beach, Navy Pier, and Northwestern University; the Magnificent Mile and Rush Street are within 2 miles. read more
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The Westin O'Hare

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6100 N River Rd, Rosemont, IL
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2 blocks from the Blue Line train to downtown Chicago, this business-oriented hotel provides complimentary shuttle service to and from O'Hare International Airport, 2 miles away. Shuttle runs every 30 minutes from 5:00AM - 7:00AM; and every 15 minutes from 7:00 AM to 10:00 PM. From 10:00PM to 12:00AM the… read more
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Westin Chicago Northwest

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400 Park Blvd, Itasca, IL
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Westin Chicago Northwest is 5 miles from Woodfield Mall shopping and the Schaumburg business district, 12 miles from O'Hare International Airport, and 27 miles from downtown Chicago. read more
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Hotel Monaco Chicago, a Kimpton Hotel

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225 N Wabash Ave, Chicago, IL
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Hotel Monaco Chicago - A Kimpton Hotel, a 14-story hotel in the Loop business district, is 4 blocks from Millennium Park and Lake Michigan, and a half-mile from the Art Institute of Chicago and Merchandise Mart. read more
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Hyatt Regency Chicago

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151 East Wacker Dr, Chicago, IL
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This Magnificent Mile hotel is located among Chicago's world-class shopping, restaurants and attractions. The Navy Pier, Millennium Park and Art Institute are less than a mile away. read more
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Hyatt Regency O'Hare

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9300 Bryn Mawr Ave, Rosemont, IL
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This hotel is 2 blocks from Rosemont Theater, 1.5 miles from O'Hare International Airport via complimentary shuttle, and within 3 miles of the Allstate Arena; Wrigley Field is less than 12 miles away. read more
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Renaissance Chicago North Shore Hotel

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933 Skokie Blvd, Northbrook, IL
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This 10-story Renaissance hotel is less than 2 miles from the Chicago Botanic Garden and the Northbrook Court Shopping Mall; downtown Chicago is 24 miles away. read more
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Raffaello Hotel

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201 E Delaware Pl, Chicago, IL
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Located on Chicago's fabled Gold Coast, this boutique hotel is adjacent to the John Hancock Tower, steps from stylish shops, and about 1 mile from Navy Pier. read more
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Congress Plaza Hotel

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520 S Michigan Ave, Chicago, IL
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Built in 1893, this downtown Chicago hotel offers a convenient location across from Grant Park and close to Lake Michigan. read more
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Upon entering the hotel I felt that I was in a gangster-era opulent resort. Marble, crystal, art deco everywhere. The hotel had a distinctly old feel to it -- as well it should, for a hotel first built in 1893! Rooms were clean and amply sized. Location was convenient to trains and cabs were easy to find. Lots of restaurants in walking distance.
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Jul 24th, 2006
The Palmer House Hilton

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17 E Monroe St, Chicago, IL
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This 1925 Beaux Arts-style Chicago hotel is steps from Millennium Park, 2 blocks from Macy's and the Art Institute, and 1 mile from Lake Michigan, Magnificent Mile shopping, and Wrigley Tower. read more
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