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Chicago Vacations

If you’re planning a trip to Chicago, Travelocity will guide you to the perfect vacation. From helping you find hotels in Chicago, flights, and car rental, Travelocity is here to help you soak up every moment of your trip to Chicago.

Top Chicago Flight + Hotel packages

Top Chicago Hotels Deals

See all 948 Hotels in Chicago
Hyatt Regency Chicago

Hyatt Regency Chicago

151 East Wacker Dr, Chicago
4.5 out of 5.0
4.1 out of 5 (251 reviews)

This Magnificent Mile hotel is located among Chicago's world-class shopping, restaurants and attractions. The Navy Pier, Millennium Park and Art Institute are ...

C$148

C$148
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

17 E Monroe St, Chicago
4.5 out of 5.0
4.3 out of 5 (340 reviews)

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 ...

C$98

C$98
Kinzie Hotel

Kinzie Hotel

20 W Kinzie St, Chicago
4.5 out of 5.0
4.6 out of 5 (117 reviews)

Within 2 blocks of Chicago's Magnificent Mile and the theater district, the Kinzie Hotel is located in the convenient River North district, a mile from the Hancock ...

C$105

C$105
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue, Chicago
3.5 out of 5.0
3.1 out of 5 (18 reviews)

Built in 1893, this downtown Chicago hotel offers a convenient location across from Grant Park and close to Lake Michigan.

C$86

C$86
The Whitehall Hotel

The Whitehall Hotel

105 E Delaware Pl, Chicago
4.5 out of 5.0
4.1 out of 5 (86 reviews)

Built in 1927, this Chicago hotel is one block from Michigan Avenue shopping and Rush Street restaurants and nightlife; Lake Michigan is within five blocks.

C$81

C$81
Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago

163 East Walton Place, Chicago
4.5 out of 5.0
4.3 out of 5 (189 reviews)

This 1927 landmark Chicago hotel is a half block from Michigan Avenue/Magnificent Mile shopping, two blocks from Oak Street shopping and Water Tower Place. Lake ...

C$95

C$95
Club Quarters Hotel, Central Loop

Club Quarters Hotel, Central Loop

111 West Adams Street, Chicago
4.5 out of 5.0
4.4 out of 5 (176 reviews)

Club Quarters is a club-like hotel in the center of the Loop, Chicago’s central business district. A short walk to Symphony Center, the Art Institute, Board ...

C$92

C$92
Hotel Felix Chicago

Hotel Felix Chicago

111 W Huron St, Chicago
4.5 out of 5.0
3.7 out of 5 (20 reviews)

Hotel Felix Chicago is 5 blocks from the Magnificent Mile, one of America’s most dazzling thoroughfares. It’s a 7-minute cab ride to the Navy Pier Ferris Wheel, ...

C$94

C$94
Edward Hotel Chicago

Edward Hotel Chicago

6600 N. Mannheim Rd, Rosemont
3.5 out of 5.0
4.0 out of 5 (66 reviews)

Situated near the airport, this hotel is 0.4 mi (0.6 km) from Allstate Arena and within 3 mi (5 km) of Rivers Casino and Donald E. Stephens Convention Center. ...

C$95

C$95
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

Ohare International Airport, Chicago
4.5 out of 5.0
3.8 out of 5 (46 reviews)

The only hotel on airport property, the Hilton Chicago O'Hare Airport is located 2 miles from the Donald E. Stephens Convention Center and the Rosemont Theatre, ...

C$161

C$161

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