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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

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See all 803 Hotels in Chicago
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue, Chicago
3.0 out of 5.0
3.1 out of 5 (12 reviews)

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

C$160

C$160
Club Quarters Hotel, Central Loop

Club Quarters Hotel, Central Loop

111 West Adams Street, Chicago
4.0 out of 5.0
4.4 out of 5 (175 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$164

C$164
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

17 E Monroe St, Chicago
4.0 out of 5.0
4.3 out of 5 (337 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$233

C$233
The Whitehall Hotel

The Whitehall Hotel

105 E Delaware Pl, Chicago
4.0 out of 5.0
4.1 out of 5 (82 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$206

C$206
Loews Chicago O'Hare Hotel

Loews Chicago O'Hare Hotel

5300 N River Rd, Rosemont
4.5 out of 5.0
4.4 out of 5 (66 reviews)

This family-friendly Rosemont hotel is located near the airport, within a 10-minute walk of Rosemont Theatre, Fashion Outlets of Chicago, and Donald E. Stephens ...

C$160

C$160
Warwick Allerton Hotel Chicago

Warwick Allerton Hotel Chicago

701 North Michigan Avenue, Chicago
4.0 out of 5.0
4.2 out of 5 (177 reviews)

Located on Michigan Avenue in the middle of Chicago's Magnificent Mile, this 1920s Italian Renaissance hotel is surrounded by fashionable shops, 1 mile from ...

C$162

C$162
Chicago's Essex Inn

Chicago's Essex Inn

800 S Michigan Ave, Chicago
3.5 out of 5.0
3.6 out of 5 (186 reviews)

Across from the greenery and attractions of Grant Park, the Essex Inn is 3 blocks from the Loop business district and Lake Michigan, 4 blocks from the Art Institute, ...

C$158

C$158
Hard Rock Hotel Chicago

Hard Rock Hotel Chicago

230 North Michigan Avenue, Chicago
4.0 out of 5.0
4.0 out of 5 (111 reviews)

On Michigan Avenue and across from Millennium Park, this rock-inspired hotel occupies the 36-story, Art Deco-style Carbide and Carbon Building in downtown's ...

C$197

C$197
Hotel Felix Chicago

Hotel Felix Chicago

111 W Huron St, Chicago
4.0 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$181

C$181
Hyatt Regency McCormick Place

Hyatt Regency McCormick Place

2233 S Martin Luther King Dr, Chicago
4.0 out of 5.0
3.9 out of 5 (58 reviews)

Connected via enclosed skybridge to the McCormick Place convention complex, the Hyatt Regency is adjacent to a Metro station, with easy access to Chicago's downtown ...

C$224

C$224

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