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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 900 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 (16 reviews)

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

C$92

C$92
Edward Hotel Chicago

Edward Hotel Chicago

6600 N. Mannheim Rd, Rosemont
3.0 out of 5.0
4.0 out of 5 (65 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$114

C$114
Hyatt Regency Chicago

Hyatt Regency Chicago

151 East Wacker Dr, Chicago
4.0 out of 5.0
4.1 out of 5 (249 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$127

C$127
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$116

C$116
Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago

163 East Walton Place, Chicago
4.0 out of 5.0
4.3 out of 5 (185 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$96

C$96
Inn of Chicago

Inn of Chicago

162 E Ohio St, Chicago
3.5 out of 5 (99 reviews)

Inn of Chicago is a half-block from the Magnificent Mile and 2 blocks from the landmark Tribune Tower. Millennium Park, Navy Pier, and the Art Institute of Chicago ...

C$88

C$88
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$103

C$103
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$101

C$101
Wyndham Chicago O'Hare

Wyndham Chicago O'Hare

1450 E Touhy Ave, Des Plaines
3.0 out of 5.0
3.5 out of 5 (24 reviews)

Complimentary shuttle service whisks guests arriving from O'Hare International to Wyndham Chicago O'Hare, a mere 2 miles away; concert-goers and hockey fans ...

C$118

C$118
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 (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$94

C$94

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