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The term “flyover” is an insult when it comes to Chicago. The Midwest’s most populated city reads like a love letter to many things—architecture, food, theater and sports to name a few—but don’t expect to do it all in one visit. Start with Millennium Park, a Cubs game and a slice of deep dish pizza and return again and again to explore its fascinating neighborhoods and hang out by the Lake.   


Hotel Deals

Wyndham Grand Chicago Riverfront $97
Wyndham Grand Chicago Riverfront

Wyndham Grand Chicago Riverfront

71 E Wacker Dr, Chicago, IL
     
    4.3
    of 5, from 151 reviews
    4.0 out of 5.0

    This 39-story Chicago hotel is across the river from Magnificent Mile shopping, six blocks from Lake Michigan, and a half-mile from the Loop's theater district and the Art Institute of Chicago.

    The Whitehall Hotel $67
    The Whitehall Hotel

    The Whitehall Hotel

    105 E Delaware Pl, Chicago, IL
       
      4.2
      of 5, from 97 reviews
      4.0 out of 5.0

      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.

      Crowne Plaza Chicago West Loop $89
      Crowne Plaza Chicago West Loop

      Crowne Plaza Chicago West Loop

      25 South Halsted Street, Chicago, IL
         
        4.3
        of 5, from 41 reviews
        3.5 out of 5.0

        Just west of the downtown business core, this hotel on Chicago's Near West Side is within a quarter mile of Greektown's restaurants and Harpo Studios. United Center and Millennium Park are within 1 mile.

        Hilton Chicago O'Hare Airport $98
        Hilton Chicago O'Hare Airport

        Hilton Chicago O'Hare Airport

        Ohare International Airport, Chicago, IL
           
          3.7
          of 5, from 50 reviews
          4.0 out of 5.0

          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, and 18 miles from downtown Chicago.

          Loews Chicago O'Hare Hotel $129
          Loews Chicago O'Hare Hotel

          Loews Chicago O'Hare Hotel

          5300 N River Rd, Rosemont, IL
             
            4.5
            of 5, from 75 reviews
            4.5 out of 5.0

            Situated near the airport, in Rosemont, this luxury hotel is close to Rosemont Theatre, Donald E. Stephens Convention Center, and Fashion Outlets of Chicago. Also nearby are Rivers Casino and MB Financial Park at Rosemont.

            Palmer House a Hilton Hotel $118
            Palmer House a Hilton Hotel

            Palmer House a Hilton Hotel

            17 E Monroe St, Chicago, IL
               
              4.3
              of 5, from 374 reviews
              4.0 out of 5.0

              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.

              Fairmont Chicago at Millennium Park $161
              Fairmont Chicago at Millennium Park

              Fairmont Chicago at Millennium Park

              200 North Columbus Drive, Chicago, IL
                 
                4.2
                of 5, from 76 reviews
                4.5 out of 5.0

                The 45-story Fairmont Chicago hotel is adjacent to Millennium Park, a half-block from Michigan Avenue, and 3 blocks from Lake Michigan; Navy Pier, Art Institute, State Street and the Museum Campus are within walking distance.

                Hyatt Regency McCormick Place $113
                Hyatt Regency McCormick Place

                Hyatt Regency McCormick Place

                2233 S Martin Luther King Dr, Chicago, IL
                   
                  4.0
                  of 5, from 69 reviews
                  4.0 out of 5.0

                  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 hub. Soldier Field, the home of the Chicago Bears, is a 15 minute walk away.

                  Chicago Athletic Association $142
                  Chicago Athletic Association

                  Chicago Athletic Association

                  12 South Michigan Avenue, Chicago, IL
                     
                    4.4
                    of 5, from 14 reviews
                    4.5 out of 5.0

                    Located in The Loop, this luxury hotel is steps from Millennium Park and Cloud Gate.

                    Trump International Hotel & Tower Chicago $260
                    Trump International Hotel & Tower Chicago

                    Trump International Hotel & Tower Chicago

                    401 N Wabash Ave, Chicago, IL
                       
                      4.7
                      of 5, from 23 reviews
                      5.0 out of 5.0

                      This family-friendly hotel is located in Chicago (River North), close to Wrigley Building, Michigan Avenue, and Water Tower Place. Also nearby are Chicago Riverwalk and Millennium Park.

                      The Langham, Chicago $271
                      The Langham, Chicago

                      The Langham, Chicago

                      330 North Wabash Avenue, Chicago, IL
                         
                        4.8
                        of 5, from 5 reviews
                        5.0 out of 5.0

                        Located in the center of Chicago, this family-friendly hotel is within a 15-minute walk of Michigan Avenue and Millennium Park. Art Institute of Chicago and John Hancock Center are also within 1 mi (2 km). State Station is 5 minutes by foot and Randolph-Wabash Station is 6 minutes.

                        Hyatt House Chicago/Evanston $116
                        Hyatt House Chicago/Evanston

                        Hyatt House Chicago/Evanston

                        1515 Chicago Avenue, Evanston, IL
                           
                          5.0
                          of 5, from 4 reviews
                          3.5 out of 5.0

                          Located in the heart of Evanston, this hotel is 0.6 mi (1 km) from Northwestern University and within 6 mi (10 km) of Loyola University Chicago and Skokie Theatre. Wrigley Field and Lincoln Park are also within 9 mi (15 km). Davis Metro Station is 6 minutes by foot and Dempster Station is 7 minutes.

                          Radisson Hotel Schaumburg $76
                          Radisson Hotel Schaumburg

                          Radisson Hotel Schaumburg

                          1998 North Roselle Road, Schaumburg, IL
                             
                            4.1
                            of 5, from 9 reviews
                            3.5 out of 5.0

                            Located in the heart of Schaumburg, this hotel is within 1 mi (2 km) of Harper College and Schaumburg Medieval Times. Woodfield Mall and Schaumburg Convention Center are also within 3 mi (5 km).

                            River Hotel $85
                            River Hotel

                            River Hotel

                            75 East Wacker Drive, Chicago, IL
                               
                              4.3
                              of 5, from 121 reviews
                              4.0 out of 5.0

                              Located in The Loop, this hotel is 0.1 mi (0.1 km) from Chicago Riverwalk.

                              Club Quarters Hotel, Central Loop $89
                              Club Quarters Hotel, Central Loop

                              Club Quarters Hotel, Central Loop

                              111 West Adams Street, Chicago, IL
                                 
                                4.3
                                of 5, from 187 reviews
                                4.0 out of 5.0

                                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 of Trade, Willis Tower, Grant Park and the Riverfront, the Theatre District and Magnificent Mile.

                                Springhill Suites by Marriott Chicago Downtown/ River North $98
                                Springhill Suites by Marriott Chicago Downtown/ River North

                                Springhill Suites by Marriott Chicago Downtown/ River North

                                410 North Dearborn Street, Chicago, IL
                                   
                                  4.5
                                  of 5, from 55 reviews
                                  3.5 out of 5.0

                                  3 blocks and the Chicago River separate the family-friendly Springhill Suites by Marriott Chicago Downtown from The Loop’s boutique stores and hip restaurants. The Magnificent Mile is 4 blocks to the west. The hotel is also surrounded by 3 CTA transit stations.

                                  Hyatt Centric Chicago Magnificent Mile $125
                                  Hyatt Centric Chicago Magnificent Mile

                                  Hyatt Centric Chicago Magnificent Mile

                                  633 N Saint Clair St, Chicago, IL
                                     
                                    4.4
                                    of 5, from 76 reviews
                                    4.0 out of 5.0

                                    This smoke-free 17-story hotel is 1 block from North Michigan Avenue's boutique and specialty stores, 3 blocks from Lake Michigan, 6 blocks from the State & Grand subway station (Red Line), and 7 blocks from the Navy Pier entertainment center.

                                    Ivy Boutique Hotel $99
                                    Ivy Boutique Hotel

                                    Ivy Boutique Hotel

                                    233 E Ontario, Chicago, IL
                                       
                                      4.5
                                      of 5, from 11 reviews
                                      4.5 out of 5.0

                                      Located in Near North Side, this luxury hotel is steps from Northwestern Memorial Hospital and Michigan Avenue. Water Tower Place and State Street are also within 10 minutes. Grand Station (Red Line) is 9 minutes by foot and Chicago Station (Red Line) is 12 minutes.

                                      Swissotel - Chicago $111
                                      Swissotel - Chicago

                                      Swissotel - Chicago

                                      323 E Wacker Dr, Chicago, IL
                                         
                                        4.4
                                        of 5, from 172 reviews
                                        4.5 out of 5.0

                                        This triangular, 43-story glass hotel is across the street from the Chicago River, 3 blocks from the lakefront running path, and 4 blocks from the Wrigley Building and the Magnificent Mile.

                                        Loews Chicago Hotel $108
                                        Loews Chicago Hotel

                                        Loews Chicago Hotel

                                        455 North Park Drive, Chicago, IL
                                           
                                          4.8
                                          of 5, from 11 reviews
                                          4.5 out of 5.0

                                          Located in Near North Side, this luxury hotel is within a 10-minute walk of Michigan Avenue, Chicago Riverwalk, and Northwestern Memorial Hospital. Navy Pier and State Street are also within 15 minutes. Grand Station (Red Line) is 11 minutes by foot and State Station is 16 minutes.

                                          The Godfrey Hotel Chicago $106
                                          The Godfrey Hotel Chicago

                                          The Godfrey Hotel Chicago

                                          127 West Huron, at LaSalle, Chicago, IL
                                             
                                            4.0
                                            of 5, from 24 reviews
                                            4.5 out of 5.0

                                            Located in River North, this luxury hotel is within a 10-minute walk of State Street and Michigan Avenue. Water Tower Place and John Hancock Center are also within 15 minutes. Chicago Station (Brown Line) is 6 minutes by foot and Chicago Station (Red Line) is 7 minutes.

                                            Hotel Lincoln $119
                                            Hotel Lincoln

                                            Hotel Lincoln

                                            1816 N Clark Street, Chicago, IL
                                               
                                              4.7
                                              of 5, from 38 reviews
                                              4.0 out of 5.0

                                              Located in Lincoln Park, this boutique hotel is within a 10-minute walk of Park West, Second City, and Chicago History Museum. Lincoln Park Zoo and Lincoln Park Conservatory are also within 15 minutes. Sedgwick Station is 12 minutes by foot and Clark-Division Station is 17 minutes.

                                              Hilton Chicago- Michigan Ave Cultural Mile $126
                                              Hilton Chicago- Michigan Ave Cultural Mile

                                              Hilton Chicago- Michigan Ave Cultural Mile

                                              720 S Michigan Ave, Chicago, IL
                                                 
                                                4.1
                                                of 5, from 183 reviews
                                                4.0 out of 5.0

                                                The Langham, Chicago resides within the 52-story riverfront AMA Plaza that is designed by architect Ludwig Mies van der Rohe. Located along the Chicago River, one block from North Michigan Avenue, Millennium Park, and Chicago's business district are just walking distance away.

                                                Thompson Chicago $159
                                                Thompson Chicago

                                                Thompson Chicago

                                                21 East Bellevue, Chicago, IL
                                                   
                                                  4.8
                                                  of 5, from 15 reviews
                                                  4.5 out of 5.0

                                                  This chic, 22-story Chicago hotel is 2 blocks from Lake Michigan and the Magnificent Mile; numerous shops, bars, and nightclubs are within a 3-block radius.

                                                  Silversmith Hotel Chicago Downtown $107
                                                  Silversmith Hotel Chicago Downtown

                                                  Silversmith Hotel Chicago Downtown

                                                  10 S Wabash Ave, Chicago, IL
                                                     
                                                    4.3
                                                    of 5, from 55 reviews
                                                    4.0 out of 5.0

                                                    The Silversmith Hotel is conveniently located within 1 block of Michigan Avenue and Millennium Park; Theatre District, Art Institute of Chicago, Soldier Field and McCormick Convention Center are within 2 miles.

                                                    Hyatt Regency Chicago $119
                                                    Hyatt Regency Chicago

                                                    Hyatt Regency Chicago

                                                    151 East Wacker Dr, Chicago, IL
                                                       
                                                      4.1
                                                      of 5, from 279 reviews
                                                      4.0 out of 5.0

                                                      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.

                                                      Hotel Felix Chicago $84
                                                      Hotel Felix Chicago

                                                      Hotel Felix Chicago

                                                      111 W Huron St, Chicago, IL
                                                         
                                                        3.8
                                                        of 5, from 24 reviews
                                                        4.0 out of 5.0

                                                        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, whose 40 gondolas command unmatched skyline and lake views. Chicago-Red Metro Station is a 6-minute walk from the hotel.

                                                        Embassy Suites Chicago Downtown Magnificent Mile $111
                                                        Embassy Suites Chicago Downtown Magnificent Mile

                                                        Embassy Suites Chicago Downtown Magnificent Mile

                                                        511 North Columbus Drive, Chicago, IL
                                                           
                                                          4.3
                                                          of 5, from 188 reviews
                                                          4.0 out of 5.0

                                                          The Embassy Suites Chicago Downtown Magnificent Mile offers a newly renovated fresh look and is located two blocks from Navy Pier, Magnificent Mile shopping, and within walking distance to Millennium Park.

                                                          The Drake, a Hilton Hotel $120
                                                          The Drake, a Hilton Hotel

                                                          The Drake, a Hilton Hotel

                                                          140 E Walton Place, Chicago, IL
                                                             
                                                            4.4
                                                            of 5, from 64 reviews
                                                            4.0 out of 5.0

                                                            Overlooking Lake Michigan, this opulent 1920s landmark Chicago hotel is set on the Magnificent Mile, with the shops of Water Tower Place a block away; Oak Street Beach is across the street.

                                                            Millennium Knickerbocker Chicago $89
                                                            Millennium Knickerbocker Chicago

                                                            Millennium Knickerbocker Chicago

                                                            163 East Walton Place, Chicago, IL
                                                               
                                                              4.2
                                                              of 5, from 200 reviews
                                                              4.0 out of 5.0

                                                              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 Michigan is three blocks away.

                                                              Crowne Plaza Hotel Chicago O'Hare $99
                                                              Crowne Plaza Hotel Chicago O'Hare

                                                              Crowne Plaza Hotel Chicago O'Hare

                                                              5440 N River Rd, Rosemont, IL
                                                                 
                                                                4.0
                                                                of 5, from 58 reviews
                                                                3.5 out of 5.0

                                                                Situated near the airport, this hotel is within a 5-minute walk of Rosemont Theatre and Donald E. Stephens Convention Center. Rivers Casino and Fashion Outlets of Chicago are also within 2 mi (3 km). Rosemont Station is 14 minutes by foot and Rosemont Station is 13 minutes.

                                                                The Talbott Hotel $97
                                                                The Talbott Hotel

                                                                The Talbott Hotel

                                                                20 E Delaware Pl, Chicago, IL
                                                                   
                                                                  4.8
                                                                  of 5, from 5 reviews
                                                                  4.0 out of 5.0

                                                                  Located in Near North Side, this boutique hotel is within a 5-minute walk of State Street, John Hancock Center, and Michigan Avenue. Water Tower Place and Chicago Water Tower are also within 10 minutes. Chicago Station (Red Line) is only a 4-minute walk and Clark-Division Station is 11 minutes.

                                                                  Kinzie Hotel $93
                                                                  Kinzie Hotel

                                                                  Kinzie Hotel

                                                                  20 W Kinzie St, Chicago, IL
                                                                     
                                                                    4.6
                                                                    of 5, from 123 reviews
                                                                    4.0 out of 5.0

                                                                    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 Tower and Lake Michigan.

                                                                    Flight Deals

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                                                                    Terms & Conditions

                                                                    Hotel deals: Offers valid at participating hotels only and are subject to availability. Minimum night stay may be required, and varies by property. Rules, restrictions, and black out dates may apply. See property pages for further details.

                                                                    Air pricing: Sample prices are quoted for one adult and include taxes and fees for round-trip travel on the promoted airline. Prices do not include baggage fees that may be charged by the applicable airline. Actual price may vary based on time/date of search, booking date, travel dates, origin, and destination. Sample prices above are updated daily; prices are found on www.Travelocity.com and quoted in U.S. dollars. Advance booking requirements, minimum/maximum stay requirements, blackout dates, and other restrictions may apply and vary by booking date, travel dates, origin city, and destination. Portions of these flights may be operated by the airlines code-share partners. Fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates. Lower fares may be available to selected destinations. Tickets are nontransferable and nonrefundable. Read the complete penalty rules for changes and cancellations applicable to the fare you're considering booking.