Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5
Due to coronavirus (COVID-19) travel advisories, some destinations may be unavailable for certain dates. Find out more.

Explore thousands of activities with free cancellation and no added fees.

Design your experience with airport transfers, excursions, day tours & more.

Get an insider's look in what to book before you travel.


Top 10 Things To Do In Chicago

See all 128 things to do in Chicago

Most Popular Booked Chicago Hotels

Trump International Hotel & Tower Chicago $315
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

401 N Wabash Ave, Chicago, IL
     
    4.8
    of 5, from 35 reviews
    5.0 out of 5.0 Stars

    A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the fitness center and perks like free WiFi.

    LondonHouse Chicago, Curio Collection by Hilton $109
    LondonHouse Chicago, Curio Collection by Hilton

    LondonHouse Chicago, Curio Collection by Hilton

    85 East Wacker Drive, Chicago, IL
       
      4.7
      of 5, from 27 reviews
      4.5 out of 5.0 Stars

      A full-service spa, 2 restaurants, and a 24-hour fitness center are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A terrace, a free grocery shopping service, and a grocery/convenience store are also on offer.

      Swissotel - Chicago $134
      Swissotel - Chicago

      Swissotel - Chicago

      323 E Wacker Dr, Chicago, IL
         
        4.4
        of 5, from 191 reviews
        4.5 out of 5.0 Stars

        This hotel features 2 bars/lounges and a 24-hour fitness center. Traveling on business? Take advantage of the business center and free WiFi in public areas. A restaurant, a 24-hour front desk, and laundry facilities are also provided.

        La Quinta Inn & Suites by Wyndham Chicago Downtown $61
        La Quinta Inn & Suites by Wyndham Chicago Downtown

        La Quinta Inn & Suites by Wyndham Chicago Downtown

        1 S Franklin Street, Chicago, IL
           
          4.3
          of 5, from 44 reviews
          3.0 out of 5.0 Stars

          A restaurant and a fitness center are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a coffee shop, and a computer station are also offered.

          Best Western Grant Park Hotel $64
          Best Western Grant Park Hotel

          Best Western Grant Park Hotel

          1100 S Michigan Ave, Chicago, IL
             
            4.2
            of 5, from 42 reviews
            2.5 out of 5.0 Stars

            This hotel features a restaurant, a fitness center, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A coffee shop, express check-in, and dry cleaning are also on offer.

            The Whitehall Hotel $71
            The Whitehall Hotel

            The Whitehall Hotel

            105 E Delaware Pl, Chicago, IL
               
              4.1
              of 5, from 122 reviews
              4.0 out of 5.0 Stars

              This boutique hotel features 2 restaurants, a bar/lounge, and a fitness center. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, express check-in, and a computer station are also offered.

              The Godfrey Hotel Chicago $90
              The Godfrey Hotel Chicago

              The Godfrey Hotel Chicago

              127 West Huron, at LaSalle, Chicago, IL
                 
                3.9
                of 5, from 16 reviews
                4.5 out of 5.0 Stars

                This luxury hotel features a full-service spa, a nightclub, and 2 restaurants. Traveling on business? Take advantage of the 3 conference rooms, free WiFi in public areas, and valet parking. Make the most of the 24-hour fitness center and a rooftop terrace, and relax with drinks at one of the 2 bars/lounges.

                The St. Clair Hotel – Magnificent Mile $87
                The St. Clair Hotel – Magnificent Mile

                The St. Clair Hotel – Magnificent Mile

                162 East Ontario Street, Chicago, IL
                   
                  3.7
                  of 5, from 33 reviews
                  2.5 out of 5.0 Stars

                  This hotel features free WiFi in public areas, luggage storage, and laundry facilities. The front desk is staffed around-the-clock and concierge services are on offer.

                  Chicago Activities

                  Places To Go In Chicago

                  The air in Chicago practically palpitates with potential. From each morning’s first rays of sunshine to the moon’s silvery rise, Chicago hotels, restaurants and shops remain abuzz with ceaseless activity. Adventurous explorers can effortlessly join the stream of wanderers that are the lifeblood of The Windy City, and no matter where the tide takes you, you’re sure to discover something quite unexpected.

                  Things to Do in Chicago

                  With an abundance of things to do in Chicago, intrepid travelers like you know to start with the culinary and cultural essentials. Come springtime, everyone’s a local if you root for the Chicago baseball team du jour, and for an authentic stadium experience, indulge in a Chicago-style frankfurter piled high with all the accoutrements. Regardless of season, no in-the-know traveler will let a day slip past without partaking in a local slice of deep-dish Chicago pizza (sauce on top, of course) and a stroll down the tree-lined Magnificent Mile. Spoil your inner shopper with luxury retail and your inner naturalist with impeccable views of Lake Michigan, best observed from atop the John Hancock Center for sweeping panoramas.

                  For a more up-close-and-personal waterfront experience, immerse yourself in one of the most romantic Chicago attractions offered—a moonlit dinner cruise upon Lake Michigan. Waltz the night away to sensual melodies after enjoying heavenly hors d'oeuvres passed out by white-gloved attendants. End the night with a champagne toast and drink in the twinkling lights of the cityscape.

                  Finding your place in the universe may be a lifelong journey, but it’s time to take the first step. Peruse Travelocity’s Chicago vacation packages to spark your exploration and chart a course towards discovering everything that Chicago has to offer.