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Chicago Flight + Hotel Packages

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Chicago Vacations

You’ve long known of Chicago’s reputation as the “The Windy City,” and now that you’re here, wise wanderer, walking amid the fountains, bike trails, and art installations of Lake Michigan’s waterfront, you’ve certainly found yourself blown away. As one of the most storied cities in the U.S., Chicago overflows with history and culture around every corner, and there’s no shortage of exciting adventures awaiting you here. And by choosing one of the Chicago vacations featured here on Travelocity, you can sink your teeth into the Chi-Town’s iconic deep-dish pizza, root for the World Series-winning Cubs, and shop along the Magnificent Mile.

Hotels in Chicago

Embarking on your first adventure in this one-of-a-kind city? Where you choose to stay makes a big difference when it comes to vacations in Chicago. To ensure you make the right choice, here are four hotels you’ll fall in love with:

  • Congress Plaza Hotel: Looking for a luxurious space to serve as home base while in Chicago? This is the place. Offering views of lush Grant Park, this iconic downtown hotel has been a presence in the city since 1893 and is just a quick walk from the Art Institute of Chicago. Choose from rooms with marble bathrooms, whirlpool tubs, and views of Lake Michigan. Fitness fanatics can workout in the on-site exercise room, while foodies can sample the offerings at the Congress Plaza’s own steakhouse or lounge. And if you need a trim before a night out on the town, there’s even a barbershop in the hotel.
  • Hyatt Regency Chicago: Located a brisk walk from Millennium Park and the Magnificent Mile, this luxurious conference hotel sports contemporary rooms with iPod docks, high-def TVs, and for-a-fee Wi-Fi. To live it up a little, upgrade to a lakeview club room that includes complimentary breakfast on weekdays, and small bites in an upscale lounge. Other on-site eateries include a steak-and-sushi restaurant and a trendy sports bar.
  • Wyndham Grand Chicago Riverfront: Situated just two miles from Millennium Park, the high-end, pet-friendly Wyndham Grand hotel invites you to spend your nights in their extravagant rooms that include hardwood accents and high-definition TVs among other amenities. You can optionally upgrade to a riverview room, or reserve a suite replete with separate living spaces and a soaking tub. In-room massages are available for an additional fee, but access to the on-site fitness center is free for all guests. And as far as food is concerned, there’s an American restaurant with a bar and in-room dining services.
  • The Palmer House Hilton: Showcasing an ornately painted lobby that complements the masterful creations found in the nearby Art Institute of Chicago, this iconic accommodation is a mere 2 miles from the McCormick Place convention center. When it comes time to fill your belly after a day of collecting swag, pay a visit to the Palmer House’s restaurant, or swing by their plush lounge. Additional offerings here include a fitness center, full-service spa, and a pool and sauna sheltered from the elements.

Major Attractions

Choose one of our vacation packages in Chicago based around the attractions or activities you’re most looking forward to. In Near South is the sprawling Museum Campus, which consists of three large museums. Stargaze at the Adler Planetarium, pay a visit to the infamous Sue the T-Rex at the Field Museum of Natural History, and finish the museum hop at the Shedd Aquarium. Architecture aficionados will be drawn to the gorgeous buildings found in the Loop, including the Fine Arts Building, The Reliance Building, and the Rookery. Use the city's popular public transportation system to get around, but if you want to explore beyond the city limits you may want to rent a car in Chicago.

Festivals and Events

Every year, the Chicago River is dyed green for St. Patrick's Day, which is celebrated with a parade the Saturday before the holiday. This popular event is only one item in a crammed calendar of city events. Head outdoors to listen to classical music during the 10-week Grant Park Music Festival or sip on favorite beers while discovering new ones at the Chicago Craft Beer Festival in July. Live music, food, and the arts are the focus of most of the festivals. Let the festivals guide you when you plan vacation package in Chicago, IL.

Travelocity makes it easy to find a cheap vacation in Chicago at any time of year. Take a look at our unbeatable Chicago package deals today, and you’ll be on the trip of your dreams in no time.

Accommodation in Chicago

Chicago is a major city, with 627 accommodations featured on Travelocity's Chicago lodging guide.

Do you have a taste for luxury and style? Chicago Downtown Condo - Michigan Ave Suite ID #14-15 and The Peninsula Chicago will be right up your alley. On the other hand, the Waldorf Astoria Chicago or the Trump International Hotel & Tower Chicago provide visitors with cozy comfort at reasonable prices.

The Northwestern University is a much-loved Chicago attraction. If you want to stay close by, the Hilton Garden Inn Chicago North Shore/Evanston is just 0.7 miles (1.1 kilometers) away, and the Hilton Orrington / Evanston is 0.7 miles (1.1 kilometers) away.


Guide to Exploring Chicago

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Top Chicago Hotels Deals

See all 994 Hotels in Chicago
Central Loop Hotel

Central Loop Hotel

111 West Adams Street, Chicago
    4.0 out of 5.0
     
     
    4.0 out of 5 (67 reviews)

    Situated in the heart of "the Loop," the contemporary Central Loop Hotel is steps from all of Chicago’s major business and cultural destinations such as Chicago ...

    River Hotel

    River Hotel

    75 East Wacker Drive, Chicago
      4.0 out of 5.0
       
       
      4.3 out of 5 (105 reviews)

      Located in The Loop, this hotel is within a 10-minute walk of Chicago Theatre, Wrigley Building, and Tribune Tower. Ford Center for the Performing Arts Oriental ...

      The Whitehall Hotel

      The Whitehall Hotel

      105 E Delaware Pl, Chicago
        4.0 out of 5.0
         
         
        4.2 out of 5 (89 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.

        The Whitehall Hotel$101

        The Whitehall Hotel$101
        Wyndham Grand Chicago Riverfront

        Wyndham Grand Chicago Riverfront

        71 E Wacker Dr, Chicago
          4.0 out of 5.0
           
           
          4.3 out of 5 (140 reviews)

          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 ...

          Wyndham Grand Chicago Riverfront$134

          Wyndham Grand Chicago Riverfront$134
          Edward Hotel Chicago

          Edward Hotel Chicago

          6600 N. Mannheim Rd, Rosemont
            3.0 out of 5.0
             
             
            4.0 out of 5 (67 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. ...

            Edward Hotel Chicago$80

            Edward Hotel Chicago$80
            Congress Plaza Hotel

            Congress Plaza Hotel

            520 South Michigan Avenue, Chicago
              3.0 out of 5.0
               
               
              3.2 out of 5 (22 reviews)

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

              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, ...

                Hotel Felix Chicago$87

                Hotel Felix Chicago$87
                Loews Chicago Hotel

                Loews Chicago Hotel

                455 North Park Drive, Chicago
                  4.5 out of 5.0
                   
                   
                  4.9 out of 5 (9 reviews)

                  Located in Near North Side, this luxury hotel is within a 10-minute walk of Tribune Tower and Wrigley Building. Navy Pier and Chicago Children's Museum are also ...

                  Loews Chicago Hotel$159

                  Loews Chicago Hotel$159
                  Hilton Chicago O'Hare Airport

                  Hilton Chicago O'Hare Airport

                  Ohare International Airport, Chicago
                    4.0 out of 5.0
                     
                     
                    3.7 out of 5 (47 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, ...

                    Hilton Chicago O'Hare Airport$93

                    Hilton Chicago O'Hare Airport$93
                    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 (345 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 ...

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