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200 customers have received free room nights by booking a Flight + Hotel together this year!
200 customers have received free room nights by booking a Flight + Hotel together this year!
200 customers have received free room nights by booking a Flight + Hotel together this year!

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Chicago Flight + Hotel Packages - 5 Night Stay

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.


Guide to Exploring Chicago

Top Chicago Hotels Deals

See all 1,384 Properties in Chicago
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue, Chicago
    3.5 out of 5.0
     
     
    3.4 out of 5 (34 reviews)

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

    Congress Plaza Hotel$79

    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 (357 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 ...

      Palmer House a Hilton Hotel$92

      Freehand Chicago

      Freehand Chicago

      19 East Ohio Street, Chicago
        3.5 out of 5.0
         
         
        4.2 out of 5 (20 reviews)

        Located in River North, this hotel is within a 10-minute walk of Chinese Consulate, Holy Name Cathedral, and Northwestern Memorial Hospital. Museum of Contemporary ...

        Freehand Chicago$69

        Comfort Inn Arlington Heights - O'Hare

        Comfort Inn Arlington Heights - O'Hare

        2120 S Arlington Heights Rd, Arlington Heights
          2.5 out of 5.0
           
           
          3.4 out of 5 (11 reviews)

          Situated near the airport, this hotel is within 1 mi (2 km) of Ned Brown Forest Preserve and Heritage Park. Arlington Lakes Golf Club and Metropolis Performing ...

          Comfort Inn Arlington Heights - O'Hare$64

          Warwick Allerton - Chicago

          Warwick Allerton - Chicago

          701 North Michigan Avenue, Chicago
            4.0 out of 5.0
             
             
            4.2 out of 5 (194 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 ...

            Warwick Allerton - Chicago$73

            Hyatt Regency Chicago

            Hyatt Regency Chicago

            151 East Wacker Dr, Chicago
              4.0 out of 5.0
               
               
              4.1 out of 5 (268 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 ...

              Hyatt Regency Chicago$104

              The Godfrey Hotel Chicago

              The Godfrey Hotel Chicago

              127 West Huron, at LaSalle, Chicago
                4.5 out of 5.0
                 
                 
                4.1 out of 5 (21 reviews)

                Located in River North, this luxury hotel is within a 15-minute walk of Magnificent Mile, John Hancock Center, and Chicago Water Tower. Merchandise Mart and ...

                The Godfrey Hotel Chicago$90

                Omni Chicago Suites - Magnificent Mile

                Omni Chicago Suites - Magnificent Mile

                676 N Michigan Ave, Chicago
                  4.5 out of 5.0
                   
                   
                  4.5 out of 5 (84 reviews)

                  Omni Chicago Suites - Magnificent Mile is at the center of Chicago’s most prestigious neighborhood, 3 blocks from the shores of Lake Michigan and around the ...

                  Omni Chicago Suites - Magnificent Mile$134

                  Hilton Chicago O'Hare Airport

                  Hilton Chicago O'Hare Airport

                  Ohare International Airport, Chicago
                    4.0 out of 5.0
                     
                     
                    3.8 out of 5 (48 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$101

                    Edward Hotel Chicago

                    Edward Hotel Chicago

                    6600 N. Mannheim Rd, Rosemont
                      3.0 out of 5.0
                       
                       
                      4.0 out of 5 (71 reviews)

                      Situated near the airport, this spa 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$68

                      Top Flight Deals

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                      *This is the largest savings for simultaneous booking of flight and hotel from July 1, 2015 to June 30, 2016, and not the discount rate or amount for your booking. Savings calculated based on the cost of a Flight + Hotel booking on Travelocity.com as compared to the aggregated price of the full published fare given by the airline and the cost of your hotel for the same travel products for the same travel dates when made separately. Savings will vary based on the origin/destination, length of trip, stay dates and selected travel supplier(s). Savings are not available on all packages. Please confirm the actual discount rate/ price on the booking page.