Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5
Book a Flight + Hotel package and you could get a free room night*
Book a Flight + Hotel package and you could get a free room night*
Book a Flight + Hotel package and you could get a free room night*

Book your ✈️ and 🏨 together | Save 💰 & 🕑

Chicago Flight + Hotel Packages

Chicago Flight + Hotel Packages - 3 Night Stay

Chicago Flight + Hotel Packages - 4 Night Stay

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 1,472 Properties in Chicago
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 (370 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$86

    Hyatt Regency Chicago

    Hyatt Regency Chicago

    151 East Wacker Dr, Chicago
      4.0 out of 5.0
      4.1 out of 5 (277 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$119

      Embassy Suites Chicago Downtown Magnificent Mile

      Embassy Suites Chicago Downtown Magnificent Mile

      511 North Columbus Drive, Chicago
        4.0 out of 5.0
        4.3 out of 5 (188 reviews)

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

        Embassy Suites Chicago Downtown Magnificent Mile$98

        Freehand Chicago

        Freehand Chicago

        19 East Ohio Street, Chicago
          3.5 out of 5.0
          4.3 out of 5 (23 reviews)

          Located in River North, this hotel is within 6 mi (10 km) of Chinese Consulate, Holy Name Cathedral, and Museum of Contemporary Art. Water Tower Place and Ann ...

          Freehand Chicago$69

          The St. Clair Hotel – Magnificent Mile

          The St. Clair Hotel – Magnificent Mile

          162 East Ontario Street, Chicago
            2.5 out of 5.0
            3.5 out of 5 (2 reviews)

            The hotel is a half-block from the Magnificent Mile and an 8-minute walk from Grand/State Metro Station. Many attractions are within a 15-minute walk, including ...

            The St. Clair Hotel – Magnificent Mile$70

            Congress Plaza Hotel

            Congress Plaza Hotel

            520 South Michigan Avenue, Chicago
              3.5 out of 5.0
              3.6 out of 5 (40 reviews)

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

              Congress Plaza Hotel$71

              Hyatt Centric Chicago Magnificent Mile

              Hyatt Centric Chicago Magnificent Mile

              633 N Saint Clair St, Chicago
                4.0 out of 5.0
                4.4 out of 5 (76 reviews)

                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 & ...

                Hyatt Centric Chicago Magnificent Mile$120

                River Hotel

                River Hotel

                75 East Wacker Drive, Chicago
                  4.0 out of 5.0
                  4.3 out of 5 (119 reviews)

                  Located in The Loop, this hotel is within a 5-minute walk of Chicago Riverwalk and Chicago Theatre. Michigan Avenue and House of Blues Chicago are also within ...

                  River Hotel$67

                  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$144

                    Warwick Allerton - Chicago

                    Warwick Allerton - Chicago

                    701 North Michigan Avenue, Chicago
                      4.0 out of 5.0
                      4.2 out of 5 (196 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$68

                      Top Flight Deals

                      Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

                      *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 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.