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Save up to $986 | Book Flight + Hotel at the same time*
Save up to $986 | Book Flight + Hotel at the same time*
Save up to $986 | Book Flight + Hotel at the same time*

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.

Guide to Exploring Chicago

Chicago FAQs

What currency is used in Chicago?

The U.S. dollar (USD) is the currency used in Chicago.

What is there to do in Chicago?

With tons of fun adventures to keep you on your toes, you’ll never be bored in this city. Here are some activities to get you started:

Where is the best place to stay in Chicago?

Located right in the heart of the downtown area, The Loop is one of the most popular neighborhoods. You’ll be within walking distance of many local and boutique stores, award-winning restaurants and major cultural institutions.

This is the place to stay if you appreciate fine art and design. It’s about a mile from the downtown area and is regarded as Chicago’s most fashionable neighborhood. The Magnificent Mile, Chicago’s premier commercial district, is a short walk away.

What is Chicago famous for?

Nicknamed the “Windy City,” here are just a few things Chicago is known for:

  • History
  • Architecture

Don’t miss Willis Tower, an iconic skyscraper that features spectacular views of the city and surrounds. The Art Institute of Chicago is also nearby; plan a visit to explore its fantastic collection of impressionist paintings and sculptures. Millennium Park and Lake Michigan are ideal for nature lovers.

Top Chicago Hotels Deals

See all 1,546 Properties in Chicago
Palmer House a Hilton Hotel $109
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

17 E Monroe St, Chicago, IL
    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.

    Hyatt Regency Chicago $119
    Hyatt Regency Chicago

    Hyatt Regency Chicago

    151 East Wacker Dr, Chicago, IL
      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.

      Embassy Suites Chicago Downtown Magnificent Mile $143
      Embassy Suites Chicago Downtown Magnificent Mile

      Embassy Suites Chicago Downtown Magnificent Mile

      511 North Columbus Drive, Chicago, IL
        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.

        Freehand Chicago $83
        Freehand Chicago

        Freehand Chicago

        19 East Ohio Street, Chicago, IL
          3.5 out of 5.0

          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 Art and Water Tower Place are also within 15 minutes. Grand Station (Red Line) is only a 2-minute walk and Chicago Station (Red Line) is 7 minutes.

          The St. Clair Hotel – Magnificent Mile $85
          The St. Clair Hotel – Magnificent Mile

          The St. Clair Hotel – Magnificent Mile

          162 East Ontario Street, Chicago, IL
            2.5 out of 5.0

            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 Wrigley Building and Navy Pier, where guests can hop on a boat cruise to see the city's famous skyscrapers from the water.

            Congress Plaza Hotel $97
            Congress Plaza Hotel

            Congress Plaza Hotel

            520 South Michigan Avenue, Chicago, IL
              3.5 out of 5.0

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

              Hyatt Centric Chicago Magnificent Mile $130
              Hyatt Centric Chicago Magnificent Mile

              Hyatt Centric Chicago Magnificent Mile

              633 N Saint Clair St, Chicago, IL
                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.

                River Hotel $72
                River Hotel

                River Hotel

                75 East Wacker Drive, Chicago, IL
                  4.0 out of 5.0

                  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 10 minutes. Randolph-Wabash Station is 5 minutes by foot and State Station is 5 minutes.

                  Things to do in Chicago

                  See all 109 things to do in Chicago

                  Top Flight Deals

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

                  *Savings based on all package bookings made with Flight + Hotel on from January 1, 2018 to December 31, 2018, as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.