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Chicago Vacation Packages

Now is the time to stop daydreaming! With a wide range of sights to see, you should start arranging your Chicago trip as soon as you can.

Save Time and Money with a Chicago Package Deal

Expedia accommodation and flight deals will help you save! You will save precious time and money when combining your flight and hotel bookings with us. Think of everything you can do in Chicago with the extra cash.

Crafty voyagers save up to $583 by booking their package deal with us.

Our enormous database has about 400 partner airlines and 321,000 hotels around the planet.

Imagine the money you'll save with some of the most competitive prices and deals via Expedia.

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Chicago Vacation Packages

The population of this area of Illinois is approximately 2,700,000.

Springfield, the state capital, is roughly 180 miles southwest of Chicago, and Whiting is 15 miles to the southeast.

This place is, without a doubt, a world-class city. It would be crazy to visit without seeing the Northwestern University and the University of Chicago. The Art Institute of Chicago and Six Flags Great America are also famous throughout the world.

Reconnect with your inner-child at the Chicago Children's Museum and the Lake County Fairgrounds. Want more? The Kane County Fairgrounds and Wagner Farm will ensure the good times keep on coming.

Gaze in awe as a variety of aquatic animals pass through the water at John G. Shedd Aquarium.

You can take loads of photos with the exotic creatures at the Brookfield Zoo and the Lincoln Park Zoo. Check out the educational programs at the Farm-in-the-Zoo to flesh out your zoological triple play.

Get set for some high-speed action at the Richard Petty Driving Experience, the area's go-to racetrack for motorsports fans.

Experienced wine taster or not, a few hours of testing vino at the region's vineyards won't disappoint. If you're considering a tour, consider adding the Lynfred Winery, the Fox Valley Winery and the Valentino Vineyards to the program. It doesn't matter what order you choose. They are all fantastic!

Let the good times roll at the Hollywood Casino or the Rivers Casino and try out your best poker face! If you need more high-energy action, why not head onwards to the Harrah's Casino or the Grand Victoria Casino?

You'll be inspired by the variety of plants on display when you and your friends make a trip to the Chicago Botanic Garden and Garfield Park Conservatory. Budding botanists might also want to take in the collection at Lincoln Park Conservatory and the Emily Oaks Nature Center.

When it's time to take five, pack a picnic and make your way over to one of the scenic urban parks, such as Millennium Park and Lincoln Park. Grant Park and Morton Arboretum are two more excellent places to while away the afternoon over a good book.

Some time spent at Oak Park Visitors Center is an enjoyable way to get some more local information about the area.

Lakes offer a range of activities for people of all ages. From skimming stones to wildlife watching, there's always fun to be had. If you feel like spending some time by the water, see what activities are available at McCullom Lake, Bubbly Creek and South Pond.

Would you like to spend a bit of time beside stretches of coastline? Pack your towel and make your way to North Avenue Beach or Illinois Beach State Park for a refreshing afternoon by the sea. Montrose Beach and Ohio Street Beach are also recommended options.

Switch your phone to silent and give yourself a break from the noises of the modern world at Montrose Harbor and Waukegan Harbor. Deer Grove Forest Preserve and Northerly Island Park are also popular with nature enthusiasts.

See the world in a new light with a visit to one of the area's fascinating cultural spaces. The Chicago Museum of Science and Industry and the Field Museum of Natural History offer a range of collections that are bound to spark your curiosity. Another two to consider are the Adler Planetarium and Astronomy Museum and the Chicago History Museum.

Build on your knowledge with a trip to the International Museum of Surgical Science, Cernan Earth and Space Center and the Museum of Science & Industry. These fascinating institutions present visitors with the latest innovations and developments in the field of science.

The natural world offers more riches than we could hope to see in just one lifetime. Fortunately, institutions such as the Peggy Notebaert Nature Museum and the Oriental Institute Museum make it easier for us by presenting them all in a single building. The Mitchell Museum of the American Indian also houses an excellent collection of specimens.

A hub for art lovers, this area boasts numerous spaces in which amateurs and professionals regularly exhibit their work. Pay a visit to the Museum of Contemporary Art and the Lake County Discovery Museum to see the best of what this creative enclave has to offer. If you're feeling inspired, wind up your day at the Smart Museum of Art and the National Vietnam Veterans Art Museum.

History comes to life at the Glessner House Museum and the Dupage County Historical Museum thanks to their variety of illuminating exhibits. The Joliet Area Historical Museum and the Gregg House Museum are also worthy choices.

To learn about the area's colorful past, pay a visit to its many historic structures and monuments. Commence your history tour at the University of Illinois Chicago and the Aurora University. You might also like to get the camera out for some photos at the Chicago Cultural Center and the Merchandise Mart.

Michigan Avenue Bridge is an impressive structure that has provided a vital crossing for local residents over the years.

Whether you think of yourself as spiritual or not, you'll be sure to enjoy a visit to Holy Name Cathedral and Unity Temple. If you'd be interested to look at a couple more religious sites, keep an eye out for tours at the Anshe Emet Synagogue and Saints Peter and Paul Catholic Church.

Chicago's most famed sights sometimes overshadow its less touristy, but equally rewarding activities. The Newberry Library and the Cloud Gate are some good options. Also, think about checking out the Grohe America and the Visual Arts Center if time allows.

Accommodation in Chicago

Chicago is well-loved by tourists, and boasts a broad range of places to stay. Expedia's Chicago lodging guide is your go-to place.

Fine examples of slightly more premium lodgings in Chicago are The Peninsula Chicago, 108 East Superior Street, and the Waldorf Astoria Chicago, 11 E. Walton Street. Cheaper accommodations worth considering include the Old Chicago Inn, at 3222 N Sheffield Ave, and the Inn at Lincoln Park, at 601 West Diversey Parkway.

One of the highlights of any trip to Chicago is McCormick Place. If you'd prefer to stay within easy walking distance of the must-see attraction, the Hyatt Regency McCormick Place and the Chicago South Loop Hotel are both popular options.

*Savings based on all vacation package bookings with Flight + Hotel on from January through December 2017, as compared to 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. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.

Guide to Exploring Chicago

Top Hotel Deals

See all 1,076 Properties in Chicago
Congress Plaza Hotel $97
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue, Chicago
    of 5, from 2,860 reviews
    3.0 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 Regency McCormick Place $134
    Hyatt Regency McCormick Place

    Hyatt Regency McCormick Place

    2233 S Martin Luther King Dr, Chicago
      of 5, from 3,720 reviews
      4.0 out of 5.0

      Connected via enclosed skybridge to the McCormick Place convention complex, the Hyatt Regency is adjacent to a Metro station, with easy access to Chicago's downtown hub. Soldier Field, the home of the Chicago Bears, is a 15 minute walk away.

      Hyatt Regency Chicago $149
      Hyatt Regency Chicago

      Hyatt Regency Chicago

      151 East Wacker Dr, Chicago
        of 5, from 9,653 reviews
        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.

        Warwick Allerton - Chicago $95
        Warwick Allerton - Chicago

        Warwick Allerton - Chicago

        701 North Michigan Avenue, Chicago
          of 5, from 9,139 reviews
          4.0 out of 5.0

          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 Lake Michigan and the Art Institute.

          Hilton Chicago- Michigan Ave Cultural Mile $157
          Hilton Chicago- Michigan Ave Cultural Mile

          Hilton Chicago- Michigan Ave Cultural Mile

          720 S Michigan Ave, Chicago
            of 5, from 4,968 reviews
            4.0 out of 5.0

            Overlooking Grant Park in downtown Chicago, this landmark Hilton hotel is within walking distance of Buddy Guy's Legends, Millennium Park, the Field Museum, Shedd Aquarium, Soldier Field, and the Loop business and shopping district.

            Crowne Plaza Hotel Chicago O'Hare $99
            Crowne Plaza Hotel Chicago O'Hare

            Crowne Plaza Hotel Chicago O'Hare

            5440 N River Rd, Rosemont
              of 5, from 1,704 reviews
              3.5 out of 5.0

              Situated near the airport, this hotel is within a 5-minute walk of Rosemont Theatre and Donald E. Stephens Convention Center. Fashion Outlets of Chicago and MB Financial Park at Rosemont are also within 10 minutes. Rosemont Station is 14 minutes by foot and Rosemont Station is 13 minutes.

              Loews Chicago O'Hare Hotel $129
              Loews Chicago O'Hare Hotel

              Loews Chicago O'Hare Hotel

              5300 N River Rd, Rosemont
                of 5, from 2,112 reviews
                4.5 out of 5.0

                This family-friendly Rosemont hotel is located near the airport, within a 10-minute walk of Rosemont Theatre, Fashion Outlets of Chicago, and Donald E. Stephens Convention Center. MB Financial Park at Rosemont and Rivers Casino are also within 2 mi (3 km). Rosemont Station is 20 minutes by foot and Rosemont Station is 15 minutes.

                Freehand Chicago $119
                Freehand Chicago

                Freehand Chicago

                19 East Ohio Street, Chicago
                  of 5, from 1,640 reviews
                  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 is only a 2-minute walk and Chicago Station is 7 minutes.

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