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Holidays in Chicago

Looking to break free and trade the daily grind for adventure and inspiration? Now's the time to make your Chicago dreams a reality!

Chicago Holidays

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Get ready to start striking off your lifetime travel dreams. Whether it's a freezing mountain peak or a beachside retreat, we'll help you satiate your wanderlust. Terms and Conditions apply.

Holidays in Chicago

The population of this city is 2,700,000.

The state capital, Springfield, sits 180 miles southwest of this destination, while Whiting is located 15 miles southeast.

In a world-renowned destination overflowing with things to discover, the Northwestern University and the University of Chicago shine brightly above the rest. The Art Institute of Chicago and Six Flags Great America are just as impressive.

If you're holidaying with the whole family, trips to the Chicago Children's Museum and the Lake County Fairgrounds will most definitely put huge smiles on everyone's faces! If you're up for a bit more adventure, the Kane County Fairgrounds and Wagner Farm are some other possibilities.

Rest your head against the glass and observe the different underwater creatures as they float around the tanks at John G. Shedd Aquarium.

Both adults and kids will have a great time getting up close to the variety of amazing animals at the Brookfield Zoo and the Lincoln Park Zoo. You can also admire the wild wonders that call the Farm-in-the-Zoo home.

You're going to need to keep your eyes wide open as the expert racers rip around the track at the Richard Petty Driving Experience. One blink at these speeds and you'll miss it!

Would you like to sip and swirl your way through the area's best wineries? The Lynfred Winery and the Fox Valley Winery are popular places to try the local blends. After that, head over to the Valentino Vineyards for an even greater insight into the winemaking industry.

There's nothing like a night out at a casino to jump start the festive spirit! Take on the baccarat dealer and get into the high-stakes action or just wander around and soak up the sights at the Hollywood Casino and the Rivers Casino. For more games, you can't go past the Harrah's Casino and the Grand Victoria Casino.

Botanical experts and novices alike will be glad to learn about this region's regional and international plant collections. For a blossom-filled day, start with a stroll around the winding pathways at the Chicago Botanic Garden. Once you're done there, head to Garfield Park Conservatory, where the array of species alone is worth beholding. If you'd like to see more, the floral displays at Lincoln Park Conservatory and the Emily Oaks Nature Center are also rather unique.

From tossing a ball around to simply relaxing on the grass, there are loads of reasons to visit a green space like Millennium Park or Lincoln Park. Alternatively, get your body moving and let the kids burn off some energy by walking around Grant Park or Morton Arboretum.

To really get under the skin of a destination, there’s nothing like picking up some local knowledge. Whatever you're on the lookout for, the dedicated staff at Oak Park Visitors Center will be able to show you the way.

McCullom Lake and Bubbly Creek truly appeal to the senses. Not just because of the soothing atmosphere and beautiful views that naturally accompany freshwater lakes, but also for the liveliness of the native birdlife that flock there, too. If you're attempting to check off every natural waterbody in the area, McCullom Lake is another one you should add to the itinerary.

An afternoon by the ocean is the ideal antidote to the fast pace of the city, so why not spend some time breathing in the fresh, salty air at North Avenue Beach or Illinois Beach State Park? Those eager to explore more can continue on to Montrose Beach and Ohio Street Beach.

Chicago has a range of natural reserves, such as Montrose Harbor and Waukegan Harbor. Two more areas to have a look at are Deer Grove Forest Preserve and Northerly Island Park.

Go to the Chicago Museum of Science and Industry or the Field Museum of Natural History if the weather's not looking nice. Study the educational exhibits or just relax in the peaceful settings. The Adler Planetarium and Astronomy Museum and the Chicago History Museum are also leading institutions.

The curious scientific objects and displays at the International Museum of Surgical Science and Cernan Earth and Space Center are bound to put your brain into gear. For even more from the wonderful world of science, make your way to the Museum of Science & Industry. Be sure to ask around about any special exhibits that may be on.

We don't quite know how the Peggy Notebaert Nature Museum and the Oriental Institute Museum have managed to jam-pack so many of earth's treasures into just two spaces. A stop at either will transfix you for hours on end. For even more exhibits from the natural world, visit the Mitchell Museum of the American Indian.

With a good range of wonderful art collections to choose from, you might need a friendly push in the right direction. We suggest grabbing a coffee and spending some time at the Museum of Contemporary Art or the Lake County Discovery Museum. The Smart Museum of Art and the National Vietnam Veterans Art Museum are two more places to stick on your schedule.

Take a step back through time and explore the people and events that have contributed to this region at the Glessner House Museum and the Dupage County Historical Museum. You can also check out fascinating exhibits which bring the past to life at the Joliet Area Historical Museum and the Gregg House Museum.

A visit to Chicago delivers the goods when it comes to historic places. You're sure to get a deeper awareness of bygone times at the University of Illinois Chicago and the Aurora University. If you're eager for more, the Chicago Cultural Center and the Merchandise Mart should also be on your itinerary.

You'll probably clap your eyes on Michigan Avenue Bridge while exploring Chicago. This historic bridge was built in a different era and will survive for a long time to come.

Regardless of what you believe in, you're sure to enjoy the tranquil atmosphere at Holy Name Cathedral and Unity Temple. The Anshe Emet Synagogue and Saints Peter and Paul Catholic Church are some other historically significant houses of prayer to add to your itinerary.

Don't hand in your hotel room key just yet, there's still lots to do! Have you visited the Newberry Library and the Cloud Gate yet? The Grohe America and the Visual Arts Center are some other options.

Best Chicago Flight + Hotel Holiday Deals

See all 1,801 properties in Chicago
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL
    3.5 out of 5.0
     
     
    3.9 out of 5 (10 reviews)

    The comfortable rooms at Congress Plaza Hotel get good marks from our customers. During your stay, you're just a quick walk from Grant Park. Enjoy features like ...

    Congress Plaza Hotel£110

    Congress Plaza Hotel£110
    Hotel Essex Chicago

    Hotel Essex Chicago

    800 S Michigan Ave, Chicago, IL
      4.0 out of 5.0
       
       
      4.0 out of 5 (1 reviews)

      Our customers tell us that they enjoy the public transport around Hotel Essex Chicago. During your stay, you're just a quick walk from Grant Park. Enjoy features ...

      Hotel Essex Chicago£92

      Hotel Essex Chicago£92
      Eurostars Magnificent Mile, previously Dana Hotel

      Eurostars Magnificent Mile, previously Dana Hotel

      660 North State Street, Chicago, IL
        4.0 out of 5.0
         
         
        4.2 out of 5 (16 reviews)

        The nightlife around Eurostars Magnificent Mile, previously Dana Hotel gets good marks from our customers. During your stay, you're just a quick walk from Chicago ...

        Eurostars Magnificent Mile, previously Dana Hotel£117

        Eurostars Magnificent Mile, previously Dana Hotel£117
        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 nightlife around The St. Clair Hotel – Magnificent Mile gets good marks from our customers. During your stay, you're just a quick walk from Tribune Tower. ...

          The St. Clair Hotel – Magnificent Mile£81

          The St. Clair Hotel – Magnificent Mile£81
          Inn of Chicago

          Inn of Chicago

          162 E Ohio St, Chicago, IL
            3.0 out of 5.0
             
             
            3.8 out of 5 (13 reviews)

            Our customers tell us that they enjoy the comfortable rooms at Inn of Chicago. During your stay, you're just a quick walk from Tribune Tower. You'll find features ...

            Inn of Chicago£68

            Inn of Chicago£68
            Warwick Allerton - Chicago

            Warwick Allerton - Chicago

            701 North Michigan Avenue, Chicago, IL
              4.0 out of 5.0
               
               
              4.2 out of 5 (18 reviews)

              Our customers tell us they enjoy Warwick Allerton - Chicago's central location. During your stay, you'll be connected to a shopping centre and just a quick walk ...

              Warwick Allerton - Chicago£108

              Warwick Allerton - Chicago£108
              DoubleTree by Hilton Chicago - Magnificent Mile

              DoubleTree by Hilton Chicago - Magnificent Mile

              300 E Ohio St, Chicago, IL
                3.5 out of 5.0
                 
                 
                4.0 out of 5 (4 reviews)

                DoubleTree by Hilton Chicago - Magnificent Mile's central location gets good marks from our customers. During your stay, you're just a quick walk from Chicago ...

                DoubleTree by Hilton Chicago - Magnificent Mile£94

                DoubleTree by Hilton Chicago - Magnificent Mile£94
                Wyndham Grand Chicago Riverfront

                Wyndham Grand Chicago Riverfront

                71 E Wacker Dr, Chicago, IL
                  4.0 out of 5.0
                   
                   
                  4.5 out of 5 (17 reviews)

                  Our customers tell us that they enjoy the nightlife around Wyndham Grand Chicago Riverfront. During your stay, you're just a quick walk from Chicago Theatre. ...

                  Wyndham Grand Chicago Riverfront£148

                  Wyndham Grand Chicago Riverfront£148
                  The Whitehall Hotel

                  The Whitehall Hotel

                  105 E Delaware Pl, Chicago, IL
                    4.0 out of 5.0
                     
                     
                    3.8 out of 5 (25 reviews)

                    Our customers tell us they enjoy The Whitehall Hotel's walkable location. During your stay, you're just a quick walk from Water Tower Place. Free WiFi in public ...

                    The Whitehall Hotel£106

                    The Whitehall Hotel£106
                    Palmer House a Hilton Hotel

                    Palmer House a Hilton Hotel

                    17 E Monroe St, Chicago, IL
                      4.0 out of 5.0
                       
                       
                      4.0 out of 5 (7 reviews)

                      Palmer House a Hilton Hotel's good location gets good marks from our customers. During your stay, you're just a quick walk from Grant Park. Free WiFi in public ...

                      Palmer House a Hilton Hotel£137

                      Palmer House a Hilton Hotel£137

                      ^Savings based on all holiday package bookings with Flight + Hotel made on ebookers.com 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.

                      *Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.