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Best Chicago Hotel Deals

Hotel Essex Chicago AU$170
Hotel Essex Chicago

Hotel Essex Chicago

800 S Michigan Ave, Chicago, IL
Hotel Essex Chicago
     
    5.0
    of 5, from 1 reviews
    4.0 out of 5.0 Stars

    Hotel Essex Chicago places you in the centre of Chicago, steps from Grant Park and within a short 5-minute stroll of State Street. Highlights at this hotel include a restaurant, a 24-hour fitness centre and a bar/lounge.

    Warwick Allerton - Chicago AU$198
    Warwick Allerton - Chicago

    Warwick Allerton - Chicago

    701 North Michigan Avenue, Chicago, IL
    Warwick Allerton - Chicago
       
      4.0
      of 5, from 3 reviews
      4.0 out of 5.0 Stars

      Warwick Allerton - Chicago puts you in the heart of Chicago, connected to a shopping centre and within steps of popular attractions like Michigan Avenue and Northwestern Memorial Hospital. Highlights at this family-friendly hotel include a restaurant, a 24-hour fitness centre and a bar/lounge.

      Congress Plaza Hotel AU$200
      Congress Plaza Hotel

      Congress Plaza Hotel

      520 South Michigan Avenue, Chicago, IL
      Congress Plaza Hotel
         
        3.8
        of 5, from 10 reviews
        3.5 out of 5.0 Stars

        Congress Plaza Hotel puts you in the heart of Chicago, within steps of Auditorium Building and Theatre and Columbia College Chicago. Highlights at this hotel include 2 restaurants, 2 bars/lounges and a restaurant.

        The Whitehall Hotel AU$163
        The Whitehall Hotel

        The Whitehall Hotel

        105 E Delaware Pl, Chicago, IL
        The Whitehall Hotel
           
          3.8
          of 5, from 5 reviews
          4.0 out of 5.0 Stars

          A romantic stay in the heart of Chicago awaits you at The Whitehall Hotel. Within steps you'll find popular attractions like John Hancock Center and Water Tower Place. Highlights at this boutique hotel include 2 restaurants and in-room free WiFi.

          Hilton Chicago O'Hare Airport AU$191
          Hilton Chicago O'Hare Airport

          Hilton Chicago O'Hare Airport

          Ohare International Airport, Chicago, IL
          Hilton Chicago O'Hare Airport
             
            3.0
            of 5, from 3 reviews
            4.0 out of 5.0 Stars

            At Hilton Chicago O'Hare Airport, you'll be connected to the airport and 4.6 km (2.8 mi) from Donald E. Stephens Convention Center. Highlights at this hotel include 2 restaurants, 2 bars/lounges and an indoor swimming pool.

            Travelodge by Wyndham Downtown Chicago AU$164
            Travelodge by Wyndham Downtown Chicago

            Travelodge by Wyndham Downtown Chicago

            65 E Harrison St, Chicago, IL
            Travelodge by Wyndham Downtown Chicago
               
              2.8
              of 5, from 4 reviews
              2.0 out of 5.0 Stars

              At Travelodge by Wyndham Downtown Chicago you'll be within steps of popular attractions like Grant Park and Columbia College Chicago. Highlights at this hotel include a restaurant and in-room free WiFi.

              Palmer House a Hilton Hotel AU$240
              Palmer House a Hilton Hotel

              Palmer House a Hilton Hotel

              17 E Monroe St, Chicago, IL
              Palmer House a Hilton Hotel
                 
                2.3
                of 5, from 3 reviews
                4.0 out of 5.0 Stars

                A romantic stay in the heart of Chicago awaits you at Palmer House a Hilton Hotel. Within a short 5-minute stroll, you'll find Art Institute of Chicago and Millennium Park. Highlights at this historic hotel include a full-service spa, a restaurant and an indoor swimming pool.

                Millennium Knickerbocker Chicago AU$180
                Millennium Knickerbocker Chicago

                Millennium Knickerbocker Chicago

                163 East Walton Place, Chicago, IL
                Millennium Knickerbocker Chicago
                   
                  4.0 out of 5.0 Stars

                  Millennium Knickerbocker Chicago puts you in the heart of Chicago, steps from John Hancock Center and within a 10-minute stroll of Museum of Contemporary Art. Highlights at this hotel include a restaurant and in-room free WiFi.

                  Top Budget Chicago Hotel Deals

                  Motel 6 Elk Grove Village - O'Hare AU$75
                  Motel 6 Elk Grove Village - O'Hare

                  Motel 6 Elk Grove Village - O'Hare

                  2881 Touhy Ave, Elk Grove Village, IL
                     
                    5.0
                    of 5, from 2 reviews
                    2.0 out of 5.0 Stars

                    At Motel 6 Elk Grove Village - O'Hare you'll be 4.9 km (3.1 mi) from Allstate Arena and 3.3 km (2.1 mi) from Lake Park. Highlights at this hotel include free in-room WiFi.

                    Freehand Chicago AU$150
                    Freehand Chicago

                    Freehand Chicago

                    19 East Ohio Street, Chicago, IL
                       
                      4.7
                      of 5, from 3 reviews
                      3.5 out of 5.0 Stars

                      Freehand Chicago puts you in the heart of Chicago, steps from Chinese Consulate and within a 10-minute stroll of Holy Name Cathedral. Highlights at this Art Deco hotel include a restaurant, a 24-hour fitness centre and a bar/lounge.

                      Travelodge by Wyndham Downtown Chicago AU$164
                      Travelodge by Wyndham Downtown Chicago

                      Travelodge by Wyndham Downtown Chicago

                      65 E Harrison St, Chicago, IL
                         
                        2.8
                        of 5, from 4 reviews
                        2.0 out of 5.0 Stars

                        At Travelodge by Wyndham Downtown Chicago you'll be within steps of popular attractions like Grant Park and Columbia College Chicago. Highlights at this hotel include a restaurant and in-room free WiFi.

                        Ohio House Motel AU$171
                        Ohio House Motel

                        Ohio House Motel

                        600 North LaSalle Street, Chicago, IL
                           
                          2.5 out of 5.0 Stars

                          Ohio House Motel places you in the centre of Chicago, within just a 15-minute stroll of Merchandise Mart and Wrigley Building. Highlights at this motel include 3 coffee shops/cafés, a restaurant and free self parking.

                          Top Luxury Chicago Hotel Deals

                          Trump International Hotel & Tower Chicago AU$478
                          Trump International Hotel & Tower Chicago

                          Trump International Hotel & Tower Chicago

                          401 N Wabash Ave, Chicago, IL
                             
                            5.0
                            of 5, from 1 reviews
                            5.0 out of 5.0 Stars

                            A luxury stay in Chicago awaits you at Trump International Hotel & Tower Chicago. Within steps you'll find Wrigley Building and Chicago Riverwalk within a short 5-minute stroll. Highlights at this family-friendly hotel include a full-service spa, a restaurant and an indoor swimming pool.

                            The Langham, Chicago AU$501
                            The Langham, Chicago

                            The Langham, Chicago

                            330 North Wabash Avenue, Chicago, IL
                               
                              5.0
                              of 5, from 2 reviews
                              5.0 out of 5.0 Stars

                              A luxury stay in the heart of Chicago awaits you at The Langham, Chicago. Within a 5-minute stroll you'll find Michigan Avenue and Millennium Park within a 15-minute walk. Highlights at this family-friendly hotel include a full-service spa, a restaurant and an indoor swimming pool.

                              The Peninsula Chicago AU$659
                              The Peninsula Chicago

                              The Peninsula Chicago

                              108 East Superior Street, Chicago, IL
                                 
                                5.0
                                of 5, from 1 reviews
                                5.0 out of 5.0 Stars

                                A luxury stay in the heart of Chicago awaits you at The Peninsula Chicago, a recipient of the prestigious Conde Nast Top 100 List award in 2012. Within steps you'll find popular attractions like Chicago Water Tower and Michigan Avenue. Highlights at this family-friendly hotel include 3 restaurants, a full-service spa and an outdoor swimming pool.

                                The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago AU$264
                                The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

                                The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

                                521 North Rush Street, Chicago, IL
                                   
                                  4.5
                                  of 5, from 2 reviews
                                  4.5 out of 5.0 Stars

                                  A luxury stay in the heart of Chicago awaits you at The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago, a recipient of the prestigious Conde Nast Top 100 List award in 2013. Within steps you'll find popular attractions like Tribune Tower and Michigan Avenue. Highlights at this romantic hotel include 2 restaurants, a restaurant and a 24-hour fitness centre.

                                  Accommodation In Chicago

                                  Don’t be shy when “Chi-Town” calls your name. Despite the rumours of cold, windy mornings, the largest city in Illinois offers a warm Midwestern welcome to travellers seeking sporting events, performing arts and a saucy piece of pizza pie. As a major political and media hub, Chicago has a serious side, but don’t underestimate the opportunities for fun and belly laughs that await you on Chicago holidays.

                                  With attractions sprinkled all over the city, from Wrigleyville to Hyde Park, hotels in Chicago are available close to the top sites on your itinerary. You can even book accommodation near Lincoln Park for instant access to the Museum of Contemporary Art Chicago and your new furry or feathered buddies at the Lincoln Park Zoo.

                                  Things to Do in Chicago

                                  First things first, traveller. Let’s go out to the ballgame. Even if sports aren’t your thing, you’re a baseball fan when you’re in Chicago. Pick up some blue and red face paint and grab seats at Wrigley Field for the next home game. Once you’ve shouted with the locals, check out the bean-shaped Cloud Gate sculpture and jog through Millennium Park, because nothing puts your life into refreshing perspective like a reflective legume.

                                  If you want to visit Chicago’s biggest hitters right off the bat, get a Chicago CityPASS and tour top attractions like Shedd Aquarium and The Field Museum. OK, we’ll stop with the baseball puns.

                                  North of Millennium Park, the Chicago Riverwalk is the perfect place to eat and shop to your heart’s content, surrounded by gorgeous views and luxurious Chicago hotels where you can relax after a long, tiring day of…being on holiday. When you’re ready for more, make your way up the Magnificent Mile to the vintage Gold Coast neighbourhood for an arvo at the beach.

                                  Next, catch a comedy show at Second City Theater in nearby Old Town. Once a nickname for Chicago’s status as the lesser of the country’s biggest cities, “Second City” is now synonymous with the funniest people of the past century, including Tina Fey, Alan Arkin and Gilda Radner.

                                  Getting To & Around Chicago

                                  Breeze into the “Windy City” via two major transit hubs: O’Hare International Airport (ORD), located about 17km northwest of downtown, or Chicago Midway International Airport (MDW), just 11km to the southwest. With an efficient light rail system and bus routes weaving through busy streets, you can easily get from the airport to popular attractions and accommodation in Chicago with public transportation. If you want to tackle traffic like a local, pick up some wheels with one of our car hire options and hit the streets.

                                  Upcoming Events

                                  Between April and October, Chicago trades in its blustery reputation for warm breezes and stylish sunnies. That’s when the events calendar is hopping, so consider booking Chicago accommodation during this time if fun in the sun is important to you—how could it not be?

                                  As summer winds down, the only thing moving at a slower pace are the smooth tunes crooning from the Chicago Jazz Festival every September. Come October, there’s a party a’brewin’—the annual Chicago Beer Hoptacular, which is a celebration of exactly what it sounds like. Bottoms up!

                                  You’ve no doubt heard that Chicago can get chilly from November through February, but these cold months are among the city’s most beautiful. The winter wonderland glows during the Magnificent Mile Lights Festival and other celebrations in November. To keep yourself warm during a brisk November holiday, join the singing, dancing and art-making at the annual Native American Pow Wow.

                                  Get Outside!

                                  If you’ve ever wondered how Chicago got its motto, “urbs in horto”, then you’re not alone. If you’ve ever wondered what “urbs in horto” means, you’re really not alone. The English translation is “city in a garden”, and Chicago sure does live by its slogan. The streets are lined with skyscrapers, but these scrappy Midwesterners will have their green spaces, doggone it. In fact, you can take a breath of fresh air surrounded by flora galore on the rooftop of City Hall!

                                  Closer to sea level, the Alfred Caldwell Lily Pool is a peaceful—and watery—oasis in already-gorgeous Lincoln Park. You’ll definitely want to snap some selfies in the stone-lined pergolas. But be advised, there is a high probability that you will either witness a marriage proposal or get the strange urge to make a lifelong commitment in this lovely garden. Hey, it happens.

                                  To run through wide open spaces in the middle of the big city, lace up your trainers and head to the Burnham Centennial Prairie, a nature preservation area on the Chicago Lakefront Trail. Tall grass grows in the breeze and wildflowers take over the sprawling fields. Located on the edge of Lake Michigan and close to the busy Loop, the Lakefront Trail is lined with some of the best places to stay in Chicago.

                                  Must-See Sights

                                  When you hit the windy streets of “Chi-Town” it’s hard not to see the tallest building in the city, but make sure you have your eyes looking up when you’re wandering through the west side of the Loop, especially if you have just one day in Chicago. “Why?” you ask? Because that’s where you’ll find Willis Tower (aka “Sears Tower”, aka “442 metres of awesome”), which was considered the highest building in the world until 1998.

                                  When you’re done staring, get out of the middle of the footpath and head to Navy Pier to graze on some of the best food in Chicago. From shopping on the boardwalk to stuffing your face with smoked smallmouth bass in waterfront restaurants, your arvo will be off to a good start. Stick around for a concert or hop on a cocktail cruise to top off the perfect holiday in style.

                                  Ready to make your way through the “Toddling Town”? Book hotels and flights to Chicago with Wotif. We’ve found great travel deals, and we’re really good at sharing.

                                  Need insider tips on must-see attractions in Chicago? Check out our Chicago travel guide!

                                  How Much is a Hotel Room in Chicago?

                                  Hotels in Chicago start at AU$75 per night. Prices and availability subject to change. Additional terms may apply.

                                  New Reviews - Best Hotels in Chicago

                                  Just Booked! Cheap Hotels in Chicago


                                  *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.