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182 customers have saved 100% on their flight when booking a Flight + Hotel together this year!
182 customers have saved 100% on their flight when booking a Flight + Hotel together this year!
182 customers have saved 100% on their flight when booking a Flight + Hotel together this year!

Chicago Flight + Hotel packages

Cheap Chicago Hotels

See all 1,473 Properties in Chicago
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

17 E Monroe St, Chicago
    4.0 out of 5.0
     
     
    3.9 out of 5 (51 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$95

    Palmer House a Hilton Hotel$95
    Hyatt Regency Chicago

    Hyatt Regency Chicago

    151 East Wacker Dr, Chicago
      4.0 out of 5.0
       
       
      4.2 out of 5 (80 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

      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 (34 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$87

        Embassy Suites Chicago Downtown Magnificent Mile$87
        Freehand Chicago

        Freehand Chicago

        19 East Ohio Street, Chicago
          3.5 out of 5.0
           
           
          4.2 out of 5 (11 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

          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
             
             
            5.0 out of 5 (1 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$65

            The St. Clair Hotel – Magnificent Mile$65
            Congress Plaza Hotel

            Congress Plaza Hotel

            520 South Michigan Avenue, Chicago
              3.5 out of 5.0
               
               
              4.0 out of 5 (12 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

              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
                 
                 
                4.1 out of 5 (32 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

                Hyatt Centric Chicago Magnificent Mile$120
                River Hotel

                River Hotel

                75 East Wacker Drive, Chicago
                  4.0 out of 5.0
                   
                   
                  4.2 out of 5 (36 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

                  River Hotel$67
                  Omni Chicago Suites - Magnificent Mile

                  Omni Chicago Suites - Magnificent Mile

                  676 N Michigan Ave, Chicago
                    4.5 out of 5.0
                     
                     
                    5.0 out of 5 (2 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

                    Omni Chicago Suites - Magnificent Mile$144
                    Warwick Allerton - Chicago

                    Warwick Allerton - Chicago

                    701 North Michigan Avenue, Chicago
                      4.0 out of 5.0
                       
                       
                      3.9 out of 5 (111 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

                      Warwick Allerton - Chicago$68
                      Map

                      Your Chicago vacation

                      From food to theater and Lake Michigan to the Loop, Chicago is home to some equally big names. But you don't need to fly in on Obama's Air Force One or have pockets as deep as Oprah to be able to experience a Chicago vacation at its fullest. Take a stroll down the Magnificent Mile, catch a Cubs game at Wrigley Field, and soak up the waterfront culture of the Second City.

                      Before you rush to Millennium Park, allow CheapTickets to help you with the planning. We'll share the city's top highlights that will blow your mind -- without blowing your budget.

                      Best time to take a vacation to Chicago

                      If you visit Chicago in the early fall you will experience the best of its weather as it retains its warm temperatures but loses the humidity of the summer months. Spring time is cooler, and it is a good time to capture those cheaper flights and hotels. The Chicago Blues Festival every June attracts headline acts from around the country and is extremely popular, as is the early three-day snow sculpturing exhibition held every winter on Navy Pier. Grant Park at the harbor hosts an annual Taste of Chicago Food Festival which, as you might expect, appeals to a wide audience.

                      Insider tips for Chicago travel

                      Alta Vista Terrace

                      Capture the history of Alta Vista Terrace close to Wrigley Field, modeled on a block of row houses in London.

                      Cafe Selmarie

                      Take lunch at the charming Cafe Selmarie overlooking the Lincoln Square Fountain and consume some mouth-watering cakes.

                      Montrose Harbor

                      Walk the lake-front trail north towards Montrose Harbor with some incredible views of the city skyline.

                      Ping Tom Memorial Park

                      Admire the Oriental architecture on a steady stroll through the pleasant and quiet surroundings of Ping Tom Memorial Park.

                      Pancho Pistolas

                      Dine out at Pancho Pistolas restaurant serving delicious Mexican cuisine in the Bridgeport neighborhood.

                      Chicago highlights

                      Magnificent Mile

                      The Mag Mile is a revered for its incredible shopping and eating scene, as well as the festivities that occur throughout the year. Lined by colorful tulips in the springtime and glittering lights during the holidays, the Mag Mile is chockablock with department stores and notable landmarks, from the Wrigley Building to Oak Street Beach. For incredible views on your Chicago travels, head to the Hancock Observatory or spend a few bucks on a cocktail in the Signature Lounge.

                      Lincoln Park Zoo

                      For an easy escape without having to spend a cent on your Chicago travels, take the afternoon to meander through the menagerie at the Lincoln Park Zoo. Not only is it brimming with wildlife exhibits and beautiful historical architecture, it's totally free and open 365 days a year.

                      Cultural Chicago

                      If you want to experience the cultural side of the Second City on your Chicago vacation, make a beeline for the Chicago Cultural Center where admission is free. After taking in the impressive architecture and stunning Tiffany dome, head to the Art Institute across the street to view the amazing collection of Impressionist art and the new Modern Wing. Take a stroll to the Buckingham Fountain and laze in the sun, or take in a nighttime light show.

                      Millennium Park

                      Chicago has plenty of parks, but this one is worth a special mention. An impressive feat of engineering, landscaping and cultural celebration, Millennium Park is home to the iconic Cloud Gate sculpture and splashy Crown Fountain video sculpture. Enjoy a concert at Jay Pritzker Pavilion, the go-to spot for the best in outdoor entertainment.

                      Navy Pier

                      For a bustling carnival vibe along Lake Michigan, wander along the Navy Pier promenade and catch the spirit of Chicago. Bring the kids to the Children's Museum, Shakespeare Theatre or Stained Glass Gallery, and marvel at the incredible skyline views from the 150-foot Ferris wheel. Grab a bite to eat at Chicago institution Harry Caray's, and rest your weary feet to enjoy the free weekly fireworks.

                      *Savings based on all holiday package bookings with Flight + Hotel on CheapTickets.com from July 1, 2015 to June 30, 2016, 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. 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.

                      * Prices reflect the lowest "base rate" found over the next 30 days. Rates are subject to change and may not include taxes and fees, hotel service charges, extra person charges, or incidentals, such as room service. All rates are displayed in USD unless otherwise noted. Converted rates are provided for your convenience. They are based on today's exchange rate, but the hotel will charge you in the local currency.