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Lowest round trip fares by airline from Chicago and Pensacola

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

Cheap flights from Chicago to Pensacola

Chicago to Pensacola

Cheap flights from Chicago to Pensacola

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Hotels in Pensacola

See all 1,568 Properties in Pensacola
Pensacola Grand Hotel

Pensacola Grand Hotel

200 E Gregory Street, Pensacola, FL
    3.5 out of 5.0
     
     
    4.5 out of 5 (16 reviews)

    Located in Downtown, this hotel is within a 15-minute walk of Pensacola Civic Center and Saenger Theatre. Historic Pensacola Village is 0.8 mi (1.3 km) ...

    Pensacola Grand Hotel$101

    Pensacola Grand Hotel$101
    Surf & Sand Hotel

    Surf & Sand Hotel

    40 Fort Pickens Road, Pensacola Beach, FL
      2.0 out of 5.0
       
       
      3.6 out of 5 (16 reviews)

      Offering direct access to the beach, this Pensacola Beach hotel is in the city center, 0.1 mi (0.2 km) from Pensacola Beach Pier, and within 9 mi (15 km) of ...

      Surf & Sand Hotel$89

      Surf & Sand Hotel$89
      Luxury Suites Pensacola

      Luxury Suites Pensacola

      6703 Pensacola Blvd, Pensacola, FL
        2.5 out of 5.0
         
         
        4.6 out of 5 (5 reviews)

        Located in Northwest Pensacola, this hotel is 0.1 mi (0.1 km) from Sam's Fun City and within 3 mi (5 km) of Marcus Pointe Golf Club and Brent Athletic Park. ...

        Luxury Suites Pensacola$59

        Luxury Suites Pensacola$59
        At Home Inn & Suites

        At Home Inn & Suites

        6550 Pensacola Boulevard, Pensacola, FL
          2.5 out of 5.0
           
           
          4.8 out of 5 (6 reviews)

          Located in Northwest Pensacola, this hotel is 0.4 mi (0.6 km) from Sam's Fun City and within 3 mi (5 km) of Marcus Pointe Golf Club and Brent Athletic Park. ...

          At Home Inn & Suites$59

          At Home Inn & Suites$59
          Best Western Beachside Resort

          Best Western Beachside Resort

          16 Via de Luna Dr, Pensacola Beach, FL
            2.5 out of 5.0
             
             
            3.7 out of 5 (12 reviews)

            Situated in Pensacola Beach, this beach hotel is within a 15-minute walk of Portofino Boardwalk and Pensacola Beach Pier. Naval Live Oaks Nature Preserve and ...

            Best Western Beachside Resort$95

            Best Western Beachside Resort$95
            Holiday Inn Resort Pensacola Beach

            Holiday Inn Resort Pensacola Beach

            14 Via De Luna Drive, Pensacola Beach, FL
              3.0 out of 5.0
               
               
              4.5 out of 5 (11 reviews)

              Nestled on the beach, this Pensacola Beach hotel is within a 10-minute walk of Portofino Boardwalk and Pensacola Beach Pier. Naval Live Oaks Nature Preserve ...

              Holiday Inn Resort Pensacola Beach$158

              Holiday Inn Resort Pensacola Beach$158
              Hampton Inn Pensacola Beach

              Hampton Inn Pensacola Beach

              2 Via De Luna Drive, Pensacola Beach, FL
                2.5 out of 5.0
                 
                 
                4.2 out of 5 (12 reviews)

                Nestled on the beach, this Plaza Primera hotel is within 1 mi (2 km) of Portofino Boardwalk and Pensacola Beach Pier. Naval Live Oaks Nature Preserve is 3 mi ...

                Hampton Inn Pensacola Beach$113

                Hampton Inn Pensacola Beach$113
                Quality Inn & Suites on the Bay near Pensacola Beach

                Quality Inn & Suites on the Bay near Pensacola Beach

                51 Gulf Breeze Pkwy, Gulf Breeze, FL
                  2.5 out of 5.0
                   
                   
                  2.5 out of 5 (6 reviews)

                  Located in Gulf Breeze, this beachfront hotel is in the city center and within 2 mi (3 km) of Woodland Park, Naval Live Oaks Nature Preserve, and Shoreline Park. ...

                  Quality Inn & Suites on the Bay near Pensacola Beach$74

                  Quality Inn & Suites on the Bay near Pensacola Beach$74
                  Margaritaville Beach Hotel

                  Margaritaville Beach Hotel

                  165 Fort Pickens Road, Pensacola Beach, FL
                    4.0 out of 5.0
                     
                     
                    4.6 out of 5 (5 reviews)

                    Located in Villa Sabine, this beachfront hotel is next to a golf course and within 1 mi (2 km) of Portofino Boardwalk and Pensacola Beach Pier. Naval Live Oaks ...

                    Margaritaville Beach Hotel$196

                    Margaritaville Beach Hotel$196
                    Country Inn & Suites by Radisson, Pensacola West, FL

                    Country Inn & Suites by Radisson, Pensacola West, FL

                    2607 Wilde Lake Blvd, Pensacola, FL
                      2.5 out of 5.0
                       
                       
                      4.7 out of 5 (6 reviews)

                      Located in Northwest Pensacola, this hotel is 1.6 mi (2.5 km) from Five Flags Speedway and within 6 mi (10 km) of Uncle Sandy's Macaw Bird Park and Sam's Fun ...

                      Country Inn & Suites by Radisson, Pensacola West, FL$84

                      Country Inn & Suites by Radisson, Pensacola West, FL$84
                      Map

                      *Savings based on all holiday package bookings with Flight + Hotel on CheapTickets.com from January through December 2017, 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.

                      *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.