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Lowest round trip fares by airline from Chicago and San Luis Obispo

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

Cheap flights from Chicago to San Luis Obispo

Cheap flights from Chicago to San Luis Obispo

Are you ready to book your flight, but feeling nervous about paying too much if the price drops? Don't play the waiting game. Our Best Price Guarantee means if you see a better fare for the same flight, we'll give you the difference in CheapCash, plus a $50 CheapCash bonus, which you can use to save on your hotel reservation.

If you have a frequent flier account, add it to your reservation to earn miles. And don't worry about getting stuck in a middle seat. Choose your seats when you book, so you'll be right where you want to be on departure day.

Save Even More Time and Money With a San Luis Obispo Travel Package

Once your flights are booked, why start all over again searching for a cheap hotel? Book your flight and hotel together, and save yourself more than time and energy. You'll also be able to take advantage of discounts and coupons on your San Luis Obispo vacation that you can't get when you book flights and hotel separately.

Relax in San Luis Obispo With Confidence and Convenience

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Hotels in San Luis Obispo

See all 726 Properties in San Luis Obispo

Estimated price for 1 night/2 adults

Oxford Suites Pismo Beach

Oxford Suites Pismo Beach

651 Five Cities Dr, Pismo Beach, CA
    2.5 out of 5.0
     
     
    4.6 out of 5 (11 reviews)

    Situated near the airport, this motel is 0.2 mi (0.3 km) from Pismo Lake Ecological Reserve and 1.5 mi (2.4 km) from Pismo Beach Pier. Pismo Beach Prime Outlets ...

    Oxford Suites Pismo Beach$139

    Aug 4 - Aug 5

    Oxford Suites Pismo Beach$139
    SeaCrest OceanFront Hotel

    SeaCrest OceanFront Hotel

    2241 Price Street, Pismo Beach, CA
      3.5 out of 5.0
       
       
      4.2 out of 5 (15 reviews)

      Nestled on the beach, this Motel District hotel is within 2 mi (3 km) of Pismo Beach Pier and Monarch Butterfly Grove. Mission San Luis Obispo de Tolosa and ...

      SeaCrest OceanFront Hotel$239

      Aug 15 - Aug 16

      SeaCrest OceanFront Hotel$239
      Holiday Inn Hotel and Suites Santa Maria

      Holiday Inn Hotel and Suites Santa Maria

      2100 N Broadway, Santa Maria, CA
        3.0 out of 5.0
         
         
        4.3 out of 5 (10 reviews)

        Situated in Santa Maria, this hotel is 0.2 mi (0.4 km) from Boomers! Santa Maria and 2 mi (3.3 km) from Santa Maria Speedway. Santa Maria Fairpark and Santa ...

        Holiday Inn Hotel and Suites Santa Maria$92

        Aug 4 - Aug 5

        Holiday Inn Hotel and Suites Santa Maria$92
        Madonna Inn

        Madonna Inn

        100 Madonna Road, San Luis Obispo, CA
          3.5 out of 5.0
           
           
          4.4 out of 5 (7 reviews)

          Situated in San Luis Obispo, this spa hotel is 0.7 mi (1.1 km) from Laguna Lake Park and 1.5 mi (2.4 km) from Mission San Luis Obispo de Tolosa. Cerro San Luis ...

          Madonna Inn$209

          Jul 23 - Jul 24

          Madonna Inn$209
          La Bellasera Hotel And Suites

          La Bellasera Hotel And Suites

          206 Alexa Ct, Paso Robles, CA
            4.0 out of 5.0
             
             
            4.6 out of 5 (5 reviews)

            Situated in a rural location, this spa resort is within 2 mi (3 km) of Firestone Walker Brewing, Peachy Canyon Winery, and Windward Vineyard. Castoro Cellars ...

            La Bellasera Hotel And Suites$149

            Jul 29 - Jul 30

            La Bellasera Hotel And Suites$149
            Olive Tree Inn & Suites

            Olive Tree Inn & Suites

            1000 Olive St., San Luis Obispo, CA
              2.5 out of 5.0
               
               
              3.5 out of 5 (2 reviews)

              Situated in San Luis Obispo, this motel is within 1 mi (2 km) of Santa Rosa Park and Mission San Luis Obispo de Tolosa. California Polytechnic State University ...

              Olive Tree Inn & Suites$75

              Aug 4 - Aug 5

              Olive Tree Inn & Suites$75
              Spyglass Inn

              Spyglass Inn

              2705 Spyglass Dr, Pismo Beach, CA
                3.0 out of 5.0
                 
                 
                4.4 out of 5 (8 reviews)

                Situated on the waterfront, this motel is 1.6 mi (2.6 km) from Avila Hot Springs and 1.7 mi (2.7 km) from Margo Dodd Park. Pismo Beach Pier and Pismo Beach Prime ...

                Spyglass Inn$213

                Aug 15 - Aug 16

                Spyglass Inn$213
                Avenue Inn Downtown San Luis Obispo

                Avenue Inn Downtown San Luis Obispo

                345 Marsh St, San Luis Obispo, CA
                  2.5 out of 5.0
                   
                   
                  4.0 out of 5 (4 reviews)

                  Located in Downtown, this motel is within a 15-minute walk of Cerro San Luis Obispo and Mission San Luis Obispo de Tolosa. California Polytechnic State University ...

                  Avenue Inn Downtown San Luis Obispo$95

                  Aug 11 - Aug 12

                  Avenue Inn Downtown San Luis Obispo$95
                  Inn at the Pier

                  Inn at the Pier

                  601 Cypress Street, Pismo Beach, CA
                    4.0 out of 5.0
                     
                     
                    5.0 out of 5 (2 reviews)

                    Located in Downtown, this beach hotel is within 1 mi (2 km) of Monarch Butterfly Grove and Pismo Beach Pier. North Beach Campground and Price Anniversary House ...

                    Inn at the Pier$239

                    Aug 11 - Aug 12

                    Inn at the Pier$239
                    La Quinta Inn & Suites by Wyndham San Luis Obispo Downtown

                    La Quinta Inn & Suites by Wyndham San Luis Obispo Downtown

                    1845 Monterey St., San Luis Obispo, CA
                      3.0 out of 5.0
                       
                       

                      Situated in San Luis Obispo, this hotel is within 1 mi (2 km) of Fremont Theater and Mission San Luis Obispo de Tolosa. California Polytechnic State University ...

                      La Quinta Inn & Suites by Wyndham San Luis Obispo Downtown$152

                      Aug 11 - Aug 12

                      La Quinta Inn & Suites by Wyndham San Luis Obispo Downtown$152
                      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.