Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Condos
Cottages
Estates
Hotels
Homes
Studios
Townhomes
Barns
Boats
Bungalows
Cabins
Castles
Chalets
Farmhouses
Lodges
Villas
Yachts

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Chicago Vacation Rentals(197)

197 Results
Book it Now!
3 - 4 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
    (109)
    Book it Now!
    3 - 4 night minimum stay
    • 1 BR,
    • 1 BA,
    • Sleeps 4
      (183)
      Book it Now!
      3 - 4 night minimum stay
      • 2 BR,
      • 2 BA,
      • Sleeps 6
        (102)
        Book it Now!
        3 - 4 night minimum stay
        • 3 BR,
        • 3 BA,
        • Sleeps 8
          (47)
          Book it Now!
          2 night minimum stay
          • 2 BR,
          • 2 BA,
          • Sleeps 8
            (61)
            Book it Now!
            2 - 4 night minimum stay
            • 3 BR,
            • 1 BA,
            • 1 HF BA,
            • Sleeps 6
              (56)
              Book it Now!
              3 - 7 night minimum stay
              • 2 BR,
              • 2 BA,
              • Sleeps 6
                (54)
                Book it Now!
                3 - 7 night minimum stay
                • 2 BR,
                • 2 BA,
                • Sleeps 6
                  (58)
                  Book it Now!
                  3 - 7 night minimum stay
                  • 2 BR,
                  • 2 BA,
                  • Sleeps 6
                    (55)
                    Book it Now!
                    3 - 7 night minimum stay
                    • 2 BR,
                    • 2 BA,
                    • Sleeps 6
                      (35)
                      Book it Now!
                      3 - 4 night minimum stay
                      • 2 BR,
                      • 1 BA,
                      • 1 HF BA,
                      • Sleeps 6
                        (31)
                        Book it Now!
                        3 - 4 night minimum stay
                        • 2 BR,
                        • 3 BA,
                        • Sleeps 8
                          (44)
                          Book it Now!
                          4 night minimum stay
                          • 2 BR,
                          • 1 BA,
                          • Sleeps 4
                            (39)
                            Book it Now!
                            2 - 5 night minimum stay
                            • 3 BR,
                            • 2 BA,
                            • Sleeps 8
                              (25)
                              Book it Now!
                              3 - 4 night minimum stay
                              • 2 BR,
                              • 2 BA,
                              • Sleeps 7
                                (31)
                                Book it Now!
                                3 - 7 night minimum stay
                                • 2 BR,
                                • 2 BA,
                                • Sleeps 6
                                  (17)
                                  Book it Now!
                                  2 - 4 night minimum stay
                                  • 4 BR,
                                  • 3 BA,
                                  • 1 HF BA,
                                  • Sleeps 24
                                    (27)
                                    Book it Now!
                                    1 - 3 night minimum stay
                                    • 1 BR,
                                    • 1 BA,
                                    • Sleeps 4
                                      (31)
                                      Book it Now!
                                      1 - 3 night minimum stay
                                      • 3 BR,
                                      • 2 BA,
                                      • Sleeps 8
                                        (25)
                                        Book it Now!
                                        1 - 3 night minimum stay
                                        • 4 BR,
                                        • 2 BA,
                                        • Sleeps 9
                                          (28)
                                          Book it Now!
                                          1 - 3 night minimum stay
                                          • 4 BR,
                                          • 2 BA,
                                          • Sleeps 9
                                            (25)
                                            3 night minimum stay
                                            • 2 BR,
                                            • 2 BA,
                                            • Sleeps 6
                                              (61)
                                              Book it Now!
                                              2 night minimum stay
                                              • 2 BR,
                                              • 2 BA,
                                              • Sleeps 8
                                                (8)
                                                Book it Now!
                                                6 night minimum stay
                                                • 1 BR,
                                                • 1 BA,
                                                • Sleeps 4
                                                  (10)
                                                  3 night minimum stay
                                                  • 5 BR,
                                                  • 3 BA,
                                                  • Sleeps 13
                                                    (26)
                                                    $260 - $335
                                                    per night
                                                    Book it Now!
                                                    3 night minimum stay
                                                    • 1 BR,
                                                    • 1 BA,
                                                    • Sleeps 4
                                                      (6)
                                                      Book it Now!
                                                      2 - 5 night minimum stay
                                                      • 2 BR,
                                                      • 2 BA,
                                                      • Sleeps 6
                                                        (21)
                                                        Book it Now!
                                                        3 - 4 night minimum stay
                                                        • 3 BR,
                                                        • 2 BA,
                                                        • Sleeps 8
                                                          (3)
                                                          Book it Now!
                                                          3 - 5 night minimum stay
                                                          • 1 BR,
                                                          • 1 BA,
                                                          • Sleeps 4
                                                            (6)
                                                            Book it Now!
                                                            3 - 7 night minimum stay
                                                            • 2 BR,
                                                            • 2 BA,
                                                            • Sleeps 6
                                                              (4)
                                                              Advertisement
                                                               

                                                              Recent Chicago Reviews

                                                              Even better than it looks on the pictures

                                                              5 of 5
                                                              Very confortable and well decorated apartment. Even better than it looks on the photos. Really close to the Brown line El train station Western. The neighbourhood (Lincoln Square) is great. With our 2 teenage daughters we enjoyed staying in this cosy apartment for 10 nights (in 2 stays). We found the 2 queenbeds quite confortable. The listing description was quite accurate. Everything was very clean and worked well. Though I am not a great cook I appreciated that the kitchen was well stocked with pans in very good condition: it is always a bit unpleasant to have to use wornout frying pans such as those often provided in rented apartments. No such thing in Carl`s apartment: everything was perfect! Carl welcomed us warmly and provided us with useful information - written detailed information is also available in the apartment - and everything we needed. Thank you Carl ! I definetly recommend this vacation rental.
                                                              • Submitted: Aug 26, 2014
                                                              • Stayed: Aug 2014

                                                              Awesome Condo, Great Location

                                                              5 of 5
                                                              The unit was very clean. It has great views and you can't beat the location. The pool was great for our kids and the grocery store located at the entrance to the building was very convenient. The property owners send you an app for your smartphone with all the details about the unit which was very helpful.
                                                              • Submitted: Aug 22, 2014
                                                              • Stayed: Jul 2014

                                                              McCool

                                                              5 of 5
                                                              Beautiful location and room. High-end furnishings and great to have grocery downstairs. The only recommendation I have is maybe get some sturdier chairs/bar stools in the dining area. A few of them were a little rickety. Close to a perfect setup overall.
                                                              • Submitted: Aug 22, 2014
                                                              • Stayed: Jul 2014