Holiday Homes in Southwest Side

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Featured Holiday Homes in Southwest Side

Belmont House, Classy & Chic/walk to Wrigley Field
Hair dryer, towels, soap, shampoo

Belmont House, Classy & Chic/walk to Wrigley Field

9.4 out of 10, Exceptional, (41)
"Perfect location. Home was very comfortable and inviting. Beds and mattresses were heavenly. We thoroughly enjoyed our stay. "
Belmont House, Classy & Chic/walk to Wrigley Field
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Fridge, microwave, oven, stovetop

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!
Interior

Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!

10.0 out of 10, Exceptional, (121)
"We had an amazing time, and this home was a large part of why we enjoyed Chicago so much! The hosts were great, and very responsive to all of our questions! The home was spacious and warm. The perfect location, so close to the train so we could travel back and forth to downtown. The kitchen has a great space for cooking, what a great stove. The ping pong/billiards table was a hit! We would definitely stay here again! "
Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!
Stunning / Spacious 6BD Home + garage - Bucktown!
Fridge, microwave, oven, stovetop

Stunning / Spacious 6BD Home + garage - Bucktown!

9.2 out of 10, Wonderful, (30)
"I invited 5 guest to join me in Chicago for a birthday trip. This home is perfectly located between MDW and ORD. We had no trouble getting to our activities, great restaurants, downtown, or quick stores (Target, CVS, etc). The layout of the home is perfect with rooms and bathrooms on each level. The homeowner is also a wonderful communicator, great at responding. We had no trouble getting a hold of them prior to the trip or during the trip. Highly recommend! "
Stunning / Spacious 6BD Home + garage - Bucktown!
Your Next Vacation Home
Private kitchen

Your Next Vacation Home

9.8 out of 10, Exceptional, (30)
"This is the second year we have stayed at this location during Thanksgiving. It is convenient for visiting family members in Park Ridge and Glenview. The four bedrooms and two bathrooms provide the space we need. There is also a well equipped kitchen. "
The price is NZ$509
includes taxes & fees
28 Jan - 29 Jan
Your Next Vacation Home
Cheery 2+bedroom home with free parking on premises
Fridge, microwave, oven, stovetop

Cheery 2+bedroom home with free parking on premises

9.8 out of 10, Exceptional, (33)
"My husband and I spent a week here with our three dogs while in town for a family wedding. I was able to work from home while my husband took the CTA into the Chicago office of his company. The home was lovely and well stocked with everything that we needed for a week away from home. Would highly recommend."
Cheery 2+bedroom home with free parking on premises
Chicago Riverhouse with private fenced in oasis
Terrace/patio

Chicago Riverhouse with private fenced in oasis

9.8 out of 10, Exceptional, (20)
"Great location for needing to be around the north park area, my grandmother easily maneuvered (87 y/o), and our 4 y/o loved watching TV on the projector. Easy parking, easy access to downtown. If you need to be in the area I’d definitely recommend staying here!"
Chicago Riverhouse with private fenced in oasis
Eddy House, Roscoe Village Hideaway
Fridge, microwave, oven, stovetop

Eddy House, Roscoe Village Hideaway

10.0 out of 10, Exceptional, (5)
"Great house . "
Eddy House, Roscoe Village Hideaway
Woodlawn Oasis...10 Minutes to Dining & Downtown
Smart TV

Woodlawn Oasis...10 Minutes to Dining & Downtown

9.6 out of 10, Exceptional, (10)
"The property has lots of space and a game room, ideal for a fun getaway with a large group. Close to bus stops and Metra station (different from metro station, we learned this the hard way). Walking distance from the U of Chicago."
Woodlawn Oasis...10 Minutes to Dining & Downtown
Luxury Home Away From Your Home
Fridge, microwave, oven, stovetop

Luxury Home Away From Your Home

9.0 out of 10, Wonderful, (116)
"Had a great time at Ms. Linnie’s place! She was incredibly responsive and helpful. The house was clean and comfortable, and I loved that there were 2 full bathrooms! I was a little nervous about the neighborhood as we were definitely looked at as outsiders, but no one bothered us and we walked to Maxwell Street Polish and back just fine (which is fantastic, btw). I did love the gated yard in back with two parking spots, so we had our own space. Would definitely stay again!"
Luxury Home Away From Your Home
Chicago Bootlegger House Sleeps 11-22 with 3 parking spots
Fridge, microwave, oven, stovetop

Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

10.0 out of 10, Exceptional, (35)
"We had a great time staying here for a family trip. Plenty of space for games, cooking, sleeping, talking. We only used a fraction of what was available. When we had trouble figuring out heating system, host was very responsive. "
Chicago Bootlegger House Sleeps 11-22 with 3 parking spots
Lincoln Park Living - 3 Queen Beds - Sleeps 6!
TV

Lincoln Park Living - 3 Queen Beds - Sleeps 6!

9.6 out of 10, Exceptional, (9)
"We needed a place to sleep with our 3 young adult sons over the Christmas holiday and this place was perfect for that. It is very basic, but also much less expensive than most other places in this area, and in an excellent location. There are 2 coffee shops just around the corner and plenty of restaurants within easy walking distance. The rooms are clean and spacious. The bedroom has blackout curtains and comfortable beds. Seeing that it is located on a fairly busy street, the apartment was very...
Lincoln Park Living - 3 Queen Beds - Sleeps 6!
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Fridge, microwave, oven, stovetop

Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS

10.0 out of 10, Exceptional, (23)
"My family gets together every fall. Our first stay in a vacation rental home was in 2015. It is with almost ten years of knowledge that I declare this house one of the best. We had an amazing stay! Craig is wonderful host. This house is filled with all sorts of extras and bonuses. Getting in the house was easy. I can't tell you how many times we stood outside of a house because the code didn't work. We walked through the house oohing and ahhing in each room. Everyone loved watching movies...
The price is NZ$1,564
includes taxes & fees
10 Feb - 11 Feb
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Elegant 3BD Chalet! 🌲15min to ORD/Train 2 Dwntwn!
Terrace/patio

Elegant 3BD Chalet! 🌲15min to ORD/Train 2 Dwntwn!

10.0 out of 10, Exceptional, (11)
"It was a great house with needed amenities and lots of space. Great location not far from downtown. Host was great to communicate with."
Elegant 3BD Chalet! 🌲15min to ORD/Train 2 Dwntwn!
The Greenleaf House—Whole House
Living area

The Greenleaf House—Whole House

9.8 out of 10, Exceptional, (27)
"The house was big enough for whole family. It was also in a great location. However, the locked bedroom doors were a big inconvenience and the carpeting was disgusting. So dirty. Did not like walking in it without shoes."
The Greenleaf House—Whole House
Cozy Home Sweet Homewood.
Fridge, microwave, oven, stovetop

Cozy Home Sweet Homewood.

9.8 out of 10, Exceptional, (17)
"We were in Homewood for a wedding and this was a perfect location. Besides its proximity to the wedding venue, we walked to the train station for a day in the city. The house is exactly as listed. It was very clean, organized and comfortable. Everything we needed was supplied. My husband especially liked the TVs. 😊 Since we were there on Halloween, we had the added bonus of seeing a truly family-oriented neighborhood in action. Lots of happy trick-or-treaters showed up accompanied by lots of...
Cozy Home Sweet Homewood.
Lincoln Park Living - Suite 2!
Fridge, microwave, oven, stovetop

Lincoln Park Living - Suite 2!

9.4 out of 10, Exceptional, (22)
"The property was exactly as advertised. Great location for our weekend visit. Very comfortable and had everything we needed for a 2 night stay. "
Lincoln Park Living - Suite 2!
Cozy 5-bedroom with lake views and spacious deck
Outdoor dining

Cozy 5-bedroom with lake views and spacious deck

10.0 out of 10, Exceptional, (8)
"This was our 2nd year in a row staying here. Everything was great yet again. I highly recommend this house for anyone staying in the area."
Cozy 5-bedroom with lake views and spacious deck
Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath
Terrace/patio

Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath

10.0 out of 10, Exceptional, (88)
"We had a fantastic trip, house great for us Cary was very helpful "
Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath
Home w/ Yard & Patio ~ 30 Mi to Downtown Chicago
Fridge, microwave, stovetop, dishwasher

Home w/ Yard & Patio ~ 30 Mi to Downtown Chicago

8.2 out of 10, Very good, (20)
"We really love the home and the setup."
Home w/ Yard & Patio ~ 30 Mi to Downtown Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Southwest Side
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Southwest Side

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (649)
"Amazing view and the apartment space was perfect. There was some cabinets that were banged up pretty good and the garbage disposal/dishwasher were not working but it was such a beautiful place that it didn't even matter. The valet was super helpful as you have to walk around the block and with alot of luggage it wasn't easy. "
The price is NZ$282
includes taxes & fees
12 Jan - 13 Jan
Sentral Michigan Avenue
Sonder South Wabash
Superior Apartment, 1 Bedroom, Balcony, City View | Living area

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (413)
"Beautiful Hotel with lots of amenities and entertainment in a walking distance "
The price is NZ$212
includes taxes & fees
30 Jan - 31 Jan
Sonder South Wabash
Sonder Market Hall
Interior

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (239)
"Wonderful experience. Easy in and out access. Very comfortable "
The price is NZ$106
includes taxes & fees
21 Jan - 22 Jan
Sonder Market Hall
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.