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Southwest Side Holiday Rentals

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Our top choices for Southwest Side holiday rentals

Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10

Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
Brighton Park
10.0 out of 10, Exceptional, (2 reviews)
"The rooms were spotless. The apartment was spacious. I enjoyed my stay. "
United States
Rachel
The price is AU$431
includes taxes & fees
4 Aug - 5 Aug
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10

Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6

Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
Brighton Park
8.6 out of 10, Excellent, (21 reviews)
"Excellent location and go anywhere so close."
United States
Yiu S.
The price is AU$383
includes taxes & fees
10 Aug - 11 Aug
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6

W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade

W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade
Brighton Park
9.4 out of 10, Exceptional, (9 reviews)
"It was great it had the basic amenities for a family to enjoy the stay"
United States
Damary T.
The price is AU$463
includes taxes & fees
10 Aug - 11 Aug
W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,211 reviews)
"Clean room, great staff, family-friendly, pet-friendly, and great rooms with a kitchen and wonderful showers. Great location!"
United States
Alessandra
The price is AU$340
includes taxes & fees
9 Aug - 10 Aug
Sentral Michigan Avenue

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line
Near North Side
9.6 out of 10, Exceptional, (8 reviews)
"Excellent, clean, modern, fully furnished apartment in downtown Chicago that is a short car ride or walk to anything you need or want to visit. The neighborhood and building are very safe and the covered parking is well worth the extra expense. We loved the extra space to spread out and the skyline views were beautiful at night. The staff responded right away to any questions we had and even helped to accommodate us an extra night when an event kept us in town longer. The beds were comfortable...
United States
Kathryn
The price is AU$1,116
includes taxes & fees
16 July - 17 July
4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line

LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
8.8 out of 10, Excellent, (10 reviews)
"Beautiful place exciting city everything was wonderful"
United States
Kyna C.
The price is AU$367
includes taxes & fees
19 July - 20 July
LIVN West Loop Chicago Queen Superior Studio

LIVN Millennium Park Downtown Chicago 1 BR

LIVN Millennium Park Downtown Chicago 1 BR
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Great location to sights, shops, and food."
United States
Adrianna W.
The price is AU$381
includes taxes & fees
19 July - 20 July
LIVN Millennium Park Downtown Chicago 1 BR

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.8 out of 10, Exceptional, (7 reviews)
"Not a bad thing to say about this experience. Host was extremely responsive and helpful, looked exactly like the pictures, had everything we needed, location was perfect and the included parking was such a perk! Highly recommend staying here. I hope to be back! "
United States
Kara B.
The price is AU$867
includes taxes & fees
19 July - 20 July
River North Rooftop With In and Out Parking 3

Modern West Loop Gem-City Views & Prime Location 4

Modern West Loop Gem-City Views & Prime Location 4
Downtown Chicago
10.0 out of 10, Exceptional, (9 reviews)
"Amazing accommodation"
United States
Jiri N.
The price is AU$1,161
includes taxes & fees
9 Aug - 10 Aug
Modern West Loop Gem-City Views & Prime Location 4

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (501 reviews)
"Very clean and loved the location and amenities with the store on the first floor was fantastic"
United States
Kimberly
The price is AU$579
includes taxes & fees
13 Aug - 14 Aug
Level Chicago – Old Town

Luxury Retreat w/ King Bed, 3-in-1 Pool Table, 15 Min to Chicago, Free Parking

Luxury Retreat w/ King Bed, 3-in-1 Pool Table, 15 Min to Chicago, Free Parking
Oak Park
The price is AU$359
includes taxes & fees
26 July - 27 July
Luxury Retreat w/ King Bed, 3-in-1 Pool Table, 15 Min to Chicago, Free Parking

4BR Retreat w/ Theater, Arcade, Gym and Firepit

4BR Retreat w/ Theater, Arcade, Gym and Firepit
Belmont Cragin
10.0 out of 10, Exceptional, (1 review)
"Great host any concerns that I had were addressed and handled!"
United States
Keana
The price is AU$830
includes taxes & fees
15 July - 16 July
4BR Retreat w/ Theater, Arcade, Gym and Firepit

South Loop Rooftop With In and Out Parking 3

South Loop Rooftop With In and Out Parking 3
Downtown Chicago
8.8 out of 10, Excellent, (5 reviews)
"Clean place. Family friendly. Location was great. A lot of restaurants close by. Great communication from the host."
United States
jaspreet
The price is AU$935
includes taxes & fees
3 Aug - 4 Aug
South Loop Rooftop With In and Out Parking 3

Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill

Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Belmont Cragin
10.0 out of 10, Exceptional, (2 reviews)
"My group and I traveled to town this weekend for a music festival and had the opportunity to stay at this place and had a great time. Communication with the host was very prompt when we had any questions which I appreciate a lot. Also, the place was clean and spacious for our group and easy to come in and out. Would recommend this place to others looking for a place to stay in town."
United States
Marcos B.
The price is AU$543
includes taxes & fees
16 July - 17 July
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill

Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (84 reviews)
"Wonderful hosts…very kind and communicative. Awesome area… highly recommended!"
United States
Andrew C.
The price is AU$277
includes taxes & fees
27 July - 28 July
Cozy studio in Andersonville Chicago

Modern 3BR Apartment Near North Ave Shops

Modern 3BR Apartment Near North Ave Shops
Near North Side
10.0 out of 10, Exceptional, (1 review)
The price is AU$1,229
includes taxes & fees
21 July - 22 July
Modern 3BR Apartment Near North Ave Shops

River North Private Deck With In and Out Parking

River North Private Deck With In and Out Parking
Downtown Chicago
9.8 out of 10, Exceptional, (12 reviews)
"Excellent location, very clean, spacious."
United States
John David K.
The price is AU$1,328
includes taxes & fees
23 July - 24 July
River North Private Deck With In and Out Parking

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
North Center
9.6 out of 10, Exceptional, (85 reviews)
"Great place to stay. Within walking distance to breweries and restaurants. "
United States
Carrie K.
The price is AU$597
includes taxes & fees
16 July - 17 July
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (77 reviews)
"The host responded quickly to my requests. Apartment was clean. Kitchen well stocked with cooking, utensils, spices, etc. He registered my car so I coiud park on the street without any problem. Close to the Blue Line stop to take the "L" into downtown Chicago."
United States
Michael
The price is AU$487
includes taxes & fees
27 July - 28 July
Cozy, Comfortable and Convenient apartment. Close to everything!

Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 • Huge Projector • Designated Workspace
Irving Park
10.0 out of 10, Exceptional, (4 reviews)
"Great location and easy on street parking. "
United States
Lori A.
The price is AU$460
includes taxes & fees
6 Aug - 7 Aug
Sleeps 7 • Huge Projector • Designated Workspace
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.
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Top Southwest Side Hotel Reviews

Find out more about Southwest Side

Everything you need to know about Southwest Side holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Southwest Side holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southwest Side holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Southwest Side holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southwest Side. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Southwest Side holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Southwest Side holiday rentals we have selected for you start as low as AU$277 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Southwest Side rentals

At Expedia, we put the best Southwest Side holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Southwest Side rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southwest Side holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southwest Side. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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