Lodging Image

Southwest Side Vacation Rentals

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Southwest Side vacation rentals

Game room

1. Large Chicago Apt 3 BR - King Bed - 12 Min Downtown w/ Arcade

Large Chicago Apt 3 BR - King Bed - 12 Min Downtown w/ Arcade
Brighton Park
9.4 out of 10, Exceptional, (13 reviews)
"It was great it had the basic amenities for a family to enjoy the stay"
United States
Damary T.
$240 nightly
The price is $269
Oct 13 - Oct 14
Total with taxes and fees
Large Chicago Apt 3 BR - King Bed - 12 Min Downtown w/ Arcade
A living room with a grey sofa, two chairs, a coffee table, and a small side table.

2. 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
$241 nightly
The price is $271
Oct 7 - Oct 8
Total with taxes and fees
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
A compact kitchen with a dining table, a refrigerator, and a trash can.

3. Spacious Apt | 4 Queen Beds | Free Parking

Spacious Apt | 4 Queen Beds | Free Parking
Brighton Park
$318 nightly
The price is $390
Oct 5 - Oct 6
Total with taxes and fees
Spacious Apt | 4 Queen Beds | Free Parking
A modern building with the name 'SENIORAL' prominently displayed on the facade.

4. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,350 reviews)
"Nice room, will stay again, highly recommend:)"
United States
Reina
$184 nightly
The price is $216
Oct 26 - Oct 27
Total with taxes and fees
Sentral Michigan Avenue
Lake

5. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (49 reviews)
"Location is perfect"
United States
Mary
$238 nightly
The price is $283
Nov 4 - Nov 5
Total with taxes and fees
Kasa Lake Shore Chicago
A modern kitchen with a large island, bar stools, and a city view.

6. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (534 reviews)
"Location and facility was very nice"
United States
Brian
$278 nightly
The price is $327
Nov 2 - Nov 3
Total with taxes and fees
Level Chicago – Old Town
A spacious hotel lobby with a high ceiling, chandeliers, and a bar area.

7. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (277 reviews)
"Really helpful staff, really nice rooms."
United States
Archita
$229 nightly
The price is $262
Oct 28 - Oct 29
Total with taxes and fees
The Gem Museum Suites
Terrace/patio

8. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
$289 nightly
The price is $330
Oct 25 - Oct 26
Total with taxes and fees
At Home in Oak Park
A modern living room with large windows, a flat-screen TV, a sofa, a coffee table, and a dining area with stools and a small table.

9. Modern West Loop Gem-City Views & Prime Location 6

Modern West Loop Gem-City Views & Prime Location 6
Downtown Chicago
10.0 out of 10, Exceptional, (28 reviews)
"Great location. "
United States
Tom S.
$645 nightly
The price is $726
Oct 28 - Oct 29
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 6
A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

10. Chic Urban Retreat Near Wrigley Field w/Parking

Chic Urban Retreat Near Wrigley Field w/Parking
Lakeview
10.0 out of 10, Exceptional, (68 reviews)
"Hosts were great, location is great, and it was a great stay."
United States
Ryan G.
$249 nightly
The price is $255
Oct 13 - Oct 14
Total with taxes and fees
Chic Urban Retreat Near Wrigley Field w/Parking
A hotel room with a large grey sofa, a small table with a copper pot, a red lamp, and a bed with white linens.

11. 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.
$287 nightly
The price is $339
Oct 7 - Oct 8
Total with taxes and fees
LIVN Millennium Park Downtown Chicago 1 BR
A modern room with a sofa, a dining table, and a window with a view of buildings.

12. LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
9.4 out of 10, Exceptional, (12 reviews)
"Great property"
United States
duane
$622 nightly
The price is $735
Oct 12 - Oct 13
Total with taxes and fees
LIVN West Loop Chicago 2 BR City View
Private kitchen

13. Cozy Boho - 10 Minutes to Downtown Chicago + Arcades

Cozy Boho - 10 Minutes to Downtown Chicago + Arcades
Lawndale
9.8 out of 10, Exceptional, (10 reviews)
"Wonderful space and convenient location. Really responsive host and super quiet neighborhood! "
United States
Jess S.
$194 nightly
The price is $217
Oct 8 - Oct 9
Total with taxes and fees
Cozy Boho - 10 Minutes to Downtown Chicago + Arcades
A modern kitchen with white cabinets, a central island with stools, a microwave, and a refrigerator.

14. 3BR Complete and Spacious Apartment in Ideal Spot

3BR Complete and Spacious Apartment in Ideal Spot
West Town
8.2 out of 10, Very good, (22 reviews)
"absolutely would stay here again. Great property and great communcation"
United States
Daniel J.
$224 nightly
The price is $247
Oct 5 - Oct 6
Total with taxes and fees
3BR Complete and Spacious Apartment in Ideal Spot
A rooftop terrace with a brick wall, large windows, and a metal railing.

15. Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Uptown
10.0 out of 10, Exceptional, (59 reviews)
"Clean, efficient, and conveniently located to plenty of transportation and culture."
United States
Michael S.
$213 nightly
The price is $256
Oct 5 - Oct 6
Total with taxes and fees
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
A modern living room with a blue sofa, a patterned rug, and a television.

16. Great Area Logan Square Apt Games Pets - Sleeps 5

Great Area Logan Square Apt Games Pets - Sleeps 5
Avondale
10.0 out of 10, Exceptional, (2 reviews)
"Place was nice and clean. Great communication from the host! Would stay here again!"
United States
Deborah J.
$191 nightly
The price is $214
Oct 13 - Oct 14
Total with taxes and fees
Great Area Logan Square Apt Games Pets - Sleeps 5
A bedroom with a bed, a wardrobe, a bench, and a floor lamp.

17. Wabash 4BR - Pool, Free In & Out Parking 4

Wabash 4BR - Pool, Free In & Out Parking 4
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Nice place to stay."
United States
William H.
$785 nightly
The price is $898
Oct 21 - Oct 22
Total with taxes and fees
Wabash 4BR - Pool, Free In & Out Parking 4
A building with a white exterior and a tree with white blossoms in front.

18. Historic Oak Park Residence

Historic Oak Park Residence
2.0 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"The house is in an amazing neighborhood, easy access to subway, extremely clean and great follow-up and follow through communication with owner!"
United States
Ann-Marie
$337 nightly
The price is $386
Oct 21 - Oct 22
Total with taxes and fees
Historic Oak Park Residence
A round table with a wooden board holding cheese, crackers, and grapes, a bottle of wine, and two glasses.

19. Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 • Huge Projector • Designated Workspace
Irving Park
9.6 out of 10, Exceptional, (8 reviews)
"Great location and easy on street parking. "
United States
Lori A.
$261 nightly
The price is $309
Oct 5 - Oct 6
Total with taxes and fees
Sleeps 7 • Huge Projector • Designated Workspace
A rooftop terrace with a fire pit, seating area, and a city skyline view.

20. Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6

Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6
West Town
9.8 out of 10, Exceptional, (6 reviews)
"Very happy with our stay. Loved the rooftop views! The host was very friendly and welcoming."
United States
Jessica C.
$200 nightly
The price is $232
Nov 4 - Nov 5
Total with taxes and fees
Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Southwest Side Hotel Reviews

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

10/10 Excellent
"Great hotel"
Carlos 2-night trip
Posted 1 hour ago
Hotel Riu Plaza Chicago

Find out more about Southwest Side

Everything you need to know about Southwest Side vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Southwest Side vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Southwest Side vacation 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 low season months. For more hustle and bustle, you may prefer to visit Southwest Side in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $72 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Southwest Side rentals

At Expedia, we put the best Southwest Side vacation 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 vacation.

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.

Explore a world of travel with Expedia