
Southwest Side Vacation Rentals
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Our top choices for Southwest Side vacation rentals

1. Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
2. Spacious Apt | 4 Queen Beds | Free Parking
Spacious Apt | 4 Queen Beds | Free Parking
3. Sentral Michigan Avenue
Sentral Michigan Avenue
4. Hyde Park Trendy Studio Apartment in Good Spot
Hyde Park Trendy Studio Apartment in Good Spot
5. Kasa Lake Shore Chicago
Kasa Lake Shore Chicago
6. Great Area Logan Square Apt Games Pets - Sleeps 5
Great Area Logan Square Apt Games Pets - Sleeps 5
7. 3BR Complete and Spacious Apartment in Ideal Spot
3BR Complete and Spacious Apartment in Ideal Spot
8. Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
9. Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
10. Chic Suite/Mins to L Train /Laundry/Free Parking
Chic Suite/Mins to L Train /Laundry/Free Parking
11. Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
12. Chic Urban Retreat Near Wrigley Field w/Parking
Chic Urban Retreat Near Wrigley Field w/Parking
13. Private Workspace • Sleeps 4 • Modern and Stylish
Private Workspace • Sleeps 4 • Modern and Stylish
14. Level Chicago – Old Town
Level Chicago – Old Town
15. Chic Studio in the Heart of the Gold Coast
Chic Studio in the Heart of the Gold Coast
16. Wrigleyville Suites
Wrigleyville Suites
17. 1BR/1BA City Comfort
1BR/1BA City Comfort
18. LIVN Millennium Park Downtown Chicago 1 BR
LIVN Millennium Park Downtown Chicago 1 BR
19. Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
20. Sleeps 7 • Huge Projector • Designated Workspace
Sleeps 7 • Huge Projector • Designated WorkspaceFind vacation rentals that suit your style
Top Southwest Side Hotel Reviews

Congress Plaza Hotel
Find out more about Southwest Side
You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Southwest Side. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.
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