A greenhouse with a glass ceiling, various cacti, and a wooden structure in the center.

West Side Holiday Rentals

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Our top choices for West Side holiday rentals

1. 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
10.0 out of 10, Exceptional, (4 reviews)
"Excellent - highly recommended."
United States
Jay J.
The price is NZ$848
includes taxes & fees
22 Oct - 23 Oct
Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6

2. Modern West Loop Gem-City Views & Prime Location 4

Modern West Loop Gem-City Views & Prime Location 4
Downtown Chicago
9.4 out of 10, Exceptional, (15 reviews)
"Amazing accommodation"
United States
Jiri N.
Modern West Loop Gem-City Views & Prime Location 4

3. Peaceful Zen Flat | 2BR Oasis with Free Parking

Peaceful Zen Flat | 2BR Oasis with Free Parking
West Town
10.0 out of 10, Exceptional, (6 reviews)
"The host was quick to respond, the place was nice and clean and there is a parking spot in the back"
United States
Gene H.
The price is NZ$782
includes taxes & fees
14 Oct - 15 Oct
Peaceful Zen Flat | 2BR Oasis with Free Parking

4. LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.6 out of 10, Exceptional, (26 reviews)
"Incredible location, very clean and easy! Would book again!"
United States
Andrea K.
The price is NZ$691
includes taxes & fees
4 Oct - 5 Oct
LIVN West Loop Chicago Queen Superior Studio

5. Modern Zen Retreat mins from Downtown

Modern Zen Retreat mins from Downtown
West Town
10.0 out of 10, Exceptional, (2 reviews)
"Perfect place to stay! We would definitely come back when we're in Chicago again."
United States
Caley C.
The price is NZ$846
includes taxes & fees
14 Oct - 15 Oct
Modern Zen Retreat mins from Downtown

6. 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.
The price is NZ$388
includes taxes & fees
8 Oct - 9 Oct
Cozy Boho - 10 Minutes to Downtown Chicago + Arcades

7. The Boho House • Two Private Suites + Parking

The Boho House • Two Private Suites + Parking
West Town
The price is NZ$1,556
includes taxes & fees
26 Oct - 27 Oct
The Boho House • Two Private Suites + Parking

8. Newly Remodeled Gem | Heart of Chicago

Newly Remodeled Gem | Heart of Chicago
Humboldt Park
9.6 out of 10, Exceptional, (7 reviews)
"Super clean, comfortable beds, easy to access, easy checkout, and a very communicable host. Overall a great stay. "
United States
Kevin R.
Newly Remodeled Gem | Heart of Chicago

9. Modern Pilsen Apt 3 Bedrooms

Modern Pilsen Apt 3 Bedrooms
Lower West Side
5.0 out of 10, (2 reviews)
"Everything was wonderful except the bathroom. When we checked in there was quite a bit of hair on the floor of the bathroom and in the tub. Everything else was very clean. Beds comfortable. Water pressure good. Felt safe in the area. Hard to find a parking spot Friday night. The kids had fun with all the games. "
United States
Naomi D.
The price is NZ$936
includes taxes & fees
16 Oct - 17 Oct
Modern Pilsen Apt 3 Bedrooms

10. Flexhome Wicker Park • Stylish 2BR • Sleeps 6

Flexhome Wicker Park • Stylish 2BR • Sleeps 6
West Town
10.0 out of 10, Exceptional, (3 reviews)
"Wouldn’t change a thing. Great location to downtown and all the things that we wanted to do."
United States
beth m.
The price is NZ$518
includes taxes & fees
14 Oct - 15 Oct
Flexhome Wicker Park • Stylish 2BR • Sleeps 6

11. Private Apartment in Fulton Market

Private Apartment in Fulton Market
West Town
Private Apartment in Fulton Market

12. 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.
The price is NZ$487
includes taxes & fees
5 Oct - 6 Oct
3BR Complete and Spacious Apartment in Ideal Spot

13. 2BR Apt with 2 Baths & Laundry

2BR Apt with 2 Baths & Laundry
Near West Side
10.0 out of 10, Exceptional, (1 review)
"The property was very clean and perfect for our overnight stay. Thank you"
United States
michele
The price is NZ$705
includes taxes & fees
7 Oct - 8 Oct
2BR Apt with 2 Baths & Laundry

14. Boho City Escape | Parking + Balcony

Boho City Escape | Parking + Balcony
West Town
The price is NZ$896
includes taxes & fees
14 Oct - 15 Oct
Boho City Escape | Parking + Balcony

15. The Zen Duplex: Two Private Suites for Groups

The Zen Duplex: Two Private Suites for Groups
West Town
The price is NZ$1,918
includes taxes & fees
7 Oct - 8 Oct
The Zen Duplex: Two Private Suites for Groups

16. Convenient 2BR Apt w/ In-Unit Laundry

Convenient 2BR Apt w/ In-Unit Laundry
West Town
The price is NZ$610
includes taxes & fees
7 Oct - 8 Oct
Convenient 2BR Apt w/ In-Unit Laundry

17. Bright & Spacious Boho Oasis: A Warm Retreat

Bright & Spacious Boho Oasis: A Warm Retreat
West Town
10.0 out of 10, Exceptional, (1 review)
"We had the best stay! Saw a show at United Center and it was minutes away. Close enough for short drives to the major sights. Beautiful decor and an ultra comfortable bed were a huge bonus. Always found close street parking at the end of the day. We would definitely come back!"
United States
Natalie M.
The price is NZ$661
includes taxes & fees
27 Oct - 28 Oct
Bright & Spacious Boho Oasis: A Warm Retreat

18. West Town 2BR | Full Kitchen + In-Unit Laundry

West Town 2BR | Full Kitchen + In-Unit Laundry
West Town
The price is NZ$560
includes taxes & fees
14 Oct - 15 Oct
West Town 2BR | Full Kitchen + In-Unit Laundry

19. Cozy Luxury 1BR - 10 Min to Downtown Chicago

Cozy Luxury 1BR - 10 Min to Downtown Chicago
Lawndale
7.8 out of 10, Good, (12 reviews)
"Don't miss out on this spot!! It's truly a must & great location!!! I really enjoyed my time here for real"
United States
Alexis R.
Cozy Luxury 1BR - 10 Min 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.
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Top West Side Hotel Reviews

Find out more about West Side

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our West Side holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up West Side. 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 West Side. Seeing all the best attractions is bound to make you fall in love with West Side. Who knows, you may even be tempted to extend your 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 holiday 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 West Side short-term rentals, that won’t be hard to do.

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