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

Holiday Rentals in West Side

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Our top choices for West Side holiday rentals

1. Cozy Urban View Retreat Near Downtown - Sleeps 7

Cozy Urban View Retreat Near Downtown - Sleeps 7
Lawndale
10.0 out of 10, Exceptional, (1 review)
The price is €187
includes taxes & fees
3 Nov - 4 Nov
Cozy Urban View Retreat Near Downtown - Sleeps 7

2. Flexhome East Village • Modern 2BR • Quiet Street

Flexhome East Village • Modern 2BR • Quiet Street
West Town
9.6 out of 10, Exceptional, (28 reviews)
"Great location! "
United States
Andrea B.
Flexhome East Village • Modern 2BR • Quiet Street

3. Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6

Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6
West Town
9.0 out of 10, Wonderful, (16 reviews)
"Great location! Comfortable and quiet. "
United States
Jonalyn B.
The price is €172
includes taxes & fees
19 Nov - 20 Nov
Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6

4. 3BR Complete and Spacious Apartment in Ideal Spot

3BR Complete and Spacious Apartment in Ideal Spot
West Town
8.4 out of 10, Very good, (24 reviews)
"My wife and I stayed here when we came to town for a concert at the united center. We actually walked to the venue and it was about 45 mins, a lovely walk. It was a very convenient location, lovely apartment, and the host communicated very well. Check in and out was easy. Great neighborhood. Would definitely stay here again."
United States
Francis
The price is €222
includes taxes & fees
9 Nov - 10 Nov
3BR Complete and Spacious Apartment in Ideal Spot

5. 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 €160
includes taxes & fees
15 Nov - 16 Nov
Flexhome Wicker Park • Stylish 2BR • Sleeps 6

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

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

Convenient 2BR Apt w/ In-Unit Laundry
West Town
The price is €207
includes taxes & fees
23 Nov - 24 Nov
Convenient 2BR Apt w/ In-Unit Laundry

8. Pilsen Sweet Life Up High

Pilsen Sweet Life Up High
Lower West Side
The price is €200
includes taxes & fees
11 Nov - 12 Nov
Pilsen Sweet Life Up High

9. Skyline View Apt - 5 minutes to Downtown - Games + Arcades - Free Parking

Skyline View Apt - 5 minutes to Downtown - Games + Arcades - Free Parking
Lower West Side
8.8 out of 10, Excellent, (6 reviews)
"Incredible place. Awesome neighborhood. Easy access to the freeways. Great neighborhood with tons of great local dining."
United States
Chad
The price is €250
includes taxes & fees
11 Nov - 12 Nov
Skyline View Apt - 5 minutes to Downtown - Games + Arcades - Free Parking

10. Modern Zen Retreat mins from Downtown

Modern Zen Retreat mins from Downtown
West Town
10.0 out of 10, Exceptional, (3 reviews)
"Perfect place to stay! We would definitely come back when we're in Chicago again."
United States
Caley C.
The price is €375
includes taxes & fees
3 Nov - 4 Nov
Modern Zen Retreat mins from Downtown

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

Peaceful Zen Flat | 2BR Oasis with Free Parking
West Town
10.0 out of 10, Exceptional, (8 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 €438
includes taxes & fees
15 Nov - 16 Nov
Peaceful Zen Flat | 2BR Oasis with Free Parking

12. 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

13. Peaceful Boho Retreat | Free Private Parking

Peaceful Boho Retreat | Free Private Parking
West Town
The price is €411
includes taxes & fees
15 Nov - 16 Nov
Peaceful Boho Retreat | Free Private Parking

14. Patio | 15 min Downtown & United Ctr+King Bed, CTA

Patio | 15 min Downtown & United Ctr+King Bed, CTA
West Town
10.0 out of 10, Exceptional, (1 review)
"Really nice apartment, perfect size. Really nice area and very Safe neighborhood. Apartment was perfect for me and my business partner, traveling and attending the Pack Expo at the McCormick Place in Downtown Chicago. 2 Nice comfortable beds, good coffee maker. I was a little scared about parking because I have never been to Chicago, but it worked out perfectly. I will 100% stay again the next time I am in Chicago. Thank you!"
United States
Joe K.
Patio | 15 min Downtown & United Ctr+King Bed, CTA

15. 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 €382
includes taxes & fees
1 Dec - 2 Dec
Bright & Spacious Boho Oasis: A Warm Retreat

16. LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.6 out of 10, Exceptional, (29 reviews)
"Clean, comfortable, effortless check-in and checkout process, and in a very convenient location. Would stay again!"
United States
Tara H.
LIVN West Loop Chicago Queen Superior Studio

17. 4BR Flat By Douglass Park & Transit - Free parking

4BR Flat By Douglass Park & Transit - Free parking
Lawndale
The price is €381
includes taxes & fees
15 Nov - 16 Nov
4BR Flat By Douglass Park & Transit - Free parking

18. Boho City Escape | Parking + Balcony

Boho City Escape | Parking + Balcony
West Town
The price is €401
includes taxes & fees
16 Nov - 17 Nov
Boho City Escape | Parking + Balcony

19. 1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
The price is €305
includes taxes & fees
15 Nov - 16 Nov
1BR Modern Luxe Apt with In-Unit Laundry

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

West Town 2BR | Full Kitchen + In-Unit Laundry
West Town
The price is €206
includes taxes & fees
10 Nov - 11 Nov
West Town 2BR | Full Kitchen + In-Unit Laundry
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

Everything you need to know about West 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 West Side holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 West Side holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

West Side holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in West 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A West 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 West Side holiday rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on West Side rentals

At Expedia, we put the best West 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 West 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 West 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 West 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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