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

West Side Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for West Side holiday rentals

A hotel room with a bed, two bedside lamps, a wall-mounted artwork, and a small table with a lamp.

1. 2BR Apt with 2 Baths & Laundry

2BR Apt with 2 Baths & Laundry
Near West Side
10.0 out of 10, Exceptional, (2 reviews)
"This made our stay in Chicago very relaxing. Everything was as expected and I do not have any complaints! Would definitely stay here again!"
United States
Matthew H.
The price is HK$1,121
HK$2,349 total
includes taxes & fees
2 Nov - 3 Nov
2BR Apt with 2 Baths & Laundry
A laundry room with a front-loading washer and dryer, a white door with a vent, and a wooden floor.

2. 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, (23 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 HK$847
HK$2,038 total
includes taxes & fees
25 Oct - 26 Oct
3BR Complete and Spacious Apartment in Ideal Spot
A corner room with a green upholstered chair, a small round table with a potted plant, and a framed picture on the wall.

3. 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 HK$445
HK$1,598 total
includes taxes & fees
3 Nov - 4 Nov
Cozy Urban View Retreat Near Downtown - Sleeps 7
A hotel room with a large bed, a window with a view of buildings, a nightstand with a lamp, and two framed pictures on the wall.

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)
"Clean, comfortable, effortless check-in and checkout process, and in a very convenient location. Would stay again!"
United States
Tara H.
The price is HK$1,208
HK$1,611 total
includes taxes & fees
25 Oct - 26 Oct
LIVN West Loop Chicago Queen Superior Studio
A hotel room with a geometric-patterned wall, a bed with white bedding and a beige throw, two bedside lamps, and a window with blinds.

5. 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 HK$633
HK$1,458 total
includes taxes & fees
16 Nov - 17 Nov
Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6
A modern kitchen with a large island, coffee maker, and a view of the city.

6. 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 HK$952
HK$2,395 total
includes taxes & fees
11 Nov - 12 Nov
Skyline View Apt - 5 minutes to Downtown - Games + Arcades - Free Parking
A bedroom with a bed, a desk, a chair, a TV, and a window with blinds.

7. 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 HK$633
HK$1,458 total
includes taxes & fees
2 Nov - 3 Nov
Flexhome Wicker Park • Stylish 2BR • Sleeps 6
A modern kitchen with a dishwasher, a sink, and a large island. There is a trash can and a dining area with a table and chairs.

8. Flexhome West Town · Spacious 2BR Duplex · Sleeps 8

Flexhome West Town · Spacious 2BR Duplex · Sleeps 8
West Town
10.0 out of 10, Exceptional, (3 reviews)
"Thank you. We had a wonderful stay."
United States
Janice G.
The price is HK$734
HK$1,490 total
includes taxes & fees
26 Oct - 27 Oct
Flexhome West Town · Spacious 2BR Duplex · Sleeps 8
A hotel room with a geometric-patterned wall, a bed with white bedding and a beige throw, two bedside lamps, and a window with blinds.

9. Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony

Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony
West Town
10.0 out of 10, Exceptional, (1 review)
"Once we were in the place it was wonderful, met all of our needs.The entrance to our unit was filthy and steps kind of dangerous for 5 year old with no railing"
United States
PAT C.
The price is HK$633
HK$1,459 total
includes taxes & fees
2 Nov - 3 Nov
Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony
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.

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

Modern West Loop Gem-City Views & Prime Location 6
Downtown Chicago
9.8 out of 10, Exceptional, (29 reviews)
"Great location. "
United States
Tom S.
Modern West Loop Gem-City Views & Prime Location 6
A modern living room with a sofa, armchair, coffee table, and a TV mounted on a wooden wall.

11. Flexhome Ukrainian Village • 2BR • Convenient Walkability · Sleeps 6

Flexhome Ukrainian Village • 2BR • Convenient Walkability · Sleeps 6
West Town
8.2 out of 10, Very good, (11 reviews)
"Excellent place and location."
United States
Josh L.
The price is HK$633
HK$1,458 total
includes taxes & fees
3 Nov - 4 Nov
Flexhome Ukrainian Village • 2BR • Convenient Walkability · Sleeps 6
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining table with a bowl.

12. 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 HK$1,084
HK$3,537 total
includes taxes & fees
2 Nov - 3 Nov
Modern Zen Retreat mins from Downtown
A room with a checkered table, a potted plant, and a bunk bed in the background.

13. Spacious Group Stay - Sleeps 12 - 3 Kings + Arcades - 10 Min to Downtown

Spacious Group Stay - Sleeps 12 - 3 Kings + Arcades - 10 Min to Downtown
Lawndale
8.0 out of 10, Very good, (4 reviews)
"Great stay, perfect for our group of 6, everyone had there own room! Necessities right around the corner if needed Cermack rd a few feet away, gets you about everywhere! We wanted a real life Chicago experience, and it was great. Owner very responsive! Permit on street parking pretty accessible most times. Definitely will stay again!"
United States
Beth
The price is HK$685
HK$2,485 total
includes taxes & fees
28 Oct - 29 Oct
Spacious Group Stay - Sleeps 12 - 3 Kings + Arcades - 10 Min to Downtown
A modern living room with a sectional sofa, a coffee table, and a TV mounted on the wall.

14. 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 HK$1,186
HK$3,548 total
includes taxes & fees
27 Oct - 28 Oct
Bright & Spacious Boho Oasis: A Warm Retreat
A modern living room with a sofa, a coffee table, and a TV mounted on the wall.

15. Zen City Escape | Patio + Free Parking

Zen City Escape | Patio + Free Parking
West Town
10.0 out of 10, Exceptional, (4 reviews)
"I had an amazing stay at Tracee's place. It was quiet, clean, plenty of parking and served all of my needs. Tracee was responsive and very accommodating of my stay."
United States
Denise R.
The price is HK$1,270
HK$3,751 total
includes taxes & fees
26 Oct - 27 Oct
Zen City Escape | Patio + Free Parking
A modern kitchen with white cabinetry, stainless steel appliances, and a central island.

16. 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.
The price is HK$529
HK$1,729 total
includes taxes & fees
26 Oct - 27 Oct
Cozy Luxury 1BR - 10 Min to Downtown Chicago
Interior

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

Convenient 2BR Apt w/ In-Unit Laundry
West Town
The price is HK$870
HK$1,956 total
includes taxes & fees
11 Nov - 12 Nov
Convenient 2BR Apt w/ In-Unit Laundry
A modern living room with a sectional sofa, a fireplace, and a dining area with a view through large windows.

18. Ukrainian Village 3BR/3BA • Private Patio, Parking

Ukrainian Village 3BR/3BA • Private Patio, Parking
West Town
10.0 out of 10, Exceptional, (41 reviews)
"Clean and convenient location for our stay. "
United States
Tony D.
Ukrainian Village 3BR/3BA • Private Patio, Parking
Private kitchen

19. Peaceful Boho Retreat | Free Private Parking

Peaceful Boho Retreat | Free Private Parking
West Town
The price is HK$915
HK$3,319 total
includes taxes & fees
2 Nov - 3 Nov
Peaceful Boho Retreat | Free Private Parking
A modern living room with a sofa, a coffee table, and a kitchen area with a bar stool.

20. Boho City Escape | Parking + Balcony

Boho City Escape | Parking + Balcony
West Town
The price is HK$1,211
HK$3,717 total
includes taxes & fees
16 Nov - 17 Nov
Boho City Escape | Parking + Balcony
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 West Side Hotel Reviews

Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

8/10 Good
"Desk staff was very helpful and kind."
Alisa 1-night trip
Posted 1 hour ago
Hampton Inn & Suites Chicago Medical District UIC

Find out more about West Side

Search for holiday rentals in West Side on Expedia! You can easily find your home rentals, villas, holiday apartments in West Side using one of the methods below:

  • View our selection of featured holiday rentals in West Side
  • Use the map to find apartments and other holiday homes in the West Side neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in West Side while they last

Look no further and take a look at our great range of rental properties in West Side!

Explore a world of travel with Expedia