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

West Side Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for West Side vacation rentals

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.

1. LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.6 out of 10, Exceptional, (21 reviews)
"Highly recommend! Will be staying here again."
United States
Sheila M.
$211 nightly
The price is $249
Sep 7 - Sep 8
Total with taxes and fees
LIVN West Loop Chicago Queen Superior Studio

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

Modern West Loop Gem-City Views & Prime Location 4
Downtown Chicago
9.6 out of 10, Exceptional, (13 reviews)
"Amazing accommodation"
United States
Jiri N.
$508 nightly
The price is $557
Sep 7 - Sep 8
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 4
A modern hotel room with a large bed, a small dining table, a bench, and a view of the city through a large window.

3. LIVN West Loop Chicago Classic Queen Studio

LIVN West Loop Chicago Classic Queen Studio
Downtown Chicago
10.0 out of 10, Exceptional, (7 reviews)
"Excellent stay. Great area and very happy with everything"
United States
Abigail B.
$181 nightly
The price is $214
Sep 7 - Sep 8
Total with taxes and fees
LIVN West Loop Chicago Classic Queen Studio
A modern room with a sofa, a dining table, and a window with a view of buildings.

4. LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
9.4 out of 10, Exceptional, (11 reviews)
"Great property"
United States
duane
$227 nightly
The price is $268
Sep 7 - Sep 8
Total with taxes and fees
LIVN West Loop Chicago 2 BR City View
A modern bedroom with a brick wall, a large bed, a sofa, a nightstand, and a mirror.

5. LIVN West Loop Chicago King Studio

LIVN West Loop Chicago King Studio
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"Amazing studio apartment style room, super clean, very helpful staff, and great location."
United States
William
$204 nightly
The price is $241
Sep 7 - Sep 8
Total with taxes and fees
LIVN West Loop Chicago King Studio
A modern living room with a sofa, armchair, coffee table, and a TV mounted on a wooden wall.

6. 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.
Flexhome Ukrainian Village • 2BR • Convenient Walkability · Sleeps 6
A compact living space with a kitchenette, a sofa, a bed, and a television mounted on the wall.

7. Ground Floor Studios in Chicago by 747 Lofts

Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
West Town
8.6 out of 10, Excellent, (25 reviews)
"It’s a really nice place. Its quite a distance from downtown Chicago. But it’s like 3 minutes from Chicago Blue line and a minute away from the bus station. Food is not a problem since there is a Korean grocery nearby. There is also a nearby Catholic church. The ameneties in this loft hotel is complete so if you are looking for a budget style trip and accommodation, I highly recommend this place."
United States
Joel
Ground Floor Studios in Chicago by 747 Lofts
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.

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

Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6
West Town
8.8 out of 10, Excellent, (14 reviews)
"Great location! Comfortable and quiet. "
United States
Jonalyn B.
Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6
A neatly made bed with white linens and a grey throw blanket, a bedside lamp, and a geometric wall design.

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

10. 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)
"Highly recommended rental. Great location near United Center. Excellent communication from landlord. Free parking! I would stay here again."
United States
DAVID
$423 nightly
The price is $485
Sep 29 - Sep 30
Total with taxes and fees
Peaceful Zen Flat | 2BR Oasis with Free Parking
A modern kitchen with stainless steel appliances, including a refrigerator, oven, and microwave, and white cabinetry.

11. 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.
$331 nightly
The price is $385
Sep 29 - Sep 30
Total with taxes and fees
Bright & Spacious Boho Oasis: A Warm Retreat
A bedroom with a bed, a desk, a chair, a TV, and a window with blinds.

12. 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.
Flexhome Wicker Park • Stylish 2BR • Sleeps 6
A modern kitchen with stainless steel appliances, a dining area with a black table and red placemats, and a living area with a red sofa and black curtains.

13. Modern 3 BR Apt - 5 Mins to Downtown Sleeps 10

Modern 3 BR Apt - 5 Mins to Downtown Sleeps 10
Lower West Side
8.0 out of 10, Very Good, (1 review)
"It was decent for what we needed. Owner sends a lot of automated messages. Place was maintained, parking free, but is difficult to find."
United States
Marie Leola K.
$269 nightly
The price is $302
Sep 2 - Sep 3
Total with taxes and fees
Modern 3 BR Apt - 5 Mins to Downtown Sleeps 10
A modern kitchen with a central island, bar stools, stainless steel appliances, and pendant lighting.

14. 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, (3 reviews)
"Excellent - highly recommended."
United States
Jay J.
$243 nightly
The price is $282
Sep 9 - Sep 10
Total with taxes and fees
Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6

15. Modern Zen Retreat mins from Downtown

Modern Zen Retreat mins from Downtown
West Town
10.0 out of 10, Exceptional, (1 review)
"Very clean and nice unit! We enjoyed it! It's right across the street from an elementary school so very safe. The neighborhood is quiet. We enjoyed walking around and meeting the friendly neighbors. Close to a Ukraine breakfast place (Ann's Bakery and Deli) and a taco place (Chavas Taco). So easy to talk to and very yummy food. You can park your car in the back, which makes getting in and out easy."
United States
Haipeng C.
$367 nightly
The price is $424
Sep 29 - Sep 30
Total with taxes and fees
Modern Zen Retreat mins from Downtown

16. Boho City Escape | Parking + Balcony

Boho City Escape | Parking + Balcony
West Town
$386 nightly
The price is $449
Sep 2 - Sep 3
Total with taxes and fees
Boho City Escape | Parking + Balcony
A modern kitchen with wooden cabinets, a microwave, and a stove. There is a purple sofa and a small table with chairs. A suitcase is on the floor next to the sofa.

17. Chicago Second Floor Studio by 747 Lofts

Chicago Second Floor Studio by 747 Lofts
2.0 star property
West Town
9.0 out of 10, Wonderful, (15 reviews)
"i loved this place! would definitely come again"
United States
adrian
Chicago Second Floor Studio by 747 Lofts
A room with a wooden door, a window with a view, a desk with a lamp, a chair, and a potted plant.

18. Karlov Inn | Stylish Chicago 2BR Retreat

Karlov Inn | Stylish Chicago 2BR Retreat
Humboldt Park
9.0 out of 10, Wonderful, (16 reviews)
"Great place, clean and comfy. "
United States
Reann J.
$355 nightly
The price is $445
Sep 2 - Sep 3
Total with taxes and fees
Karlov Inn | Stylish Chicago 2BR Retreat
A modern kitchen with white cabinets, a stainless steel refrigerator, a built-in oven, and a window above the sink.

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

Flexhome East Village • Modern 2BR • Quiet Street
West Town
9.6 out of 10, Exceptional, (23 reviews)
"Great location! "
United States
Andrea B.
$294 nightly
The price is $363
Sep 3 - Sep 4
Total with taxes and fees
Flexhome East Village • Modern 2BR • Quiet Street
A modern living room with a sofa, armchair, coffee table, and a TV mounted on a wooden wall.

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

Flexhome Ukrainian Village • 2BR • Convenient Walkability · Sleeps 6
West Town
8.0 out of 10, Very Good, (1 review)
"On busy street so was a little noisy."
United States
Diane M.
Flexhome Ukrainian Village • 2BR • Convenient Walkability · 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.
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Top West Side Hotel Reviews

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

8/10 Good
"Clean room and nice staff. Didn’t love the breakfast."
Christine 2-night trip
Posted 2 hours ago
Crowne Plaza Chicago West Loop by IHG

Find out more about West Side

Everything you need to know about West 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 West 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 West Side vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

West Side vacation 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 low season months. For more hustle and bustle, you may prefer to visit West 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 $249 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 West Side rentals

At Expedia, we put the best West 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 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 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 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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