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 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for West Side vacation rentals

1 bedroom, iron/ironing board, travel crib, WiFi

1. 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
$193 nightly
The price is $228
Aug 23 - Aug 24
Total with taxes and fees
LIVN West Loop Chicago King Studio
TV, offices

2. Modern West Loop Gem-City Views & Prime Location 1

Modern West Loop Gem-City Views & Prime Location 1
Downtown Chicago
9.0 out of 10, Wonderful, (4 reviews)
"Great location, HUGE space, and great service at a great rate!"
United States
Ernest C.
$594 nightly
The price is $663
Sep 1 - Sep 2
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 1
1 bedroom, iron/ironing board, travel crib, WiFi

3. LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.4 out of 10, Exceptional, (19 reviews)
"Highly recommend! Will be staying here again."
United States
Sheila M.
$194 nightly
The price is $229
Aug 23 - Aug 24
Total with taxes and fees
LIVN West Loop Chicago Queen Superior Studio
1 bedroom, iron/ironing board, travel crib, WiFi

4. 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.
$169 nightly
The price is $200
Aug 23 - Aug 24
Total with taxes and fees
LIVN West Loop Chicago Classic Queen Studio
Interior

5. River West, Third Floor Chicago by 747 Lofts

River West, Third Floor Chicago by 747 Lofts
2.0 star property
West Town
8.8 out of 10, Excellent, (19 reviews)
"Loved the space and location "
United States
Caroline
$194 nightly
The price is $228
Aug 23 - Aug 24
Total with taxes and fees
River West, Third Floor Chicago by 747 Lofts
Smart TV, fireplace, video-game console, books

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

Ukrainian Village 3BR/3BA • Private Patio, Parking
West Town
10.0 out of 10, Exceptional, (38 reviews)
"Clean and convenient location for our stay. "
United States
Tony D.
$718 nightly
The price is $901
Aug 30 - Aug 31
Total with taxes and fees
Ukrainian Village 3BR/3BA • Private Patio, Parking
Terrace/patio

7. 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
9.6 out of 10, Exceptional, (5 reviews)
"Comfortable apartment and the rooftop deck was a great bonus. Street parking was convenient. Would absolutely stay again. "
United States
Dennis R.
$280 nightly
The price is $325
Sep 9 - Sep 10
Total with taxes and fees
Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6
Coffee/tea maker, fridge, microwave, oven

8. 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
$374 nightly
The price is $433
Aug 24 - Aug 25
Total with taxes and fees
Peaceful Zen Flat | 2BR Oasis with Free Parking
2 bedrooms, iron/ironing board, travel crib, WiFi (free)

9. 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.
$409 nightly
The price is $470
Sep 8 - Sep 9
Total with taxes and fees
Modern Zen Retreat mins from Downtown
Interior

10. 10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades

10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades
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
$309 nightly
The price is $346
Sep 14 - Sep 15
Total with taxes and fees
10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades
Dining

11. 5 Mins to Downtown CHI Sleeps 10 - Parking + Games

5 Mins to Downtown CHI Sleeps 10 - Parking + Games
Lower West Side
9.0 out of 10, Wonderful, (4 reviews)
"We loved the location, the area is awesome! Great stay, highly recommend. "
United States
Db D.
$337 nightly
The price is $378
Sep 8 - Sep 9
Total with taxes and fees
5 Mins to Downtown CHI Sleeps 10 - Parking + Games
Smart TV, books

12. 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.
$154 nightly
The price is $190
Aug 31 - Sep 1
Total with taxes and fees
Flexhome Ukrainian Village • 2BR • Convenient Walkability · Sleeps 6
Interior

13. Sleeps 12 - Games - 10 Min to Downtown - Arcades - Walking Distance to Train

Sleeps 12 - Games - 10 Min to Downtown - Arcades - Walking Distance to Train
Lawndale
10.0 out of 10, Exceptional, (1 review)
$339 nightly
The price is $381
Aug 25 - Aug 26
Total with taxes and fees
Sleeps 12 - Games - 10 Min to Downtown - Arcades - Walking Distance to Train
Coffee/tea maker, fridge, microwave, oven

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.
$344 nightly
The price is $401
Sep 8 - Sep 9
Total with taxes and fees
Bright & Spacious Boho Oasis: A Warm Retreat
Studio | Living area

15. 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
$147 nightly
The price is $172
Sep 9 - Sep 10
Total with taxes and fees
Ground Floor Studios in Chicago by 747 Lofts
Interior

16. Boho City Escape | Parking + Balcony

Boho City Escape | Parking + Balcony
West Town
$466 nightly
The price is $536
Sep 1 - Sep 2
Total with taxes and fees
Boho City Escape | Parking + Balcony
2 bedrooms, desk, iron/ironing board, WiFi

17. 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.
$149 nightly
The price is $184
Sep 1 - Sep 2
Total with taxes and fees
Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony
TV, offices

18. The Boho House • Two Private Suites + Parking

The Boho House • Two Private Suites + Parking
West Town
$739 nightly
The price is $863
Aug 31 - Sep 1
Total with taxes and fees
The Boho House • Two Private Suites + Parking
Terrace/patio

19. Sleeps 18 • 7BR • Gym • Game Room • Theater

Sleeps 18 • 7BR • Gym • Game Room • Theater
Austin
6.0 out of 10, (1 review)
"Ok place to fit large families if no other option available. Not suitable for kids with allergies as there are some opportunities in the cleanness and maintenance of the property.The communication were ok for reserving but very limited during the stay.The floor os severely damaged as well."
United States
Adrian Cesar C.
$760 nightly
The price is $940
Aug 24 - Aug 25
Total with taxes and fees
Sleeps 18 • 7BR • Gym • Game Room • Theater
Coffee/tea maker, fridge, microwave, oven

20. The Zen Duplex: Two Private Suites for Groups

The Zen Duplex: Two Private Suites for Groups
West Town
$776 nightly
The price is $890
Aug 24 - Aug 25
Total with taxes and fees
The Zen Duplex: Two Private Suites for Groups
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

Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

10/10 Excellent
"The hotel is located close to the hospital and not far from downtown area where shopping is and concerts. Also, there are several fast food restaurants within walking distance, such as Starbucks, Chipotle, etc. Our room was clean and cozy. Everyone who worked there was super nice. Very nice complimentary breakfast also. You do need to purchase a parking permit."
Kelli 1-night trip
Posted 2 hours ago
Hampton Inn & Suites Chicago Medical District UIC

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 $213 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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