West Side Vacation Rentals

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Check prices for these dates

In two weeks
Jan 30 - Feb 1
In two months
Mar 13 - Mar 15
In three months
Apr 10 - Apr 12
In four months
May 8 - May 10

Our top choices for West Side vacation rentals

TV, offices

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
9.8 out of 10, Exceptional, (11 reviews)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
$153 nightly
The price is $168
Jan 18 - Jan 19
Total with taxes and fees
Modern Comfort: 1BR Unit w/ Laundry
TV, offices

Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
$153 nightly
The price is $168
Jan 19 - Jan 20
Total with taxes and fees
Sun-Drenched 1BR Apartment
1 bedroom, iron/ironing board, travel crib, WiFi

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (6 reviews)
"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."
United States
Jeffrey
$153 nightly
The price is $168
Jan 22 - Jan 23
Total with taxes and fees
West Loop Living – Bright 1BR
1 bedroom, WiFi, bed sheets

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
$153 nightly
The price is $168
Jan 19 - Jan 20
Total with taxes and fees
1BR Modern Luxe Apt with In-Unit Laundry
Interior

Spacious 3-bedroom apartment near downtown, FREE PARKING

Spacious 3-bedroom apartment near downtown, FREE PARKING
Near West Side
9.4 out of 10, Exceptional, (10 reviews)
"Great place to stay that was close to downtown"
United States
Michelle B.
$269 nightly
The price is $332
Jan 20 - Jan 21
Total with taxes and fees
Spacious 3-bedroom apartment near downtown, FREE PARKING
Interior

Your Perfect 2BR Home

Your Perfect 2BR Home
Near West Side
8.2 out of 10, Very Good, (14 reviews)
"Great stay by the United Center "
United States
Brian H.
$192 nightly
The price is $211
Jan 19 - Jan 20
Total with taxes and fees
Your Perfect 2BR Home
Smart TV

NEW Private West Loop 1br with Backyard near Green Line and CTA

NEW Private West Loop 1br with Backyard near Green Line and CTA
East Garfield Park
9.4 out of 10, Exceptional, (3 reviews)
"Clean, and was exactly how described in the booking. Host was quick to respond to any questions we had. "
United States
Cyril M.
$197 nightly
The price is $243
Jan 18 - Jan 19
Total with taxes and fees
NEW Private West Loop 1br with Backyard near Green Line and CTA
Interior

River West, Third Floor Chicago by 747 Lofts

River West, Third Floor Chicago by 747 Lofts
2.0 star property
West Town
9.0 out of 10, Wonderful, (17 reviews)
"Loved the space and location "
United States
Caroline
$296 nightly
The price is $347
Jan 25 - Jan 26
Total with taxes and fees
River West, Third Floor Chicago by 747 Lofts
Interior

3BR Complete and Spacious Apt

3BR Complete and Spacious Apt
West Town
8.4 out of 10, Very Good, (10 reviews)
"Clean, Good Location easy to find. If in the area would definitely stay again. "
United States
tyler
$200 nightly
The price is $218
Jan 22 - Jan 23
Total with taxes and fees
3BR Complete and Spacious Apt
Dining

Flexhome Wicker Park 2BR DV3

Flexhome Wicker Park 2BR DV3
West Town
9.6 out of 10, Exceptional, (4 reviews)
"Great location. The apartment has everything you will need. Had a great time . Thanks"
United States
Wayne M.
$146 nightly
The price is $180
Jan 25 - Jan 26
Total with taxes and fees
Flexhome Wicker Park 2BR DV3
Dining

Urban Comfort • 2BR in West Town

Urban Comfort • 2BR in West Town
West Town
9.8 out of 10, Exceptional, (6 reviews)
"Good location, close to airport, downtown Chicago, Wrigleyville and United Center. "
United States
David M.
$172 nightly
The price is $188
Jan 25 - Jan 26
Total with taxes and fees
Urban Comfort • 2BR in West Town
Fridge, microwave, oven, stovetop

Spacious 4BR Near Wicker Park

Spacious 4BR Near Wicker Park
West Town
9.4 out of 10, Exceptional, (8 reviews)
"Very clean very spacious very comfortable great location"
United States
Maxwell H.
$319 nightly
The price is $342
Jan 20 - Jan 21
Total with taxes and fees
Spacious 4BR Near Wicker Park
Interior

Flexhome West Town 2BR Apt T1

Flexhome West Town 2BR Apt T1
West Town
9.6 out of 10, Exceptional, (4 reviews)
"Awesome location, great views and comfortable."
United States
Steve L.
$154 nightly
The price is $178
Jan 19 - Jan 20
Total with taxes and fees
Flexhome West Town 2BR Apt T1
TV, offices

Upscale 4BR Retreat: Wicker Park

Upscale 4BR Retreat: Wicker Park
West Town
8.0 out of 10, Very Good, (7 reviews)
"Great place in a great area. Would definitely stay here again!"
United States
John R.
$319 nightly
The price is $342
Jan 19 - Jan 20
Total with taxes and fees
Upscale 4BR Retreat: Wicker Park
Fridge, microwave, oven, stovetop

Flexhome Ukrainian Village 2BR D2

Flexhome Ukrainian Village 2BR D2
West Town
9.4 out of 10, Exceptional, (6 reviews)
"Great size space and very comfortable!"
United States
Jennifer H.
$183 nightly
The price is $226
Jan 30 - Jan 31
Total with taxes and fees
Flexhome Ukrainian Village 2BR D2
Exterior

Cabin 306 by 747 Lofts

Cabin 306 by 747 Lofts
West Town
6.6 out of 10, (4 reviews)
"You changed my room but the room key code did not work in the new room so I had to call the concierge who gave me a new code. The bed in the new room was a single and not what I reserved. There were no instructions on how to turn on hot water. No instructions on TV either which was very confusing. The TV was on the wall above the bed - to watch meant sitting on one of the two stools - very uncomfortable. Cute that in the bowl of snacks there were two sets of ear plugs - didn't use them but...
United States
Leigh C.
$172 nightly
The price is $204
Jan 25 - Jan 26
Total with taxes and fees
Cabin 306 by 747 Lofts
Fridge, microwave, oven, stovetop

Gated Family Home w/ Chef’s Kitchen

Gated Family Home w/ Chef’s Kitchen
2.0 star property
Humboldt Park
$458 nightly
The price is $470
Jan 19 - Jan 20
Total with taxes and fees
Gated Family Home w/ Chef’s Kitchen
Terrace/patio

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

Sleeps 18 • 7BR • Gym • Game Room • Theater
2.0 star property
Austin
$724 nightly
The price is $895
Jan 19 - Jan 20
Total with taxes and fees
Sleeps 18 • 7BR • Gym • Game Room • Theater
Dining

Flexhome Wicker Park 2BR DV3

Flexhome Wicker Park 2BR DV3
2.0 star property
West Town
$146 nightly
The price is $180
Jan 25 - Jan 26
Total with taxes and fees
Flexhome Wicker Park 2BR DV3
Smart TV, books

Flexhome Ukrainian Village 2BR D1

Flexhome Ukrainian Village 2BR D1
West Town
9.6 out of 10, Exceptional, (5 reviews)
"It was clean and ready for our arrival. A big plus is having a washer and dryer on the premises."
United States
Ray R.
$227 nightly
The price is $280
Feb 13 - Feb 14
Total with taxes and fees
Flexhome Ukrainian Village 2BR D1
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

Hyatt House Chicago West Loop

Hyatt House Chicago West Loop

10/10 Excellent
"It was very quiet and clean. The staff were all very friendly. They seemed to be struggling to keep up with the needs at the breakfast buffet. "
Jane 1-night trip
Posted 1 day ago
Hyatt House Chicago West Loop

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 $168 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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