West Side Vacation Rentals

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Check prices for these dates

In two weeks
Jan 16 - Jan 18
In two months
Feb 27 - Mar 1
In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26

Our top choices for West Side vacation rentals

Fridge, microwave, oven, stovetop
West Loop Living – Bright 1BR

Apartment in Downtown Chicago

West Loop Living – Bright 1BR
10.0 out of 10, Exceptional, (6)
"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 4 - Jan 5
Total with taxes and fees
West Loop Living – Bright 1BR
Fridge, microwave, oven, stovetop
Sun-Drenched 1BR Apartment

Apartment in Downtown Chicago

Sun-Drenched 1BR Apartment
10.0 out of 10, Exceptional, (2)
"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 4 - Jan 5
Total with taxes and fees
Sun-Drenched 1BR Apartment
Fridge, microwave, oven, stovetop
Stylish 1BR in West Loop

Apartment in Downtown Chicago

Stylish 1BR in West Loop
10.0 out of 10, Exceptional, (10)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
$153 nightly
The price is $168
Jan 4 - Jan 5
Total with taxes and fees
Stylish 1BR in West Loop
1 bedroom, WiFi, bed sheets
1BR Modern Luxe Apt with In-Unit Laundry

Apartment in Downtown Chicago

1BR Modern Luxe Apt with In-Unit Laundry
10.0 out of 10, Exceptional, (1)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
$153 nightly
The price is $168
Jan 5 - Jan 6
Total with taxes and fees
1BR Modern Luxe Apt with In-Unit Laundry
Studio | Private kitchen | Fridge, oven, coffee/tea maker, toaster
River West, Third Floor Chicago by 747 Lofts

Aparthotel in West Town

River West, Third Floor Chicago by 747 Lofts
2.0 star property
9.0 out of 10, Wonderful, (17)
"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
Private kitchen
Spacious 3-bedroom apartment near downtown, FREE PARKING

Apartment in Near West Side

Spacious 3-bedroom apartment near downtown, FREE PARKING
9.4 out of 10, Exceptional, (10)
"Great place to stay that was close to downtown"
United States
Michelle B.
$269 nightly
The price is $332
Jan 4 - Jan 5
Total with taxes and fees
Spacious 3-bedroom apartment near downtown, FREE PARKING
Fridge, microwave, oven, stovetop
Flexhome Ukrainian Village 2BR D1

Apartment in West Town

Flexhome Ukrainian Village 2BR D1
9.6 out of 10, Exceptional, (5)
"It was clean and ready for our arrival. A big plus is having a washer and dryer on the premises."
United States
Ray R.
$146 nightly
The price is $180
Jan 4 - Jan 5
Total with taxes and fees
Flexhome Ukrainian Village 2BR D1
Fridge, microwave, oven, stovetop
NEW Private West Loop 1br with Backyard near Green Line and CTA

Apartment in East Garfield Park

NEW Private West Loop 1br with Backyard near Green Line and CTA
9.4 out of 10, Exceptional, (3)
"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 4 - Jan 5
Total with taxes and fees
NEW Private West Loop 1br with Backyard near Green Line and CTA
Fridge, microwave, oven, stovetop
Your Perfect 2BR Home

Apartment in Near West Side

Your Perfect 2BR Home
8.2 out of 10, Very Good, (14)
"Great stay by the United Center "
United States
Brian H.
$177 nightly
The price is $193
Jan 4 - Jan 5
Total with taxes and fees
Your Perfect 2BR Home
Fridge, microwave, oven, stovetop
Flexhome Wicker Park 2BR DV3

Apartment in West Town

Flexhome Wicker Park 2BR DV3
9.6 out of 10, Exceptional, (4)
"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
Fridge, microwave, oven, stovetop
Flexhome West Town 2BR Apt T1

Apartment in West Town

Flexhome West Town 2BR Apt T1
9.0 out of 10, Wonderful, (2)
"Awesome location, great views and comfortable."
United States
Steve L.
$154 nightly
The price is $178
Jan 5 - Jan 6
Total with taxes and fees
Flexhome West Town 2BR Apt T1
Fridge, microwave, oven, stovetop
3BR Complete and Spacious Apt

Apartment in West Town

3BR Complete and Spacious Apt
8.4 out of 10, Very Good, (10)
"Clean, Good Location easy to find. If in the area would definitely stay again. "
United States
tyler
$199 nightly
The price is $217
Jan 8 - Jan 9
Total with taxes and fees
3BR Complete and Spacious Apt
2 bedrooms, iron/ironing board, travel crib, WiFi
Urban Comfort • 2BR in West Town

Apartment in West Town

Urban Comfort • 2BR in West Town
9.8 out of 10, Exceptional, (6)
"We had a wonderful stay! The location was perfect and was close to everything we needed. The apartment was very clean and the host was excellent with communication. The check-in and our overall experience smooth and stress-free. Would definitely recommend staying here!"
United States
Jared P.
$172 nightly
The price is $188
Jan 11 - Jan 12
Total with taxes and fees
Urban Comfort • 2BR in West Town
Exterior
Cabin 306 by 747 Lofts

Aparthotel in West Town

Cabin 306 by 747 Lofts
6.6 out of 10, (4)
"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

Vacation Home in Humboldt Park

Gated Family Home w/ Chef’s Kitchen
2.0 star property
$473 nightly
The price is $487
Jan 4 - Jan 5
Total with taxes and fees
Gated Family Home w/ Chef’s Kitchen
Property grounds
Sleeps 18 • 7BR • Gym • Game Room • Theater

Vacation Home in Austin

Sleeps 18 • 7BR • Gym • Game Room • Theater
2.0 star property
$824 nightly
The price is $1,019
Jan 5 - Jan 6
Total with taxes and fees
Sleeps 18 • 7BR • Gym • Game Room • Theater
Fridge, microwave, oven, stovetop
Spacious 4BR Near Wicker Park

Apartment in West Town

Spacious 4BR Near Wicker Park
9.2 out of 10, Wonderful, (7)
"Had an amazing stay at this Vrbo. Very cozy and comfortable for everyone!"
United States
Wendy P.
$318 nightly
The price is $340
Jan 4 - Jan 5
Total with taxes and fees
Spacious 4BR Near Wicker Park
TV
Bold 3BR West Town Sleeps 8 | Patio + Free Parking

Apartment in West Town

Bold 3BR West Town Sleeps 8 | Patio + Free Parking
2.0 star property
$396 nightly
The price is $493
Jan 19 - Jan 20
Total with taxes and fees
Bold 3BR West Town Sleeps 8 | Patio + Free Parking
Fridge, microwave, oven, stovetop
Upscale 4BR Retreat: Wicker Park

Apartment in West Town

Upscale 4BR Retreat: Wicker Park
8.0 out of 10, Very Good, (7)
"Great place in a great area. Would definitely stay here again!"
United States
John R.
$318 nightly
The price is $340
Jan 4 - Jan 5
Total with taxes and fees
Upscale 4BR Retreat: Wicker Park
Fridge, microwave, oven, stovetop
Flexhome Wicker Park 2BR DV3

Apartment in West Town

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

10/10 Excellent
"Great stay "
Aidan 1-night trip
Posted 19 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 $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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