West Side Vacation Rentals

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Our top choices for West Side vacation rentals

Sunlit 1BR Apartment | Warm & Welcoming Space

Sunlit 1BR Apartment | Warm & Welcoming Space
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.
The price is CA $138
CA $297 total
includes taxes & fees
May 26 - May 27
Sunlit 1BR Apartment | Warm & Welcoming Space

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
9.8 out of 10, Exceptional, (10 reviews)
"Great spot next to the green line train a few restaurants and a Starbucks right up the street I will book again for sure "
United States
2k G.
The price is CA $138
CA $297 total
includes taxes & fees
May 26 - May 27
West Loop Living – Bright 1BR

LIVN West Loop Chicago King Studio

LIVN West Loop Chicago King Studio
Downtown Chicago
10.0 out of 10, Exceptional, (4 reviews)
"Amazing studio apartment style room, super clean, very helpful staff, and great location."
United States
William
The price is CA $231
CA $309 total
includes taxes & fees
May 27 - May 28
LIVN West Loop Chicago King Studio

Modern West Loop Gem-City Views & Prime Location 6

Modern West Loop Gem-City Views & Prime Location 6
Downtown Chicago
10.0 out of 10, Exceptional, (23 reviews)
"Everything was walking distance and had everything needed for a comfortable stay "
United States
Daniel
The price is CA $404
CA $1,056 total
includes taxes & fees
Jun 17 - Jun 18
Modern West Loop Gem-City Views & Prime Location 6

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
8.8 out of 10, Excellent, (3 reviews)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is CA $174
CA $344 total
includes taxes & fees
May 26 - May 27
1BR Modern Luxe Apt with In-Unit Laundry

LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
9.4 out of 10, Exceptional, (3 reviews)
"Super clean, great communication! Thanks for a great stay."
United States
Tracey L.
The price is CA $226
CA $306 total
includes taxes & fees
May 25 - May 26
LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago Classic Queen Studio

LIVN West Loop Chicago Classic Queen Studio
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Excellent stay. Great area and very happy with everything"
United States
Abigail B.
The price is CA $179
CA $244 total
includes taxes & fees
May 25 - May 26
LIVN West Loop Chicago Classic Queen Studio

LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
The price is CA $189
CA $256 total
includes taxes & fees
May 25 - May 26
LIVN West Loop Chicago Queen Superior Studio

Cozy Boho Chicago - 10 Minutes to Downtown Chicago

Cozy Boho Chicago - 10 Minutes to Downtown Chicago
Lawndale
9.8 out of 10, Exceptional, (10 reviews)
"Wonderful space and convenient location. Really responsive host and super quiet neighborhood! "
United States
Jess S.
The price is CA $127
CA $311 total
includes taxes & fees
Jun 16 - Jun 17
Cozy Boho Chicago - 10 Minutes to Downtown Chicago

Modern West Loop Gem-City Views & Prime Location 5

Modern West Loop Gem-City Views & Prime Location 5
Downtown Chicago
9.4 out of 10, Exceptional, (3 reviews)
"Great location, plenty of space and clean home. "
United States
Brittany T.
The price is CA $559
CA $1,253 total
includes taxes & fees
Jun 3 - Jun 4
Modern West Loop Gem-City Views & Prime Location 5

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
8.8 out of 10, Excellent, (3 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 CA $139
CA $405 total
includes taxes & fees
May 26 - May 27
10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades

Cabin 105 by 747 Lofts

Cabin 105 by 747 Lofts
2.0 star property
West Town
10.0 out of 10, Exceptional, (1 review)
The price is CA $160
CA $279 total
includes taxes & fees
Jun 10 - Jun 11
Cabin 105 by 747 Lofts

LIVN West Loop Chicago 1 BR

LIVN West Loop Chicago 1 BR
Downtown Chicago
The price is CA $215
CA $286 total
includes taxes & fees
May 25 - May 26
LIVN West Loop Chicago 1 BR

Newly Remodeled Gem | Heart of Chicago

Newly Remodeled Gem | Heart of Chicago
Humboldt Park
9.4 out of 10, Exceptional, (6 reviews)
"Super clean, comfortable beds, easy to access, easy checkout, and a very communicable host. Overall a great stay. "
United States
Kevin R.
The price is CA $223
CA $681 total
includes taxes & fees
Jun 8 - Jun 9
Newly Remodeled Gem | Heart of Chicago

15 mins DT| HumboldtPark Gem | Sleeps 8 | FreePark

15 mins DT| HumboldtPark Gem | Sleeps 8 | FreePark
West Town
10.0 out of 10, Exceptional, (2 reviews)
"Fun neighborhood "
United States
gregory m.
The price is CA $119
CA $383 total
includes taxes & fees
May 25 - May 26
15 mins DT| HumboldtPark Gem | Sleeps 8 | FreePark

Luxurious, Cozy Beauty 10 min from Downtown Chicago

Luxurious, Cozy Beauty 10 min from Downtown Chicago
Lawndale
8.6 out of 10, Excellent, (9 reviews)
"Close to public transport, clean, helpful host"
United States
Aaron W.
The price is CA $100
CA $293 total
includes taxes & fees
May 27 - May 28
Luxurious, Cozy Beauty 10 min from Downtown Chicago

Urban Comfort • 2BR in West Town

Urban Comfort • 2BR in West Town
West Town
9.6 out of 10, Exceptional, (8 reviews)
"The place was very clean and accommodating."
United States
Mark E.
The price is CA $178
CA $378 total
includes taxes & fees
May 25 - May 26
Urban Comfort • 2BR in West Town

Flexhome Wicker Park • Stylish 2BR • Sleeps 6

Flexhome Wicker Park • Stylish 2BR • Sleeps 6
West Town
9.8 out of 10, Exceptional, (6 reviews)
"Great location. The apartment has everything you will need. Had a great time . Thanks"
United States
Wayne M.
The price is CA $202
CA $379 total
includes taxes & fees
Jun 21 - Jun 22
Flexhome Wicker Park • Stylish 2BR • Sleeps 6

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
The price is CA $150
CA $431 total
includes taxes & fees
Jun 1 - Jun 2
Sleeps 12 - Games - 10 Min to Downtown - Arcades - Walking Distance to Train

Vintage Arcade Apt with Parking

Vintage Arcade Apt with Parking
Lawndale
6.0 out of 10, (6 reviews)
"Very clean and private"
United States
Anthony B.
The price is CA $95
CA $271 total
includes taxes & fees
May 26 - May 27
Vintage Arcade Apt with Parking
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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You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with West Side. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.