Search Vacation Homes in West Side

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Vacation Homes in West Side

Stylish 1BR in West Loop
Fridge, microwave, oven, stovetop

Stylish 1BR in West Loop

10.0 out of 10, Exceptional, (5)
$207 nightly
The price is $232
Sep 10 - Sep 11
Total with taxes and fees
Stylish 1BR in West Loop
Sun-Drenched 1BR Apartment
Fridge, microwave, oven, stovetop

Sun-Drenched 1BR Apartment

$220 nightly
The price is $247
Sep 22 - Sep 23
Total with taxes and fees
Sun-Drenched 1BR Apartment
NEW Private West Loop 1br with Backyard near Green Line and CTA
Fridge, microwave, oven, stovetop

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

9.0 out of 10, Wonderful, (2)
"The apartment was clean and the host was very responsive and helpful. "
$169 nightly
The price is $208
Sep 9 - Sep 10
Total with taxes and fees
NEW Private West Loop 1br with Backyard near Green Line and CTA
3BR Complete and Spacious Apt
TV

3BR Complete and Spacious Apt

9.6 out of 10, Exceptional, (4)
"Spacious and well appointed. Great location with plenty of eating/drinking options within walking distance. "
$247 nightly
The price is $274
Sep 10 - Sep 11
Total with taxes and fees
3BR Complete and Spacious Apt
Cabin 308 by 747 Lofts
Fridge, microwave, oven, dishwasher

Cabin 308 by 747 Lofts

9.4 out of 10, Exceptional, (15)
"Nice place, interesting neighborhood. Very convenient location!"
$157 nightly
The price is $185
Sep 7 - Sep 8
Total with taxes and fees
Cabin 308 by 747 Lofts
Modern 3 BR Apt - 5 Mins to Downtown Sleeps 10
Exterior

Modern 3 BR Apt - 5 Mins to Downtown Sleeps 10

$285 nightly
The price is $320
Sep 10 - Sep 11
Total with taxes and fees
Modern 3 BR Apt - 5 Mins to Downtown Sleeps 10
Urban Comfort • 2BR in West Town
2 bedrooms, iron/ironing board, travel crib, WiFi

Urban Comfort • 2BR in West Town

10.0 out of 10, Exceptional, (2)
"Very clean. Host was exceptionally communicative. Would stay again!"
$232 nightly
The price is $259
Sep 24 - Sep 25
Total with taxes and fees
Urban Comfort • 2BR in West Town
HUGE! 3BR Private Home+Garage+360° Roof Deck+Hot Tub+EV+Sleeps 12
Outdoor dining

HUGE! 3BR Private Home+Garage+360° Roof Deck+Hot Tub+EV+Sleeps 12

10.0 out of 10, Exceptional, (9)
"Great property and very kind and responsive hosts. I would be happy to stay here again. "
$799 nightly
The price is $986
Sep 17 - Sep 18
Total with taxes and fees
HUGE! 3BR Private Home+Garage+360° Roof Deck+Hot Tub+EV+Sleeps 12
The One: A 1BR Stay That Feels Like Home
Fridge, microwave, oven, stovetop

The One: A 1BR Stay That Feels Like Home

8.0 out of 10, Very Good, (1)
"The apartment looked exactly like the pictures and was very well kept. Everything was clean and functional and we didn’t have any issues. The neighborhood is very quiet and safe and also has a target nearby for quick grocery trips. Connectivity wise, there’s a busy stop within walking distance but no train stations.The host was also very responsive and helpful. We didn’t have any trouble checking in or checking out.Overall a great experience and comfortable stay."
$194 nightly
The price is $217
Sep 16 - Sep 17
Total with taxes and fees
The One: A 1BR Stay That Feels Like Home
Cozy house in the city
Outdoor dining

Cozy house in the city

2.0 star property
8.8 out of 10, Excellent, (3)
"it was nice"
$369 nightly
The price is $395
Sep 11 - Sep 12
Total with taxes and fees
Cozy house in the city
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Exterior detail

Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.

2.0 star property
10.0 out of 10, Exceptional, (10)
"Very clean in a safe neighborhood. I would stay here again"
$178 nightly
The price is $199
Sep 7 - Sep 8
Total with taxes and fees
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Master qtr close to nature & easy urban facilities
Exterior detail

Master qtr close to nature & easy urban facilities

9.8 out of 10, Exceptional, (61)
"Great spot."
$192 nightly
The price is $204
Sep 8 - Sep 9
Total with taxes and fees
Master qtr close to nature & easy urban facilities
2BR, Sleeps7 • Coffee Station, Backyard w/ Grill
Travel crib, free WiFi, bed sheets

2BR, Sleeps7 • Coffee Station, Backyard w/ Grill

10.0 out of 10, Exceptional, (1)
"The house was amazing. The beds were so comfortable. The stay was so fun. Thank you for everything!"
$325 nightly
The price is $402
Sep 9 - Sep 10
Total with taxes and fees
2BR, Sleeps7 • Coffee Station, Backyard w/ Grill
Cozy studio in Andersonville Chicago
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cozy studio in Andersonville Chicago

9.2 out of 10, Wonderful, (26)
"Great studio apartment. Needed just one night and worth the price. Would recommend."
$140 nightly
The price is $173
Sep 9 - Sep 10
Total with taxes and fees
Cozy studio in Andersonville Chicago
Charming 2-bedroom house with WiFi in peaceful Hazel Crest
Fridge, microwave, oven, stovetop

Charming 2-bedroom house with WiFi in peaceful Hazel Crest

7.4 out of 10, Good, (9)
"The property was very spacious and clean and customer service is very responsive and quick. "
$293 nightly
The price is $313
Sep 9 - Sep 10
Total with taxes and fees
Charming 2-bedroom house with WiFi in peaceful Hazel Crest
4BR Retreat w/ Theater, Game Room & Backyard
Dining

4BR Retreat w/ Theater, Game Room & Backyard

7.4 out of 10, Good, (9)
$408 nightly
The price is $496
Sep 23 - Sep 24
Total with taxes and fees
4BR Retreat w/ Theater, Game Room & Backyard
Peaceful 1BR Escape in Evanston
1 bedroom, iron/ironing board, travel crib, WiFi

Peaceful 1BR Escape in Evanston

9.4 out of 10, Exceptional, (3)
"Quiet, clean and spacious! A peaceful neighborhood. "
$187 nightly
The price is $205
Sep 24 - Sep 25
Total with taxes and fees
Peaceful 1BR Escape in Evanston
Great Layout – Spacious 2BR Apt
Fridge, microwave, oven, stovetop

Great Layout – Spacious 2BR Apt

10.0 out of 10, Exceptional, (4)
"Clean, comfortable, and would definitely stay again!"
$194 nightly
The price is $214
Sep 17 - Sep 18
Total with taxes and fees
Great Layout – Spacious 2BR Apt
Cozy Studio in Portage Park
Iron/ironing board, travel crib, WiFi, bed sheets

Cozy Studio in Portage Park

$168 nightly
The price is $188
Sep 10 - Sep 11
Total with taxes and fees
Cozy Studio in Portage Park
Cozy 2BR Apt for a Seamless Stay
2 bedrooms, WiFi, bed sheets

Cozy 2BR Apt for a Seamless Stay

8.0 out of 10, Very Good, (1)
"Everything as advertised. The only part that I was unsure of was what to do with the keys as this was not stated in any of the information provided. So I left them on the table. "
$230 nightly
The price is $257
Oct 5 - Oct 6
Total with taxes and fees
Cozy 2BR Apt for a Seamless Stay
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

The Emily Hotel

The Emily Hotel

10/10 Excellent
"We have stayed at The Emily Hotel twice and has become our go to for our yearly trip for an event in town. Every time we visit the staff goes above and beyond to ensure a great experience from check in, valet parking, amenities, and room service."
Saud 4-night trip
Posted 2 days ago
The Emily Hotel

Find out more about West Side

Find out more about West Side

West Side Vacation Homes information

Number of reviews
Accommodation
82 Vacation Homes
Lowest Price
Highest Price

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