West Side Vacation Rentals

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Sep 19 - Sep 21
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Oct 31 - Nov 2
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Nov 28 - Nov 30
In four months
Dec 26 - Dec 28

Vacation Rentals in West Side

Our top choices for West Side vacation rentals

Sonder by Marriott Bonvoy Market Hall Apartments West Loop
1 bedroom, individually decorated, individually furnished, desk

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.2 out of 10, Very Good, (352)
"Great stay!"
$149 nightly
The price is $175
Sep 3 - Sep 4
Total with taxes and fees
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
The Neighborhood Hotel-Little Italy
Front of property

The Neighborhood Hotel-Little Italy

4.0 star property
9.6 out of 10, Exceptional, (194)
"Property was extremely comfortable in a great area."
The Neighborhood Hotel-Little Italy
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Lobby

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
9.0 out of 10, Wonderful, (209)
"Great location, room was very nice. Vent in the bathroom wasn’t working and the walls are paper thin so you can hear other people talking loud. Otherwise a great stay! "
$195 nightly
The price is $229
Sep 21 - Sep 22
Total with taxes and fees
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Art Villa
Hot tub

Art Villa

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
$980 nightly
The price is $1,240
Sep 8 - Sep 9
Total with taxes and fees
Art Villa
Sonder by Marriott Bonvoy Greektown Apartments
Apartment, 1 Bedroom | Living room | 40-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
8.6 out of 10, Excellent, (59)
"loved our stay there. close to UIC and Greektown. will stay again"
$212 nightly
The price is $248
Sep 28 - Sep 29
Total with taxes and fees
Sonder by Marriott Bonvoy Greektown Apartments
Stylish 1BR in West Loop
Fridge, microwave, oven, stovetop

Stylish 1BR in West Loop

10.0 out of 10, Exceptional, (5)
$194 nightly
The price is $217
Sep 3 - Sep 4
Total with taxes and fees
Stylish 1BR in West Loop
Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown
Terrace/patio

Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown

2.0 star property
9.0 out of 10, Wonderful, (9)
"We got all the help and instructions needed to easily find this clean, well-supplied apartment with lovely outdoor space attached. And with the Pink Line just a few minutes walk and The Loop just 6 stops away, it was the perfect home base for getting to all that Chicago has to offer!"
Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown
Amazing 3-bedroom house with WiFi and AC in awesome Chicago
Iron/ironing board, WiFi, bed sheets

Amazing 3-bedroom house with WiFi and AC in awesome Chicago

Amazing 3-bedroom house with WiFi and AC in awesome Chicago
Spacious 3-bedroom apartment near downtown, FREE PARKING
Private kitchen

Spacious 3-bedroom apartment near downtown, FREE PARKING

9.4 out of 10, Exceptional, (3)
"Extremely clean space that was perfect for our group. We didn't spend a lot of time in the home during our stay, but when we did it was fantastic. Only minor gripe would be the upstairs neighbors, they were occasionally quite loud and woke us up a few times in the middle of the night. Would absolutely stay here again, if/when we come back to the area."
$286 nightly
The price is $353
Sep 3 - Sep 4
Total with taxes and fees
Spacious 3-bedroom apartment near downtown, FREE PARKING
HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony
Property grounds

HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony

9.2 out of 10, Wonderful, (52)
"The building is from the 19th century which made it a really unique experience. The hosts were amazing and quick to respond. We went to check out the Linkin Park concert in the United Center and it was a 5min walk from the property. "
HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony
Ground Floor Studios in Chicago by 747 Lofts
Exterior

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
9.4 out of 10, Exceptional, (17)
"Its was in a good location for anyone who has family close by. Bed was wonderful. "
$168 nightly
The price is $198
Sep 15 - Sep 16
Total with taxes and fees
Ground Floor Studios in Chicago by 747 Lofts
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
Outdoor dining

3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

10.0 out of 10, Exceptional, (251)
"Well stocked, spacious and beautifully decorated, excellent location, attentive host. We had a great stay!"
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
Your Perfect 2BR Home w/ Parking
Fridge, microwave, oven, stovetop

Your Perfect 2BR Home w/ Parking

8.6 out of 10, Excellent, (7)
"Our stay was great, the apartment was close to the bus line and the train. The beds were very comfortable and it was a good size for our family. It was nice to have the off street parking in the back although the rear entrance was a bit disheveled. The building was secure but not entirely sound proof, but that is expected in a basement appartment. I would stay here again on a trip to Chicago. "
$228 nightly
The price is $253
Sep 3 - Sep 4
Total with taxes and fees
Your Perfect 2BR Home w/ Parking
1F Chicago's Little italy Graystone nearDowntown
Exterior

1F Chicago's Little italy Graystone nearDowntown

10.0 out of 10, Exceptional, (152)
"This is an awesome place to stay in Chicago."
1F Chicago's Little italy Graystone nearDowntown
4 br/3ba, Great for Large Groups, Garage Parking. Spacious and updated!
Fridge, microwave, oven, stovetop

4 br/3ba, Great for Large Groups, Garage Parking. Spacious and updated!

10.0 out of 10, Exceptional, (5)
4 br/3ba, Great for Large Groups, Garage Parking. Spacious and updated!
Urban Farm Fun with Goats 10 Minutes To Downtown!
Interior

Urban Farm Fun with Goats 10 Minutes To Downtown!

8.0 out of 10, Very Good, (2)
"So overall the stay was amazing the goats and chickens were a perfect addition to the stay BUT the neighbors upstairs literally didn’t sleep at al they were banging around moving things at all hours of the night one night it was 2am and they were still going strong so that’s why my rating was low but the host was amazing and sweet. "
Urban Farm Fun with Goats 10 Minutes To Downtown!
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. "
$254 nightly
The price is $282
Sep 4 - Sep 5
Total with taxes and fees
3BR Complete and Spacious Apt
Bright & Roomy 4BR in Pilsen
Dining

Bright & Roomy 4BR in Pilsen

8.0 out of 10, Very Good, (8)
$297 nightly
The price is $329
Sep 22 - Sep 23
Total with taxes and fees
Bright & Roomy 4BR in Pilsen
Elizabeth by Coast to Cactus | Chic Artists Loft
Interior

Elizabeth by Coast to Cactus | Chic Artists Loft

9.2 out of 10, Wonderful, (21)
"Great place, excellent location and close to the trains!!!!"
Elizabeth by Coast to Cactus | Chic Artists Loft
Spacious 4BR Near Wicker Park
Fridge, microwave, oven, stovetop

Spacious 4BR Near Wicker Park

10.0 out of 10, Exceptional, (2)
"Had an amazing stay at this Vrbo. Very cozy and comfortable for everyone!"
$362 nightly
The price is $393
Sep 3 - Sep 4
Total with taxes and fees
Spacious 4BR Near Wicker Park
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 19 hours ago
The Emily Hotel

Find out more about West Side

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 $175 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia