Holiday Rentals in West Side

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In two weeks
3 Oct - 5 Oct
In two months
14 Nov - 16 Nov
In three months
12 Dec - 14 Dec
In four months
9 Jan - 11 Jan

Holiday Rentals in West Side

Our top choices for West Side holiday 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
8.0 out of 10, Very good, (360)
"Great stay!"
The price is €128
includes taxes & fees
24 Sept - 25 Sept
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Lobby

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
8.8 out of 10, Excellent, (223)
"Great location and lovely amenities. "
The price is €157
includes taxes & fees
25 Sept - 26 Sept
Sonder by Marriott Bonvoy The Burnham Apartments Loop
The Neighborhood Hotel-Little Italy
Front of property

The Neighborhood Hotel-Little Italy

4.0 star property
9.6 out of 10, Exceptional, (202)
"This place was perfect "
The Neighborhood Hotel-Little Italy
Art Villa
Hot tub

Art Villa

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
Art Villa
Stylish 1BR in West Loop
Fridge, microwave, oven, stovetop

Stylish 1BR in West Loop

10.0 out of 10, Exceptional, (5)
The price is €188
includes taxes & fees
22 Sept - 23 Sept
Stylish 1BR in West Loop
Sonder by Marriott Bonvoy Greektown Apartments
Apartment, 1 Bedroom | Living room

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
8.6 out of 10, Excellent, (62)
"loved our stay there. close to UIC and Greektown. will stay again"
The price is €189
includes taxes & fees
28 Sept - 29 Sept
Sonder by Marriott Bonvoy Greektown Apartments
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, (18)
"Its was in a good location for anyone who has family close by. Bed was wonderful. "
The price is €121
includes taxes & fees
30 Sept - 1 Oct
Ground Floor Studios in Chicago by 747 Lofts
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."
The price is €313
includes taxes & fees
22 Sept - 23 Sept
Spacious 3-bedroom apartment near downtown, FREE PARKING
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)
"Great"
Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown
Your Perfect 2BR Home w/ Parking
Fridge, microwave, oven, stovetop

Your Perfect 2BR Home w/ Parking

8.8 out of 10, Excellent, (8)
"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. "
The price is €207
includes taxes & fees
6 Oct - 7 Oct
Your Perfect 2BR Home w/ Parking
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, (253)
"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
Experience Chicago living near United Center
Fridge, microwave, oven, stovetop

Experience Chicago living near United Center

9.2 out of 10, Wonderful, (26)
"Plenty of room, very nice amenities, short walk to bus line. Felt great coming back every day to that rather than a hotel room. Much more personal."
Experience Chicago living near United Center
3BR Complete and Spacious Apt
TV

3BR Complete and Spacious Apt

8.0 out of 10, Very good, (5)
"Spacious and well appointed. Great location with plenty of eating/drinking options within walking distance. "
The price is €209
includes taxes & fees
23 Sept - 24 Sept
3BR Complete and Spacious Apt
Bright & Roomy 3BR in Pilsen
Dining

Bright & Roomy 3BR in Pilsen

8.4 out of 10, Very good, (10)
The price is €261
includes taxes & fees
22 Sept - 23 Sept
Bright & Roomy 3BR in Pilsen
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, (53)
"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
Amazing 3-bedroom house with WiFi and AC in awesome Chicago
Interior

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

Amazing 3-bedroom house with WiFi and AC in awesome Chicago
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, (6)
"We were travelling with extended family for our niece's graduation from DePaul and this place was a short ride from everyplace we needed to be. We were a large group staying under one roof which can be challenging if there aren't enough private spaces to 'get away' sometimes, but this place had plenty..step away to a bedroom, sit on the deck, or walk to the park. On the flipside, the public spaces were great, too. With 4 young people under the age of 23, the hangout space downstairs made for...
4 br/3ba, Great for Large Groups, Garage Parking. Spacious and updated!
River West, Third Floor Chicago by 747 Lofts
Studio | Private kitchen

River West, Third Floor Chicago by 747 Lofts

2.0 star property
8.8 out of 10, Excellent, (15)
"Overall solid property, I will return."
The price is €143
includes taxes & fees
24 Sept - 25 Sept
River West, Third Floor Chicago by 747 Lofts
Experience Chicago living near United Center
Fridge, microwave, oven, stovetop

Experience Chicago living near United Center

8.8 out of 10, Excellent, (19)
"Immaculately clean property"
Experience Chicago living near United Center
1F Chicago's Little italy Graystone nearDowntown
Exterior

1F Chicago's Little italy Graystone nearDowntown

10.0 out of 10, Exceptional, (155)
"Very comfortable place, Great location for visiting the city!"
1F Chicago's Little italy Graystone nearDowntown
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 Place Chicago/Wicker Park

Hyatt Place Chicago/Wicker Park

10/10 Excellent
"We enjoyed our stay at the Hyatt. Our room was clean, the employees were helpful and the breakfast was great. It was a walkable neighborhood and we felt safe at all times. We will be back. "
Beatrice 2-night trip
Posted 1 day ago
Hyatt Place Chicago/Wicker Park

Find out more about West Side

Find out more about West Side

Everything you need to know about West Side holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the West Side holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

West Side holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A West Side holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of West Side holiday rentals we have selected for you start as low as €121 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on West Side rentals

At Expedia, we put the best West Side holiday 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 holiday.

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.