West Side Holiday Rentals

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Our top choices for West Side holiday rentals

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (4)
"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."
United States
Jeffrey
The price is AU$254
includes taxes & fees
4 Jan - 5 Jan 2026
West Loop Living – Bright 1BR

Stylish 1BR in West Loop

Stylish 1BR in West Loop
Downtown Chicago
10.0 out of 10, Exceptional, (10)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is AU$254
includes taxes & fees
1 Jan - 2 Jan 2026
Stylish 1BR in West Loop

Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment
Downtown Chicago
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.
The price is AU$254
includes taxes & fees
4 Jan - 5 Jan 2026
Sun-Drenched 1BR Apartment

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is AU$254
includes taxes & fees
1 Jan - 2 Jan 2026
1BR Modern Luxe Apt with In-Unit Laundry

Cozy Boho Chicago - 10 Minutes to Downtown Chicago

Cozy Boho Chicago - 10 Minutes to Downtown Chicago
Lawndale
10.0 out of 10, Exceptional, (8)
"Very nice apartment close to downtown!"
United States
Dariana
The price is AU$299
includes taxes & fees
29 Dec - 30 Dec
Cozy Boho Chicago - 10 Minutes to Downtown Chicago

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

NEW Private West Loop 1br with Backyard near Green Line and CTA
East Garfield Park
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.
The price is AU$384
includes taxes & fees
13 Jan - 14 Jan 2026
NEW Private West Loop 1br with Backyard near Green Line and CTA

Flexhome Ukrainian Village 2BR D1

Flexhome Ukrainian Village 2BR D1
West Town
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.
The price is AU$246
includes taxes & fees
1 Jan - 2 Jan 2026
Flexhome Ukrainian Village 2BR D1

15mins DT | Wicker Park Gem | Sleeps 7 | FreePark

15mins DT | Wicker Park Gem | Sleeps 7 | FreePark
East Garfield Park
The price is AU$422
includes taxes & fees
26 Dec - 27 Dec
15mins DT | Wicker Park Gem | Sleeps 7 | FreePark

Spacious 3-bedroom apartment near downtown, FREE PARKING

Spacious 3-bedroom apartment near downtown, FREE PARKING
Near West Side
9.4 out of 10, Exceptional, (10)
"Nice place to stay. Good communication with the owner."
United States
Ryan
The price is AU$484
includes taxes & fees
20 Jan - 21 Jan 2026
Spacious 3-bedroom apartment near downtown, FREE PARKING

10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades

10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades
2.0 star property
Lawndale
8.0 out of 10, Very good, (2)
"While it was a great price, you get what you pay for. "
United States
Deya R.
The price is AU$439
includes taxes & fees
7 Jan - 8 Jan 2026
10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades

Flexhome East Village 2BR H1

Flexhome East Village 2BR H1
West Town
9.8 out of 10, Exceptional, (7)
"great place! clean, comfortable, safe and in a great area! highly recommend. "
United States
CJ M.
The price is AU$307
includes taxes & fees
24 Jan - 25 Jan 2026
Flexhome East Village 2BR H1

Cabin 203 by 747 Lofts

Cabin 203 by 747 Lofts
West Town
8.6 out of 10, Excellent, (7)
"Was prefect for a mother/son spring break excursion. "
United States
Julie R.
The price is AU$232
includes taxes & fees
1 Jan - 2 Jan 2026
Cabin 203 by 747 Lofts

Flexhome Wicker Park 2BR DV3

Flexhome Wicker Park 2BR DV3
West Town
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.
The price is AU$246
includes taxes & fees
30 Dec - 31 Dec
Flexhome Wicker Park 2BR DV3

Your Perfect 2BR Home

Your Perfect 2BR Home
Near West Side
8.2 out of 10, Very good, (14)
"Great stay by the United Center "
United States
Brian H.
The price is AU$293
includes taxes & fees
4 Jan - 5 Jan 2026
Your Perfect 2BR Home

Chicago Third Floor Studio by 747 Lofts

Chicago Third Floor Studio by 747 Lofts
2.0 star property
West Town
9.8 out of 10, Exceptional, (6)
"Cute little studio that was clean. There was a nice size kitchen and was close to our activities in the West loop of Chicago. There was also assistance with parking located in the lofts."
United States
Jennifer
The price is AU$346
includes taxes & fees
30 Dec - 31 Dec
Chicago Third Floor Studio by 747 Lofts

5 Mins to Downtown CHI Sleeps 10 - Parking + Games

5 Mins to Downtown CHI Sleeps 10 - Parking + Games
Lower West Side
10.0 out of 10, Exceptional, (1)
"We loved the location, the area is awesome! Great stay, highly recommend. "
United States
Db D.
The price is AU$439
includes taxes & fees
13 Jan - 14 Jan 2026
5 Mins to Downtown CHI Sleeps 10 - Parking + Games

3BR Complete and Spacious Apt

3BR Complete and Spacious Apt
West Town
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
The price is AU$318
includes taxes & fees
30 Dec - 31 Dec
3BR Complete and Spacious Apt

Flexhome West Town 2BR Apt T1

Flexhome West Town 2BR Apt T1
West Town
9.0 out of 10, Wonderful, (2)
"Awesome location, great views and comfortable."
United States
Steve L.
The price is AU$243
includes taxes & fees
21 Jan - 22 Jan 2026
Flexhome West Town 2BR Apt T1

King Bed with Chefs Kitchen and Free Parking - Pets OK

King Bed with Chefs Kitchen and Free Parking - Pets OK
2.0 star property
West Town
The price is AU$557
includes taxes & fees
30 Dec - 31 Dec
King Bed with Chefs Kitchen and Free Parking - Pets OK

Urban Comfort • 2BR in West Town

Urban Comfort • 2BR in West Town
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.
The price is AU$284
includes taxes & fees
1 Jan - 2 Jan 2026
Urban Comfort • 2BR in West Town
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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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, 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 favourite 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 depend 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 AU$254 per night. Entering your travel dates in the search wizard might find you 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.