West Side Holiday Rentals

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Check prices for these dates

Our top choices for West Side holiday rentals

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,420 reviews)
"Great for extended stays."
United States
Jeff
The price is NZ$406
includes taxes & fees
13 Dec - 14 Dec
Sentral Michigan Avenue

2. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (313 reviews)
"The rooms were clean, and the staff was courteous and the Breakfast was excellent."
United States
Ernest
The price is NZ$410
includes taxes & fees
16 Dec - 17 Dec
The Gem Museum Suites

3. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (95 reviews)
"The bathroom was really clean. The beds were really comfortable"
United States
Jair
The price is NZ$435
includes taxes & fees
22 Nov - 23 Nov
Kasa Lake Shore Chicago

4. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (565 reviews)
"Super clean and friendly staff! Would definitely stay here again"
United States
Robert Edward
The price is NZ$410
includes taxes & fees
23 Nov - 24 Nov
Level Chicago – Old Town

5. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.6 out of 10, Exceptional, (53 reviews)
"The area was nice! Many restaurants and stores are at walking distance Room was very nice and clean"
United States
Francisco
The price is NZ$247
includes taxes & fees
16 Nov - 17 Nov
Wrigleyville Suites

6. Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
8.8 out of 10, Excellent, (6 reviews)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
The price is NZ$645
includes taxes & fees
16 Nov - 17 Nov
Historic Oak Park Home

7. Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line
3.0 star property
Forest Park
The price is NZ$859
includes taxes & fees
16 Nov - 17 Nov
Classic Forest Park Foursquare < 1 Mi to Blue Line

8. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (14 reviews)
"Great location with parking included"
United States
Melissa
At Home in Oak 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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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 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 NZ$309 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.

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