
Holiday Rentals in West Side
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Our top choices for West Side holiday rentals

1. Cozy Urban View Retreat Near Downtown - Sleeps 7
Cozy Urban View Retreat Near Downtown - Sleeps 7
2. Flexhome East Village • Modern 2BR • Quiet Street
Flexhome East Village • Modern 2BR • Quiet Street
3. Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6
Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6
4. 3BR Complete and Spacious Apartment in Ideal Spot
3BR Complete and Spacious Apartment in Ideal Spot
5. Flexhome Wicker Park • Stylish 2BR • Sleeps 6
Flexhome Wicker Park • Stylish 2BR • Sleeps 6
6. Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6
Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6
7. Convenient 2BR Apt w/ In-Unit Laundry
Convenient 2BR Apt w/ In-Unit Laundry
8. Pilsen Sweet Life Up High
Pilsen Sweet Life Up High
9. Skyline View Apt - 5 minutes to Downtown - Games + Arcades - Free Parking
Skyline View Apt - 5 minutes to Downtown - Games + Arcades - Free Parking
10. Modern Zen Retreat mins from Downtown
Modern Zen Retreat mins from Downtown
11. Peaceful Zen Flat | 2BR Oasis with Free Parking
Peaceful Zen Flat | 2BR Oasis with Free Parking
12. Cozy Luxury 1BR - 10 Min to Downtown Chicago
Cozy Luxury 1BR - 10 Min to Downtown Chicago
13. Peaceful Boho Retreat | Free Private Parking
Peaceful Boho Retreat | Free Private Parking
14. Patio | 15 min Downtown & United Ctr+King Bed, CTA
Patio | 15 min Downtown & United Ctr+King Bed, CTA
15. Bright & Spacious Boho Oasis: A Warm Retreat
Bright & Spacious Boho Oasis: A Warm Retreat
16. LIVN West Loop Chicago Queen Superior Studio
LIVN West Loop Chicago Queen Superior Studio
17. 4BR Flat By Douglass Park & Transit - Free parking
4BR Flat By Douglass Park & Transit - Free parking
18. Boho City Escape | Parking + Balcony
Boho City Escape | Parking + Balcony
19. 1BR Modern Luxe Apt with In-Unit Laundry
1BR Modern Luxe Apt with In-Unit Laundry
20. West Town 2BR | Full Kitchen + In-Unit Laundry
West Town 2BR | Full Kitchen + In-Unit LaundryFind holiday rentals that suit your style
Top West Side Hotel Reviews

Hyatt Place Chicago Medical/University District
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 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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