
West Side Vacation Rentals
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Our top choices for West Side vacation rentals

1. LIVN West Loop Chicago King Studio
LIVN West Loop Chicago King Studio
2. Modern West Loop Gem-City Views & Prime Location 1
Modern West Loop Gem-City Views & Prime Location 1
3. LIVN West Loop Chicago Queen Superior Studio
LIVN West Loop Chicago Queen Superior Studio
4. LIVN West Loop Chicago Classic Queen Studio
LIVN West Loop Chicago Classic Queen Studio
5. River West, Third Floor Chicago by 747 Lofts
River West, Third Floor Chicago by 747 Lofts
6. Ukrainian Village 3BR/3BA • Private Patio, Parking
Ukrainian Village 3BR/3BA • Private Patio, Parking
7. 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
8. Peaceful Zen Flat | 2BR Oasis with Free Parking
Peaceful Zen Flat | 2BR Oasis with Free ParkingFind vacation rentals that suit your style
Top West Side Hotel Reviews

Hampton Inn & Suites Chicago Medical District UIC
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, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in. The selection of West Side vacation rentals we have selected for you start as low as CA $317 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 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.
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