West Side Vacation Rentals

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Tonight
Oct 27 - Oct 28
Tomorrow
Oct 28 - Oct 29
This weekend
Oct 31 - Nov 2
Next weekend
Nov 7 - Nov 9

Vacation Rentals in West Side

1 bedroom, individually decorated, individually furnished, desk
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
3.5 star property
8.0 out of 10, Very Good, (394)
"Great location. Was there for the marathon and had a great stay. "
United States
HELGA
$110 nightly
The price is $129
Nov 10 - Nov 11
Total with taxes and fees
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Lobby
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Sonder by Marriott Bonvoy The Burnham Apartments Loop
3.5 star property
8.8 out of 10, Excellent, (244)
"Great stay. "
United States
Teresa
$135 nightly
The price is $159
Nov 10 - Nov 11
Total with taxes and fees
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Front of property
The Neighborhood Hotel-Little Italy
The Neighborhood Hotel-Little Italy
4.0 star property
9.6 out of 10, Exceptional, (213)
"Perfect location and area was wonderful."
United States
Thomas
The Neighborhood Hotel-Little Italy
Apartment, 1 Bedroom | Living room | 40-inch flat-screen TV with digital channels, TV
Sonder by Marriott Bonvoy Greektown Apartments
Sonder by Marriott Bonvoy Greektown Apartments
3.5 star property
8.6 out of 10, Excellent, (65)
"The kitchen had everything we needed, great space overall, safe location, clean, near everything we needed, access to bus and rail very close, we really enjoyed our stay. "
United States
Samuel
$118 nightly
The price is $139
Nov 10 - Nov 11
Total with taxes and fees
Sonder by Marriott Bonvoy Greektown Apartments
Interior
Art Villa
Art Villa
5.0 star property
10.0 out of 10, Exceptional, (2)
" "
United States
tomonobu
$823 nightly
The price is $1,031
Oct 28 - Oct 29
Total with taxes and fees
Art Villa
Terrace/patio
NEW LUXURY PENTHOUSE CONDO
NEW LUXURY PENTHOUSE CONDO
10.0 out of 10, Exceptional, (197)
"Great house with a great rooftop. "
United States
Francisco
NEW LUXURY PENTHOUSE CONDO
Outdoor dining
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
10.0 out of 10, Exceptional, (263)
"Very clean and you can't beat the location!"
United States
Kenix F.
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
Fridge, microwave, oven, stovetop
Experience Chicago living near United Center
Experience Chicago living near United Center
9.2 out of 10, Wonderful, (27)
"We were in town with our rowing team for a regatta, and this was a perfect spot to stay! Amenities were perfect for our needs, the living room is super spacious for some morning yoga, and the owners were responsive to any questions we had. Will definitely be saving this location for our trip here next year?"
United States
McKenzie J.
Experience Chicago living near United Center
Studio | Exterior
Ground Floor Studios in Chicago by 747 Lofts
Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
9.0 out of 10, Wonderful, (20)
"The stay lacked in shelf space as well as other amenities that could be useful. "
United States
Zugeily
$119 nightly
The price is $139
Nov 5 - Nov 6
Total with taxes and fees
Ground Floor Studios in Chicago by 747 Lofts
Fridge, microwave, oven, stovetop
Stylish 1BR in West Loop
Stylish 1BR in West Loop
10.0 out of 10, Exceptional, (7)
"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"
United States
Jacob D.
$186 nightly
The price is $207
Nov 3 - Nov 4
Total with taxes and fees
Stylish 1BR in West Loop
Fridge, microwave, oven, stovetop
Luxury Home Away From Your Home
Luxury Home Away From Your Home
9.0 out of 10, Wonderful, (133)
"House was very nice extremely comfortable bed"
United States
Kris B.
Luxury Home Away From Your Home
Exterior
1F Chicago's Little italy Graystone nearDowntown
1F Chicago's Little italy Graystone nearDowntown
10.0 out of 10, Exceptional, (162)
"Very comfortable place, Great location for visiting the city!"
United States
Calvin D.
1F Chicago's Little italy Graystone nearDowntown
Interior
Remodeled West Loop Apartment Near United Center
Remodeled West Loop Apartment Near United Center
9.0 out of 10, Wonderful, (54)
"This apartment is very close to downtown with easy parking right outside! The unit is very well maintained with spacious rooms and amenities! The host has thought of everything to make it feel like your own home! Would love to come back and stay here again!"
United States
kiran
Remodeled West Loop Apartment Near United Center
TV
Bright & Roomy 3BR in Pilsen
Bright & Roomy 3BR in Pilsen
7.8 out of 10, Good, (13)
"We had a great time and the host was very responsive. Pilsen is a great neighborhood, very safe, and super close to down town."
United States
Jonathan M.
$260 nightly
The price is $286
Oct 28 - Oct 29
Total with taxes and fees
Bright & Roomy 3BR in Pilsen
Terrace/patio
Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown
Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown
2.0 star property
9.0 out of 10, Wonderful, (11)
"Stay was great!"
United States
Augustus L.
Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown
3 bedrooms, iron/ironing board, travel crib, free WiFi
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
10.0 out of 10, Exceptional, (316)
"Listing as described. We would definitely stay here again!"
United States
Lauren O.
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
Fridge, microwave, oven, stovetop
Experience Chicago living near United Center
Experience Chicago living near United Center
8.6 out of 10, Excellent, (21)
"Immaculately clean property"
United States
cody m.
Experience Chicago living near United Center
Private kitchen
Spacious 3-bedroom apartment near downtown, FREE PARKING
Spacious 3-bedroom apartment near downtown, FREE PARKING
9.4 out of 10, Exceptional, (8)
"Nice place to stay. Good communication with the owner."
United States
Ryan
$269 nightly
The price is $332
Oct 29 - Oct 30
Total with taxes and fees
Spacious 3-bedroom apartment near downtown, FREE PARKING
Exterior
Million Dollar Views! Luxury Downtown Skyhouse!
Million Dollar Views! Luxury Downtown Skyhouse!
10.0 out of 10, Exceptional, (115)
"Great location. As advertised. "
United States
Paul C.
Million Dollar Views! Luxury Downtown Skyhouse!
Studio | Private kitchen | Fridge, oven, coffee/tea maker, toaster
River West, Third Floor Chicago by 747 Lofts
River West, Third Floor Chicago by 747 Lofts
2.0 star property
9.0 out of 10, Wonderful, (17)
"Overall solid property, I will return."
United States
Fletcher
$155 nightly
The price is $181
Oct 30 - Oct 31
Total with taxes and fees
River West, Third Floor Chicago by 747 Lofts
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

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

10/10 Excellent
"Staff was friendly upon check in and the premise was very clean."
Kelan 2-night trip
Posted 13 hours ago
Crowne Plaza Chicago West Loop by IHG

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit West Side in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $129 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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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