Far Southwest Side Vacation Rentals from $151: Search Short-Term Rentals

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Our top choices for Far Southwest Side vacation rentals

A modern building with the name 'SENIORAL' prominently displayed on the facade.

1. Sentral Michigan Avenue

Downtown Chicago

Jacob

$143 nightly

Nov 9 - Nov 10

Total with taxes and fees

A modern living room with a sofa, a round coffee table, and a dining area with a table and chairs.

2. Kasa Lake Shore Chicago

Downtown Chicago

Iliana

$202 nightly

Nov 25 - Nov 26

Total with taxes and fees

A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

3. Wrigleyville Suites

Lakeview

Diana

$165 nightly

Oct 26 - Oct 27

Total with taxes and fees

A modern kitchen with a large island, bar stools, and a city view.

4. Level Chicago – Old Town

Downtown Chicago

Robert Edward

$279 nightly

Nov 1 - Nov 2

Total with taxes and fees

A large brick house with a central chimney, a covered porch, and a brick pathway leading to the entrance.

5. The Oak Park Loft

Oak Park

Linda

$294 nightly

Oct 27 - Oct 28

Total with taxes and fees

A spacious living room with a grand piano, a comfortable sofa, and a dining area with a chandelier.

6. Historic Oak Park Home

Oak Park

Janette

$276 nightly

Oct 27 - Oct 28

Total with taxes and fees

A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

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

Forest Park

$444 nightly

Oct 27 - Oct 28

Total with taxes and fees

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Top Far Southwest Side Hotel Reviews

River Hotel

10/10 Excellent

"I had a wonderful experience at the hotel. The staff was friendly, welcoming, and professional. Everything made my stay comfortable and enjoyable. Thank you for providing such excellent service. I would definitely recommend this hotel and look forward to staying here again!"

The Chicago Hotel Collection - Magnificent Mile

8/10 Good

"Solo Raymond fue la única persona amable, una señora la cual no me sé su nombre fue muy grosera con nosotros, nos habló muy golpeado y no nos explicó amablemente nada. No te hace sentir bienvenido, solo Raymond lo hace. Gracias a Dios solo nos cobraron los 150 dolares del depósito, pero escuché que te pueden cobrar 50 dólares por noche y un 18% de impuestos, la verdad no sé bien en qué casos, yo me estuve manteniendo en contacto con los de expedia para todas mis dudas. Así que aconsejo reservar cuarto sin desayuno incluido. Lo bueno del lugar es que el cuarto es amplio y que la ubicación es maravillosa. Y que el precio no es tan elevado como el de los hoteles cercanos a este (no por eso es barato) No esperen algo lujoso, es más bien algo útil. Ah, y la TV nunca funcionó, no pudimos poner música de mientras. A mi no me molesta tanto eso, pero a mi novio sí y otra cosa, el internet es muy lento."

Club Quarters Hotel, Central Loop, Chicago

10/10 Excellent

"My husband and I went for 2 nights and our stay was very pleasant, staff was super friendly, I loved that they were able to hold our luggage after checking out so we can explore the city a little longer since our flight was in the evening. Theres a lot of places to ear and visit and its very walkable, I would stay here again next time."

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good

"We had a larger king bed room….it had space but no comfortable seating after a long day. That was disappointing and a misuse of space. It should have had two cushioned/fabric accent chairs or a small sofa. Nobody wants to sit on their bed to read or watch TV before dinner or just to relax. That was unfortunate."

Hotel Saint Clair- Magnificent Mile

8/10 Good

"St. Clair hotel lists the room as premium, even though the two windows in the room had no view. Both windows faced the building outter exterior brick walls from all sides. Dim lightning with no direct sunlight, very depressing to look out. The room should have been listened and offered as standard, at best, not premium."

Find out more about Far Southwest Side

Everything you need to know about Far Southwest 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 Far Southwest 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 Far Southwest Side vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Far Southwest Side vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Far Southwest 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 Far Southwest 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 $151 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 Far Southwest Side rentals

At Expedia, we put the best Far Southwest 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 Far Southwest 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 Far Southwest 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 Far Southwest 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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Check prices for these dates

Our top choices for Far Southwest Side vacation rentals

1. Sentral Michigan Avenue

2. Kasa Lake Shore Chicago

3. Wrigleyville Suites

4. Level Chicago – Old Town

5. The Oak Park Loft

6. Historic Oak Park Home

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

Find vacation rentals that suit your style

Top Far Southwest Side Hotel Reviews

River Hotel

Arlo Chicago

The Chicago Hotel Collection - Magnificent Mile

Club Quarters Hotel, Central Loop, Chicago

The Chicago Hotel Collection Ambassador Gold Coast

Eurostars Magnificent Mile

Congress Plaza Hotel

Hotel Saint Clair- Magnificent Mile

Find out more about Far Southwest Side

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