West Side, IL Vacation Homes from ￥32,437

A greenhouse with a glass ceiling, various cacti, and a wooden structure in the center.

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Our top choices for West Side vacation homes

A circular fire pit with chairs around it, string lights overhead, and a house in the background.

1. Sleeps 18 • 7BR • Gym • Game Room • Theater

Austin

Adrian Cesar C.

￥148,821 total

includes taxes & fees

Sep 30 - Oct 1

2. Theater • Game Room • Gym • Firepit • 4BR Home

Belmont Cragin

Jason

￥88,379 total

includes taxes & fees

Sep 24 - Sep 25

A large, multi-story building with a prominent stone facade and a distinctive triangular roof.

3. A quiet stay while you are away

Oak Park

Fred D.

￥45,295 total

includes taxes & fees

Oct 12 - Oct 13

A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

4. Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Maywood

Eduardo

￥45,693 total

includes taxes & fees

Sep 23 - Sep 24

A modern living room with a sectional sofa, a coffee table, and a TV.

5. Attractive Coach House Apartment for rent in Oak Park.

Oak Park

kerston b.

￥35,381 total

includes taxes & fees

Sep 23 - Sep 24

6. Arcade • Theater • Gym • Office • Sleeps 15

Portage Park

Daniel J.

￥117,414 total

includes taxes & fees

Sep 30 - Oct 1

A single-story house with a covered porch, a front door, and a small garden area.

7. Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard

Oak Park

Willow M.

￥53,828 total

includes taxes & fees

Oct 6 - Oct 7

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

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

Forest Park

LEM R.

￥75,356 total

includes taxes & fees

Sep 27 - Sep 28

A white two-story house with a porch, steps, and a small table with chairs.

9. Oak Park Victorian by FLW Studio

Oak Park

Margaret L.

￥89,865 total

includes taxes & fees

Sep 30 - Oct 1

A cozy living room with a neon sign, a fireplace, a television, and a guitar.

10. Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops

Lincoln Park

"We had a really nice stay at the Village Inn. We appreciated that artistic furnishings and decorations, and the thoughtful touches throughout. (We are a white noise family, so we were very happy to find a white noise machine in every bedroom!)The neighborhood is very quiet and also close to great shops and restaurants as well as the train. We enjoyed being able to walk to dinner in the evening, and walk to the train to take a short ride right to the Art Institute. The kitchen was great for...

Andrea M.

A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

11. LUXE 3 BR, 2 BA + Hot Tub

Elmhurst

Jeff

￥57,733 total

includes taxes & fees

Sep 24 - Sep 25

A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

12. Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

Westmont

Tomas R.

￥33,510 total

includes taxes & fees

Sep 30 - Oct 1

A hotel room with a large bed, two pillows, a teal throw blanket, and a view of buildings through a window.

13. Bronzeville Gem: Balcony, Gym & Rooftop Deck

Near South Side

Kathy

￥121,908 total

includes taxes & fees

Sep 26 - Sep 27

A staircase with a wooden finish and black railings, leading to a room with a large wooden door and a white ceiling.

14. Cozy Home by O'Hare + EV Plug

Des Plaines

Richie S.

￥50,150 total

includes taxes & fees

Oct 5 - Oct 6

A modern kitchen with stainless steel appliances, wooden cabinets, and a tiled backsplash.

15. PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

Westchester

Carl M.

￥87,097 total

includes taxes & fees

Sep 28 - Sep 29

A wooden deck with a railing, a staircase, and a window with a wreath.

16. Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

Robertsdale

Jusu K.

￥32,437 total

includes taxes & fees

Sep 29 - Sep 30

A covered patio with a hammock, a barbecue grill, and a dining area with a table and chairs.

17. Chicago Riverhouse with private fenced in oasis

North Park

Robert S.

￥109,459 total

includes taxes & fees

Oct 8 - Oct 9

A living room with a flat-screen TV mounted on the wall, a plant on a stand, and a window with blinds.

18. 4 BR • Theater Room • Gym • Walk to Lincoln Park!

Lincoln Park

A beach with people sunbathing and swimming, a lighthouse, and a pier extending into the water.

19. Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

Lincoln Park

Ann V.

￥147,912 total

includes taxes & fees

Oct 5 - Oct 6

A hotel room with a large bed, dark curtains, a ceiling fan, and a bedside lamp.

20. Back Unit Patio, Balcony, Yard, Smart TVs, W/D

Westmont

￥50,003 total

includes taxes & fees

Sep 28 - Sep 29

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Top West Side Hotel Reviews

Hyatt House Chicago/West Loop-Fulton Market

8/10 Good

"We arrived before 3pm check in and did not get our room until close to 4. Cleaning service was behind. Despite the delay, the room was spacious and fit the 5 of us comfortably. We were here for kids to go to a concert so didn’t stay in hotel long, but could walk (about 20 mins) to United Center. The adults then walked for dinner to Fulton Market area. Felt safe doing all that- so the hotel is in a good location. The staff had comped us 2 drinks at the bar for the check in delay, which we did use. The bartender was friendly. Never got to the pool. The gym was satisfactory for a hotel gym. We were on the 8th floor and it was quiet. In and out valet was pricey but super convenient and quick. Would stay here again."

Chicago Parthenon Hostel

10/10 Excellent

"Stayed in the 8 female dorm for a few hrs before my early flight outta OHare. Room was clean, bed was comfy- decent sheets, comforter and pillows. Everyone was super respectful and quiet except for 1 girl who was taking on her phone pretty loud so that was annoying but other than that nice place. easy check in / out, front desk man was super nice. Would def stay again."

STAY

8/10 Good

"The advertisement for the room should not have included the couch as it was in a communal area. AC broke down halfway through our stay and if it wasn't for the cool weather, it would have been miserable. Amenities were replaced at least twice a day, and luckily one just happened to show up after a chair fell apart. It was adequate in all."

Level Chicago Fulton Market

10/10 Excellent

"I loved the balcony and the great view! The kitchenette was a plus along with the provided utensils and necessary items. The laundry are was not something that I used but I could see how it would be a bonus feature. The area by the bed was a little cramped, but it ended up being comfortable. The staff was extremely friendly and helpful and the check in was seamless. The elevators were especially private and convenient. Overall, the extra $ that I paid for my stay was well worth it!"

The Neighborhood Hotel-Little Italy

10/10 Excellent

"Great location with nearby bars, restaurants and a few mini marts. We did wish there was a larger grocery store closer, but not a deal breaker by any means. Close to many bus stops and maybe 1/2 mile to the pink line and 3/4 mile to the blue line. Spacious room with a kitchen. They provide about 2 full pots of coffee which is a bonus. They respond to questions almost immediately. The room Is very spacious, as is the bathroom. The soap, gel, shampoo, conditioner and lotion they provide has a very nice scent, but not too strong. There is a good size closet for storage, hanging clothes etc. There is a dishwasher and a clothes washer and I presume also acts as a dryer (2 in 1). These are kind of knit picking but, the bed is pretty soft. If you like soft beds you’ll be stoked. The water pressure in the shower was a little weak. Overall this is a great hotel, great location and a fair price. I would definitely stay here again."

Find out more about West Side

West Side Vacation Homes information

Number of reviews	423
Accommodation	54 Vacation Homes
Lowest Price	￥32,437
Highest Price	￥148,821

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for West Side vacation homes

1. Sleeps 18 • 7BR • Gym • Game Room • Theater

2. Theater • Game Room • Gym • Firepit • 4BR Home

3. A quiet stay while you are away

4. Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

5. Attractive Coach House Apartment for rent in Oak Park.

6. Arcade • Theater • Gym • Office • Sleeps 15

7. Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard

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

9. Oak Park Victorian by FLW Studio

10. Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops

11. LUXE 3 BR, 2 BA + Hot Tub

12. Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

13. Bronzeville Gem: Balcony, Gym & Rooftop Deck

14. Cozy Home by O'Hare + EV Plug

15. PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

16. Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

17. Chicago Riverhouse with private fenced in oasis

18. 4 BR • Theater Room • Gym • Walk to Lincoln Park!

19. Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

20. Back Unit Patio, Balcony, Yard, Smart TVs, W/D

Find vacation rentals that suit your style

Top West Side Hotel Reviews

Hyatt House Chicago/West Loop-Fulton Market

Chicago Parthenon Hostel

Hyatt House Chicago Medical/University District

Hyatt Place Chicago Medical/University District

STAY

Level Chicago Fulton Market

The Emily Hotel

The Neighborhood Hotel-Little Italy

Hampton Inn & Suites Chicago Medical District UIC

Find out more about West Side

West Side Vacation Homes information

Explore a world of travel with Expedia

Search Vacation Homes in West Side

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for West Side vacation homes

1. Sleeps 18 • 7BR • Gym • Game Room • Theater

2. Theater • Game Room • Gym • Firepit • 4BR Home

3. A quiet stay while you are away

4. Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

5. Attractive Coach House Apartment for rent in Oak Park.

6. Arcade • Theater • Gym • Office • Sleeps 15

7. Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard

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

9. Oak Park Victorian by FLW Studio

10. Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops

11. LUXE 3 BR, 2 BA + Hot Tub

12. Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

13. Bronzeville Gem: Balcony, Gym & Rooftop Deck

14. Cozy Home by O'Hare + EV Plug

15. PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

16. Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

17. Chicago Riverhouse with private fenced in oasis

18. 4 BR • Theater Room • Gym • Walk to Lincoln Park!

19. Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

20. Back Unit Patio, Balcony, Yard, Smart TVs, W/D

Find vacation rentals that suit your style

Top West Side Hotel Reviews

Hyatt House Chicago/West Loop-Fulton Market

Find out more about West Side

West Side Vacation Homes information

Explore a world of travel with Expedia