West Side Holiday Homes from €92: Search Top House Rentals

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 holiday homes

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

Austin

Adrian Cesar C.

includes taxes & fees

30 Sept - 1 Oct

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

Belmont Cragin

Jason

includes taxes & fees

24 Sept - 25 Sept

3. A quiet stay while you are away

Oak Park

Fred D.

includes taxes & fees

21 Oct - 22 Oct

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

Maywood

Eduardo

includes taxes & fees

23 Sept - 24 Sept

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

Oak Park

kerston b.

includes taxes & fees

23 Sept - 24 Sept

7 bedrooms, desk, iron/ironing board, travel cot

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

Portage Park

Daniel J.

includes taxes & fees

30 Sept - 1 Oct

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

Oak Park

Willow M.

includes taxes & fees

6 Oct - 7 Oct

Coffee/tea maker, fridge, microwave, stovetop

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

Forest Park

LEM R.

includes taxes & fees

27 Sept - 28 Sept

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Top West Side Hotel Reviews

Hyatt House Chicago Medical/University District

10/10 Excellent

"The hotel is immaculate. Room was so nice. First hotel that I could stream movie apps from my phone. Really great for off times. Best hotel I’ve stayed at."

Crowne Plaza Chicago West Loop by IHG

10/10 Excellent

"This hotel has become my family's go-to for trips to Chicago. It's very easy to drive to. Love the on-site parking, which is not free, but I'd say was worth the ~$42/night for the convenience. The property is very clean and beautifully maintained. The staff is excellent. Close proximity to public transportation, which we used to get to and from Riot Fest in Douglas Park. Will definitely stay here 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 Holiday Homes information

Number of reviews	10,405
Accommodation	55 Holiday Homes
Lowest Price	€92
Highest Price	€531

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Chicago Holiday Rentals

Room 1

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Treat yourself

Be picky

Check prices for these dates

Our top choices for West Side holiday 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 holiday rentals that suit your style

Top West Side Hotel Reviews

Hyatt House Chicago Medical/University District

Hyatt Place Chicago Medical/University District

Crowne Plaza Chicago West Loop by IHG

STAY

Chicago Parthenon Hostel

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 Holiday Homes information

Explore a world of travel with Expedia

Holiday Homes in West Side

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for West Side holiday 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 holiday rentals that suit your style

Top West Side Hotel Reviews

Hyatt House Chicago Medical/University District

Find out more about West Side

West Side Holiday Homes information

Explore a world of travel with Expedia