West Side Vacation Rentals from ￥54,975: Search Short-Term Rentals

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Our top choices for West Side vacation rentals

A hotel room with a bed, two bedside lamps, a wall-mounted artwork, and a small table with a lamp.

1. 2BR Apt with 2 Baths & Laundry

Near West Side

michele

￥46,275 total

includes taxes & fees

Nov 2 - Nov 3

A hotel room with a geometric-patterned wall, a bed with white bedding and a beige throw, two bedside lamps, and a window with blinds.

2. Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6

West Town

Jonalyn B.

￥28,723 total

includes taxes & fees

Nov 2 - Nov 3

3. Cozy Boho - 10 Minutes to Downtown Chicago + Arcades

Lawndale

Jess S.

A modern kitchen with white cabinets, a central island with stools, a microwave, and a refrigerator.

4. 3BR Complete and Spacious Apartment in Ideal Spot

West Town

Francis

￥40,673 total

includes taxes & fees

Oct 20 - Oct 21

A modern living room with a sofa, armchair, coffee table, and a TV mounted on a wooden wall.

5. Flexhome Ukrainian Village • 2BR • Convenient Walkability · Sleeps 6

West Town

Josh L.

￥30,012 total

includes taxes & fees

Nov 1 - Nov 2

A neatly made bed with white linens and a grey throw blanket, a bedside lamp, and a geometric wall design.

6. Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony

West Town

PAT C.

￥28,292 total

includes taxes & fees

Nov 2 - Nov 3

A rooftop terrace with a fire pit, seating area, and a city skyline view.

7. Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6

West Town

Jessica C.

￥37,893 total

includes taxes & fees

Nov 4 - Nov 5

A modern kitchen with white cabinets, a stainless steel refrigerator, a built-in oven, and a window above the sink.

8. Flexhome East Village • Modern 2BR • Quiet Street

West Town

Andrea B.

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Top West Side Hotel Reviews

Hyatt House Chicago/West Loop-Fulton Market

10/10 Excellent

"Such a great hotel. Easy, clean, enjoyable."

Hampton Inn & Suites Chicago Medical District UIC

10/10 Excellent

"I took my granddaughter to a concert at the United Center. This is the perfect place to stay! I used to travel weekly for work, and this is one of the nicer properties I've stayed at. It's a 15-minute walk to the United Center, and there are lots of food options within a block or two of the hotel. The staff is super-friendly. Six stars!"

LIVN - West Loop Chicago

10/10 Excellent

"Amazing location and great place to stay! The only negative is that you hear a lot throughout the building, with thin walls. That didn’t bother us and realistically you won’t be spending that much time in the room, but something to note if it’s something that would annoy you. Bed was super comfy, kitchen was well equipped and it was easy to store luggage after checkout. Definitely recommend!"

The Neighborhood Hotel-Little Italy

10/10 Excellent

"The location offered great proximity to restaurants, green space, smaller exceptional museums like Public Housing History and National Museum of Mexican Art. Easy to get to downtown via the Pink line Polk station. Hotel advised the Blue Line Halsted station. It’s a pleasant walk thru the UIC campus but it’s about a mile vs 10 minutes to Polk. We would definitely stay again."

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Our top choices for West Side vacation rentals

1. 2BR Apt with 2 Baths & Laundry

2. Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6

3. Cozy Boho - 10 Minutes to Downtown Chicago + Arcades

4. 3BR Complete and Spacious Apartment in Ideal Spot

5. Flexhome Ukrainian Village • 2BR • Convenient Walkability · Sleeps 6

6. Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony

7. Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6

8. Flexhome East Village • Modern 2BR • Quiet Street

9. Convenient 2BR Apt w/ In-Unit Laundry

10. Pilsen Sweet Life Up High

11. The Banksy-Greystone Rooftop Firepit United Center

12. Skyline View Apt - 5 minutes to Downtown - Games + Arcades - Free Parking

13. Flexhome Wicker Park • Stylish 2BR • Sleeps 6

14. West Town 2BR | Full Kitchen + In-Unit Laundry

15. Modern Comfort: 1BR Unit w/ Laundry

16. Ukrainian Village 3BR/3BA • Private Patio, Parking

17. LIVN West Loop Chicago Queen Superior Studio

18. Modern West Loop Gem-City Views & Prime Location 4

19. Private Apartment in Fulton Market

20. Newly Remodeled Gem | Heart of Chicago

Find vacation rentals that suit your style

Top West Side Hotel Reviews

Hyatt House Chicago/West Loop-Fulton Market

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