West Side Holiday Rentals - Holiday Homes in West Side

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Our top choices for West Side vacation rentals

1. River West, Second Floor Chicago by 747 Lofts

West Town

Anonymous traveler

P20,017 total

includes taxes & fees

Aug 14 - Aug 15

2. Ground Floor Studios in Chicago by 747 Lofts

West Town

P15,281 total

includes taxes & fees

Aug 12 - Aug 13

3. River West, Third Floor Chicago by 747 Lofts

West Town

Caroline

P10,340 total

includes taxes & fees

Aug 12 - Aug 13

4. Chicago Second Floor Studio by 747 Lofts

West Town

adrian

P9,700 total

includes taxes & fees

Aug 12 - Aug 13

5. Sentral Michigan Avenue

Downtown Chicago

Michael

P13,180 total

includes taxes & fees

Aug 30 - Aug 31

Full-size fridge, microwave, oven, stovetop

6. Level Chicago – Old Town

Downtown Chicago

Martha

P18,349 total

includes taxes & fees

Sep 1 - Sep 2

7. Kasa Lake Shore Chicago

Downtown Chicago

Erica

P21,451 total

includes taxes & fees

Sep 7 - Sep 8

8. The Gem Museum Suites

Downtown Evanston

Nuriye

P10,802 total

includes taxes & fees

Aug 16 - Aug 17

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Top West Side Hotel Reviews

LIVN - West Loop Chicago

10/10 Excellent

"This was a very nice boutique experience . Would book again"

Hampton Inn & Suites Chicago Medical District UIC

10/10 Excellent

"This Hampton was well appointed, close enough to the action to park there and Uber pretty much anywhere fairly reasonably, with super friendly and helpful staff and very clean, modern, and well-appointed rooms. Loved that we could listen to Sirius XM on the TV! The choice of different pillows on each bed was appreciated, too; I am super picky about pillows and found one I liked even better than the one I had brought from home! The room and hotel were quiet, the only possibly distracting noise being the occasional siren, as it is located in the Medical District. Breakfast was plentiful with a good variety, including Western omelets and make-your-own waffles. And FREE breakfast at a hotel in Chicago is a rare find no matter what! I would definitely stay here again and recommend it to anyone who is looking for a great place to call Home Base while enjoying the Windy City!"

The Hoxton, Chicago

10/10 Excellent

"This property is IT! I traveled in for Lollapalooza, and had no idea I was in for such a treat with my hotel alone! The Hox is in the Fulton Market District which is perfect for my fellow foodies, and nightlifers. The hotel lobby features one of two restaurants on site- the bar being quite the local attraction in the evening, especially weekends! Make SURE you stop by the speakeasy in the basement for alllll the swanky vibes. It features a live band thurs-sat & has a way of stopping time. The local artwork on display throughout the hotel is quite mesmerizing, too! I highly recommend The Hoxton, could not be more fulfilled with my experience!"

Hyatt Place Chicago Medical/University District

10/10 Excellent

"We were late for an event but had to go the hotel first and the check-in clerk was so helpful in assisting us to get to our room fast so we could change and leave. The room was comfortable and quiet. The breakfast was delicious and lastly, the staff around the hotel was courteous and very polite!! I would definitely stay here again!!!"

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Check prices for these dates

Our top choices for West Side vacation rentals

1. River West, Second Floor Chicago by 747 Lofts

2. Ground Floor Studios in Chicago by 747 Lofts

3. River West, Third Floor Chicago by 747 Lofts