Search Vacation Homes in West Side

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Vacation Homes in West Side

Stylish 1BR in West Loop

10.0 out of 10, Exceptional, (4)
"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"
The price is ¥16,050
¥32,742 total
includes taxes & fees
Aug 18 - Aug 19
Stylish 1BR in West Loop

Sun-Drenched 1BR Apartment

The price is ¥17,376
¥35,207 total
includes taxes & fees
Aug 25 - Aug 26
Sun-Drenched 1BR Apartment

NEW Private West Loop 1br with Backyard near Green Line and CTA

9.0 out of 10, Wonderful, (2)
"The apartment was clean and the host was very responsive and helpful. "
The price is ¥9,913
¥36,215 total
includes taxes & fees
Aug 21 - Aug 22
NEW Private West Loop 1br with Backyard near Green Line and CTA

3BR Complete and Spacious Apt

10.0 out of 10, Exceptional, (2)
"Spacious and well appointed. Great location with plenty of eating/drinking options within walking distance. "
The price is ¥17,228
¥40,538 total
includes taxes & fees
Aug 25 - Aug 26
3BR Complete and Spacious Apt

Modern 3 BR Apt - 5 Mins to Downtown Sleeps 10

The price is ¥16,787
¥46,210 total
includes taxes & fees
Sep 2 - Sep 3
Modern 3 BR Apt - 5 Mins to Downtown Sleeps 10

Urban Comfort • 2BR in West Town

10.0 out of 10, Exceptional, (2)
"Very clean. Host was exceptionally communicative. Would stay again!"
The price is ¥16,198
¥35,850 total
includes taxes & fees
Sep 2 - Sep 3
Urban Comfort • 2BR in West Town

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

2.0 star property
10.0 out of 10, Exceptional, (7)
"Very clean in a safe neighborhood. I would stay here again"
The price is ¥21,071
¥29,868 total
includes taxes & fees
Aug 28 - Aug 29
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.

Charming 1-bedroom townhome with WiFi, AC in enjoyable Thornton

8.6 out of 10, Excellent, (4)
"Was a good stay, my only suggestions are that the a/c be turned on for guests checking in that day, at least on low. It was so hot our first night that we couldn't sleep comfortably, 2nd provide full size bath towels. Only saw hand towels in the bath room, so we used the full size bath towels I had with me. Otherwise it was a pleasant stay."
The price is ¥18,406
¥25,992 total
includes taxes & fees
Aug 23 - Aug 24
Charming 1-bedroom townhome with WiFi, AC in enjoyable Thornton

Nice cozy home to experience on your vacation

The price is ¥106,020
¥219,595 total
includes taxes & fees
Aug 15 - Aug 16
Nice cozy home to experience on your vacation

2 Connecting Suites at a 4⭐️ Hotel

The price is ¥80,178
¥108,300 total
includes taxes & fees
Sep 2 - Sep 3
2 Connecting Suites at a 4⭐️ Hotel

Brand New Modern Bedroom with AC, TV & WiFi in Chicago Near Wind Creek Casino

The price is ¥18,995
¥25,992 total
includes taxes & fees
Aug 26 - Aug 27
Brand New Modern Bedroom with AC, TV & WiFi in Chicago Near Wind Creek Casino

Brand New Modern Beautiful Room in Chicago, with WiFi, AC and TV.

The price is ¥19,732
¥26,623 total
includes taxes & fees
Aug 21 - Aug 22
Brand New Modern Beautiful Room in Chicago, with WiFi, AC and TV.

2 Connecting Suites at a 5⭐️ Hotel

The price is ¥392,301
¥526,518 total
includes taxes & fees
Sep 1 - Sep 2
2 Connecting Suites at a 5⭐️ Hotel

“The Marlowe” A Couples Getaway

10.0 out of 10, Exceptional, (1)
"Loved everything communication was good definitely a vibe will be booking again "
The price is ¥51,538
¥68,168 total
includes taxes & fees
Aug 17 - Aug 18
“The Marlowe” A Couples Getaway

Cozy Room with Rooftop Lounge & City Views in River North

10.0 out of 10, Exceptional, (1)
"The hotel was very nice and the location was excellent. Was able to walk to many locations. Noise wasn't bad for a city experience. Hotel restaurant was very good."
The price is ¥25,445
¥37,510 total
includes taxes & fees
Sep 1 - Sep 2
Cozy Room with Rooftop Lounge & City Views in River North

Luxury Unit with Rooftop Lounge & Spectacular City Views

The price is ¥21,557
¥32,399 total
includes taxes & fees
Aug 17 - Aug 18
Luxury Unit with Rooftop Lounge & Spectacular City Views

Spacious Room with Rooftop Lounge & Scenic Views of Chicago

The price is ¥26,741
¥39,395 total
includes taxes & fees
Aug 17 - Aug 18
Spacious Room with Rooftop Lounge & Scenic Views of Chicago

Modern Suite with Rooftop Lounge & Views of Downtown Chicago

The price is ¥30,510
¥44,725 total
includes taxes & fees
Aug 17 - Aug 18
Modern Suite with Rooftop Lounge & Views of Downtown Chicago

2 Spacious King Room with Rooftop Lounge & Scenic Views of Chicago

The price is ¥43,115
¥65,163 total
includes taxes & fees
Aug 17 - Aug 18
2 Spacious King Room with Rooftop Lounge & Scenic Views of Chicago

2 Suites with Rooftop Lounge & Beautiful Views of Chicago Skyline

The price is ¥53,363
¥79,011 total
includes taxes & fees
Aug 17 - Aug 18
2 Suites with Rooftop Lounge & Beautiful Views of Chicago Skyline
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top West Side Hotel Reviews