Far Southwest Side Vacation Rentals from ￥32,060: Search Short-Term Rentals

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Our top choices for Far Southwest Side vacation rentals

Sentral Michigan Avenue

Downtown Chicago

Alessandra

￥32,060 total

includes taxes & fees

Aug 17 - Aug 18

Full-size fridge, microwave, oven, stovetop

Level Chicago – Old Town

Downtown Chicago

Serigne abdou

￥63,529 total

includes taxes & fees

Aug 13 - Aug 14

Wrigleyville Suites

Lakeview

Kate

￥32,777 total

includes taxes & fees

Jul 19 - Jul 20

1 bedroom, iron/ironing board, travel crib, WiFi

LIVN West Loop Chicago Queen Superior Studio

Downtown Chicago

Kyna C.

￥39,821 total

includes taxes & fees

Jul 19 - Jul 20

LIVN Millennium Park Downtown Chicago Prem Studio

Downtown Chicago

Raquel W.

￥44,611 total

includes taxes & fees

Jul 19 - Jul 20

Modern West Loop Gem-City Views & Prime Location 4

Downtown Chicago

Jiri N.

￥131,651 total

includes taxes & fees

Aug 9 - Aug 10

River North Rooftop With In and Out Parking 6

Downtown Chicago

Amy L.

￥88,373 total

includes taxes & fees

Aug 16 - Aug 17

W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade

Brighton Park

Damary T.

￥49,298 total

includes taxes & fees

Aug 10 - Aug 11

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Top Far Southwest Side Hotel Reviews

Hotel Riu Plaza Chicago

10/10 Excellent

"what a great location, and the rooftop bar was sensational. Service was friendly and solid, breakfast was enough to last you till dinner, and the rooms (especially the showers) were great."

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent

"This was a great place to stay for a quick weekend trip. This was convenient to get to off the interstate and was so convenient to walk to all the shops along magnificent mile. Raymond was such a bright welcoming and the two valet drivers were great as well. They even let me keep my vehicle parked later than check out so we could explore some more of the city before we left town. I would stay here again. I wish we could have made it up to the rooftop bar but timing wasn’t our friend. Rooms were slightly outdated and I’ve stayed at places with softer sheets but I’m easy to please!"

The Allegro Royal Sonesta Hotel Chicago Loop

10/10 Excellent

"This property and staff was amazing! We planned a small event for my daughters marriage proposal in one of their lounges as well as stayed in one of the rooms. The staff was so appreciatively attentive to our needs to pull off the proposal as a secret. My family felt they went above and beyond when they attended to us during our small event. Because of a plane delay we were scrambling to get things set up, they recognized that and stepped right in to help wherever they could including bringing much needed refreshing glasses of water since we were hot, scrambling and parched. Three families including my husband and I stayed at the Allegro. This hotel is iconic, historic and absolutely beautiful. Our room offered everything we needed: was clean and the mattress was great. All staff from doorman to check-out was very kind and helpful, including the Allegro Lounge with great service and drinks. If we have opportunity to stay in Chicago again we will be staying here."

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Far Southwest Side Vacation Rentals

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Our top choices for Far Southwest Side vacation rentals

Sentral Michigan Avenue

Level Chicago – Old Town

Wrigleyville Suites

LIVN West Loop Chicago Queen Superior Studio

LIVN Millennium Park Downtown Chicago Prem Studio

Modern West Loop Gem-City Views & Prime Location 4

River North Rooftop With In and Out Parking 6

W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade

River North Rooftop With In and Out Parking 3

Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6

Downtown Chicago Stay with Free In & Out Parking 3

South Loop Rooftop With In & Out Parking 1

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

LIVN West Loop Chicago King Studio

LIVN West Loop Chicago Classic Queen Studio

LIVN Millennium Park Downtown Chicago 1 BR

LIVN Millennium Park Downtown Chicago Studio

LIVN West Loop Chicago 2 BR City View

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

Modern West Loop Gem-City Views & Prime Location 5

Find vacation rentals that suit your style

Top Far Southwest Side Hotel Reviews

Hotel Riu Plaza Chicago

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The Comfy King RanchKing Bed Suite*Fast Wi-Fi