Vacation rentals in West Side

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Top-rated vacation rentals in West Side

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Guest favorite

Guesthouse in Chicago

4.99 out of 5 average rating, 776 reviews

Polk Street Coach House Apartment, Little Italy/Medical Dist

Cook in a kitchen with everything from a KitchenAir convection range and Kitchen Aid food processor to Calphalon pots and pans. The mid-century look includes a comfy American Leather sofa, Gansgo Mobler dining table, and Frem Rolje teak chairs. Welcome to Polk Street Guest House: a well-appointed, completely private, 2-bedroom carriage house in Little Italy near the Medical District. Decorated with mid-century antiques and paintings, our 2nd floor coach house apartment is perfect for guests looking for a home-away-from-home. It has a fully-equipped kitchen, teak furnishings, comfortable queen size beds, and a private entrance accessible though a side gate from the street. For folks with kids, please note there is no child gate near the top of the stairs. Enjoy quiet parks and have easy access to all of Chicago. Major hospitals at Rush, University of Illinois, Hines, VA and Stroger are within 3 to 6 blocks. Chicago's elevated pink line train is 2 blocks away; the Blue line is 3 blocks. Take a quick cab ride to “the loop" downtown for $10, or take a Divvy bike. Chicago's famed Little Italy restaurants on Taylor Street are a block South. Free street parking with 24-hour zoned pass. Your hosts: Ken & Curt Want privacy? You have privacy! Use an entry code to access the coach house through the side gate to the left of our main house. Your private entrance, which also has keypad entry, is on the left side of the vine-covered brick building in back. The main living area is upstairs. There will be a 24-hour zoned parking pass waiting for you on a shelf as you enter the Coach with instructions on how to fill out the parking pass. We regret that the Coach House is not ADA/wheelchair accessible. For those arriving early than check-in, or who are staying later than check-out, we have an area beneath the coach house where you may leave your luggage. Just ask. Our space is your space. The coach house is entirely separate from our main house where we live. The coach house has a separate entrance and full amenities. You’re welcome to use the seating area in the courtyard, and the Weber grill. We're happy to provide any tips about the city, or to help show you how to use anything in the apartment. Just call our cell phones (they are listed in the apartment), or step across the yard and say hello. Three blocks to the Medical District and major hospitals, walk from this tree-lined Little Italy neighborhood to restaurants of all kinds. Host recommendations include Rosebud for classic Italian, and Indian cuisine on Taylor Street. Stroll in Garibaldi Park on the doorstep, with Arrigo Park a block away. We are conveniently located for transit, bike, car and Uber. Public Transportation: -Pink Line, Polk Station, CTA: 3 blocks west of us, this rail line gets you downtown in 10 minutes (plan 30 minutes total time with walking for most destinations) and is useful for most site-seeing. -Blue Line, Racine Station, CTA: 4 blocks east or west of us, this rail line gets you to O'Hare airport in less than an hour, or downtown in about 10 minutes (it's a bit longer walk to the Blue Line than to the Pink Line) . -#157 Bus (Streeterville): This super convenient bus 1 block south of us on Taylor Street runs during the daytime only and takes you to the Magnificent Mile for upscale shopping on North Michigan Avenue in 25 minutes. -#12 Bus (Roosevelt): This is about 3-4 blocks south of us, runs east-west, and takes you to the Soldier Field stadium and the Roosevelt Road shopping area with Whole Foods, Nordstrom Rack, Best Buy, Core Power Yoga, and much more. Bicycle: You bike? We bike. There is a DIVVY bike share station a block east in Arrigo Park. Get at DIVVY bike-share 24-hour pass with unlimited half-hour rides. Switch out bikes for longer distances. If you have your own bike, you can park it safely on the ground floor of your coach house apartment. It takes 15 to 20 minutes to bike to most downtown locations. Car: Our home is 3 blocks south of I-290 (the Eisenhower), and near I-55 (the Stevenson), I-90 and I-94 (the Dan Ryan and Kennedy). Parking: We provide parking passes for free zoned street parking available on a small shelf as you enter the Coach House along with instructions. Please be very careful about filling out the pass, as City workers seem motivated to issue tickets if the pass is not filled out correctly. We travel a lot and know what it's like to be away from home. That's why we've furnished the apartment with appealing furniture, comfortable beds, plenty of towels (and more towels), soaps, shampoos, and a kitchen outfitted with all the basics plus a few more: Kitchen Aid food processor, toaster, microwave, baking and cooking tools, Calphalon pots & pans. Please note there is no dishwasher. Enjoy complimentary Nespresso coffee, Bigelow teas, bottle water, and snacks. Three blocks to the Medical District. Walk the tree-lined streets of the Little Italy to restaurants of all kinds. Host recommendations include Rosebud for classic Italian, and Asian cuisine on Taylor Street. Stroll in Garibaldi Park steps away, or Arrigo Park a block away.

Dec 11 – 18

$111 per night
Guest favorite

Condo in Chicago

4.83 out of 5 average rating, 296 reviews

Peaceful & Airy Modern-Chic Condo in Trendy Pilsen

Brand New Private Modern 2 bd 2bth apt for your stay in Chicago. We are located 2 blocks form the CTA line in the heart of Pilsen, a neighborhood Time Out labeled the 10th coolest in the world. Newly renovated, hardwood tiled floors throughout, chefs kitchen, toiletries, brand new furnishings including 2 queen beds, 1 twin sleeper, fresh linen, smart TV (HBO, Netflix, Hulu) wifi, tons of books,coloring books,board games & puzzles! We truly want you to feel like this is your home away from home.

Feb 3 – 10

$107 per night
Superhost

Apartment in Oak Park

4.84 out of 5 average rating, 482 reviews

Sunny Jumbo Studio NO cleaning fee!

Bright and sunny Oak Park jumbo garden studio, steps from cute downtown, train to Chicago, and amazing local tourist destinations- like the Hemingway Home and the Wright Studio. This welcoming studio was completely rehabbed and updated. We put a lot of care into designing a relaxing apartment with all the amenities. The main room features a king-sized bed, office nook, and fully stocked entertainment area, with games, books, and a TV. The spacious kitchen and luxurious bathroom are brand new!

Dec 31 – Jan 7

$110 per night

Popular amenities for West Side vacation rentals

Other great vacation rentals in West Side

Superhost

Condo in Chicago

4.88 out of 5 average rating, 104 reviews

Spacious Duplex in Great Location

Sep 6 – 13

$116 per night
Guest favorite

Guest suite in Chicago

4.93 out of 5 average rating, 111 reviews

Entirely Private Suite - Urban Oasis - Pilsen/UIC

Jun 18 – 25

$97 per night
Guest favorite

Apartment in Berwyn

4.86 out of 5 average rating, 132 reviews

The Green Bungalow: Charming 1-BR apt. with patio

Jul 9 – 16

$84 per night
Superhost

Apartment in Chicago

4.92 out of 5 average rating, 584 reviews

Explore Chicago from an Urban Sanctuary with Free Parking

Apr 17 – 24

$109 per night
Guest favorite

Home in Chicago

4.97 out of 5 average rating, 316 reviews

Cozy garden apartment historic Jackson Bvld.

Dec 20 – 25

$157 per night
Superhost

Apartment in Oak Park

4.85 out of 5 average rating, 216 reviews

Cozy and Character-Rich Chicago Style, Tv NFL PASS

Jul 23 – 30

$89 per night
Superhost

Apartment in Chicago

4.91 out of 5 average rating, 22 reviews

15min/Loop, PilsenTreasure, Sunny1BR Apt w/Parking

Aug 28 – Sep 4

$112 per night
Guest favorite

Apartment in Chicago

4.87 out of 5 average rating, 52 reviews

Bright & Cozy 1-Bedroom Apartment in Logan Square

Nov 21 – 28

$84 per night
Guest favorite

Guesthouse in Oak Park

4.99 out of 5 average rating, 70 reviews

Stylish Coachhouse in lovely Oak Park!

Nov 7 – 14

$115 per night
Guest favorite

Home in Chicago

4.87 out of 5 average rating, 68 reviews

Live Like a Local + Roomy home by Mexican Museum

Apr 4 – 11

$54 per night
Superhost

Apartment in South Lawndale

4.81 out of 5 average rating, 48 reviews

Cozy Little Village Studio

Feb 3 – 10

$77 per night
Guest favorite

Home in Chicago

4.88 out of 5 average rating, 32 reviews

Brand New Spacious Duplex

Sep 4 – 11

$146 per night

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