Holiday rentals in West Loop, Chicago

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Top-rated holiday rentals in West Loop, Chicago

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Guest favourite

Guest house in Little Italy

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.

11–18 Dec

₹10,733 per night
Superhost

Flat in West Town

4.92 out of 5 average rating, 324 reviews

Bright, Modern Apartment in a Vintage Greystone

Enjoy morning coffee by the sunny bay window in this vintage apartment with classic modern style. The apartment features vintage charm with modern amenities, queen memory foam bed in bedroom and queen sofa bed in living room. Parking is available in the back lot for an additional $25 per night. For reservations over three weeks, we require a cleaning every 2 weeks at a cost of $60 per cleaning. Apartment is located on the 3rd floor of a three story building and you will need to climb stairs. This is a large 1100 square foot fully renovated 1 bedroom apartment on the third floor of a beautiful vintage Chicago Grey Stone. Located directly on Chicago Ave. The space was thoughtfully designed by the design firm of Inside Home with the modern traveler in mind. The furnishings are a mix of vintage and new pieces specially curated for the space. The bedroom features a queen memory foam mattress as well as a 42" TV. The kitchen is equipped with cutlery, cooking utensils, coffee maker, espresso machine, pots & pans, baking sheets. Walking Rating of 96! You will have access to the full 1100 square foot apartment as well as a parking spot if needed located directly out back for an additional $20 per night, please notify us at the time of booking if you will require parking and we will add this fee to your reservation. There is also a washer and dryer in the basement if need (please request access) We will be on site at the furniture store located on the ground floor of the building should you need anything during your stay. Ukrainian Village is a historic community known for the contemporary restaurants, bars, and shops along bustling Chicago and Division Streets, but explore the neighborhood further to discover homes and businesses as old as the city itself. You are steps away from the 66 bus, which will take you directly to Navy Pier, rent a bike and explore the city or catch a cab right out side the front door or jump on the blue line "EL" train. This apartment has a walk rating of 96, bike rating of 90 and a transit rating of 72! This apartment is located on the third floor of a three story walk up. There is a additional queen bed in the sofa of the main room and all the additional bed linens are located in the bedroom night stand and closet.

27 Oct – 3 Nov

₹13,680 per night
Superhost

Apartment in West Town

4.87 out of 5 average rating, 433 reviews

Humboldt Park Traveler's Lodge

Come stay at my gorgeous condo! Featuring exposed brick, a private entrance, stainless steel appliances, and a queen bed --> all on a quiet tree lined street! It's a perfect place to re-energize between big city adventures. Free street parking, and a 5 min walk to some of the best independently owned shops, restaurants, and bars in the city. Also, the massive and incredible Humboldt Park is also just a 5 min walk away! Please reach out for recommendations - I love giving them to people!

5–12 Apr

₹7,693 per night

Popular amenities for West Loop, Chicago holiday rentals

Stay near West Loop, Chicago's top sights

Chicago Union Station82 locals recommend
Greek Islands50 locals recommend
Union Park29 locals recommend
wndr museum22 locals recommend
Lyric Opera of Chicago44 locals recommend
Soho House Chicago53 locals recommend

Other great holiday rentals in West Loop, Chicago

Superhost

Apartment in West Loop

4.81 out of 5 average rating, 111 reviews

West Loop is the Best Loop 3Bed Condo

24–31 Dec

₹28,323 per night
Guest favourite

Flat in Wicker Park

4.97 out of 5 average rating, 235 reviews

Stylish First Flr. Studio. Best Location Division+Hermitage.

21–28 Mar

₹13,689 per night
Superhost

Flat in Irving Park

4.92 out of 5 average rating, 584 reviews

Explore Chicago from an Urban Sanctuary with Free Parking

17–24 Apr

₹10,954 per night
Guest favourite

Flat in West Loop

4.92 out of 5 average rating, 206 reviews

✨Spacious Centrally Located West Loop Loft✨

10–17 Nov

₹16,520 per night
Guest favourite

Flat in West Town

4.9 out of 5 average rating, 116 reviews

Spacious & New Modern-Chic Condo Close to Downtown

6–13 Dec

₹15,489 per night
Guest favourite

Home in West Town

4.95 out of 5 average rating, 166 reviews

Paradise on the Park

17–24 Aug

₹15,383 per night
Guest favourite

Guest suite in West Loop

4.95 out of 5 average rating, 76 reviews

Cozy one-bedroom suite in the heart of West Loop

10–17 Dec

₹11,691 per night
Superhost

Flat in West Town

4.96 out of 5 average rating, 28 reviews

The Secret West Loop Oasis/walk to Fulton market

19–26 Jan

₹8,509 per night
Guest favourite

Flat in West Town

5.0 out of 5 average rating, 32 reviews

Cozy Studio in Perfect Location

22 Feb – 1 Mar

₹12,123 per night
Guest favourite

Flat in West Loop

4.96 out of 5 average rating, 28 reviews

Fulton House #1 - Studio Only

19–24 Apr

₹16,583 per night
Guest favourite

Guest suite in West Town

4.92 out of 5 average rating, 39 reviews

Renovated basement studio w/ independent entrance

21–28 Oct

₹10,828 per night
Guest favourite

Flat in West Loop

4.94 out of 5 average rating, 32 reviews

West Loop Oasis: Roomy 1BR Unit w/ In-Unit Laundry

5–12 Dec

₹14,499 per night

Quick stats about holiday rentals in West Loop, Chicago

Total rentals

500 properties

Rentals with dedicated workspaces

320 properties have a dedicated workspace

Rentals with a pool

270 properties have a pool

Pet-friendly rentals

290 properties allow pets

Family-friendly rentals

200 properties are a good fit for families

Total number of reviews

13T reviews

Destinations to explore

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Chicago
  6. West Loop