Vacation rentals in West Loop, Chicago

Guesthouse in Little Italy

A spacious living area features a comfortable black leather sofa and a distinctive black chair. Natural light filters through large windows, illuminating the mid-century cabinetry and vibrant area rug. Light-colored curtains frame the windows, and a circular coffee table sits at the center.

4.99 out of 5 average rating, 858 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.

Superhost

The exterior of the building features a multi-level deck with wooden stairs leading to the upper levels. A secure black metal fence encloses a private garden area, showcasing colorful outdoor chairs and a small table, inviting relaxation in a shared space.

4.85 out of 5 average rating, 405 reviews

Explore the City from an Elegant, Urban Retreat

- Queen Size bed in the private bedroom for two guests. - Sofa Bed with Full Size mattress for the 3rd and 4th guests (light weight and easy to setup). - Additional portable twin size cot can be set up per request. - Private Bathroom has a ceiling speaker and night light. - Living Room has an HD cinema projector with 100" screen. - A private garden with a gas grill and patio dining table/chairs. - Entry gate and door are Keyless/ Secured Key-coded. - Attached Private Parking space is available per request (subject to availability). - Easy Street Parking: Street parking is zoned (Chicago Residential Zone Parking) and we provide daily zone permits for parking on the street in front of the apartment. - Garden Space offers gas grill for Summer/Fall cookout (Share with two other apartments in the building). Text or phone call for quick reply The apartment is near the popular West Loop and West Town neighborhoods and close to public transit. Downtown parks, museums, and shops are less than two miles away. There's a Divvy Bikes station and a Starbucks across the street. Short walk to public transit ("L", bus, or Divvy bikes) 1 min drive to I-90/94. Less than 2 miles to downtown parks, museums, and shopping destinations. Less than 10 min drive to Lincoln Park, Old Town, and 5 min drive to Wicker Park, and Bucktown.

The studio apartment features an open layout with exposed brick walls and modern furnishings. A cozy sleeping area is shown, alongside a living space with a television. A small dining table with three stools is positioned near the kitchen area, which includes stainless steel appliances.

4.98 out of 5 average rating, 105 reviews

Cozy Studio in Perfect Location

Recently remodeled English garden studio apartment in the perfect location! Exposed brick with skylights added to this lower level apartment in a great neighborhood! Steps away from the CTA Blue Line train in an area featuring great cafes, bars and restaurants! The apartment was recently renovated and the bed is a Bob-O-Pedic memory foam mattress. If you're coming to Chicago for concerts, sporting events, restaurants, museums or other cultural activities, this location is ideal and pretty chill!

Superhost

An ivy-covered brick facade presents a charming entrance. A black door with decorative window details is centered, flanked by a small garden featuring well-maintained greenery. A gravel pathway leads to the entrance, showcasing the unique character of the historic coach house.

Guesthouse in West Loop

4.86 out of 5 average rating, 434 reviews

Pro Cleaned & Isolated West Loop Coach House

Mimi & Paul's historic ivy-covered two-level coach house has a private entrance and an airy queen bedroom. The renovated kitchen is outfitted with European-sized appliances, though you'll probably have no time to cook since you're surrounded by the best restaurants Chicago has to offer. All of the essentials are provided to make your stay easy and comfortable...paper products, soaps, shampoo/conditioner/body wash, towels, linens and even coffee/tea! (See layout in "Other Details To Note" below)

A private balcony features minimalist outdoor furniture, including a two-seater sofa and armchairs arranged around a glass-top coffee table. Natural wood fencing provides privacy, while the view extends to tree-lined streets below.

4.97 out of 5 average rating, 173 reviews

Great Location & Bright 2BR+2BA | Mapletree Suites

Welcome to Mapletree Suites! Our stylish, clean, and contemporary 2 bed+2 bath suites are located in a boutique building in Chicago’s booming West Loop neighborhood. Keyless entry, blazing fast WiFi, bright white linens, in-unit laundry, 10ft ceilings, balconies, Italian cafe, host on-site, plus much more! Steps from Target store, parks/athletic field, CTA, and close to United Center, world-class restaurants, loop/lakefront, Med District, UIC, corporate offices and highway network. Book today!

Apartment in Humboldt Park

A spacious living area is highlighted by sloped ceilings and wooden beams. A comfortable sectional sofa and a coffee table are nestled on a well-kept area rug. A television is positioned against the wall, while natural light filters in through two skylights.

4.99 out of 5 average rating, 138 reviews

Humboldt Park Loft

Bright and spacious loft style 1 bedroom/1 bathroom apt in the Humboldt Park neighborhood of Chicago. Renovated A-frame large attic space on the second floor of our house. Private apartment with open lay-out plan, full kitchen, and lots of natural light. Close to Logan Square and Wicker Park neighborhoods. Walking distance to Humboldt Park and the 606 trail. Two blocks to Kimball/Homan and North Ave buses. Quiet residential street with free and easy street parking. Smoke and pet free space.

Apartment in Noble Square

A modern kitchen features wooden cabinetry and a black refrigerator. A granite countertop is combined with a small dining area, equipped with a chair. The space has tile flooring, and a framed artwork is displayed above the countertop, adding a touch of style.

4.97 out of 5 average rating, 535 reviews

Fully Furnished Apartment Wicker Park Free Parking

Hello and welcome to all seeking a comfortable and convenient place to stay in Chicago! Please enjoy your time away from home in our fully furnished apartment located in the trendy neighborhood of Wicker Park! Please view the list below of all the wonderful amenities we offer to every guest staying out apartment. Again if you have any questions or comments please do not hesitate to ask. I look forward to seeing you and having your apartment ready soon! Thank you! One night available

4.98 out of 5 average rating, 356 reviews

The exterior of a historic brick building is framed by lush green trees and plants. A decorative wrought-iron gate leads to a set of stairs, which rise to a large wooden front door. Sunlight filters through the foliage, creating a serene entrance.

Home in West Loop

Cozy garden apartment historic Jackson Bvld.

Just a short walk to the United Center our cozy 1 bdrm garden apt is located on Historic Jackson Blvd's tree lined st. Stop back & warm up by the fireplace before heading out to near by shopping & restaurants. Less than an hour from Midway or O'Hare. Walking distance to Randolph St. Restaurant Row, Little Italy, Greek Town, Union Pk, Fulton Warehouse Dist, Rush Hospital and UIC. A quick train/bus to The Loop, Theater Dist, Mag Mile, Wicker Pk. Free, convenient street pkg.

4.96 out of 5 average rating, 230 reviews

The kitchen features a modern design with a spacious island surrounded by stylish bar stools. Exposed brick walls provide a warm contrast to the sleek cabinetry. A spiral staircase is visible, leading to the upper levels, while large windows allow natural light to brighten the space.

Condo in West Loop

Updated Designer Duplex In Fulton Market W/parking

We completed our luxury renovation in kitchen, bathrooms, and patio with a fire pit! We hope you enjoy! The first thing you notice stepping into my house are the sky-high ceilings! Enormous floor to ceiling windows allow light to stream into the the 2 floor home. The stylish and very large terrace are great for summer nights. Walk out the front door & you are in the heart of restaurant row with all the best bars and restaurant in the city. Parking included!

A modern apartment building is shown, characterized by a sleek glass facade reflecting the sunlight. Nearby structures vary in height and design, featuring a mix of blue-tinted glass and bold graphic elements along the lower level, suggesting an urban environment.

4.93 out of 5 average rating, 120 reviews

Spacious Downtown 3BR with Free Parking

A beautiful, modern, three bedroom two bath apartment located in the heart of Fulton Market in downtown Chicago. You'll have the whole space to yourself with easy access to some of the best restaurants in the city, a free parking space on premise, and nearby access to public transportation to quickly get around the city. The interior is recently renovated with new furnishings, and provides a beautiful space to relax and recharge between outings.

Guest suite in River West

A well-lit hallway showcases exposed brick walls and polished wood flooring. A cozy seating area includes a spacious bed draped with a blanket, accompanied by a side table and lamp. A large television is mounted on the wall, while barn doors lead to another room.

4.91 out of 5 average rating, 120 reviews

The Huron Haven

A beautiful, one-of-a-kind, hidden gem in the heart of River West. Private entry. Front & Back Patios. Full office space. Large Living Room. Exposed brick walls, 11.5’ tall ceilings. Large barn doors lead from the living room / office to a large master bedroom with large modern bathroom. The bedroom has French doors which open to private balcony with a beautiful back patio, dining space, and thriving garden. On Property Parking

4.99 out of 5 average rating, 243 reviews

Beautiful and spacious West Loop apartment.

This sunny & spacious 2bd / 2ba is the perfect getaway in the epicenter of the bustling Fulton Market neighborhood. Find Chicago’s most eclectic restaurant scene steps from your apartment. Explore the many coffee houses, shops, and galleries the West Loop has to offer. Downtown and Millennium Park are a short "El" ride away. Complimentary assorted coffee, fluffy towels and a beautiful deck await!

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Popular amenities for West Loop, Chicago vacation rentals

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Stay near West Loop, Chicago's top sights

United Center50 locals recommend

Millennium Park213 locals recommend

Magnificent Mile104 locals recommend

Other great vacation rentals in West Loop, Chicago

4.6 out of 5 average rating, 15 reviews

Modern 1BR in Prime West Loop Location

RossRating, 5 stars1 week ago

We had an incredible stay in Chicago’s West Loop last week! The place was spotlessly clean and perfectly located, just steps away from fantastic restaurants, bars, and the vibrant heart of the West Loop. The digital keypad on the door made getting in and out incredibly easy, and the building felt very safe. The host was exceptional—clear instructions, always reachable, and stayed in touch throughout our trip to ensure everything went smoothly. Highly recommend this spot for anyone visiting Chicago!

An outdoor deck is furnished with a table and four light gray chairs. Soft cushions are placed on two chairs, and a potted plant sits at the center. The space is surrounded by wooden railings, with nearby buildings visible in the background.

5 out of 5 average rating, 27 reviews

Here on Huron—spacious classic Chicago 2flat

KatieRating, 5 stars3 weeks ago

We loved our stay at Jon's place! The apartment was clean and comfortable & the balcony was an added bonus! The location is awesome - I have visited Chicago many times and this was probably my favorite airbnb that I've stayed in because of access to some of the best restaurants in the city. It's a really charming neighborhood and walkable to tons of restaurants, bakeries, and vintage shops. Jon was an awesome host, I would definitely stay here again!

A compact laundry area features a stacked washer and dryer in white. Shelves above hold a container of laundry detergent. The space is enclosed by a door, ensuring a neat and organized appearance.

Apartment in Chicago

4.8 out of 5 average rating, 319 reviews

Sophisticated River West 2 Bedroom - Near the L

GregRating, 5 stars2 weeks ago

Beautiful place. Clean, modern, fully equipped. Roomy bathroom, to boot One block to the CTA (subway) and as an added bonus, that line (Blue) goes straight to O'Hare when it's time to leave! Bus stop right outside the door, too. Starbucks, 7-11, and Guinness brewery/restaurant (and local bars) within a couple of blocks. Overall, it is a great jumping off point for exploring Chicago as it is just outside the Loop area (one stop on the CTA). We would use this place again when coming to town!

Private room in South Loop

A spacious balcony features a black metal table surrounded by two red chairs and a small seating area. A grill is positioned against the wall, and patterned outdoor rugs cover the floor. Overhead, string lights enhance the inviting atmosphere.

5 out of 5 average rating, 119 reviews

Urban Oasis Pilsen - guest room in townhouse

LaceyRating, 5 stars2 weeks ago

I unfortunately had to cancel at the last minute - but Christianne and Patrick were still so incredibly thoughtful. They sent me the weather forecast in advance as a heads up for packing, and even some encouragement for getting through an emergency situation at home (despite the fact that I was doing them a total disservice with a last minute cancellation). I would look to stay with them again in the future as priority #1 if in Chicago! They clearly understand what it means to go above and beyond on the hospitality front!!

The exterior of a three-story building is framed by lush trees and greenery. The structure features a welcoming entrance with stairs leading up to the front door, partially obscured by foliage. The facade showcases a combination of siding and decorative elements, reflecting classic architectural details.

4.98 out of 5 average rating, 64 reviews

West Town 1-Bedroom Full Remodel

JessicaRating, 5 stars1 week ago

This spot was absolutely perfect for our trip! The blue line stop was an easy walk away, there were plenty of restaurants and coffee shops less than 5 minutes away, and even a walkable grocery store with a pharmacy. Ubers/Lyfts are also super easy. The space was spotlessly clean from top to bottom, check-in was seamless, and the hosts left a lovely little guidebook with local recommendations and helpful tips.

An entryway is presented, featuring a dark blue wall contrasted by a light-colored door with a large window. A small table is positioned to the left, and a rug lies beneath. A bathroom is visible through a doorway, displaying a white toilet against a light background.

Home in West Loop

4.93 out of 5 average rating, 40 reviews

Entire lofted space in West Town

NeilRating, 5 stars1 week ago

This was a great space all to ourselves. brought the family to the city to go to the museums and it was super comfortable and felt like our own space. Great location and not far from about anywhere you wanna go.

A view of historic skyscrapers along a river at dusk, with reflections of city lights shimmering on the water's surface. The image captures the iconic clock tower and ornate architectural details, surrounded by modern buildings and a bridge in the background.