Holiday rentals in West Loop, Chicago

4.98 out of 5 average rating, 105 reviews

Flat in West Town

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!

4.95 out of 5 average rating, 95 reviews

Fulton House #1 - Studio Only (Nightly)

Unique & stylishly designed by Chicago's own Outline Interiors, this highly sought after location is for those that want to stay on a calm side street around the corner from city's best, award-winning restaurants and trendiest shopping. The fully-serviced studio has the business-travel amenities you want: ultra speed wifi, work station, top tier dining options within steps, Nespresso coffee maker, bottled water and more. Paid parking next door $20/day, subject to avail - inquire in advance.

5 out of 5 average rating, 13 reviews

Chicago Luxury Long Term 30+

Enjoy a stylish experience at this centrally-located place. This home is a lovely city terrace modern loft in a quiet nook of the Fulton Market / West Loop Area. Furnished beautifully for working from home or coming home. Very walkable with all of the best smart home features: digital light controls, Sony 65” TV, Sonos BEAM, smart lock, solid marble dining table with modern chairs, comfortable bed and pillows, and quality sheets for a great night sleep! Ultra high speed internet at 500mbps

4.97 out of 5 average rating, 227 reviews

Flat in Chicago

Comfy River West, Free Parking

Comfy, sunny 2 bedroom apt with free gated parking. Level 2 EV charging available for electric cars. Beautiful hardwood floors and high ceilings. Fully stocked kitchen with Coffee, tea and snacks. Both bedrooms have ceiling fans. Full length mirror in 1 bedroom and bath. Views of the property gardens and Willis Tower from both bedroom windows. Communal gardens, backyard has table and chairs, BBQ grill and bocce ball. An additional 2 bedroom apt in the same building may also be available.

4.97 out of 5 average rating, 535 reviews

Flat in Noble Square

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

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.

4.99 out of 5 average rating, 230 reviews

Flat in Chicago

Modern Apt with style & comfort in Pilsen Chicago

Enjoy a nicely updated studio in a safe, family-owned building located in Pilsen/Heart of Chicago conveniently located near Downtown, Chinatown, & Hyde Park to name a few. Public transportation is walking distance or you can go on a short drive to museums, parks, cafes, restaurants, bars, venues, and hip neighborhoods. Chicago has a full line up of festivals happening this year so feel confident in choosing my lovely space to be part of your experience.

5 out of 5 average rating, 33 reviews

Gym | Garage Parking | Balcony | Sleeps 6

Stunning 2 bedroom West Loop apartment with Private Balcony, Gym, 1 Garage Parking with 1 king bed and 2 full beds. Perfect for groups & families up to 6. You are a 5 min walk to Fulton Market, and a 12 min drive away from restaurants in downtown, Millennium Park, and 15 mins drive away from Navy Pier! This is the perfect place for tourists to immerse themselves in the central vibe of Chicago, and enjoy all the activities that West Loop has to offer.

Superhost

Apartment in River West

4.86 out of 5 average rating, 118 reviews

Cabin 308 at 747 Lofts

This studio apartment is in the perfect location in Chicago for getting to Downtown via the Blue Line L or to the Hot West Loop and Randolph street restaurant row. Walk to bars, shops, restaurants, coffee liquor stores and transportation with ease! You will love our spa baths, in unit laundry and full modern kitchens to make it feel like a home away from home. One of the best pizza spots in Chicago is only steps away!

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!

5 out of 5 average rating, 57 reviews

Apartment in West Town

Sun-Soaked West Loop Penthouse - Private Rooftop

This Sun Soaked West Loop Penthouse is the perfect home away from home. With it's expertly designed living areas and alluring outdoor spaces, there is nothing this unit doesn't have. It is equipped to be lived in full-time and is owner occupied and maintained as a primary residence for a portion of the year. NOTE: Photos are up-to-date as of 5/5/2024 www.westlooppenthouse. com

4.88 out of 5 average rating, 91 reviews

Flat in West Town

Garden on Warren

Near West Side / West Loop location, less than 10 minute walk to United Center for Chicago Blackhawks, Chicago Bulls, music, concerts, shows, and events. Close proximity to CTA Pink & Green lines, Union Park, Randolph & Fulton Street dining districts, University of Illinois at Chicago and Rush Medical District. Private entry, very secure and quiet apartment.

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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 holiday rentals in West Loop, Chicago

5 out of 5 average rating, 5 reviews

Stylish 1BR with Laundry In-unit - Aberdeen G

KirbyRating, 5 stars1 week ago

Great spot for a stay in Chicago! Apartment is large, with a full living/kitchen, two bathrooms, and a bedroom with a big closet. It is walkable to the Fulton Market area and the blue line train. Aberdeen Tap is a great spot right down the street! Nick was quick to communicate and there were no issues with check-in. Place was clean and it was a great stay. Would book again!

Superhost

Hotel room in West Loop

4.89 out of 5 average rating, 9 reviews

Art-inspired design and Malin+Goetz bath products

MikaylaRating, 5 stars3 months ago

Near everything we wanted to do in the west loop. Excellent personal care amenities. Lobby and bar have cool decor.

5 out of 5 average rating, 28 reviews

Flat in West Town

Here on Huron—spacious classic Chicago 2flat

TobiasRating, 5 stars1 week ago

The apartment was exactly as described – maybe even better! Everything was very clean and tastefully furnished. The location is fantastic: super central yet quiet, with direct access to the Blue Line and several bus routes – perfect for exploring the city. Host Jon was incredibly friendly, helpful, and always easy to reach. I felt welcome right away. Communication before and during the stay was smooth and uncomplicated. I would definitely stay here again – a great choice for anyone looking for a clean, well-located, and comfortable place to stay!

Private room in Little Italy

4.78 out of 5 average rating, 79 reviews

Beautiful Private Room 5 min to the City

IngridRating, 5 stars2 weeks ago

Super close to UIC, located in a quiet and safe neighborhood. It’s also not far from downtown Chicago. The apartment has five rooms, with a toilet on the first floor and a full bathroom on the second floor. It can get a bit crowded on weekends, which might make the bathrooms busier, but in my experience, they’ve remained clean despite being shared. That said, cleanliness may vary depending on the tenants. Also, the walls are a bit thin, so noise from the first floor can sometimes be heard upstairs. However, people generally keep quiet after 11 p.m.

Private room in South Loop

5 out of 5 average rating, 120 reviews

Urban Oasis Pilsen - guest room in townhouse

GretchenRating, 5 stars2 days ago

My friend and I enjoyed staying with them. They are a very nice couple. Very helpful. We would definitely recommend staying there to anyone in the future.

Private room in West Town

4.94 out of 5 average rating, 34 reviews

Stylish Condo BR w/Skyline Views – Walk Score 95

StevensonRating, 5 stars2 weeks ago

Tejal was extremely responsive, sweet, and hospitable! She was always available for questions and even recommendations! Her place was very clean and lovely to stay in!

4.89 out of 5 average rating, 27 reviews

1 Bedroom unit in Heart of Downtown| Skyline view

KathleenRating, 5 stars1 month ago

Good things: Host always responded quickly, fabulous view, very sunny, gorgeous sunsets, comfortable place, easy walks to the riverwalk and Fulton market, grocery store very close. just a fun, active place to be! Challenges: a bad smell randomly came up from the kitchen sink and maintenance could not fix it, so we burned candles; no a/c available bc it gets turned on (switched over from heat) when the whole building switches it which made it quite warm some days in April; only had one key for the two of us which made it hard to split up and do different things; saw 1 cockroach, but pest control took care of it immediately and there were never anymore, and we stayed there 1 month!...just being honest here because some of the 5 star reviews are not completely honest. We would stay here again, despite the challenges!