Condo vacation rentals in West Loop, Chicago

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Top-rated condo rentals in West Loop, Chicago

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Guest favourite

Condo in Chicago

4.86 out of 5 average rating, 334 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.

Guest favourite

Condo in West Town

4.88 out of 5 average rating, 252 reviews

2 King Bed Condo Easy Downtown Free Street Parking

Welcome to your private home away from home in Ukrainian Village, a Top 10 neighborhood in the nation! Our super comfy 2 King Serta pillowtop mattress in the garden (lower) level condominium with everything you need during your stay and more. We have been told over & over the photos do not do this place justice. Walk to a wide variety of award winning restaurants, hip shopping/coffee shops, grocery, public transport, bars and more! A quiet neighborhood with quick access to all Chicago offers!

Superhost

Condo in West Town

4.86 out of 5 average rating, 212 reviews

Bold Ukrainian Village 2 Bedroom w/Garage Parking

Our bright Ukrainian Village apartment is on a quiet, tree-lined street, but near some of the most exciting restaurants, bars, and vintage shops in the city, and only a mile north of the United Center - it's the best of all worlds! The layout is equally ideal for friends traveling together as it is families, as well as work from home life. We've got a backyard and patio for you to share, we're walking distance to Wicker Park, and close to plenty of CTA options that'll get you down to the Loop.

Superhost

Condo in Near West Side

4.85 out of 5 average rating, 115 reviews

Tri-Taylor/Medical Dist. near West Loop

Enjoy this stylish Newly Rehabbed condo equipped with 3 bedrooms and 2 bathrooms. Modern kitchen with stainless steel appliances. ~UNITED CENTER home of the Chicago Bulls and Blackhawks located within 2-3 min walk *2 blocks*. 4-7 min drive to little Italy restaurants/Tri Taylor/Medical District. Near Downtown (5-7min drive). 2 Blocks from the blue line ~Free street parking ~Washer Dryer ~Dishwasher ~spacious Back patio Parties are restricted due to COVID guidelines for the city of Chicago.

Guest favourite

Condo in Humboldt Park

4.96 out of 5 average rating, 127 reviews

Stylish 3BR + Free Parking 10-15mins from Downtown

This apartment is located in Historical Humboldt Park, a residential area that is an easy 10-15mins drive to Downtown, Medical District, Wicker Park, West Town, Logan Square, and Ukranian Village. Due to the proximity, we host guests visiting for tourism, fests,concerts, sport events , work conferences, weddings, birthdays, and visiting family. There are grocery stores closeby. There’s street parking and a gated private parking available. Location wise, you are close enough to everything.

Guest favourite

Condo in Little Italy

4.97 out of 5 average rating, 145 reviews

Private hot tub - King bed suite - Free parking

Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

Superhost

Condo in West Town

4.81 out of 5 average rating, 131 reviews

Cabin 207 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! Early Check-Ins and Late Check-Outs are difficult to accommodate.

Guest favourite

Condo in West Loop

4.95 out of 5 average rating, 197 reviews

Updated Designer Duplex In Fulton Market W/parking

UPDATE: We just completed our luxury renovation March 2023! New kitchen, bathrooms, and patio with a firepit. 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!

Guest favourite

Condo in West Town

5 out of 5 average rating, 126 reviews

Spacious 4 Bedroom Condo

Located in West Town in the heart of Noble Square, just north of West Loop with access to all the best restaurants and only minutes away from River North and Old town, enjoy this 4 bedroom, 3.5 bath condo with private parking, 2 living spaces, heated floors throughout the entire lower level and steam showers. A gourmet kitchen stocked with everything you will need including an espresso maker. This home is perfect for families, couples, friends or traveling for business.

Superhost

Condo in Near West Side

4.93 out of 5 average rating, 232 reviews

The Upscale Getaway Near Downtown

This cozy apartment features custom furniture in every room and a fireplace to warm up next to on a chilly night. Make use of the well-stocked kitchen to cook a hearty breakfast before setting out to explore the city! The primary bedroom has a King Bed, the second bedroom as queen bed and the pull out sofa in the living room has a queen bed. All of the mattresses are high quality memory foam. Parking: 1 gated parking spot included & plenty of free street parking

Guest favourite

Condo in Lincoln Park

4.97 out of 5 average rating, 119 reviews

Lincoln Park 2bed/2bath in Historic Neighborhood

Just steps from the lively center of Chicago's Lincoln Park and poised above the quiet, tree-lined streets of the coveted Arlington-Deming neighborhood, this residence on the top floor of a three-story walkup is the perfect for families that want to be close to it all! Lake Michigan, Lincoln Park Zoo, multiple parks, transportation, dining, nightlife, and more. We provide one daily parking permit per night of your stay so you can access free street parking.

Guest favourite

Condo in Wrigleyville

4.98 out of 5 average rating, 310 reviews

Sunny Apartment Just 2 Blocks from Wrigley and Boystown

Located on a quiet, tree-lined street, the apartment sits on the second storey of a classic Chicago house in Lakeview—a vibrant lakefront community with arts and culture, green space, eateries, boutiques, nightlife, and transportation options. Street parking passes available upon request. Less than five minute walk to red line El (subway train) stop and several bus lines.